Always planning, never booking? Here's how to commit to a trip

I am incapable of booking a trip more than 2 weeks before departure. Months go by while I bookmark hotels, file restaurant recommendations in about a dozen cities and add flights to my cart, only to panic at the last minute and close the tab in a fit of indecision. In the meantime, my wishlist grows and grows.

Here's how I've adapted – and embraced – my travel-planning tendencies, plus my top tips on how to commit to a trip.

My trip-planning habits

When organizing trips for other people, I am a woman on a mission. I laser-focus on one destination and spring into action with personalized Google Maps, flight deals, a doc with links to vibey places on Instagram that I think they'll like, restaurant reservations made in their name and hour-by-hour itineraries. I get very into it – maybe, one might say, a little too into it.

After a friend mentioned that she was considering going to Barcelona, I sent her a 2000-word email with advice (“Instagram will tell you this market is good, but this one is better”) and links to nearly every Lonely Planet article we’ve published on Barcelona, plus the link to our Spain guidebook in case she extended the trip. When coworkers visited Dublin, and someone mentioned they’d tried a restaurant not on my meticulously curated list, I gasped. Who authorized this deviation? Was it a random person on TikTok? Someone unfamiliar with the exact vibe this person was looking for? What if this restaurant was terrible and their night – no, their entire trip – was ruined? And I was only half joking.

At this stage, I know I need to chill, but I also want to ensure that everyone is having a good time at all times, and I get paid to be this annoying, so it’s actually fine.

Finding new travel inspiration

Working at Lonely Planet makes it especially difficult to progress beyond the inspiration phase, especially when you’re surrounded by travel ideas all day (check out our Substack, and you'll see what I mean). Part of my job involves interviewing our guidebook writers for a monthly newsletter that showcases our latest titles, which only ever adds more places to my list. Our writers are either locals or people who immerse themselves in destinations for months on end, so they’re incredibly passionate about their topics. Just when I’m about to commit, they’ll share a cool story about a new spot, and I immediately want to go there instead.

Take Virginia diGaetano, who has a way of making Italy, a destination that’s so widely covered, feel like it's off the beaten track. She’ll casually mention an old-school bar in Genoa that makes traditional Genovese wine and is “hardly visible until you stumble upon it,” and suddenly, I want to return to Italy. Or Chawadee Nualkhair in Thailand, whose descriptions of Thai ingredients and culture are so vivid that I can almost taste the lemongrass. I start looking up flights to Thailand (it’s been on my wishlist for years), derailing whatever travel plans I was this close to finalizing.

Dreaming is part of my process

Despite the absolute lack of clear direction, I genuinely embrace my frantic travel-planning style. Having thousands of ideas bubbling around in my head brings me joy. Getting excited about other people’s trips is such a buzz. Chatting with our writers and falling in love with the places they’re passionate about is truly one of the best parts of my job. Let’s be honest, the dreaming stage is a huge part of the fun of travel.

Eventually, though, something clicks. Maybe it’s a hotel deal too good to pass up or the sudden realization that summer is slipping away. Whatever the trigger, I finally commit, the countdown is on, and once I’ve settled on a place, I always have the best time. Perhaps that’s the secret: the longer the daydreaming phase, the sweeter the actual adventure.

How to commit to a destination

1. Three is the magic number

When overwhelmed by choice, narrow down your planning to three destinations. Then identify nonnegotiable elements you want from your experience – like great beaches, no crowds and a walkable city – and one absolute deal-breaker. Soon you'll get a clearer picture of what you want, and you'll eventually land on that one perfect place.

2. Center your trip around an experience and book that first

Instead of beginning with the daunting task of finding flights, research restaurants or cute hotels or experiences that excite you. Once you've made dinner reservations or booked concert tickets, you'll feel more pressure to book the flights to get there.

3. Use flight deals as a decision-maker

When torn between destinations, sign up for flight alerts for all of them. Then let the best deal make the decision for you.

4. Travel offseason

Sometimes the pressure to have amazing summer travel plans is off-putting. So maybe take a little break in the summer, then go on a big trip in the offseason, when you can ease into the planning phase. You'll be doing your bit for sustainable travel, and the pressure won't feel so intense.