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A Travel Blogger’s Step-by-Step Guide to Planning Unforgettable Trips
As a former flight attendant turned part-time travel blogger, I’ve had the privilege of exploring countless destinations and picking up many travel planning tips along the way. I’ve also had my fair share of complete travel planning f*ck ups so I’ve put together a step-by-step guide on how to successfully plan your next trip!
And how to NOT make any of the same travel planning mistakes I’ve made before (like getting turned away at the boarding gate because my visa to Kenya was expired).
Even though I personally enjoy the travel planning process (which is probably pretty rare when compared to the rest of the population), I recognize that many find it completely overwhelming. However, with a little help from me and a more structured approach, you can significantly reduce stress associated with travel planning and ultimately relax more while preparing for your trip
So here’s my step-by-step guide to making your dream trip a reality.
This site contains affiliate links. I may receive a small commission for purchases made through these links however, this has no impact on the integrity of my reviews. All thoughts and opinions are my own.
The dream begins: where should I travel to next?
The hardest part is probably figuring out where the heck you want to go?! First, you should start by considering what type of trip this is. I always say there’s a huge difference between traveling and going on vacation. “Traveling” to me means busy days, packed itineraries, absorbing the culture, learning, etc whereas “going on vacation” means deleting slack from my phone and laying by a beach.
There’s a time and place for both but they are both very different experiences.
How to choose your next travel destination
Like I said, you’ll want to first start by asking yourself a series of questions.
- Who am I traveling with?
- What am I looking to get out of the trip?
- What time of year am I planning to go?
- What do I ultimately want to see and do?
- How many days can I get off?
- What’s my budget? (if applicable)
- Should I go on a roadtrip or take a plane?
- Do I want to go somewhere new or am I okay going somewhere I’ve already been?
I’ll tell you a little bit about how I choose my travel destinations but it’s a bit unique to my situation. Up until recently, I’ve been working full time at a tech company based in San Francisco. We had to go into the office 3x a week but there was flexibility on working remote for a week here and there. I also used to travel to NYC a lot for work, so I used to back up my trips with a personal / blogging business trip on either end.
So for me, I was always looking for destinations that were easy to get to/from SFO and/or EWR Airport (because I’m a loyal United flyer. More on this later)
Since I work full-time, I very much value my time. So I’ll almost always look for a direct flight and/or one with little connections. As a former flight attendant, I’ve seen how 1 flight delay can screw up an entire agenda.
I’m also engaged to someone from South Africa and he personally has no desire to visit some of the countries I want to visit. So if I’m doing solo travel, I’ll usually pick from my list of countries that I know we’ll never go to in our lifetime together.
A few things I always keep top of mind as a solo female traveler are: safety, access to reliable wifi, and ease of difficulty logistically (ie. do i have to take 2 planes and 1 train and rent a car? if so, i’m probably not going to go alone to this destination).
Lastly, I follow a lot of travel bloggers for a reason! I’m always getting introduced to new destinations on social media and will save them to a “wishlist” folder to revisit when I’m in the mood to travel plan.
Prioritizing a travel wishlist (budget, interests, and time)
Okay so once I’ve narrowed it down to a few destinations — how do I actually pick where to go?
For me, it usually comes down to a few things…
- Ease of logistics (this is usually my #1 criteria for any trip)
- Access to reliable wifi (this is only if i’m working but 99% of the time i am)
- Things to do (food, culture, activities, photography spots, etc)
- Budget (this is usually a last consideration for me as I no longer focus on budget travel)
Ease of logistics when travel planning
Logistics are often my top consideration when choosing a destination. I look for places with good transportation networks, including reliable public transport and easy access to airports or train stations.
I can be an anxiety-ridden traveler so the simplicity of getting around can greatly influence my overall travel experience and honestly, my mood.
This is mainly why I do a lot of city travel with day trips sprinkled in. Ultimately, I love nothing more than a destination with straightforward logistics.
Access to reliable wifi
Given that I’m typically working during my travels, having access to reliable WiFi is crucial. Depending on the destination, I’ll sometimes reach out to hotels or airbnb hosts before booking to ask about their wifi speed.
I’ve found that anything above 50 mbps is usually sufficient for being on meetings all day. Anything below and you’re bound to run into issues.
If the hotels or hosts don’t know how to check their internet speeds, I ask them to head to https://www.speedtest.net/ and they can check it directly from there.
This is mostly for destinations that aren’t big cities. For big cities, I’m almost certain there’s a WeWork or some sort of coworking space around that I can book.
Things to do / activities in the area
A wide array of activities (or mouthwatering food) is essential for when I travel. I use GetYourGuide a lot to book walking tours, food tours, hidden gems, and museum entry tickets. I also use them sometimes to book private transportation to/from an airport. They’re so easy to use and their UI is great.
(Sorry but Viator was built like a million years ago and they need some serious updates to their UI/UX to be stay relevant).
I ultimately love going on day trips, exploring historical landmarks, tasting local delicacies, or capturing stunning portraits and landscapes through photography. Put me anywhere with all 3 of those and I’m a happy camper 😊
Budget
While budget isn’t my primary focus anymore, it still remains a factor in my decision-making process. I definitely take into consideration the overall cost and also how much hotels will cost me, as they’re usually the most expensive part of any trip.
