Late-summer getaways, warm-weather vacations for the coming winter, and once-in-a-lifetime experiences that you need to book a year out: These are the destinations you should be booking trips to right now. Follow our advice and you’ll still have a range of accommodations to choose from, the best guides won’t already be taken, and our Trusted Travel Experts will have enough time to work their magic and optimize every aspect of your trip. (Note: If you prefer to know which destinations are ideal for traveling to in any given month, see our Where to Go When series.)
London
For: August
London is ideal in August (see The August Travel Deal You’ve Been Waiting For) because the lack of business travelers drives down hotel rates, the weather is mild, and everything is open but the crowds are gone—so it’s easier to get great seats to the city’s renowned theater events, for example. The U.S. dollar was already strong against the pound before the vote to leave the European Union sent the British currency plunging even lower, and it’s even stronger now.
Why book in July? It’s your last chance to snag some of the best deals of the year—such as four nights for the price of three, or guaranteed room upgrades—at the city’s top four- and five-star hotels.
—Jonathan Epstein, Trusted Travel Expert for England, Ireland, and Scotland
Contact Jonathan through our site to get the best possible trip.
Mexico’s Caribbean Coast
For: August or Early September
For a few months each year, whale sharks congregate along Mexico’s Caribbean coast, feeding on plankton. These gentle creatures are not actually whales at all, but the world’s largest fish, weighing as much as 20 tons, with a length of up to 40 feet. They will even let you swim near them; and unlike many other sea life encounters, this is one that happens naturally, without the animal confined to a cage. You can arrange such an excursion from Isla Mujeres, Isla Holbox, the Riviera Maya, Tulum, or Cancun.
Why book in July? You still have access to the best accommodation, guides, and boats before the whale sharks swim away from the Mexican coast in early September; if you wait until August to make arrangements, you’ll have to settle for mediocre outfitters.
—Zachary Rabinor, Trusted Travel Expert for Mexico
Read Zachary’s Insider’s Guide to the Riviera Maya, and contact him to get the best possible trip.
Bhutan
For: September, October, November
Fall is the height of “tsechu season,” or festival season, in the tiny country of Bhutan; each district holds its own colorful tsechu, full of dancing, Buddhist blessings, and socializing that draws locals from near and far.
Why book in July? Only one airline, Druk Air, flies into the country’s sole international airport (Paro), so seats are extremely limited. July is your last chance to get the fall flights you want, without having to compromise on logistics. Moreover, many of the top hotels are tiny, so those convenient to the most famous tsechus are often sold out by September.
—Antonia Neubauer, Trusted Travel Expert for Bhutan
Read Antonia’s Insider’s Guide to Bhutan, and contact her to get the best possible trip.
St. Barts
For: November
November is one of the best times to be in St. Barts: Many shops and restaurants have just reopened after hurricane season, so everything is fresh and new, but prices are still up to 40% lower than during high season—even over Thanksgiving.
Why book in July? Come the end of summer, many people start making Thanksgiving plans. Savvy travelers have their choice of villas or hotel rooms for the holiday by booking in July.
—Peg Walsh, Trusted Travel Expert for St. Barts
Read Peg’s Insider’s Guides to St. Barts Beach Vacations and St. Barts Villa Vacations, and contact her to get the best possible trip.
Machu Picchu, Peru
For: November
November is the last chance to trek the Inca Trail to Machu Picchu before the wet season hits. It is magical to approach the ruins on foot, getting your first glimpse of them from the Sun Gate, as many Incans did. On a private trek, it’s possible to arrange for tents large enough to stand up in, inflatable mattresses, and even a massage therapist.
Why book in July? Permits typically sell out four months in advance, so by August you’ll have to choose between hiking and camping in inclement weather, or holding off until next year.
—Tom Damon, Trusted Travel Expert for Peru
Read Tom’s Insider’s Guide to Machu Picchu, and contact him to get the best possible trip.
Los Cabos, Mexico
For: December
If you want to be in Cabo over Christmas or New Year’s, July is the latest that you will still be able to find space in a villa or hotel for your preferred travel dates.
Why book in July? Because if you wait until August (or even later), you’ll likely be stuck picking among accommodations that don’t quite match your requirements—a long hike to the beach, perhaps, or not enough bedrooms to fit your group comfortably.
—Julie Byrd, Trusted Travel Expert for Los Cabos
Read Julie’s Insider’s Guides to Los Cabos Beach Vacations and Los Cabos Villa Vacations, and contact her to get the best possible trip.
Costa Rica
For: December
Christmas kicks off the dry season in Costa Rica, so it’s a great place to take your family for an eco-friendly holiday surrounded by nature. While you’ll feel good about helping preserve the country’s environment, your kids will love the abundance of available activities, including hiking, kayaking, and snorkeling.
Why book in July? By August, the top-rated eco-lodges are selling out for the busy December period. Since most families have a fixed window to travel during the school holidays, waiting to book will mean compromising on your accommodations.
—Irene Edwards, Trusted Travel Expert for Costa Rica
Read Irene’s Insider’s Guide to Costa Rica Luxury Eco-Travel, and contact her to get the best possible trip.
French Polynesia
For: January, February, or March 2017
January 15th through the end of March is the low season for French Polynesia, which means 15 to 20% lower prices for hotels and airfare. While it will be hotter and a bit more humid than in August, there is not an El Nino forecast for this coming year, so there will be less rain, and very little chance of hurricanes.
Why book in July? Europeans tend to make their winter plans before they leave on holiday in August; if you book in July, you’ll still be able to get an overwater bungalow.
—Kleon Howe, Trusted Travel Expert for French Polynesia and the Cook Islands
Read Kleon’s Insider’s Guide to Bora Bora, Tahiti and French Polynesia, and contact him to get the best possible trip.
Siena, Italy
For: July 2017
The Palio di Siena—a centuries-old, famously colorful horse race with bareback jockeys representing each of the city’s contrade, or districts—is held twice a year: on July 2ndand August 16th. More than just a 90-second-long race, the multi-day Palio festivities typify the pride and spirit of community felt throughout the city.
Why book in July? Seats for each of next year’s Palios go on sale as soon as this year’s event for that date is over. If you book as soon as the July Palio winds down, we can reserve an exclusive vantage point (such as a balcony overlooking the Mossa spot or the Curva di San Martino) for next year’s July race.
