Travel Planning in 2026: What’s Worth Booking Early (and What Can Wait)

Every year, I see the same pattern: some travelers rush to book everything the moment they decide on a destination, while others wait a little too long and end up scrambling. The truth is, travel planning isn’t one-size-fits-all. Some pieces really do need to be locked in early—sometimes months early—while others are far more flexible than people realize. As we head into 2026 planning season, it feels like the perfect time to talk honestly about what deserves your urgency and what you can safely leave for later.

Let’s start with the big one: where you stay. Hotels in high-demand destinations—think the Amalfi Coast in summer, Paris during event weeks, the Greek Islands in late June—truly do fill up fast. The best rooms disappear before most travelers even start looking. If your dream trip involves a particular hotel, a sea-view balcony, or a boutique property with limited rooms, this is something to secure months in advance. The earlier you book, the better your options and your pricing. It’s one of the few pieces of a trip where being proactive really pays off.

A question I get often from clients is why I make the hotel the very first priority—long before the cute cafés, the day trips, or the must-do experiences. The answer is simple: your hotel shapes everything else. Where you stay influences how you move through a city, what neighborhoods you explore, how much time you spend commuting, and the overall rhythm of your days. The best hotels book quickly, and once those are gone, everything else becomes harder to plan around. Securing the right place early gives you a home base that supports the rest of the trip. Then the smaller details—those fun, personalized touches—can fall into place with much less stress.

Flights follow a similar rhythm, though with a bit more flexibility. For long-haul international travel, booking three to six months out tends to hit the sweet spot. Too early and you’re often paying more; too late and availability gets messy, especially around holidays and school breaks. If your dates are fixed or you’re hoping for premium cabins, booking early helps you get what you want. If you’re flexible, you can afford to monitor things a little longer—but waiting until the last minute rarely works anymore.

Then there are the experiences that anchor a trip: the Vatican at sunrise, the Eiffel Tower summit, the Alhambra, a beloved food tour, a cooking class that only runs twice a week. These are the moments people dream about long before they ever step off the plane. Spots can disappear weeks—or months—before your travel date in cities that stay busy year-round. If something is a non-negotiable part of your itinerary, book it early and give yourself peace of mind. It becomes one less thing to juggle and one more thing to look forward to.

On the other hand, many parts of a trip don’t require early planning at all. Local trains across Europe are often easy to book closer to travel. Ferries—especially around southern Italy or the Greek Islands—release schedules later than you’d expect, so stressing about them too early only leads to frustration. And restaurants, unless you’re targeting a Michelin-starred table or a viral hotspot, can usually be booked closer to your travel date. Some of the best meals you’ll ever have are found by wandering into a tiny spot you didn’t even know to search for.

There’s also a whole category I think of as “don’t overthink it.” Metro tickets, small museums, casual cafés, beach clubs with day-of availability—these don’t need advance planning. Not everything has to be scheduled, and honestly, leaving space for spontaneity often ends up creating the moments you remember most. Some of my favorite travel memories came from hours that weren’t planned at all.

Travel planning in 2026 doesn’t need to feel overwhelming. Start with the pieces that truly benefit from being booked early: the hotels that set the tone of your trip, the flights that determine your pace and budget, and the experiences you’d be heartbroken to miss. Then give yourself permission to relax about the rest. Knowing what actually matters—and what doesn’t—makes the whole process feel lighter.

And if you’re unsure where your plans fall on that spectrum, that’s exactly where I come in. I help travelers figure out the right timing, the right priorities, and the right balance between organization and ease. 2026 is full of possibility, and the earlier you start thinking about your next adventure, the more options you’ll have—without the stress.

Here’s to planning smarter, not busier, and giving yourself room to enjoy the kind of travel that actually feels good.