By balancing all of these factors (ease of logistics, wifi access, activities, and budget), I can usually choose a destination that aligns with both my practical needs and personal interests!
(And yes, it’s almost always going to be an international destination outside of the US).
Visa requirements: what do I need to know?
Take it from someone who’s f*cked up her visa situation a number of times. I know it’s easy for those with a United States passport (aka myself) to get complacent about visa requirements but things are definitely changing for us soon (ie. Europe visa requirements, Brazil visa requirements, the UK, etc).
Understanding visa requirements is a crucial step in the travel planning process.
Each country has its own set of rules regarding entry, and it’s important to research these well in advance of your trip. Start by checking whether your destination requires a visa for travelers from your country.
The first thing you should be googling before seriously booking flights to any destination is – “DO I NEED A VISA FOR XYZ COUNTRY”
Some countries offer visa-free entry or visas on arrival, while others require you to apply in advance. The application process can vary significantly, with some requiring online applications and others necessitating a visit to an embassy or consulate.
Some of my favorite websites for checking travel requirements include:
Keep in mind, while these websites are usually up to date – you’ll always want to actually cross reference it to the government website of the country you’re visiting.
Lastly, you’ll want to ensure your passport is valid for the required duration beyond your planned departure date (usually 6 months is the norm). You also want to make sure you have enough blank pages for a stamp.
I almost got turned away in Germany for not having an open page for them to stamp on and they eventually found a tiny sliver of space and let me go but I wouldn’t always bank on getting so lucky.
Planning the journey: logistics & getting there
Finding the best deals: tips for booking flights
Finding the best flight deals can be a bit of a treasure hunt! I’m not sure I’ll be able to give universal advice on flight deals because I live in a major city and am extremely loyal to United Airlines. BUT I do have decades of experience with travel, travel planning, and research so I have some great tools and recommendations for those who aren’t tied to a specific loyalty program.
Price-conscious flight shopping
For the most budget-friendly options, I’d probably start with Google Flights. You can set price alerts pretty easily and they aggregate flight deals from ALL of the airlines (not just one). Going (Formerly Scott’s Cheap Flight’s) is also a great tool to find cheap flights.
Hopper is another great tool as they can show you a heatmap calendar of ticket prices and allow you to also set alerts.
Travel planning like an expert: maximizing credit cards & points
If you’re a credit card points enthusiast, then Roame Travel and seats.aero are excellent resources for maximizing your rewards. Both of these are premium products and require a monthly subscription to get the most out of the tool.
I recently signed up for seats.aero and was super impressed. I set an alert for a business class flight to Rio for under 85,000 points for a certain date and was sent an email/text alerting me that a flight existed so I immediately booked it!
Another travel creator friend of mine did the same thing and found a kickass business class deal to Japan for under 70,000 miles.
You can still use both of these sites for free, you just won’t be able to access specific routes and/or receive alerts without paying. So it’s still good for browsing flights though!
Ps. I’m working on an article about my specific credit card strategy so stay tuned!
Is airline loyalty worth It?
Everyone always asks me this and my answer is always the same — it depends.
Again, I live in a major city in a major airport hub so it makes sense. If you live in the US and are within a 45 minute drive of a major airline’s hubs (LAX, SFO, IAH, ORD, MIA, JFK, EWR, ATL, etc), then I think it totally makes sense to start building loyalty.
I also personally have a lot of family that live in Taiwan and Milan and United Airlines is the most convenient nonstop from SFO to both of these destinations. I also have a personal goal of becoming a United “million-miler” which means you fly 1,000,000 miles with them and receive United/Star Alliance Gold status for life.
Again – I recognize this probably doesn’t make sense for everyone but these are things that are important to me.
This is for United Airlines specifically — aside from the convenience factor, I also love the perks of getting to board early, free checked bags, free economy plus seating at booking, and the most important part — being as close to the top of the list for business class upgrades.
While getting upgraded out of SFO is hard in general because there are so many business travelers with status, it’s definitely still possible and I’ve gotten upgraded many times.
The secret is to use expert mode when browsing for flights and you can always call the help desk and ask how many people are on the upgrade list already and what # you would be on the list if you were to be added to the flight.
Ultimately, if your travel schedule is unpredictable or you prioritize the lowest possible price regardless of airline, a loyalty program is probably not right for you.
Packing smart: essential packing tips & travel planning checklist
After years and years of being on the road as a flight attendant, I’d like to think that I’ve actually perfected my packing strategy! I wrote an article awhile back (one of my first blog posts ever) outlining my Top 5 Packing Tips in detail, but here they are in a nutshell 🥜 ⬇️
1. NEVER CHECK A BAG
I’ve seen waaaaaaay too many bags get lost during my time at American Airlines so I generally try to avoid checking a bag as much as possible to reduce the risk of it getting lost at the start of my trip.
If I absolutely have to check a bag, then I make sure to always bring a spare set of clothes and underwear into my carry on or backpack.
2. ROLL YOUR CLOTHES
Awhile back, I conducted my own very scientific study involving a mix of 20 tops, 5 denim jeans, 2 sweaters, and 2 pairs of shoes to see which method yielded more room in my suitcase.
