How to Successfully Choose Your Travel Destination

Do you want to travel but don’t know where you should go? Are you looking for a little clarity and inspiration to get your trip planning started? You’re in the right place!

This post has the questions you should ask yourself and 5 tips on where you can go to find and choose your travel destination.

You want your trip to be a success and that starts with a right-fit destination. But, choosing your travel destination can feel overwhelming. No worries.

This can happen whether you’re planning your first trip or you’re a seasoned traveler. Break the process down into smaller pieces to sort out what’s practical (or not) and awaken your travel inspiration!

Choose your Travel Destination: Start with the Basics

How much time do you have? 

Are you thinking about a long weekend getaway, a 2-week trip, extended travel, or something in between? Depending on where you live and the amount of time you have to travel, certain destinations will make more sense than others.

Regardless of whether you want to relax or have an active adventure, traveling too far or cramming in too much can make for a rushed, ungratifying trip.


Who are you traveling with? 

Are you traveling as a couple, with children, for a girl’s/guy’s trip, or taking a solo adventure?

The people you travel with or the lack thereof might make specific places and experiences more practical than others. You have to ask what kind of destination would be enjoyable for everyone traveling.

If you’re traveling solo, is it your first time or have you been on your own before? Are you looking for an experience out of your comfort zone? Or would you prefer to keep things easy for yourself by taking a tour?

There’s no right or wrong answer. Just follow what makes sense and feels right for your situation.

Family Travel Stock

What kind of weather suits your travel style? 

Do you want to sightsee when it’s warm or work on your tan? Or do you prefer cooler temperatures and hope to see a perfect winter white landscape?

Obviously, your weather preference can help narrow down possible travel destinations based on when you intend to travel. Keep in mind that traveling during peak seasons comes with higher prices.

Would you be ok traveling during a shoulder season in order to save money? Oftentimes, the weather is pleasant, but may not be what you imagine when you think of enjoying a particular destination.

On the upside, fewer people visit during the shoulder season, which means you’ll be less affected by crowds. I prefer visiting Europe in the off-season exactly for this reason.

Cuba Stock

What is your budget?

You certainly don’t need to be rich to travel, but you also want to feel comfortable with the destination you choose, the seat class you fly in, and where you’re staying without blowing a hole in your budget.

Ask yourself:

  • Are you a budget traveler or a luxury traveler?
  • Will you fly coach or only in business or first class?
  • Will you stay in a hotel like this or like that?
  • Do you prefer boutique hotels? Or will you stay in a vacation rental?
  • Will your destination require specific travel gear that you’ll need to factor into the overall costs?
  • If you participate in airline or hotel loyalty programs, can you use miles and/or points to offset some or all of the costs?
  • Do you know which countries are more affordable with a favorable exchange rate?

financially savvy traveler knows the answers to these questions and plans accordingly.

With the above questions asked and answered, you’ve finished the practical first steps to choosing your travel destination. 

The next step is my favorite part, though. It’s where you can put your right brain to work and envision the kind of destination that matches the experience for which you’re hoping.

What kind of journey or travel experience do you want?

Certainly, you need to decide if you prefer mountains or beaches, city sightseeing or an outdoor adventure, a foodie holiday or a historical visit to famous cultural sights.

Beyond this, though, travel planning is about crafting a journey or experience for you and your travel companions.

  • What do you hope to gain from your travels? What will your travel companions gain from the trip?
  • What experiences do you want to have with your travel companions, or if solo, on your own?
  • How do you want to remember this trip? Is there a lasting impact you’re hoping for?

If your answer is having downtime and spending time together, perhaps a beachside or mountain retreat is the right fit.

Maybe you’re traveling with children and want the travel to be educational in some way. Consider, then, sightseeing, age-appropriate museums, and cultural experiences.

If you want an adventure as a couple, it might be the right time to finally make that epic hike or learn how to scuba dive.

Blyde RIver Canyon South Africa
Blyde River Canyon, South Africa

Understanding the type of journey or experience you want is the essence of choosing the right destination and making your trip a success. Too often, people are heard saying “I need a vacation from my vacation.”  It doesn’t have to be this way.

Travel can be so fulfilling if you take the time to plan a meaningful getaway that meets the needs, hopes, and wants of you and your travel companions.

But, when you choose your travel destination because it’s where you think you should take your kids or where everyone else you know goes, your trip can end up feeling lackluster and not worth your time and money.

5 Tools to Find and Choose Your Travel Destination

1. Use Pinterest’s Visual Search Engine

“A picture speaks a thousand words” is so cliche, but also resonates with truth. We are visual creatures in the same way my dogs relate to the world around them by using their keen sense of smell. Our brains are hardwired to process visuals quickly, which impacts how we feel, what we think, and even what we do.

Why not use this scientific rationale (as I have!) to explain an obsession with Pinterest and Instagram?! 😉

But, it also helps to understand why 100s of millions of people use these visual platforms for everything from home decor to travel planning. We’ve all seen photos of places that have grabbed us, causing an emotional, visceral reaction. These feelings can be a huge help when choosing your travel destination.

