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The Best Trips to Book in September: What to Lock in Now

Brook Wilkinson | August 18, 2017

From New Year’s Eve in Sydney to Carnevale in Venice, festivals make already gorgeous cities shine even brighter. So if you’re considering a trip to experience either of these iconic events—as well as others happening around the globe in the coming months—act now.

In this monthly series, we point you to the places you should be booking trips to right away, while the best-value rooms and savviest private guides are still available, and while our Trusted Travel Experts still have enough time to work their magic.

(Don’t miss the rest of our series on what trips to book in each month of the year. If you prefer to know which destinations are ideal for traveling to in any given month, see our Where to Go When series, and don’t miss our comprehensive guide to the benefits of booking early.)

Cambodia’s Water Festival

Water Festival in Siem Reap Cambodia

Water Festival in Siem Reap. Photo: Ploy Photography

For: November

The Water Festival in Cambodia marks the end of the rainy season—when the flow of the Tonle Sap River actually changes direction—and the start of the fishing season. You can experience boat races, fireworks displays, and a “Srouch Tec” ceremony in which a monk splashes water on you to wash away sins and bad luck. “The Water Festival is my favorite festival in the entire region; this year, it’s falling earlier in the month than usual, allowing travelers to see it and still be home in time for Thanksgiving,” says Andrea Ross.

Why book in September? For now, there is still availability at Andrea’s favorite hotels and with her preferred guides—but that won’t last into October.

Wendy recommends: Andrea Ross, Trusted Travel Expert for Southeast Asia. Contact Andrea through our site to be marked as a VIP and get the best possible trip.

New Year’s in Sydney, Australia

Sydney Opera House New Years Fireworks

New Year’s Eve fireworks over the Sydney Opera House are something to see. Photo: Robert Wallace/Tourism Australia

For: December

A massive New Year’s Eve celebration takes place in Sydney Harbour, with the famous “coathanger” bridge lit up by fireworks not once but twice (first at 9 p.m. for families, then again at midnight). Be there, and you’ll be among the first to ring in 2018.

Why book in September? While most Sydney hotels—and certainly all of those with harbor views—have been fully reserved for many months already, most properties have payments due in September; as a result, last-minute rooms may become available when people cancel. Tickets for some of Sydney’s most iconic vantage points from which to watch the fireworks—from Barangaroo to Taronga Zoo—also go on sale in the coming weeks, and always sell out fast.

Wendy recommends: Stuart Rigg, Trusted Travel Expert for Australia. Contact Stuart through our site to be marked as a VIP and get the best possible trip.

Costa Rica for Spring Break

hammock overlooking costa rica greenery

American winter is Costa Rica’s high season, so give yourself plenty of time to secure the best hotels. Photo: Kura Design Villas

For: December through March

Costa Rica’s busy season (and also, not coincidentally, its driest season) starts in mid-December and continues through Easter; December and March are the most popular times to visit. Many families arrange their spring break trip in the fall, so it’s important to stay ahead of the planning curve.

Why book in September? You’ll secure spots at your preferred lodges and resorts, in rooms with those all-important views of the ocean, volcanoes, and tropical forests; by October, many of them will have waiting lists. Earlier bookers also have a better shot at the family suites, which are usually a better value than separate rooms.

Wendy recommends: Irene Edwards, Trusted Travel Expert for Costa Rica. Contact Irene through our site to get the best possible trip.

A Family Trip to Israel

Dormition Abbey at Sundown, Jerusalem, Israel

Israel is a popular spring break destination. Photo by Noam Chen.

For: December and March

Winter and spring school breaks in the U.S. make December and March popular months to visit Israel; many Jewish families come as a bar/bat mitzvah celebration, and groups of college kids travel on trips through the Birthright Israel organization.

Why book in September? The last great guides, who have been holding out for long, private tours using their own luxury vans during these busy periods, will now be available to the first booking that comes along; if you wait until October, you’ll likely have to settle for subpar hotels too.

Wendy recommends: Joe Yudin, Trusted Travel Expert for Israel. Contact Joe through our site to get the best possible trip.

Cuba Over the Winter

Cuba street view

Now is still a good time to go to Cuba. Photo: Cultural Cuba

For: December to April

The changes announced by President Trump mean that people can no longer legally travel independently to Cuba—but the private and small-group tours arranged by our Trusted Travel Expert are still allowed. His connections on the island can get you access to the private paladar and photo studio of Fidel Castro’s son, a meeting with the city planner of Havana, or a rum tasting with the Havana Club brand’s sommelier; private trips are fully customized to each traveler’s interests. Winter and spring are the best time to visit Cuba, given the cooler temperatures and lower humidity.