The final verdict? I was able to fit way more clothes into my suitcase when I rolled them!
3. AN EMPTY DUFFEL BAG IS YOUR BEST FRIEND
By now, you probably think I’m a crazy person that just travels insanely light all the time. That’s definitely not the case. I always remember to pack an empty duffel bag that can be used for anything I buy abroad.
You can check out all of the packing gear I use on my Amazon storefront.
4. WEAR YOUR HEAVIEST SHOES ON THE PLANE
These will typically be tennis shoes (or maybe booties for women), but by doing so, you’ll end up leaving extra room in your suitcase for things that matter more! This rule applies for heavy winter coats as well!
5. SIGN UP FOR AN AIRLINE CREDIT CARD
Lastly, I’d suggest signing up for an airline branded credit card. Almost all airline credit cards offer complimentary checked bags as a perk for cardholders, potentially saving you significant costs over time. This benefit can be particularly valuable for families or those who just can’t leave those full-size skincare products behind!
For example, United’s Chase Explorer card gives travelers their first checked bag for free! Don’t let the airlines sucker you into paying extra fees for luggage when there are ways around it.
Finding the perfect place to stay: accommodation abroad
If this is your first time to the blog, then you might not know that I specialize in featuring aesthetically pleasing, design-forward, super dreamy boutique hotels around the world. Which is why finding a place to stay when traveling is one of my absolute favorite parts of trip planning.
Keep reading to better understand how you should think about booking accommodation and to learn more about the tools I use for booking accommodations abroad!
What type of Accommodation is right for me? (hotels, airbnb, hostels, etc)
Similar to figuring out where to travel to next – I usually start by asking myself a short series of questions when it comes to deciding on the type of accommodation I’ll be staying in.
- Am I traveling alone?
- Will I be working during my trip?
- How close do I need to be to public transportation?
- Is this destination small? Will I need a car to get around?
- Will I be staying onsite a lot?
- When will I be arriving at this destination?
All of these are important factors when deciding what type of accommodation to book. I’ll NEVER book a hostel so it’s usually a toss up between a hotel and/or an Airbnb.
I’m also very much Team Hotel. I love beautiful hotel lobby interiors, being able to drop my bags off and wander around if the room isn’t ready, and there’s usually a history behind the building itself.
There’s also just something about getting pampered (room service, plush robes, slippers, onsite spas, etc) that make paying a higher price tag totally worth it. Or maybe it’s because it’s the opposite of how I live at home so it really feels like I’m experiencing something new.
How do I find the best accommodation? My favorite travel rewards program
SAFARA SAFARA SAFARA! I wish I could scream this as loud as possible from the rooftops.
Ask anyone, I used to be the MOST loyal Hotels.com fan. My whole family was, we were all gold members for a really long time. But then Expedia bought them and absorbed all their brands into this combined “One Key” rewards program which is absolute crap.
You used to get a 10th night free (that was worth the average of your 9 previous bookings) but now they basically give you pennies on the dollar back in rewards.
Ever since my former coworker’s husband started the company (shout out to Doug and Maxine), I’ve been a loyalist to Safara Travel. Not only due to the personal connection, but it’s just so much better for hotel reward bookings than any other platform out there.
On every single booking, you’re earning money off your next booking, and the more you book, the more you earn back. You start off getting 2.5% cashback; after you spend $1,000, you’ll earn 5%; and after $5,000 in annual spend, you get 10% back for every single booking.
Using Safara also avoids the hassle of managing points with various credit cards and transferring them. The credits are all in one place and automatically applied to your next booking.
If you’ve read any of my other posts, you’ll know that I genuinely love this platform.
Seriously – run don’t walk to Safara Travel. Plus, they immediately give you $100 towards your next hotel just for signing up.
Where should I stay? How to choose the right neighborhood during your trip
There are so many different ways to figure out where to stay when traveling. I don’t think there’s ONE right way to do it so I’m going to tell you about how I figure out where to stay when travel planning.
First, I use social media a lot. I use instagram to figure out what the hottest restaurants are and to look for photogenic spots that I know I’m going to want to visit. I’ll often just type in “Japan restaurants” and start scrolling or “Paris things to do” and see what’s out there.
Once I find something I like, I start a folder in Instagram and save all of the posts, reels, carousels, etc to this folder. You can also use a travel planning app like Travogram that shows you real places that other people have been recently on their trip.
Once I have enough places (over time), I’ll pull up my computer and open Google Maps.
Then, I’ll create a list in Google Maps and start pinning and saving the spots onto the map that I saw on Instagram. Once I have a decent amount of pins (like 15-20, usually more) then I’ll look to see which area all of my pins are in.
Sometimes all my pins are concentrated in one area and other times, my pins are super spread out. There’s usually a pretty common theme that emerges though and then I’ll start to do more research on the neighborhoods themselves based on my saved pins.
My research usually consists of reading travel blogs (like this), scrolling through reddit questions, and asking friends or fellow bloggers on Instagram if they’ve gone to XYZ destination.
My method isn’t perfect but it definitely works for me!
Here’s an example of a Google Maps Pin List that I used during my last trip to Copenhagen. (This is an example of a city that was pretty compact so I based my hotel stay on where the highest concentration of pins were)
Crafting your itinerary: what to see & do
Are you a “have everything planned by the minute” or an “ill wake up and just see where the day takes me” person?
