I plan bucket-list trips for a living. Here are 4 mistakes I see travelers make when booking their own vacations.

• I’m a professional trip planner who builds itineraries for solo travelers around the globe.
• Many people planning their own trips make the same mistakes, like leaving no space for downtime.
• Some stick to the highlight reel and miss out on destinations’ local cultures and communities.

As an adventure designer for Flash Pack, a company that plans trips for solo travelers, I put together cool itineraries for a living.

I pay razor-sharp attention to all of the logistical details that go into planning our clients’ excursions. Although it’s really fun, it can be quite difficult.

In my experience, here are the biggest mistakes I see travelers make when they plan their own itineraries and trips.

Limiting themselves by only visiting popular destinations and attractions

It’s amazing how far a little research can go in bringing an extra thrilling twist to your trip.

I used to lead tours through New Orleans, and the French Quarter’s bright lights were always a major draw. However, I discovered that some of the best local bars featuring live, world-class jazz music were actually located in less-touristed neighborhoods.

These spots just weren’t on the cookie-cutter tourist itineraries, so it took a bit of research to find them.

This isn’t to say you should skip popular spots, but you should also try to add unexpected activities and under-the-radar places to your itinerary, too.

If you hike through Patagonia, you might also dine in a cave, surrounded by prehistoric rock art and candlelight. And when you take a cable car up Cape Town’s Table Mountain, consider abseiling back down.

This mentality might also mean approaching a mainstream attraction in a new way.

Hike a backdoor route to Petra, camp out on a secret island in the Philippines, or arrange a private masterclass with a luchador — one of Mexico’s legendary masked wrestlers.

Overplanning instead of going with the flow

It’s tempting to plan your dream vacation down to a “T,” but that strategy doesn’t always account for the unpredictable nature of travel. Regardless of how much planning you do, some things will likely go wrong — and your trip will still be OK.

Too much rigidity in your itinerary means there’s zero chance of spontaneity, and those unplanned, impromptu moments are often the best parts of an adventure.

For example, if the restaurant you earmarked in Marrakech is fully booked, you may end up wandering the medina instead, soaking up street-food flavors and live performances.

Or, a disappointing flight delay can lead to a conversation with other travelers, who might introduce you to a new culture and become your lifelong friends.

On one trip, I fell in love with a Danish woman I’d just met, shelved my plans, and lived with her on a pig farm in Scandinavia.

In my opinion, the best trips blend both activities and downtime. The latter allows you to leisurely explore a place in your own way, at your own pace.

Remember that just because you can do everything, it doesn’t mean that you should. Be selective and open to the reality that some things might change on a whim.

Discounting the importance of relationships and the people along the way

My job wouldn’t be possible without the many great relationships I’ve cultivated.

Activities, accommodations, and weather all play a role in a trip’s success. But it’s the people, both those you bring with you and those you meet along the way, who make a trip great.

So when you’re planning your vacation, it’s just as important to think about the people you’re traveling with as it is to think about anything else in your itinerary.

In my many years of planning adventures and working as a tour guide, I’ve found that an easygoing, curious attitude works best. Even if you love someone dearly, you might not want to share a room, sit on a long flight, or ride on an overnight train with them.

You may also choose to travel alone or with strangers to try out new experiences and different dynamics.

If you travel by yourself, consider slotting in some group activities, such as island-hopping in Thailand or a food tour through Lisbon, that will introduce you to locals and other like-minded travelers.

Not immersing themselves in local life

Every time you visit a new place, seek out experiences that you can’t find anywhere else in the world. Usually, you’ll be able to find something unique to the location, whether it be a landscape, music, art, or culture.

It’s up to you to do your homework and make sure you tap into the hotels, cafés, activities, and excursions that immerse you in the landscape. Local people and businesses are the beating heart of towns, villages, and cities around the world.

If you have the luxury of spare time, spend a few days getting to know one particular neighborhood. Take half an hour to chat with the hotel manager or the bar owners down the road. Hang out in a local restaurant and observe the place’s rhythm.

I also enjoy booking my accommodations in residential neighborhoods because I’ve often found a destination’s pulse to be outside of the city center.

And in my experience, the locals you meet have the power to expose you to ideas and secrets you’d never know otherwise.

This story was originally published on November 13, 2022, and most recently updated on November 4, 2025.

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