Why book in September? Despite the political changes, you still need to book far ahead to assure that you’ll have a room in one of Havana’s few centrally located, top-rated hotels. If you’re considering traveling during these months—especially between Christmas and New Year’s—now is the time to reserve those spots.

Wendy recommends: David Lee, Trusted Travel Expert for Cuba. Contact David through our site to get the best possible trip.

Venice’s Carnevale

Photo: armelle76/Pixabay

Plan now for Venice’s Carnevale 2018. Photo: armelle76/Pixabay

For: January and February

Carnevale is the high point in Venice’s social calendar, a masked extravaganza where elegance and style come together in transgression. In 2018, it will happen January 27–February 13. The most sought-after masquerade balls are those that take place in Venice’s great palaces, where you are surrounded by rich furnishings and a wealth of historic art.

Why book in September? These exquisite costume parties draw visitors from around the world; by October, tickets for the most anticipated events will be sold out, as will the most desirable hotels.

Wendy recommends: Andrea Grisdale, Trusted Travel Expert for Italy. Contact Andrea through our site to get the best possible trip.


Festivals in Brazil

The Estrela d’Agua pousada on Praia dos Nativos, Trancoso, Brazil

Picture yourself at the Estrela d’Agua pousada on Praia dos Nativos,Trancoso, Brazil. Photo: Thomas Robinson

For: February and March

Want a dose of winter sun? Brazil offers several options, depending on your style. Head to Trancoso in early February for two traditional festivals—dedicated to Iemanja (the goddess of the sea) on the 2nd and Sao Bras (the patron saint of Trancoso) on the 3rd—that give travelers a rare glimpse of authentic Bahia culture. In early March, this chic tropical beach resort becomes home to Music in Trancoso, a classical music festival that takes place in an amphitheater overlooking the red cliffs of Terravista. And of course there’s Rio’s Carnival; our Trusted Travel Expert can set you up with a local stylist to design personalized costumes both for the street carnival and the glamorous fancy-dress balls to which he can also obtain tickets.

Why book in September? This is around the time that Brazilians start thinking about summer vacations—so book now to make sure you can get rooms at the hotels you want before space gets tight.

Wendy recommends: Paul Irvine, Trusted Travel Expert for Brazil. Contact Paul through our site to be marked as a VIP and get the best possible trip.

New Year’s in Uzbekistan (in March!)

People dressed up in traditional costumes for Navruz holiday in Uzbekistan

In March, Uzbekistan celebrates the New Year’s festival of Navruz. Photo: Zulya Rajabova

For: March

From March 18 to 25, every country in Central Asia celebrates Navruz, a New Year’s festival with public displays of traditional singing, dancing, and handicrafts, and the sharing of sumalak, a sweet made from fresh, sprouted wheat. There are torchlight processions, concerts, sporting events, and other events happening around the clock in Bukhara and Tashkent. In 2018, our Trusted Travel Expert will be guiding a group of travelers during this celebratory season, taking them to cook pilaf in her parents’ home and procuring premium seats for various Navruz events.

Why book in September? Those who book this trip in September will benefit from discounted pricing; come October, prices will increase. The earliest to book will also get to reserve the hotel rooms with the best views.

Wendy recommends: Zulya Rajabova, Trusted Travel Expert for Uzbekistan and the Silk Road. Contact Zulya through our site to be marked as a VIP and get the best possible trip.

Canada’s Northern Lights

January and February and some of the best times to visit British Columbia. The weather is perfect for winter sports, and you also have a good chance of seeing the Northern Lights. 

September and October offer a good chance of seeing the Northern Lights in Canada. Photo: Entrée Canada.

For: September and October

Roughly the same size as Spain with a population of 37,000 (most of whom reside in the capital city of Whitehorse), northern Canada’s Yukon territory is wild and remote—making it ideal for catching the aurora borealis. Command your own dogsled team as you move from one wilderness lodge to the next, following the light show across frozen lakes and wide-open tundra.

Why book in September? This natural spectacle is so popular—and so short-lived—that accommodations in the area sell out a year in advance; book now to ensure your spot for 2018.

Wendy recommends: Marc Telio, Trusted Travel Expert for Western Canada. Contact Marc through our site to be marked as a VIP and get the best possible trip.

Be a smarter traveler: Use Wendy’s WOW List to plan your next trip. You can also follow her on Facebook and Twitter @wendyperrin, and sign up for her weekly newsletter to stay in the know.

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