I’d like to think that I’m a mix of both but I can also admit that I definitely lean towards the former. I mean, I’m writing a blog post about travel planning so you can assume there’s some level of planning and organization to me as a person. But yes, I’m also pretty Type A in real life.
Creating an Itinerary: Balancing Flexibility and Structure
However, when I travel – it’s important to me to not cram too much into an itinerary. I usually pick 2-3 things each day that are must-see places or activities, and then leave the rest of the day free for other things that might come along.
This is where having that Google Maps Pins List is helpful because if I have free time to wander around, I’ll usually just pull up the map and see what else is around that I’ve bookmarked.
For major attractions, I also like to get up early and get it out of the way so that I can beat the crowds and be happy I saw whatever it was by ~10am, leaving the rest of my day pretty free for whatever.
Booking Tours & Activities: Making the Most of My Trip
As for tools, I pretty much always use GetYourGuide to book activities. Yes, I’m an affiliate partner of theirs but I’ve also been using them for years even before I started this blog. They were founded in 2009 whereas Viator was founded in 1995 and it shows.
Here another screenshot of other activities I’ve booked through GetYourGuide. (I paid for all of these out of pocket).
Viator’s UI/UX is terrible. It runs like it was built in 1995 which is totally fine but they NEED to invest in updating it to be more mobile friendly. Their app crashes all the time and it’s so hard to access your bookings.
My parents always laugh at me nowadays when I tell them that I’ve booked a walking tour or a guided tour in XYZ destination because I HATED tours as a kid. (Some of them are still awful but they’ve gotten much better recently, or maybe it’s because I’ve gotten older).
When I was younger, you couldn’t have paid me to go on a tour. I loved just wandering around, going to restaurants, going out to the bars, etc. but now I really enjoy finding a couple hour history tour, or guided museum visit, or a food tour with locals, etc.
Oh how times have changed.
Travel essentials: staying connected, health, & safety
I’m honestly laughing as I write this post because there’s a lot of things I prepare for now (as a 33 year old) that I would NEVER have spent money on a few years ago. Like, travel insurance but I now realize how valuable it is (especially if you’re traveling to countries where you’re at high risk of disease).
Staying Connected: International Roaming & Local SIM Cards
It’s crazy to think how much has changed in the travel world, including SIM cards and how data plans work. Assuming you have a newish model of an iphone or Android, there are two e-sim companies that I recommend when traveling abroad: Airalo and Holafly
Airalo and Holafly are both eSIM providers that offer affordable and flexible data plans for international travelers. They both have great coverage (over 200 countries) and allow you to purchase internet and install the eSIM directly to your phone. I’ve listed out some differences between the two and my top choice below.
Airalo vs. Holafly:
- Pricing: Airalo generally offers more budget-friendly options with various data packages, while Holafly focuses on unlimited data plans at a higher price point.
- Coverage: Both companies offer extensive global coverage and are necessary for making sure you’re not stuck with offline access.
- Data Plans: Airalo provides more flexibility with various data options, while Holafly specializes in unlimited data plans.
- Features: Airalo offers a wider range of features, including some plans with local phone numbers and voice/SMS services, while Holafly primarily focuses on data services.
The winner for me? Holafly due to the fact that every sim card comes with unlimited data!
(I used Airalo for awhile but just kept running out of data which was frustrating so I’d either have to keep topping up or just go on airplane mode so I decided to just stick with Holafly because every sim is unlimited).
Ps. you can use my referral link for 5% off your next Holafly purchase.
Travel Insurance: what coverage do I need? Health and safety
Raise your hand if you’ve never purchased travel insurance?
Yep, that was me too.
Until my friend broke her arm while on a scooter in Bali.
Or until another friend had her baby 2 months premature while on a trip to South America and they had to stay in the ICU in Chile for 6 months.
After that happened… I said never again.
Travel insurance is like a safety net for your trip. It protects you from unexpected costs if things go wrong. Imagine getting sick overseas, your flight getting canceled, flight delays, or losing your luggage – travel insurance can help cover those expenses. So, if you want to travel worry-free, consider getting insurance. It’s a small price to pay for peace of mind.
I usually get travel insurance through Allianz because their plans are pretty reasonable, starting as low as $27/person for short trips.
(I mostly only get it for fear of something crazy happening to me from a health perspective, but I know loads of people that pay for it in case they run into delays or cancellations. I usually wing it with that sort of stuff but you won’t catch me dead without health insurance when traveling).
Step-by-Step Guide to Travel Planning: Final Thoughts
If you’ve made it this far — congrats 👏 and thanks for reading all of my tips and tricks on travel planning!
Even though I have extensive experience with traveling, I always advise people to still do their own research before arriving in a destination because the world changes quickly and some of my personal preferences won’t always align to yours.
Planning a trip can feel totally overwhelming, but breaking it down into manageable steps makes it so much easier and way more fun. I hope this guide was helpful and you incorporate some of these strategies into your next trip or vacation!
Did you use any of these tips and tricks for travel planning? Let me know in the comments below!
Looking for some travel inspiration?
Check out all my international travel guides here!
