Choosing a destination for your most awesome trip

Look the other way from Kirkjufell

How to choose the perfect destination for your next trip

Choosing a destination for your next trip or vacation can be one of the most enjoyable aspects of travel. It’s a time filled with anticipation and possibility. But sometimes, choosing a destination can also be stressful or frustrating. As I note quite often in Hidden Travel: The Secret to Extraordinary Trips, where you go matters less than how you go. By that I mean that a good attitude, one filled with openness and wonder, can make an otherwise ho-hum destination magical. But the most beautiful location can fall flat if you’re ill or not in your happy place.


When choosing a destination, start with “Know thyself”

Martin Gobsch at work

Still, there are several factors to consider in choosing a destination for your trip that will improve the likelihood of an amazing experience. I’ll cover most of these factors below. But first, let’s look at the main factor: you.

The starting point for choosing a destination for your vacation or even long-term trip is understanding your Traveler Type. And the best way to do that is to take the Traveler Type quiz, then review the corresponding workbook you get at the end of the quiz.

Once you know a bit more about yourself and the type of travel you prefer, it’s time to think about the type of places to visit.


When choosing a destination, ask, “What makes a place special to me?”

Travel is all about places. But you may not have considered all the ways that place can affect you or your trip, particularly as you’re choosing a destination for your next one. Thus, when choosing a destination, answer these questions to get a sense of what you like best about places.

Let’s start with this open-ended question: What factors draw you to a place? That could be colors, smells, nature, architecture, the people (in what way?), food, activities, history, cultural sights and events, etc.

If that seems too vague, check out this article on what appeals to you visually about a place.

Now let’s be more specific. Think of one of your favorite trips. What are some of the key elements — not just magic moments — that stood out or that you’d like to experience more of elsewhere? It can help to think in terms of your senses: things you saw, heard, smelled, tasted, touched or did. For example, my favorite trips all have these elements in common: natural beauty (a gorgeous setting or hiking experience or even a lovely garden), distinctive architecture (preferably old or ancient) and encounters with locals who end up being friends. What about you?

Your goal is to identify the factors that delighted you on past trips and learn from them for choosing a destination for future trips. To help even further, let’s get very specific with the key factors that tend to influence where you’ll go on a trip.

FYI, this list is part of a larger downloadable guide on How to Prepare Now for Better Trips Later. That guide provides additional information on how to choose the right traveling companion, how to connect your internal interests with your trips, how to practice more sustainable travel, and how to build your empathy skills, both at home and on a trip. You can download this useful guide over in the Resources section if you’ve already signed up or get it right here:


Key factors for choosing a destination for your next trip

Now let’s get to the heart of choosing a destination for your next trip. Here are some key factors (in alphabetical order so you can prioritize based on what matters to you) to consider when planning where to go. Use these to build your own list to determine where to travel next.

  • Activities: These may relate to your hobbies or could be new adventures you’ve never tried before. Some destinations are well-known for certain activities, so if the activity matters most to you, plan your trip around that. For example, you won’t find a lot of ziplining in Nebraska, but you would in Jamaica. Or, you could orient an entire trip around a single activity such as skiing, surfing, fishing, backpacking, and other sports. But you can do the same for indoor activities such as theater, museums, restaurants, dancing, etc.
  • Amount of time you have: This relates to distance and budget as well, but remember that short trips built around purpose, themes or defining moments can be as powerful as long ones.
  • Bucket list: Where have you always wanted to go? If you have several locations on your bucket list, use some of these other factors to choose the one that works best right now.
  • Budget: Your budget can affect where you go, how long you’re gone, what level of places you stay at, how you eat, etc. But it can also influence the style of travel you choose.
  • Comfort level: You define what this means in terms of the cush factor for the places you stay, the kinds of transport you use, the nature of the places where you eat, as well as risk and safety concerns. It can also relate to how comfortable you are with trying new things and being in very strange (to you) environments. If you don’t like dealing with hassles, consider having someone else plan the trip for you or go to someplace known for taking good care of their guests.
  • Distance: How far are you willing to go? How much time do you want to spend in transition? How comfortable are you with less-than-comfortable transport (crowded busses, hours in a van over rough roads, etc.)?
  • Environmental impact: Can you take public transportation or minimize short flights in one destination better than in another? Can you avoid overly popular cities in favor of lesser-visited ones in the same country?
  • Events: Are there sporting events, festivals, concerts, fairs or other activities in a certain place at a certain time you want to see? This can affect the season in which you travel and also how long in advance you have to make reservations (i.e., longer for more popular events).
  • Food: Is there a particular cuisine you long to try? Or do you want to build your trip around restaurants, markets, or types of food? How about cooking classes or regional specialties?
  • Friends: This can apply to who you go with, who you go to meet, etc. It relates to whether to travel solo or with others, but also how important is it for you to meet or meet up with others on a trip? Some locations and the types of places where you stay will make it easier to meet locals or other travelers.
  • Language Do you want a place that speaks your language everywhere (e.g. Australia), in most places (e.g. Norway), hardly anywhere (e.g. rural China)? Or do you want to go learn or practice a particular language?
  • Mood: Do you want a trip that is adventurous, relaxing, people and parties, quiet and introspective, etc.?
  • Opportunities: Similarly, is there a wedding or business trip that could be extended? Are you traveling to one country that is close to another you’ve never visited where you could add even a quick side trip? Do you have a friend who has recently moved to a particular country or location that you could now visit?
  • Personal interests: These include hobbies, areas of curiosity, personal passions or can relate to Activities as noted above. This is where you can apply purpose, quests or themes to your trip as well.
  • Popularity: If you’ve never traveled, perhaps you want to visit the popular places. But because over-tourism is such a growing issue, how might you plan a trip to places that others rarely visit?
  • Sales: Maybe the biggest opportunity of all is this: Is there a deal going on right now? Many a great trip has occurred by getting email alerts on travel deals and then responding.
  • Time of year: What season can you go or what is a place known for in a particular season (e.g., fall foliage in New England)? This also includes intentionally going somewhere in the off-season to avoid crowds.
  • Transportation choices: Do you want to avoid planes? Sail on a freighter? Try riding horseback or on a camel? Is cost more important or is the experience? For example, in Europe, renting a car will likely be cheaper than the train for more than two people but trains offer a unique experience. Also, if using airline miles for a ticket, are there restrictions or limited seats to one destination but plenty to another? 
  • Type of place: What appeals to you most, beach, mountain, desert, city, small town, nature, etc.? Rural or urban? Big city or small village? As with most of these factors, you can build a trip around a mixture. But knowing what you gravitate towards helps avoid less-than-stellar trips. If the countryside bores you senseless, don’t plan a trip around a rural location just because other people enjoy that.
  • Weather: Hot or cold or someplace in between? Rainy or dry? Cloudy or clear? Some may seem like obvious choices. After all, who wants to travel in stormy weather? But if your purpose is to take beautiful landscape photographs of a place, you may actually choose a place or season with inclement weather, at least part of the time, for more interesting skies.
  • Other?  

One of the best ways to figure out where you want to go on a big trip is to take these factors, prioritize them for you, and apply them to a short trip closer to home. You likely won’t be able to work in all the factors you might on a big trip, but if you’re thinking about traveling in the off-season, for example, when you know the weather might be rainier than you’re used to, don’t wait until you’re in Bangladesh during the monsoon season to determine your tolerance for rain. Find someplace domestically with similar weather to see how you do.

Any factors I’ve missed here that are important to you when choosing a destination? If so, leave a comment since it always helps to share what we know with other travelers.