by Annie 

Published: November 4, 2021

Updated:  August 29, 2022
choose a destination map

When it comes time to choose a destination for your next vacation, it’s easy to go down the rabbit hole of internet research only to find yourself with an even longer list of ideas than you started with! That’s not just me, right? I swear, this is one of the hardest parts of travel planning -- narrowing down a world full of amazing places to just a few you can string together with the time and money you have to spend on your next trip. 

Over the years, I’ve come up with a few tips and tricks to help both myself and my clients make this seemingly impossible choice with more ease. Save this post for next time you’re planning a trip and find your head swimming with all the possibilities! Below are the simple steps we’ll cover in this post so choosing where to go on vacation is a much easier process! If you're planning a trip to Europe, here's a step-by-step guide with everything you need to create an incredible experience. 

*This post contains affiliate links, which means if you make a purchase using the link, I receive a small commission at no additional charge to you. This helps me keep the lights on around here. I ONLY recommend products and services I personally use and love. 

How to choose a travel destination?

  1. Create your list of possibilities: Set a timer for 3 minutes and make a list of all the destinations that come to mind for this trip. Narrow your choices with the following questions. 
  2. What’s your travel budget? Eliminate any places that will cost more than you want to spend.
  3. What type of traveler are you? This will help you figure out what types of experiences you'll enjoy most.
  4. How many days do you have for this trip and how much of it are you willing to spend getting to/from your destination? Remove options that take more time than you want to spend in transit.
  5. How do you want to spend your days? Decide what kind of vacation you want to have (relaxing, active, city adventure, outdoors, etc.) and cross-out options that don’t fit your desired experience. 
  6. Consider other factors: entry requirements, climate & weather, events, high season vs. shoulder season, etc.
  7. Look at flights, hotels, activities, and transportation options for your remaining destinations and finalize your decision.

3 Questions to Help You Choose a Destination

When you’re craving a change of scenery and have a zillion ideas about where to go and what to do, here are three important questions that will help you narrow your choices: what is your budget? How much time do you have for this trip and how much are you willing to spend in transit? How do you want to spend your days? Once you answer these, it will not only help you choose a destination, but give you guidelines for the rest of your travel planning too. If you’re traveling with other people, I highly recommend going through these activities together so you’ll find the perfect vacation spot for everyone!

What is your budget for this trip? 

This is one of the most important things to determine when you’re ready to start designing your next vacation. Knowing how much you have to spend will help you narrow down your destination options quickly! For example, if you have $2,000 to spend, that’s going to go pretty quickly in a place like Denmark, but it can stretch for weeks, maybe even months, in a place like Albania. 

Once you nailed down your travel budget, look at your list and cross off any destinations that you know are more expensive. Something like this --I desperately want to go to Tanzania to see Mt. Kilimanjaro and take a safari. I know this is going to be a more expensive trip, so if my budget is $2,000 I have to cross that one off my list for this trip. Once you know your travel budget, check out this post with tips for saving money and maximizing your time on vacation

How much time do you have for this trip and how much of that are you willing to spend in transit?

Time is another element that can help you narrow down your destination choices quickly. If you have a week for your vacation, you’ll probably want to skip countries that have a total travel time (from the time you leave home until you arrive at your accommodation) of more than 20 hours. Though it’s doable (anything is possible!), go into it knowing that you’ll spend two of your seven days just getting to your destination and home again. 

If you have a traditional (in the US) schedule of ten vacation days you can still go anywhere, if you’re willing to use a chunk of them at once. When I was working in the corporate world, I found lots of ways to stretch that PTO so I could travel more. Every year I would take seven or eight of my PTO days at once and, when combined with weekends and holidays, take nearly two full weeks off and travel to Europe. Some of the places I was able to visit using less than ten days of PTO include London & Southern England, Iceland, Spain + Rome + Paris, Christmas & New Years in Germany + Prague. If you want it, you can find a way!

Depending on your organization, time off without pay may be an option for you. At my last day job, we had a few really busy times of year and, outside of those, my boss would let me take time off without pay. Granted, this meant budgeting for it and saving money from all my other paychecks to make up the difference, but it worked! One year, I took six weeks off and traveled to Romania, Ireland, and even took a road trip to the Oregon Coast when I got back. 

Once you’ve decided how much time you have for your vacation and see how it fits in with your work, cross off any of the places you know you’ll want more time to experience in the way you want. Even if you have to eliminate some places you really want to go, it’s only for this trip. This isn’t a one-time deal. When it’s time to choose a destination again and that place will be back on the list! 