Looking for more travel planning tips and tricks?
Check out all my other travel tips from a former flight attendant turned travel blogger!
As a former flight attendant turned part-time travel blogger, I’ve had the privilege of exploring countless destinations and picking up many travel planning tips along the way. I’ve also had my fair share of complete travel planning f*ck ups so I’ve put together a step-by-step guide on how to successfully plan your next trip!
And how to NOT make any of the same travel planning mistakes I’ve made before (like getting turned away at the boarding gate because my visa to Kenya was expired).
Even though I personally enjoy the travel planning process (which is probably pretty rare when compared to the rest of the population), I recognize that many find it completely overwhelming. However, with a little help from me and a more structured approach, you can significantly reduce stress associated with travel planning and ultimately relax more while preparing for your trip
So here’s my step-by-step guide to making your dream trip a reality.
This site contains affiliate links. I may receive a small commission for purchases made through these links however, this has no impact on the integrity of my reviews. All thoughts and opinions are my own.
The dream begins: where should I travel to next?
The hardest part is probably figuring out where the heck you want to go?! First, you should start by considering what type of trip this is. I always say there’s a huge difference between traveling and going on vacation. “Traveling” to me means busy days, packed itineraries, absorbing the culture, learning, etc whereas “going on vacation” means deleting slack from my phone and laying by a beach.
There’s a time and place for both but they are both very different experiences.
How to choose your next travel destination
Like I said, you’ll want to first start by asking yourself a series of questions.
- Who am I traveling with?
- What am I looking to get out of the trip?
- What time of year am I planning to go?
- What do I ultimately want to see and do?
- How many days can I get off?
- What’s my budget? (if applicable)
- Should I go on a roadtrip or take a plane?
- Do I want to go somewhere new or am I okay going somewhere I’ve already been?
I’ll tell you a little bit about how I choose my travel destinations but it’s a bit unique to my situation. Up until recently, I’ve been working full time at a tech company based in San Francisco. We had to go into the office 3x a week but there was flexibility on working remote for a week here and there. I also used to travel to NYC a lot for work, so I used to back up my trips with a personal / blogging business trip on either end.
So for me, I was always looking for destinations that were easy to get to/from SFO and/or EWR Airport (because I’m a loyal United flyer. More on this later)
Since I work full-time, I very much value my time. So I’ll almost always look for a direct flight and/or one with little connections. As a former flight attendant, I’ve seen how 1 flight delay can screw up an entire agenda.
I’m also engaged to someone from South Africa and he personally has no desire to visit some of the countries I want to visit. So if I’m doing solo travel, I’ll usually pick from my list of countries that I know we’ll never go to in our lifetime together.
A few things I always keep top of mind as a solo female traveler are: safety, access to reliable wifi, and ease of difficulty logistically (ie. do i have to take 2 planes and 1 train and rent a car? if so, i’m probably not going to go alone to this destination).
Lastly, I follow a lot of travel bloggers for a reason! I’m always getting introduced to new destinations on social media and will save them to a “wishlist” folder to revisit when I’m in the mood to travel plan.
Prioritizing a travel wishlist (budget, interests, and time)
Okay so once I’ve narrowed it down to a few destinations — how do I actually pick where to go?
For me, it usually comes down to a few things…
- Ease of logistics (this is usually my #1 criteria for any trip)
- Access to reliable wifi (this is only if i’m working but 99% of the time i am)
- Things to do (food, culture, activities, photography spots, etc)
- Budget (this is usually a last consideration for me as I no longer focus on budget travel)
Ease of logistics when travel planning
Logistics are often my top consideration when choosing a destination. I look for places with good transportation networks, including reliable public transport and easy access to airports or train stations.
I can be an anxiety-ridden traveler so the simplicity of getting around can greatly influence my overall travel experience and honestly, my mood.
This is mainly why I do a lot of city travel with day trips sprinkled in. Ultimately, I love nothing more than a destination with straightforward logistics.
Access to reliable wifi
Given that I’m typically working during my travels, having access to reliable WiFi is crucial. Depending on the destination, I’ll sometimes reach out to hotels or airbnb hosts before booking to ask about their wifi speed.
I’ve found that anything above 50 mbps is usually sufficient for being on meetings all day. Anything below and you’re bound to run into issues.
If the hotels or hosts don’t know how to check their internet speeds, I ask them to head to https://www.speedtest.net/ and they can check it directly from there.
This is mostly for destinations that aren’t big cities. For big cities, I’m almost certain there’s a WeWork or some sort of coworking space around that I can book.
Things to do / activities in the area
A wide array of activities (or mouthwatering food) is essential for when I travel. I use GetYourGuide a lot to book walking tours, food tours, hidden gems, and museum entry tickets. I also use them sometimes to book private transportation to/from an airport. They’re so easy to use and their UI is great.
(Sorry but Viator was built like a million years ago and they need some serious updates to their UI/UX to be stay relevant).
I ultimately love going on day trips, exploring historical landmarks, tasting local delicacies, or capturing stunning portraits and landscapes through photography. Put me anywhere with all 3 of those and I’m a happy camper 😊
Budget
While budget isn’t my primary focus anymore, it still remains a factor in my decision-making process. I definitely take into consideration the overall cost and also how much hotels will cost me, as they’re usually the most expensive part of any trip.