If you’ve never used Pinterest, think of it not as a social platform, but as a search engine that delivers results in photos. You’ll need a Pinterest account to search, so sign up for one if you haven’t yet.

You can follow me on Pinterest and also find a ton of great travel inspiration by other travel bloggers on my Pinterest group boards!

Like Google, Pinterest’s search engine lets you search for specific keywords. It also suggests additional keywords as you type and shows more of them in boxes just above your search results.

Pinterest search screenshot How to choose a travel destination

In the search above, I searched for travel destinations. “Bucket lists” appeared as I was typing so I added it to my keywords. (I’ve cut off the search results to focus just on the keywords.)

You can click any of the keyword boxes to refine your search further. The arrows on either side of the keywords let you scroll through all the keyword options. For example, if you wanted bucket list travel destinations in Europe, choose Europe from the keyword boxes.

pinterest how to choose a travel destination

You’ll begin to see visual results for incredible bucket list travel destinations in Europe. Repeat the search by refining it with different keywords and click on the pins you like to see even more information about that destination.

Then, save the pins you like to one of your Pinterest travel boards and use them to choose your travel destination and for future trip inspiration. Just be forewarned! You may look up and wonder how on earth X number of hours has passed!

2. Follow Inspiring Instagram Accounts and Hashtags

Instagram is the place to share photos and videos whether you’re a seasoned photographer or just sharing a photo of your new shoes. There are 60 million new photos uploaded to Instagram every day. Luckily, there’s no shortage of photos highlighting travel and amazing places around the globe.

San Juan Puerto Rico

You’ll need to join the 500 million active Instagrammers if you haven’t already by downloading the app to your mobile device. Once you’re up and running, use the search feature to enter a keyword like travel or the name of a place to find photos and people to follow.

You can follow me on Instagram and use this Matador article to find more inspiring travel Instagrammers. You’ll likely not only choose your travel destination but also have a long list of places you want to visit in the future!

3. Buy Coffee Table Travel Books

With everything digitalized or online these days, don’t underestimate the power of travel books. You know the ones, with their oversized, smooth pages and glossy colorful photos that fill your eyes and heart with wanderlust.

They’re perfect for perusing whether you want to choose your travel destination or just float away into your travel dreams. I love opening these books to random pages and seeing what I find. Sometimes I take a photo of a photo or keep the book open to a specific page for a couple of days just to see if a place feels like the right one for my next trip.

Here are a few of my favorite travel picture books.

This Amazon bestseller, along with its sister book Journeys of a Lifetime, can excite a passion for traveling the world in just about anyone! The photos carry you into the scene, while the text about each place transports you to lush rain forests and medieval architecture. I especially love how the chapters are organized by place type, like mountains, beaches, etc.

I have a previous version of this book, which I’ve continually picked up through the years. By looking at each country individually, you can glimpse its culture, cities, countryside, and people. I particularly love the dos and don’ts and the book and movie suggestions to prepare for your visit.

This book is perfect for choosing experiences that match the journeys you imagine for yourself and others. The ideas in this book are for those who want to explore versus lounge beachside. From Patagonia to the Canadian Rockies to the world’s best dive spots, you’ll be packing your backpack as you stare wide-eyed at all the possible adventures awaiting.

Of course, while I was getting these book thumbnails from Amazon, I spied a travel book to add to my holiday wishlist!

Aren’t you always wondering which destinations are the best for the times you want to travel? Or maybe you look for the best value times to travel to a specific place? This book looks to be the perfect blend of practical information and travel inspiration. 

4. Read Travel Blogs

Ok, you had to know this was coming! 😉

But, in all seriousness, there are a ton of travel blogs out there with a lot of inspiring, incredible content. Find someone you like on social media? Take some time to explore their blog. The hidden gem content is often discovered by those who take a few minutes and dig beyond just the most recent posts. Have you seen my posts on Perito Moreno Glacier in Patagonia, camping in the Okavango Delta, or discovering beautifully, historic Cordoba, Spain?

5. Follow the Deals

Maybe you’re an open-minded, flexible person who’s just happy to travel anywhere. Perhaps you’re looking to get away for the least possible money! Sign up for hotel and airline loyalty programs and their emails to learn about the destinations with low airfares or hotel rates.

If you collect miles and points, look for loyalty program award discounts to specific places or for particular hotels. For instance,  hotel brands like IHG offer promotions throughout the year like 50% off award nights at select hotels in Mexico, the Caribbean, and Central America.

airplane window - best websites to find cheap flights

Airfare websites I follow are The Flight Deal and Secret Flying because they list mistake fares and other great value airfares. The deals are timely and often need to be booked right away.

Momondo is another great tool for choosing your travel destination and finding the best airfare. They have an explore anywhere feature that lets you choose destinations by continent, month, budget, and theme (beaches, cities, etc.).Momondo Search Anywhere

Skyscanner is another tool to search for the best prices on flights even when you don’t where you want to go. Type your home airport as the departure and “everywhere” as the destination. Skyscanner will show you the lowest-priced flights to a range of destinations.

If you need more tips about how to find cheap flights, check out more tools I use and the tips I use to find cheap flights.