How do you want to spend your days?

This is one of the most crucial questions to ask yourself when it comes to choosing a destination. Spend some time thinking about what you’d like to do on this vacation. Knowing what type of traveler you are can really help you figure this out! If you’ve been working a lot of hours and really want a chance to relax and unwind, think about which places feel rejuvenating. Sometimes a big city full of sights can feel too busy and overwhelming if I just want some time to chill and relax. Other times, I’m ready to spend my days on the move and exploring. There’s no right answer, but get clear on how you want to feel on this trip and what types of activities will allow you to get what you want.

Take your time with this question. When it’s time to choose a destination, the process doesn’t have to be completed in ten minutes. Give yourself time to daydream. This is part of why I typically start my travel planning at least six months before I actually leave. It gives me time to ponder what I want from my next travel experience and research the different options. Take the time to envision yourself in each of the places you’re considering. Which ones feel the most awesome when you think about how you would spend your time there? Keep those and cross out the rest on your list. 

Now that you’ve answered these three questions, your list should be significantly shorter than when you started. If you still have more than five places on your list, here’s one more question to help you get to your top 5 -- If you only get to take one more trip, which of the places on your list would you most want to visit? I can never choose just one, but it usually helps me get to five or less.

Listen, you’re going to take way more than one more trip. The whole point of independent travel is having flexibility in how you spend your time and money. You can travel more often this way then if you use the traditional, more expensive, generic options. Also, there are a variety of ways to save money on the different elements of travel using the value travel approach

Other Considerations to Help You Choose a Destination

Hopefully, you’ve managed to get your list down to a top 5. Now, let’s think about some of the specific factors related to each place on your list. It’s time to dig into things like entry requirements, events, climate, and the busiest tourist seasons. Let’s do it!

Covid-19 Entry Requirements

Navigating travel during a global pandemic makes the entry and quarantine requirements a huge factor in choosing your destination. When planning my 40th birthday trip for the fall of 2021, Vietnam and Argentina were the places at the top of my list. Unfortunately, neither were allowing non-essential visitors so I had to eliminate those and see where I could visit more easily. The New York Times has created an article with the places that are currently open to vaccinated US citizens, and they update it regularly. It’s a good starting point, but be sure to visit the specific country’s website for the most up-to-date info. A simple internet search of “country entry requirements” will get you all the details for current entry requirements for any of the countries on your list. 

Events in Your Destination

Big events happening in the destination you’re considering can either be a reason to visit or a reason to stay away. It totally depends on the type of experience you want to have, which you’re clear about now! For example, going to Munich in late September means Oktoberfest. This has always sounded like a crowded, sloppy, expensive headache to me. I’d rather visit when the beer halls aren’t jam packed and prices are lower. Someone else will think it sounds like an amazing once-in-a-lifetime party they don’t want to miss! There are no right or wrong answers here, just be honest with yourself about what kind of experience you want to have. 

Do a quick search for events in the place you’re considering during the season or month you’d like to visit. There may be some you want to attend -- like the time we went to Edinburgh during the Military Tattoo and Fringe Festivals (so epic and super fun!), and others you want to avoid so spend five to ten minutes researching.

Weather & Climate

Personally, this is an important one when I’m trying to choose a destination. If you’re like me and don’t love the heat, Southeast Asia in the middle of summer, which is during their monsoon season, might be miserable. Or, you may want to avoid the Caribbean during hurricane season (June through November).

Running a search for the average temperatures in the destinations on your list will show you what to expect and give you info about average rainfall and hours of daylight as well. Also search for the best times to visit the places you’re considering. This is super helpful for giving you specific information so you can choose a destination that’s going to be enjoyable while you’re there!

Depending on the reason you’ve got a place on your list, the weather may not make much difference to you. Stan and I went to Germany and Czechia for Christmas one year, knowing full well that it was going to be cold and snowy, which it was! We drank lots of gluhwein to stay warm and quickly learned to see any of the outdoor attractions first thing because it was dark by about 4 PM. That’s when we headed for the museums and beer halls! You can totally plan around the weather and pack appropriately for anything. Just keep it in mind as you’re thinking through your list of destinations.

High Season vs. Shoulder Season

This particular element can be a tough decision because the time when most tourists visit (aka high season) is usually when the weather is nice and a lot of events are happening. However, flights and accommodations also tend to be most expensive during these times because the demand is high. (Check out these posts to help you save money on flights and another to save on accommodations, regardless of when you’re going). 

