What to Book Now for 2027

Supply and demand. We all know its ins and outs, and we know what happens when supply is constrained but demand rises. Prices go up, choices evaporate, and availability eventually disappears completely.

The travel industry is governed by those laws as much as any other. And there are places in the world, and experiences deeply worth having, where the supply is much more constrained than you might think.

Like the yacht with the crew you want, the hotel that offers your family the right rooms in the right part of the South of France, the safari camp with only a few tents available, or a high-end hotel in Kyoto when the cherry trees are blooming.

These are five trips to start thinking about now for 2027, because they’re likely to be sold out at least six months in advance.

Yachts: Ensuring You Get the Best Crew and the Best Boat

A yacht trip is a unique way to travel. Your hotel, transportation, dining, and concierge all move with you daily. Over the course of your journey you get to know your crew in a way you rarely do with staff even at the most boutique hotels. They learn your preferences, surprise you with little touches, and delight you with warmth, knowledge, and hospitality.

It takes a special team of people to pull that off at the level we expect for our clients. And like in any industry, the best teams are in high demand. Our best-in-class yacht broker personally inspects many of the yachts in Europe every year, so we know who they are, and we know how big a difference it makes to travel with them.

If you’re thinking about waking up each morning somewhere new without repacking a suitcase, moving from olive oil and stone-carving traditions to wine and oysters in Croatia or sailing past the crowds to visit the hidden gems of the Aegean Sea in Greece, we highly recommend you start early. With yachting, it makes all the difference to sail with one of the best crews in the world.

The South of France: Beloved Locations with Limited Inventory

Long lunches, blue water, small villages, the scent of lavender, sea salt on the breeze. A trip to the south of France offers so much. Provence brings you vineyards, historic villages, markets, and the countryside. The Riviera means the Mediterranean, boating, beaches, Cannes, and Saint-Tropez. Some of our clients’ favorite properties are located in each.

But the region isn’t exactly a well-kept secret. Millions of French residents take their holidays there every year, and millions of foreigners join them. Many of them book properties like Château de la Messardière and Hotel du Cap Eden Roc in the Riviera or Villa La Coste in Provence for the same dates every year, which means room inventory dries up as far as nine months in advance during the most popular times to travel.

So if you want a private sandy beach in Antibes, unforgettable winery tours in Provence, or the perfect mixture of buzz and privacy in Saint-Tropez, you’re far better off booking your trip early, while you still have plenty of top-shelf options to choose from.

Safaris: Where the Best Camps Are Small On Purpose

Few trips create as much anticipation as a safari does. You leave early in the morning without knowing what the day will bring. You watch and wait, sinking into stillness as you realize how enormous the landscape really is. The wildlife comes out on its own schedule, one your guides work to meld you into without disrupting it. There’s deep craftsmanship to a good safari, one that too many visitors at once spoils.

So many of the best safari camps, like those at Angama Mara, Singita Ebony Lodge, or Royal Malewane, are deliberately small, with only a dozen or so tents available at any given time. And that means that they can fill up a long way ahead, especially during times of the year like migration season. Waiting too long can mean losing out on the best camps, the best routes, and the best experience overall. 

We suggest you book a year in advance, then enjoy the anticipation of the trip. It’ll be worth the wait.

Costa Rica: Getting the Balance Right

Costa Rica makes an unusually good family trip because it can satisfy two very different ideas of vacation at once. It’s practically dripping with waterfalls, zip lines, hanging bridges, tropical forests, and guided hikes for the adventure-minded. For those looking for a more relaxed week, its beaches, swimming, boating, and afternoons at the resort spa or pool are top-notch as well. And because there’s very little time change, it’s easy to adapt to even for younger kids.

The resorts that offer the best of both options while still delivering five-star quality, like Nayara Gardens and Four Seasons Resort Peninsula Papagayo, often book up months in advance. The new Ritz Carlton Reserve adds a new option for the beach, but jungle adventures still go fast. Spring break in particular concentrates families wanting a trip to Costa Rica into just a few weeks, so if you wait until the last minute, the rooms and trip flows we’d normally pick for you will already be reserved.

Starting early preserves the element our clients love most about a trip to Costa Rica: enough adventure that everyone comes home with stories, and enough relaxation that you still feel like you got a vacation.

Cherry Blossom Season in Japan: Planning Around a Cultural Moment

Cherry blossom season makes Japan almost irresistible. For a few weeks, streets, canals, gardens, and temple grounds erupt in a riot of gorgeous, ephemeral color that’s been a central anchoring point of Japan’s cultural calendar for centuries. 

But because viewing the cherry blossoms is so popular (there’s even a word for it in Japanese: hanami), and the bloom varies from year to year and moves through different parts of Japan at different times, you need a plan and an expert’s touch to make the most of it.

Every year, there’s a cherry blossom forecast, and hotel, transportation, and experience bookings for the dates predicted to be peak fill up fast. Late March and early April face intense demand, particularly for well-located properties, family configurations, and anything in or around the Tokyo to Kyoto corridor (a classic itinerary we recommend for first-timers in Japan). Inventory for Spring 2027 is already drying up in some places.

So even though spring feels a world away, fall is the time to book. We’ll plan a trip that syncs up your availability with the most reliable forecasts, the best properties, and your personal preferences, so you end up with a view of the cherry blossoms you’ll never forget.

When to Book for 2027

Your ability to travel well in 2027 isn’t about to disappear. Even if these places sell out, we can find you something off the beaten path that will delight you.

But supply is already starting to get squeezed, and as it does, choices will come off the board one by one. If you book too late, you may never know what you missed out on, but we will, and we implore you: if you want to visit one of these places next year, let us know now, and keep the following timetables in mind:

• African Safari: 12–24 months in advance

  
  

• Mediterranean Yacht Trip: 9–12 months in advance

  
  

• South of France Vacation: 9–12 months in advance

  
  

• Cherry Blossoms in Japan: 6–12 months in advance

  
  

• Spring Break in Costa Rica: 6+ months in advance

  
  

Starting early gives you the luxury of choosing exactly the trip you want, rather than fitting into what’s still available.