Selecting a Travel Destination


How did you decide to go there? When talking to friends and family about travel, I frequently get that question. On our recent trip to Europe, we did a stopover in Iceland and it brought more than a few inquiries. We’re now in the midst of deciding between going back to Iceland later in the year or heading to Montreal, Canada this summer. As we work our way through that process, I thought I would turn it into a blog post, which might help inspire readers to select a fun destination for summer. 

Make a list:

Melanie and I keep a running list of places we want to go and then use it in our annual planning process that includes budgeting for travel. Our typical sources for deciding on destinations are travel magazines, social media, friends and family, and occasssional work travel. I joined Instagram (username @troywgregory) a few years ago. Some of the users that I follow on Instagram were posting amazing photos from all over the world and that, along with my lovely, nomadic wife, lit a burning desire to go see some of these places first hand. As the travel bug took hold of us, we began to seek out travel magazine articles (Conde Nast Traveler is my current favorite). After subscribing, we discovered that we could get a lot of content by following the magazines on social media or by signing up for their free email lists. For instance, I now follow CN Traveler on Twitter, Facebook, and Snapchat; all of which offers slightly different yet equally inspiring content. Finally, as the saying goes, birds of a feather flock together. We’ve come across quite a few people in our daily lives who also like to travel and they have great stories to tell about their destinations. 
We found ourselves jotting down notes and creating non-permanent lists in notebooks, but the travel destination ideas were coming in more quickly than we could keep organized, so we wanted a better solution. Obviously the list can take any format, but we use Wunderlist, a truly simple mobile and desktop app for making and sharing checklists. We maintain an in-app travel destination list that either of us can add to or check off as complete. I could go on and on about the criteria we use to add a destination to our list, but it simply revolves around our interests. For instance, we really like live sporting events. Well, I should say that I really like live sporting events and that my wife loves me, any dazzling spectacle, and to travel – in no certain order. So… we’ve been prioritizing travel to some of the bigger and more historic locations for live sporting events over the past few years. We’ve seen the Sugar Bowl in New Orleans, a Red Sox game at baseball’s oldest and weirdest: Fenway Park, we’ve been to a Cleveland Cavs home game (no stretch for us as Ohio natives) and for me, the top of the bucket list check mark was seeing El Clasico: Real Madrid vs. FC Barcelona at Camp Nou in Barcelona, Spain. In all cases, we took the opportunity to go see the city (or more) that we were visiting and had some great experiences along the way. The tip here is to dream big. I’ve been an FC Barcelona fan since 1978, but I never thought that I’d actually make the trip. And yet I have, now twice! Put those big, audacious goals on the list and it might be surprising just how accessible they become.
We organize our destination list into long weekends or weeklong visits depending on what there is to do and the complexity of travel from our home. My wife and I call ourselves “tapas people” because we both like a small sampling of a lot of different things. Therefore, we find long weekends or a touring vacation with several destinations most appealing. Note: after talking with several non-Americans, we’ve decided that “tapas people” is a charming name for “American travelers,” because we Americans apparently have a reputation for hurry-up vacationing. Whether we’re “tapas travelers” or simply Americans, Melanie and I are just not the sort of people who can schedule a weeklong trip to the beach and unwind. After about 3 days, we’ll both be on the search for an Internet cafe so we can begin planning our next adventure. I would like to point out that this kind of self-knowledge is vitally important when selecting and planing a trip. Or better yet, having this kind of knowledge of everyone in the group you’re planning for is critical because it helps prioritize destinations, transportation methods, and itineraries. Our most recent trip abroad included our two young adult children as well as my son’s girlfriend and the itinerary took quite a while to develop in order to accommodate everyone’s interests and needs. 

Selecting the destination:

As I mentioned above, we have an annual planning process. Explaining our planning process could probably be a blog post by itself, but I’ll try to briefly describe it here. Several years ago when my wife and I were getting organized in our new relationship, we sat down and talked about our big directional goals. Near the end of every year, we have a formal discussion to reevaluate those goals and then set sub-goals for the coming year. In recent years, one top goal that has emerged has been to prioritize experiences over material things, which results in travel. Obviously, we take care of household necessities first, but we really do look at travel experience as a gift that’s much more rewarding than – for instance – having every possible cable channel that only seems to motivate us to stay home and huddle around the tube. We include the kids in our directional goals as well. We took our family of 6 (and added a cousin -why not?) to New York City a couple of years ago for the family Christmas instead of giving material gifts. The kids still talk about that trip and look forward to the next one. As we go through our planning process, we look at our available budget and then consult our list to pick what we would like to do.  
When making our destination selection, we factor in the timing of related events as well. For example, we knew that one of the best midfielders of all time for FC Barcelona (Xavi Hernandez) was leaving the club at the end of the 2014-15 season. So we prioritized our trip that included the big game at Camp Nou for my 40th Birthday celebration. On a more somber note, the other obvious “related events” that we also consider is security. The BBC offers current events news for most countries around the world and I usually begin immersing myself in my destination’s local events a couple of months ahead of time. While the US State Department website doesn’t offer a lot of specifics, it’s also a good idea to check their listing of travel advisories before making plans. When we have a couple of top ideas, we’ll run through some quick pricing on flights, hotels and other details to make sure we can meet the budget. Once confirmed, we usually have our direction for the year set and the trip planning process begins. We start up to 6 months beforehand for something like a a multi-week trip to Europe and as little as a week for a spur of the moment weekend trip. I’ll provide more details on trip planning in a future post. Occasionally, we’ll run across low cost opportunities and we may add a short trip to a destination from the list, but most of the time our trips result from a very purposeful planning and budgeting process. Hopefully, this post will inspire a few readers to start their own list and to perhaps go see something new.
Want more information about a topic mentioned or have your own story to share? Let’s connect! Send me your destination selection insights or any related travel story to
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