The good news is that there’s usually a chunk of time on either side of high season (aka shoulder season) that’s a great time to travel to most places. During shoulder season, the weather is still pretty good (better, in some cases), but the crowds are smaller and prices are lower. For Europe, the high season is June through August, but visiting in late spring or early fall, their shoulder season, is perfect! Now, I actually plan to go during shoulder season because it’s the sweet spot for all the things that are important to me. 

When I was planning my 40th birthday trip to the Balkans, I was looking for places in Europe that would be nice from the end of September through October. Turns out, the beaches in Albania were perfect for me (temps in the 70s & 80s) and it was super easy to find accommodations on the fly because it was outside the main tourist season. Dubrovnik was one of the stops and there was a day where it was way more crowded than I enjoy due to busloads of people coming from the cruise ships. The guide from our walking tour told us that, during the summer, you can hardly walk through the old city and there’s a line of people just to get into the gate. Even though it was more crowded than I like, it turns out things were actually chill compared to the high season. I probably would have lost my mind between the heat and the crowds. Lol! Know thyself. 

Start Researching Flights & Accommodations

By now, your list of destinations should be at five or less. You can narrow it further and start putting together different route options with a quick look at flights using Skyscanner.com. Start by searching from your home airport to the specific destinations. Next, you can expand your search to see if it’s cheaper to fly somewhere nearby. For example, if you want to go to Berlin, it may be cheaper to fly to Paris and then take a short flight or a train ride the rest of the way to Berlin. Plus, you get to see some of Paris while you’re there too! 

Finding cheap flights is a huge part of how I choose a destination. Saving money on flights is one of the things that lets me travel more often, so I’m all about finding a great deal and working my trip around that!

For accommodations, have a look at Booking.com see all the different types of accommodations and prices available for when you’re looking to visit. This will also give you a clearer picture for how this destination will work for your budget. 

Dig Deeper Into Your Destinations

By this point, you have a top 2 or 3 places left on your list, at the most. Maybe you’ve already made your decision and are ready to start building your itinerary, the next phase of travel planning. Now it’s time to start gathering more information about these destinations. Many times, I’ll buy a guidebook (DK is my favorite!) to learn more about the places I’m considering. Usually, I’ll buy used ones (Thriftbooks.com is my favorite!) because the information I care about doesn’t really change too much over time. I use them to learn about the history, culture, food, main attractions, different regions, etc.  Also, you can find a ton of helpful information on the country’s tourism website. 

Can you see how this all starts to come together?! It’s easy with small, manageable pieces, which is why I like to give myself lots of time for researching and travel planning before the actual trip. This makes the whole process less overwhelming and you get to actually enjoy the process of creating your travel experience instead of dreading it. Also, by planning well in advance, you can usually find great deals on flights and accommodations before everyone else is looking too! 

Europe is my specialty. I've planned (and taken) dozens of indie trips all over the continent. If you're looking for more information on planning a trip to Europe, here's a complete guide that will walk you through the steps!

Conclusion

Maybe you'd like to talk to a real person, get some answers or help with the details, and move on with the planning. I've got you covered! Check out these travel consulting services designed specifically for indie travelers! Get only the help you want without turning your trip over to someone or listening to a pitch about some generic vacation package. 

I'd love to stay connected! You can sign up for the newsletter so you'll get updates and know anytime a new post is out. You can also find me over on Instagram or Facebook where I share my adventures and would love to hear about yours too!

Now get out there. The world is waiting for you!

Your Turn

How do you usually choose a destination for your next trip? We’d love to hear your process and any tips you have!

Share yours in the comments.

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About the author 

Annie

Fun Lover. Food Eater. Bold Explorer. Big Dreamer.

Annie is a fiercely independent traveler who loves to create unique and interesting experiences. She thrives on finding the magical moments and hidden gems waiting around every corner. Her passion for helping others make their travel dreams come true fuels her work as a travel planner, consultant, educator, and community builder.

  • Great ideas. There are so many places that I want to visit, narrowing it down is the challenge. Sometimes my husband and I figure out the best place to fly to and then plan a trip from there.

    • Yes! I totally do the same thing. It’s fun to build around the cheap flights and figure out a route. You can find all sorts of hidden gems along the way!

  • Great ideas. I think of destinations a lot and I usually have a lot of travel wishes and sometimes I decide depending on cheap flights, but sometimes I just follow my heart.

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