When it comes to travel, forget “Top 10” and “Best of” lists. For your next vacation, determining your best itinerary means focusing on what most appeals to you and your travel companions.

“What’s the best day of the week to book airfare?”

“Where’s the best hotel in Paris?”

“Who has the best lobster roll on Cape Cod?”

When it comes to travel, I often get some variation of these questions from friends and family—and it makes sense at first glance. We work hard and get precious little time off each year, as such, we want to make sure we’re making the most of our vacation. Hence the pursuit of bests—if we’re only getting a week in Jamaica, or a long weekend in San Francisco, we want to make sure we’ll enjoy it and have an ideal experience.

Any and all major magazines have their “10 Best” lists popping up for everything from airlines to airports, hotels to restaurants. (I may even be guilty of having authored a few such stories in my previous life.)

But here’s the secret: Even after 10+ years of studying consumer travel trends, I’m here to tell you that the word “best” is—at best—a fallacy. Think about it: It’s a means of finding a quality experience that will appeal to the most people, across all walks of life. It’s a way to quickly distill something complex and nuanced into an easy-to-digest format. And it’s a method for busy travelers to save time during trip planning—after all, consulting a “best of” list is the quickest way to research a new place.

But by focusing on the generic “best”, ironically, you might miss the experience that would be best for you. So it’s time to remove the term from your Grownup traveler vocabulary.

Whenever I chat with travelers and get asked about “best (fill-in-the-blank),” my answer is always the same: “It depends. What do you like?” or “I’m not quite sure how to answer that. What are you looking for?”

The best experience is slightly different for every Grownup traveler. So in planning your next trip, shift your thinking ever so slightly and consider a very personalized ideal instead. Focus on places, activities, and experiences that would resonate most with you and your travel companions.

Here are a few helpful questions to help you determine your ideal travel experience:

  • What does the backdrop of the destination look like?
  • Who’s with you?
  • What are you doing?

Once you’ve answered the “where, what, and with whom” of your trip, determine how much you have to spend on your vacation. Now you’re ready to start looking into the particulars.

As you start planning your trip, tweak your research based on your budget, time off, and season you’re traveling. For example, instead of asking, “What’s the best hotel in Miami?” the question might change to “What’s an ideal hotel in South Beach, based around $200 per night, for travel in October?”

Adding in specifics will help you zero in on options that embody what’s important to you, and in the process ensure you’ll put together a customized itinerary that accurately reflects your taste. Once you’ve found some possibilities that work for you and your travel companions, you can book with confidence, knowing you’ve found something as close to “best” as one can get.

Of course, “best” lists aren’t going anywhere anytime soon. But if you use them as a jumping off point for your own trip research, you’ll be in a much better position to find your best trip. That’s going to be money well spent, and a wonderfully memorable vacation.


A lifelong traveler and bookworm, Sarah spends her days thinking of new ways to explore and tell stories.

Any third-party resources or websites referenced above are not under Society of Grownups control. Society of Grownups cannot guarantee and are not responsible for the accuracy of the resources, websites, or any products or services available through such resources or websites.

While Society of Grownups hopes the information is useful, it’s only intended to provide general education. It’s not legal, tax, or investment advice, and may not apply or be useful to your specific financial situation. If you need recommendations geared to your personal financial situation, schedule time with a financial planner.

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