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

by Brook Wilkinson | June 4, 2020




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.)

Italy’s Chocolate Festival

piles of Baci chocolate kisses in bins at the Perugina chocolate factory in Perugia Italy

The Perugina factory (famous for its Baci chocolate kisses) is only one reason to visit Perugia during the annual EuroChocolate Festival. Photo: Billie Cohen

For: October

If you like chocolate, you’ll love Perugia’s EuroChocolate festival, an annual celebration of all things cacao. From October 18–27, the city hosts a range of chocolate-themed activities, from sculpting to cooking classes—and of course, chocolate tastings.

Why book in September? Since the event is largely attended by locals, it’s not too late to find room at one of Perugia’s excellent hotels and enjoy autumn in the Umbrian countryside.

For a WOW trip, contact Italy expert Andrea Grisdale via Wendy’s “Start a Trip” questionnaire. You’ll be marked as a VIP and get a trip like this.

Botswana’s Newest Safari Camp

view from the deck of Tuludi safari camp in Botswana with sunset, Okavango delta and tree

Tuludi is a new tented safari camp in Botswana’s Okavango Delta.

For: October 2019 through June 2020

Tuludi is a brand-new tented safari camp that brings a new level of sophistication to the vast wilderness of the game-rich Okavango Delta. The luxurious high-pitched tented rooms harmonize with the surrounding landscape, and each has its own private pool. Located within the 800-square-mile Khwai Private Reserve, Tuludi offers potential encounters with the elusive wild dog, black and white rhino, and dense numbers of elephant, buffalo, zebra, giraffe, antelope, and big cats.

Why book in September? Our Trusted Travel Expert has negotiated an extra 15% off any 3-night stay at Tuludi, booked via this month, for travel between October 2019 and June 2020 or between October and December 2020.

For a WOW trip, contact Africa expert Cherri Briggs via Wendy’s “Start a Trip” questionnaire. You’ll be marked as a VIP and get a trip like this.

Cuba Over Fall and Spring

family in old fashioned red car on the streets of Havana cuba

Yes, you can still travel to Cuba. Photo: Cultural Cuba

For: October/November 2019 and March/April 2020

Yes, you can still travel to Cuba. While cruise ships and people-to-people tour groups have been banned, our Trusted Travel Expert’s custom private tours are complaint with U.S. regulations and let you experience Cuba in a way that the cruise masses and large groups never could. These itineraries include full-time, top-notch guides, dedicated drivers and air-conditioned vehicles, reservations at private restaurants and paladares, exclusive interactions with Cuban artists and musicians, and behind-the-scenes access at certain sites. Late fall, winter, and spring are the best time to visit Cuba, given the cooler temperatures and lower humidity.

Why book in September?  Jump on one of our Trusted Travel Expert’s three- or four-day weekend trips for late fall, or plan ahead so that you can reserve your preferred dates and the most convenient and affordable flights for spring.

For a WOW trip, contact Cuba expert David Lee via Wendy’s “Start a Trip” questionnaire. You’ll be marked as a VIP and get a trip like this.

Athens in Fall

For: November

Athens is perfect in autumn, when the weather is mild—ideal for taking advantage of the city’s many rooftop bars—and the summer crowds have dissipated. The Athens Marathon takes place on the second Sunday in November, following the same course from the first modern Olympics in 1896. Casual runners may want to just watch this one, though, as the route is a famously difficult one.

Why book in September? Since many travelers don’t think to head to Europe in November, it’s not too late to book your hotel or reserve one of the top cultural guides to show you around the city.

Contact Wendy to find the right Trusted Travel Expert to plan your best possible trip.

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.

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

For a WOW trip, contact Southeast Asia experts Andrea Ross and April Cole via Wendy’s “Start a Trip” questionnaire. You’ll be marked as a VIP and get a trip like this.

Australia: New Year’s in Sydney

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 2020.

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.

Contact Wendy to find the right travel specialist for your needs and to get the best possible trip.

Costa Rica for Spring Break

A capuchin monkey in a tree on Costa Rica’s Osa Peninsula

See capuchin monkeys on Costa Rica’s Osa Peninsula. Credit:

For: December 2019 through March 2020

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.