By balancing all of these factors (ease of logistics, wifi access, activities, and budget), I can usually choose a destination that aligns with both my practical needs and personal interests!
(And yes, it’s almost always going to be an international destination outside of the US).
Visa requirements: what do I need to know?
Take it from someone who’s f*cked up her visa situation a number of times. I know it’s easy for those with a United States passport (aka myself) to get complacent about visa requirements but things are definitely changing for us soon (ie. Europe visa requirements, Brazil visa requirements, the UK, etc).
Understanding visa requirements is a crucial step in the travel planning process.
Each country has its own set of rules regarding entry, and it’s important to research these well in advance of your trip. Start by checking whether your destination requires a visa for travelers from your country.
The first thing you should be googling before seriously booking flights to any destination is – “DO I NEED A VISA FOR XYZ COUNTRY”
Some countries offer visa-free entry or visas on arrival, while others require you to apply in advance. The application process can vary significantly, with some requiring online applications and others necessitating a visit to an embassy or consulate.
Some of my favorite websites for checking travel requirements include:
Keep in mind, while these websites are usually up to date – you’ll always want to actually cross reference it to the government website of the country you’re visiting.
Lastly, you’ll want to ensure your passport is valid for the required duration beyond your planned departure date (usually 6 months is the norm). You also want to make sure you have enough blank pages for a stamp.
I almost got turned away in Germany for not having an open page for them to stamp on and they eventually found a tiny sliver of space and let me go but I wouldn’t always bank on getting so lucky.
Planning the journey: logistics & getting there
Finding the best deals: tips for booking flights
Finding the best flight deals can be a bit of a treasure hunt! I’m not sure I’ll be able to give universal advice on flight deals because I live in a major city and am extremely loyal to United Airlines. BUT I do have decades of experience with travel, travel planning, and research so I have some great tools and recommendations for those who aren’t tied to a specific loyalty program.
Price-conscious flight shopping
For the most budget-friendly options, I’d probably start with Google Flights. You can set price alerts pretty easily and they aggregate flight deals from ALL of the airlines (not just one). Going (Formerly Scott’s Cheap Flight’s) is also a great tool to find cheap flights.
Hopper is another great tool as they can show you a heatmap calendar of ticket prices and allow you to also set alerts.
Travel planning like an expert: maximizing credit cards & points
If you’re a credit card points enthusiast, then Roame Travel and seats.aero are excellent resources for maximizing your rewards. Both of these are premium products and require a monthly subscription to get the most out of the tool.
I recently signed up for seats.aero and was super impressed. I set an alert for a business class flight to Rio for under 85,000 points for a certain date and was sent an email/text alerting me that a flight existed so I immediately booked it!
Another travel creator friend of mine did the same thing and found a kickass business class deal to Japan for under 70,000 miles.
You can still use both of these sites for free, you just won’t be able to access specific routes and/or receive alerts without paying. So it’s still good for browsing flights though!
Ps. I’m working on an article about my specific credit card strategy so stay tuned!
Is airline loyalty worth It?
Everyone always asks me this and my answer is always the same — it depends.
Again, I live in a major city in a major airport hub so it makes sense. If you live in the US and are within a 45 minute drive of a major airline’s hubs (LAX, SFO, IAH, ORD, MIA, JFK, EWR, ATL, etc), then I think it totally makes sense to start building loyalty.
I also personally have a lot of family that live in Taiwan and Milan and United Airlines is the most convenient nonstop from SFO to both of these destinations. I also have a personal goal of becoming a United “million-miler” which means you fly 1,000,000 miles with them and receive United/Star Alliance Gold status for life.
Again – I recognize this probably doesn’t make sense for everyone but these are things that are important to me.
This is for United Airlines specifically — aside from the convenience factor, I also love the perks of getting to board early, free checked bags, free economy plus seating at booking, and the most important part — being as close to the top of the list for business class upgrades.
While getting upgraded out of SFO is hard in general because there are so many business travelers with status, it’s definitely still possible and I’ve gotten upgraded many times.
The secret is to use expert mode when browsing for flights and you can always call the help desk and ask how many people are on the upgrade list already and what # you would be on the list if you were to be added to the flight.
Ultimately, if your travel schedule is unpredictable or you prioritize the lowest possible price regardless of airline, a loyalty program is probably not right for you.
Packing smart: essential packing tips & travel planning checklist
After years and years of being on the road as a flight attendant, I’d like to think that I’ve actually perfected my packing strategy! I wrote an article awhile back (one of my first blog posts ever) outlining my Top 5 Packing Tips in detail, but here they are in a nutshell 🥜 ⬇️
1. NEVER CHECK A BAG
I’ve seen waaaaaaay too many bags get lost during my time at American Airlines so I generally try to avoid checking a bag as much as possible to reduce the risk of it getting lost at the start of my trip.
If I absolutely have to check a bag, then I make sure to always bring a spare set of clothes and underwear into my carry on or backpack.
2. ROLL YOUR CLOTHES
Awhile back, I conducted my own very scientific study involving a mix of 20 tops, 5 denim jeans, 2 sweaters, and 2 pairs of shoes to see which method yielded more room in my suitcase.
