Snorkeling Trunk Bay, St. John, USVI

Choosing the right travel destination

Two considerations when picking a locale

If I’ve learned one major thing while traveling, and can give one piece of advice for those choosing the location for their next getaway, it’s this: be true to yourself. 

When someone returns from a getaway with a sub-par reaction and an unenthusiastic response about the place, I see one of two major issues at play (perhaps both). The following happened during their planning process:

  1. They weren’t honest with themselves about what they were looking to achieve in a vacation
  2. They took glossy ads as being reality

Having a couple of mediocre experiences myself juxtaposed with a whole lot of great experiences, I’ve learned how to navigate the destination-picking phase of travel. Newsflash: it involves some work.

Know what you’re looking for in an experience and know yourself

Istanbul, Bucket List Experiences
At the mosque near the Spice Bazaar.

1First and foremost, what are you looking to achieve with your upcoming getaway? Do you want to do absolutely nothing on a stunning stretch of beach? Do you want to explore museums and dine at Michelin-starred restaurants? Do you want a middle-of-nowhere-chateau or an adventure trip?

This seems obvious, but I genuinely believe that people begin planning getaways based on what they’ve heard is a great destination (I’ll talk more about this with point number two below) without giving much bearing to their travel style or desires. If you prefer packaged trips that take the work out of planning for you, cruises and group tours may be a good option. If, on the other hand, you dislike the idea of a schedule and being roped into more touristed routes, a group tour would likely leave you unsatisfied. Know how much planning you want to put into a trip and if you’re one who is likely to get out and explore without the help of a guide.

This brings me to the next component: knowing yourself and being honest about what you want. If you want to visit Machu Picchu but don’t want to hike, there’s nothing wrong with that. Don’t tell yourself that a 27 mile hike sounds fun and book the Inca Trail hike. You’ll spend a lot of money and time doing something you don’t actually enjoy. Opt for the train instead and you’ll be much happier. If you’re not much of a wine drinker, don’t feel like you have to put the Napa Valley or French countryside on your list because every travel blogger and tour book has raved about it. Maybe a Bourbon tour in Kentucky is more up your alley.

The same thing can be said about planning an itinerary when visiting your dream locale. You’re in Paris for four days and simply want to shop, dine and people-watch? Planning a day filled with art history and museums might not necessarily tickle your fancy. Instead, integrate a couple of the most renowned museums into your itinerary but leave yourself time for a leisurely lunch in a great location or pack a picnic for the park. Don’t just visit places that every guide christens a ‘must’; figure out what you want in your trip and what makes you tick. If you’re someone who prefers the comfort of being a part of a larger group, book a guided bike tour or find complimentary walking tours of a city. You’ll be part of a group and have the benefit of a guide to help narrate your experience.

I went to Munich for Oktoberfest when I first moved to Europe. I wanted to experience a new country and a new culture and wanted to do it with friends. Also note that I don’t drink beer and I’m a vegetarian. As you can imagine, visiting a major meat-eating city during a time when people were on a mission to see who could chug the most beers? Probably not the best time for me to visit Munich despite it being such a renowned celebration. I genuinely think I would have left Germany with fonder feelings had I gone during a non-festival period where I could have truly explored Munich without having to be at a beer tent during the whole trip.

Here’s the truth: I personally appreciate getting a sense of the local culture when we travel — through food, through sightseeing, through chatting with locals — but that’s not for everyone. It’s okay to not appreciate fine dining or expensive wine. It’s okay to not want to spend a night at the opera. It’s okay to not understand the appeal of paying five-star prices for an ‘adventure’ experience. The most important thing is to know if spending $200 on a fancy meal is going to leave you disappointed and searching for a burger joint. To know if you’d rather spend a night at a great pub in lieu of an opera house or theatre. To know that you’d rather spend money on a week shopping in Paris than a week on a cruise in Vietnam. Know yourself, know what you want and what types of activities you enjoy when you’re picking your destination and planning activities.

Research and planning goes a long way

Lower Trail, Iguazu Falls, Argentina

2I personally find the planning and researching component of travel to be half the fun. I love the anticipation of upcoming travel and learning about the history and must-sees in a location. I like a major city destination as much as the next traveler, but I also appreciate being able to find those locations that are off the beaten path. That’s where research comes into play.

Those glossy ads that you peeped in your in-flight magazine? Don’t count that single snapshot as reality. Every tourist board’s job is to sell their destination. There’s no way a single snapshot and a slogan can capture the nuances of an entire country. A pretty ad may pique your interest, but do research and dig deeper. If you’re convinced you want to do head on a Mediterranean getaway, where in the Mediterranean? To lump the region together as a homogenous group is to entirely discount the unique cultures, activities and topography of each island. The south of France, for example, is entirely different than Malta which is entirely different than Greece. Think about the cost of traveling in the region, the hotel experience, what types of activities you would be interested in, if you prefer doing a guided tour, etc. Research and solid planning ahead of time ensures that you pick a location that matches your personality and interests, plus having activities planned ahead of time helps make your trip much more enjoyable.

As great as Frommers, Rick Steves, and Lonely Planet are, find other sources of information. Naturally, I’m a lover of blogs (shocker) because I like reading about different people’s perspectives on the same experience. Sites driven by peers sharing their take on a hotel, restaurant, or attraction are much more valuable to me than one person’s point of view.  There are so many factors that shape a good trip (weather, number of tourists, site closures, interactions with locals, etc.) and reading different thoughts on the same topic helps me think about where I might stand and factors I need to take into consideration. Beyond blogs, I find sites like TripAdvisor and AFAR incredibly valuable. Always utilize local knowledge when you can. If you have like-minded friends that have visited a destination or have family  abroad, reach out to them to gather some insight. Remember, don’t let one person’s bad experience dissuade you from a trip — everyone’s idea of what constitutes a great trip is different.

For planning and researching, my rule of thumb is this: Have a list (mental or physical) of must-sees in an area, an idea of restaurants, bars or lounges that would be worth experiencing, plus a few other ‘maybe’ attractions to round out the list. I always depart with an idea of what I want to accomplish, but never plan out a set-in-stone itinerary. Some flexibility is key to making sure you enjoy the random sights and hidden gems of a destination. Sometimes it’s those serendipitous outings with newfound friends/fellow travelers or a lazy afternoon dining al fresco that create the best memories. If you’re too strict with what you think you should be doing or seeing, you don’t get to enjoy the organic experiences that come your way.

What are your tips for finding destinations that are a good fit for you? Do you do a lot of research in advance or do you prefer to wing it?

Shannon Kircher, The Wanderlust Effect

More about Shannon Kircher

Shannon Kircher is the founder and editor of The Wanderlust Effect, formerly The Traveling Scholar. Founded in 2009, she has continued to document her international escapes as an expat in Europe and the Caribbean. She is a former resident of London and San Francisco and now calls the island of Anguilla home. In addition to The Wanderlust Effect, Shannon is the Director of Marketing for the Frangipani Beach Resort and is on the Board of Directors of the Omololu International School in Anguilla.