So, how do you choose the right destination? 

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How to Choose Your Best Travel Destination
Save for later! Pin this guide to your Pinterest travel board.

36 thoughts on “How to Successfully Choose Your Travel Destination”

    1. Jackie Sills-Dellegrazie

      Thanks, Kelly! How could I forget Kayak’s explore, tool!? Thanks for the reminder and for adding to this guide with such a great tip!

  1. Haha, I am definitely guilty of saying ‘I need a vacation from my vacation’. These are great pieces of advice, especially deciding what type of adventure you want, and who you’ll be with so that your expectations matches the reality!

    1. Jackie Sills-Dellegrazie

      Lol, Annie. I don’t think you’re alone on that one! It’s such a disappointment when you have one idea in mind and then the trip turns out not like you wanted.

  2. I really use pinterest for visual searches. I love that you included that. My friends and I already peg the places we want and the moment there is a sale— we just go for it.

    1. Jackie Sills-Dellegrazie

      I love how you said, “we just go for it.” So awesome, Karla. You can plan forever, but in the end, you just have to take action! 🙂

  3. Really nice I like that you added tools to go along with how to choose your travel destination! Pinterest is a great place to get information and what I like about it is getting a picture preview before you get to the website to peak interest instead of print list on google search 🙂

    1. Jackie Sills-Dellegrazie

      Thanks for reading. I so agree! The Pinterest visual is really great and so much more helpful than just a text link.

    1. Jackie Sills-Dellegrazie

      Flexibility is key to being a successful traveler, right Chrysoula?! So, following the deals is smart.

    1. Jackie Sills-Dellegrazie

      Thanks for sharing, Jennifer. It’s always great to get a good deal! Good for you for being so open and flexible.

  4. Great post! I abide by most of these tips myself! I’d say I usually pick where to go based on three things: length of visit (I’m not going to plan a trip to Australia with only 3 days) who I’m going with (is my boyfriend coming along? Maybe I’ll go somewhere that is more iffy for solo travelers) and the weather (I don’t want to go anywhere during monsoon season)!.

    And of course, blogs, Pinterest and Instagram are where I get much of my inspiration!

    1. Jackie Sills-Dellegrazie

      Thanks for reading, Erika. I do the same and I always have to think differently when I travel solo versus with my husband. (Shh..I can be more adventurous without him! lol)

  5. These are all very practical things to think of and helpful advices! Some things didn’t work out as planned but it happens, least we could do is try and prevent them 🙂 I’ll check against this list the next time I plan to go!

    1. Jackie Sills-Dellegrazie

      Exactly, Mar. We can’t prevent everything but thoughtful planning means you tried your best. 🙂 Thanks for reading.

  6. Great tips. It is a struggle every time I have some time of but I think I basically ask all those questions myself – and I am very strongly influenced by social media of course 🙂

    1. Jackie Sills-Dellegrazie

      Absolutely, Arzo! Isn’t is perfect when a photo or a post on social media just speaks to you? 😉 Thanks for reading.

  7. Great tips and amazing write up Jackie! I love how you made it look simple yet contains lots of important informations. Totally loving your tips and will absolutely use some of your tips in choosing where to go next in the future! Thanks!

  8. Ridley Fitzgerald

    It’s good to know more about finding a vacation destination and hotel. I like how you said that it depends on if we’re traveling with our kids. This summer we plan on taking our two kids with us, so we’ll have to find a destination and a hotel that will work for two rowdy children!

    1. Jackie Sills-Dellegrazie

      Thanks for reading, Ridley. I edited out your link as they’re not allowed in comments. Thanks!

  9. Skylar Williams

    Thank you for your tip to consider what type of lodgings you will be staying at. My brother wants me to visit the sea with him and his family. I’ll be sure to talk to him about whether we’ll be staying in a motel or hotel and what type of accommodations they offer.

  10. I loved the tip that you gave to consider following deals while you are looking for a place to visit. Me and some of my classmates are wanting to find a tour to go on for a project for our photography project, and it will be important for us to know that we could find the right tour. I will be sure to follow the deals, so we could stick to our tight budgets.

  11. Kristofer Van Wagner

    Thanks for these tips! I like that you mentioned we should think about what sort of experiences we want to gain from the trip so that it helps us in determining the perfect holiday destination. My wife and I are planning to go on a couple’s vacation next month and I’ll be sure to speak with her on her preference.

    1. Jackie Sills-Dellegrazie

      Thanks for reading, Kristofer. Also so important to think about the types of experiences. Hope you have a great trip.

  12. I like your tip about reading travel blogs to help decide where to vacation since they may have some hidden gems you didn’t know about. My husband and I have been looking for somewhere to go to celebrate our one year anniversary. I think we should find a vacation rental somewhere that is less well known so that we can spend quality time together.

    1. Jackie Sills-Dellegrazie

      Thanks for reading, Charlotte. Hope you have a great anniversary trip.

  13. Hi, interesting article and useful tips. I especially like that you recommended tools that help to choose a destination. When I travel I always spend a lot of time searching for the ideal place for my trip.

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