The final verdict? I was able to fit way more clothes into my suitcase when I rolled them!
3. AN EMPTY DUFFEL BAG IS YOUR BEST FRIEND
By now, you probably think I’m a crazy person that just travels insanely light all the time. That’s definitely not the case. I always remember to pack an empty duffel bag that can be used for anything I buy abroad.
You can check out all of the packing gear I use on my Amazon storefront.
4. WEAR YOUR HEAVIEST SHOES ON THE PLANE
These will typically be tennis shoes (or maybe booties for women), but by doing so, you’ll end up leaving extra room in your suitcase for things that matter more! This rule applies for heavy winter coats as well!
5. SIGN UP FOR AN AIRLINE CREDIT CARD
Lastly, I’d suggest signing up for an airline branded credit card. Almost all airline credit cards offer complimentary checked bags as a perk for cardholders, potentially saving you significant costs over time. This benefit can be particularly valuable for families or those who just can’t leave those full-size skincare products behind!
For example, United’s Chase Explorer card gives travelers their first checked bag for free! Don’t let the airlines sucker you into paying extra fees for luggage when there are ways around it.
Finding the perfect place to stay: accommodation abroad
If this is your first time to the blog, then you might not know that I specialize in featuring aesthetically pleasing, design-forward, super dreamy boutique hotels around the world. Which is why finding a place to stay when traveling is one of my absolute favorite parts of trip planning.
Keep reading to better understand how you should think about booking accommodation and to learn more about the tools I use for booking accommodations abroad!
What type of Accommodation is right for me? (hotels, airbnb, hostels, etc)
Similar to figuring out where to travel to next – I usually start by asking myself a short series of questions when it comes to deciding on the type of accommodation I’ll be staying in.
- Am I traveling alone?
- Will I be working during my trip?
- How close do I need to be to public transportation?
- Is this destination small? Will I need a car to get around?
- Will I be staying onsite a lot?
- When will I be arriving at this destination?
All of these are important factors when deciding what type of accommodation to book. I’ll NEVER book a hostel so it’s usually a toss up between a hotel and/or an Airbnb.
I’m also very much Team Hotel. I love beautiful hotel lobby interiors, being able to drop my bags off and wander around if the room isn’t ready, and there’s usually a history behind the building itself.
There’s also just something about getting pampered (room service, plush robes, slippers, onsite spas, etc) that make paying a higher price tag totally worth it. Or maybe it’s because it’s the opposite of how I live at home so it really feels like I’m experiencing something new.
How do I find the best accommodation? My favorite travel rewards program
SAFARA SAFARA SAFARA! I wish I could scream this as loud as possible from the rooftops.
Ask anyone, I used to be the MOST loyal Hotels.com fan. My whole family was, we were all gold members for a really long time. But then Expedia bought them and absorbed all their brands into this combined “One Key” rewards program which is absolute crap.
You used to get a 10th night free (that was worth the average of your 9 previous bookings) but now they basically give you pennies on the dollar back in rewards.
Ever since my former coworker’s husband started the company (shout out to Doug and Maxine), I’ve been a loyalist to Safara Travel. Not only due to the personal connection, but it’s just so much better for hotel reward bookings than any other platform out there.
On every single booking, you’re earning money off your next booking, and the more you book, the more you earn back. You start off getting 2.5% cashback; after you spend $1,000, you’ll earn 5%; and after $5,000 in annual spend, you get 10% back for every single booking.
Using Safara also avoids the hassle of managing points with various credit cards and transferring them. The credits are all in one place and automatically applied to your next booking.
If you’ve read any of my other posts, you’ll know that I genuinely love this platform.
Seriously – run don’t walk to Safara Travel. Plus, they immediately give you $100 towards your next hotel just for signing up.
Where should I stay? How to choose the right neighborhood during your trip
There are so many different ways to figure out where to stay when traveling. I don’t think there’s ONE right way to do it so I’m going to tell you about how I figure out where to stay when travel planning.
First, I use social media a lot. I use instagram to figure out what the hottest restaurants are and to look for photogenic spots that I know I’m going to want to visit. I’ll often just type in “Japan restaurants” and start scrolling or “Paris things to do” and see what’s out there.
Once I find something I like, I start a folder in Instagram and save all of the posts, reels, carousels, etc to this folder. You can also use a travel planning app like Travogram that shows you real places that other people have been recently on their trip.
Once I have enough places (over time), I’ll pull up my computer and open Google Maps.
Then, I’ll create a list in Google Maps and start pinning and saving the spots onto the map that I saw on Instagram. Once I have a decent amount of pins (like 15-20, usually more) then I’ll look to see which area all of my pins are in.
Sometimes all my pins are concentrated in one area and other times, my pins are super spread out. There’s usually a pretty common theme that emerges though and then I’ll start to do more research on the neighborhoods themselves based on my saved pins.
My research usually consists of reading travel blogs (like this), scrolling through reddit questions, and asking friends or fellow bloggers on Instagram if they’ve gone to XYZ destination.
My method isn’t perfect but it definitely works for me!
