Here’s a topic that I thought would make for a fun discussion — what are your favorite places that you’ve traveled to? It’s a question that I’m often asked, but struggle to answer. That’s not because I never leave the airport (contrary to what some people may believe), but rather because I have a hard time picking some destinations over others. Let me explain.
My challenge with picking “best” travel destinations
Before I share some of my favorite places I’ve traveled to, let me talk a bit about why I struggle with the concept of making recommendations in this area, and why I’m cautious when taking recommendations from some people (just as you shouldn’t put too much weight in my recommendations). This comes down to several factors, so let me share them in no particular order.
What determines our enjoyment from a trip
Simply put, our perception of a trip comes down to the experience we actually had, compared to the experience we thought we were going to have. Let me give a non-travel example involving ice cream:
- Say your friend says that X place has the world’s best ice cream, and no other ice cream can compare
- Then you go to that place and have ice cream, and it’s really good, but perhaps not memorable; you’d probably feel disappointed, since you were expecting a life changing experience
- Now compare that to what your perception would be if your friend hadn’t given that recommendation; you’d probably be thrilled, and would think “that was so much better than I was expecting”
The same principle applies to travel. If you ask me, the best trips are those where we don’t have many expectations, or where our expectations of the experience are exceeded. For example, there are some objectively great travel destinations, but if they don’t quite live up the hype of what you were expecting, it’s natural to feel disappointed (Paris syndrome comes to mind).
For example, Santorini couldn’t be more picturesque, and it’s perhaps one of the travel destinations you see the most photos of. Everyone posts a picture that makes it look like they have all of Oia to themselves, given the beautiful backdrops. If you go in late July and then discover the crowding levels, the whole thing might feel a bit less charming than you pictured it to be. It’s natural to feel like it maybe didn’t quite live up to your expectations, assuming you were expecting that the real experience would be like the carefully curated photos that others shared.
Meanwhile if you go to a place no one really recommended where you don’t have many expectations, and you end up having a great experience, your expectations may be exceeded, and you’ll probably be quite happy.
Admittedly this is probably just a reality we have to live with, as the world is increasingly online. If you traveled somewhere 20 years ago, you weren’t as influenced by everyone on the internet. That’s no longer the case.
Social media & recommendation culture change travel
This ties in to the above, but I think it’s worth expanding on a bit more. I think social media, and our general “recommendation culture,” has kind of fundamentally changed travel, and the ability of people to objectively share their thoughts on a place. This can come in many different forms, so let me give a few examples.
For example, take the Maldives. It’s an absolutely picturesque destination, but I’d almost argue that it’s nicer in pictures than in real life. In pictures, you just see the beautiful sunshine and crystal clear waters. What you don’t see is how outrageously hot it can be, that the UV is an 11 for much of the day, the number of bugs you’re going to be dealing with, the reality of jet lag and exhaustion for having traveled so far to get there, etc.
That’s not at all to say that the Maldives isn’t worth visiting. It’s just that I think that pictures make it look like heaven on earth, while there are some realities to deal with when traveling there.
We live in an era where social media is such a large part of peoples’ lives. For many people, travel isn’t just about having a good time, but it’s about presenting to their friends and family like they had a good time. After all, people want to share the highlights of their life with friends and family. You don’t see people captioning pictures with “I had a pretty nice time in the Maldives, but it wasn’t quite what I was expecting.”
Instead there’s almost a bias going into a trip of wanting it to be amazing — and I guess that’s a good attitude to have. But then this is also how we create a cycle of sort of fake feedback (or at least feedback that omits important details). Your friend says “oh my gosh, your trip to Santorini looked amazing,” and then you say “yeah, it was totally amazing.”
I’m not saying there’s anything inherently wrong with that, but I also think that collectively we’re not necessarily honest or thorough with sharing our impressions of places. Like, you’ll sound like a total Debbie Downer if you go to Rome and say “it was great, but it was really damn hot, and the crowds were wild.”
So many factors impact our travel perceptions
I also think it’s important to reflect on how so many factors can impact our perception of a travel experience. This includes things like crowding levels and weather.
But it also includes who you’re traveling with, and the kind of experiences that you’re having. Travel experiences are almost always better if you’re with a local friend, or someone very familiar with an area. For example, last summer we went to San Sebastian with some friends who were very familiar with the area, and we absolutely loved it.
I know one thing for sure, though — I definitely wouldn’t have had the same perception if we had traveled there alone, and had to come up with our own plan. There’s something so nice about someone just guiding you to their favorite places, and not having to do all the work. And there’s also a difference when you have friends showing you, vs. when you hire a guide, since it’s less transactional.
The places that I’ve enjoyed traveling to
With the above out of the way, I don’t have a top X list of my favorite places I’ve been to, though I’ll share some of the places that I’ve very much enjoyed visiting. Let me start by saying that I’m not a huge fan of visiting cities, and prefer places that either have a totally different culture, or are more outdoor-focused.
With that in mind, here are several of my favorites:
- Hong Kong is one of my favorite cities in the world; it’s the first city in Asia that I visited, it’s so indescribably electric, and and it holds a special place in my heart
- I absolutely love everything about visiting Japan, and it’s probably the place I most enjoy traveling to; I’m not meaning to fetishize it, and Japan has its problems, but culturally Japan couldn’t be more different than my home city of Miami, and that’s why I enjoy it so much
- Bhutan is a unique country, unlike anywhere else I’ve ever seen, and I can’t recommend it enough, especially given the lack of crowding (due to how visitor permits in the country work)
- New Zealand has so much to offer, and is also a great outdoors destination
- Mexico is an easy getaway from the United States, so I generally prefer that to the Caribbean, especially thanks to the friendly people and great food; personally I’m not a huge fan of the Cancun area, but that’s just because it’s so similar to what I’m used to in Miami in terms of climate
- I’ve absolutely loved the nature focused destinations I’ve been to, from Svalbard to Iceland; I’m hoping to visit Greenland next summer
- I’ve very much enjoyed traveling to the “stans” (like Kazakhstan, for example), simply because they’re a part of the world that isn’t discussed much in the United States; so it’s fascinating to come in with no expectations, and see these places firsthand
- Parts of Africa are amazing for their safari opportunities, because it’s truly a vacation unlike any other, and it gives you a new appreciation for nature and the cycle of life
Next, let me say that nowadays France, Greece, and Italy, are among the most popular summer travel destinations for Americans, and I largely think that’s for good reason. I love visiting all three of the countries, but try to be strategic about when I go:
- France has so much to offer, from amazing food, to incredible hotels, to diversity in destinations — Paris is a dynamic city, the South of France is gorgeous in summer, Courchevel and the surrounding area is lovely in winter, Provence is awesome in spring and fall, French Basque Country is beautiful year-round, etc.
- Greece has endless places to travel to, and even as so many tourists flock to Mykonos and Santorini (with a stopover in Athens), there are so many places that are less busy that can still be visited; I love the weather, the food, and the scenery
- Italy also has so much to offer, from the best food, to a variety of experiences; Italy has some of my favorite cities (even though I’m not a city person), and also has beautiful countryside, beaches, and mountains
Bottom line
I think just about every place has its charms as a visitor, and it all comes down to what expectations you come in with, and through what lens you see things. A lot of the most visited tourist destinations are popular for good reason, though I can’t help but feel like they may sometimes lead to disappointment, given the high expectations that people have going in.
There’s no denying that social media and the internet at large have shaped our travel patterns, and that’s both a blessing and a curse.
What are your favorite places you’ve traveled to?