For a WOW trip, contact Costa Rica expert Irene Edwards via Wendy’s trip request form. You’ll be marked as a VIP and get a trip like this.

Israel: A Memorable Family Trip

Dormition Abbey at Sundown, Jerusalem, Israel

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

For: December 2019 and March 2020

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. Wendy took her own kids there in spring; you can read about their trip in What the Right Local Fixer Can Do for You in Israel (or Anywhere).

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.

For a WOW trip, contact Israel expert Joe Yudin and Jonathan Rose via Wendy’s “Start a Trip” questionnaire. You’ll be marked as a VIP and get a trip like this.

Venice’s Carnevale

Photo: armelle76/Pixabay

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

For: February 2020

Carnevale is the high point in Venice’s social calendar, a masked extravaganza where elegance and style come together in transgression. In 2020, it will happen February 8–25. 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.

For a WOW trip, contact Italy expert Andrea Grisdale via Wendy’s “Start a Trip” questionnaire. You’ll be marked as a VIP and get a trip like this.

Nepal: Big Savings at a Jungle Lodge

green fields with mountains in background in Chitwan Nepal

Chitwan, Nepal. Photo: Shutterstock

For: February 2020

February is the best month to visit Chitwan National Park, as the grass is short and the conditions prime for wildlife viewing; here you’ll find rhinos, royal Bengal tigers, elephants, and more. Barahi Jungle Lodge, carefully designed to blend into the jungle ecosystem, lies just across a river from a quiet region of the park; while you’re there, you can take part in jeep safaris, canoe trips, village visits, and spa treatments. February is also an ideal month for a larger trip that takes in the Kathmandu Valley, plus Pokhara and the surrounding villages, before the weather gets too hot.

Why book in September? Our Trusted Travel Expert has negotiated a complimentary two-night/three-day stay at Barahi Jungle Lodge for any travelers who book a 10-day or longer trip to Nepal; that’s a savings of nearly $1,000 for two travelers. This deal is available until it’s sold out.

For a WOW trip, contact Nepal expert Toni Neubauer via Wendy’s “Start a Trip” questionnaire. You’ll be marked as a VIP and get a trip like this.

Brazil’s Summer Festivals

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 2020

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.

For a WOW trip, contact Brazil expert Paul Irvine via Wendy’s “Start a Trip” questionnaire. You’ll be marked as a VIP and get a trip like this.

Uzbekistan Premier Festivals

Registan Square in Samarkand Uzbekistan

Visit Registan Square in Samarkand, Uzbekistan, during the countries two big annual festivals. Photo: Surapon Supratya

For: March and May 2020

Uzbekistan’s rich culture is on full display during two spring festivals: New Year’s in March, and Bukhara’s Silk and Spice Festival in May. In the days around the spring equinox on March 21, 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. During the Silk and Spice Festival from May 25-27, performers and craftspeople from all over the country gather to celebrate the traditions of Central Asia, from ikat fabric to wood carvings, with exuberant parades on the first and last days.

Why book in September? The earliest travelers to book during these periods will get the hotel rooms with the best views. Prices for a New Year’s tour led by our Trusted Travel Expert will also increase come October.

For a WOW trip, contact Uzbekistan expert Zulya Rajabova via Wendy’s “Start a Trip” questionnaire. You’ll be marked as a VIP and get a trip like this.

Canada’s Prime Bear-Viewing Opportunity

bear looking at camera on Nakina River in British Columbia canada

September and October are British Columbia’s prime bear-viewing months. Photo: Entree Canada

For: September and October 2020

Canada is home to three ursine species: grizzly, black, and polar bears (four if you count the Kermode or spirit bear, a sub-species of the black bear). Late August ushers in the arrival of salmon to rivers throughout British Columbia (which has one of the world’s highest populations of black bears), and their run peaks in September and October. With the salmon come hungry bears, looking for their next meal!

Why book in September?  Bear-watching is so popular that the lodges in the wilderness areas where the animals are most likely to be spotted sell out a year in advance; book now to ensure your place for 2020.

For a WOW trip, contact Western Canada expert Marc Telio via Wendy’s “Start a Trip” questionnaire. You’ll be marked as a VIP and get a trip like this.

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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