Here’s an example of a Google Maps Pin List that I used during my last trip to Copenhagen. (This is an example of a city that was pretty compact so I based my hotel stay on where the highest concentration of pins were)
Crafting your itinerary: what to see & do
Are you a “have everything planned by the minute” or an “ill wake up and just see where the day takes me” person?
I’d like to think that I’m a mix of both but I can also admit that I definitely lean towards the former. I mean, I’m writing a blog post about travel planning so you can assume there’s some level of planning and organization to me as a person. But yes, I’m also pretty Type A in real life.
Creating an Itinerary: Balancing Flexibility and Structure
However, when I travel – it’s important to me to not cram too much into an itinerary. I usually pick 2-3 things each day that are must-see places or activities, and then leave the rest of the day free for other things that might come along.
This is where having that Google Maps Pins List is helpful because if I have free time to wander around, I’ll usually just pull up the map and see what else is around that I’ve bookmarked.
For major attractions, I also like to get up early and get it out of the way so that I can beat the crowds and be happy I saw whatever it was by ~10am, leaving the rest of my day pretty free for whatever.
Booking Tours & Activities: Making the Most of My Trip
As for tools, I pretty much always use GetYourGuide to book activities. Yes, I’m an affiliate partner of theirs but I’ve also been using them for years even before I started this blog. They were founded in 2009 whereas Viator was founded in 1995 and it shows.
Here another screenshot of other activities I’ve booked through GetYourGuide. (I paid for all of these out of pocket).
Viator’s UI/UX is terrible. It runs like it was built in 1995 which is totally fine but they NEED to invest in updating it to be more mobile friendly. Their app crashes all the time and it’s so hard to access your bookings.
My parents always laugh at me nowadays when I tell them that I’ve booked a walking tour or a guided tour in XYZ destination because I HATED tours as a kid. (Some of them are still awful but they’ve gotten much better recently, or maybe it’s because I’ve gotten older).
When I was younger, you couldn’t have paid me to go on a tour. I loved just wandering around, going to restaurants, going out to the bars, etc. but now I really enjoy finding a couple hour history tour, or guided museum visit, or a food tour with locals, etc.
Oh how times have changed.
Travel essentials: staying connected, health, & safety
I’m honestly laughing as I write this post because there’s a lot of things I prepare for now (as a 33 year old) that I would NEVER have spent money on a few years ago. Like, travel insurance but I now realize how valuable it is (especially if you’re traveling to countries where you’re at high risk of disease).
Staying Connected: International Roaming & Local SIM Cards
It’s crazy to think how much has changed in the travel world, including SIM cards and how data plans work. Assuming you have a newish model of an iphone or Android, there are two e-sim companies that I recommend when traveling abroad: Airalo and Holafly
Airalo and Holafly are both eSIM providers that offer affordable and flexible data plans for international travelers. They both have great coverage (over 200 countries) and allow you to purchase internet and install the eSIM directly to your phone. I’ve listed out some differences between the two and my top choice below.
Airalo vs. Holafly:
- Pricing: Airalo generally offers more budget-friendly options with various data packages, while Holafly focuses on unlimited data plans at a higher price point.
- Coverage: Both companies offer extensive global coverage and are necessary for making sure you’re not stuck with offline access.
- Data Plans: Airalo provides more flexibility with various data options, while Holafly specializes in unlimited data plans.
- Features: Airalo offers a wider range of features, including some plans with local phone numbers and voice/SMS services, while Holafly primarily focuses on data services.
The winner for me? Holafly due to the fact that every sim card comes with unlimited data!
(I used Airalo for awhile but just kept running out of data which was frustrating so I’d either have to keep topping up or just go on airplane mode so I decided to just stick with Holafly because every sim is unlimited).
Ps. you can use my referral link for 5% off your next Holafly purchase.
Travel Insurance: what coverage do I need? Health and safety
Raise your hand if you’ve never purchased travel insurance?
Yep, that was me too.
Until my friend broke her arm while on a scooter in Bali.
Or until another friend had her baby 2 months premature while on a trip to South America and they had to stay in the ICU in Chile for 6 months.
After that happened… I said never again.
Travel insurance is like a safety net for your trip. It protects you from unexpected costs if things go wrong. Imagine getting sick overseas, your flight getting canceled, flight delays, or losing your luggage – travel insurance can help cover those expenses. So, if you want to travel worry-free, consider getting insurance. It’s a small price to pay for peace of mind.
I usually get travel insurance through Allianz because their plans are pretty reasonable, starting as low as $27/person for short trips.
(I mostly only get it for fear of something crazy happening to me from a health perspective, but I know loads of people that pay for it in case they run into delays or cancellations. I usually wing it with that sort of stuff but you won’t catch me dead without health insurance when traveling).
Step-by-Step Guide to Travel Planning: Final Thoughts
If you’ve made it this far — congrats 👏 and thanks for reading all of my tips and tricks on travel planning!
Even though I have extensive experience with traveling, I always advise people to still do their own research before arriving in a destination because the world changes quickly and some of my personal preferences won’t always align to yours.
Planning a trip can feel totally overwhelming, but breaking it down into manageable steps makes it so much easier and way more fun. I hope this guide was helpful and you incorporate some of these strategies into your next trip or vacation!
Did you use any of these tips and tricks for travel planning? Let me know in the comments below!
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Check out all my international travel guides here!
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