Make Your Next Trip Extraordinary

It’s September and This is Your Monthly Guide to What Trips to Book Now

Brook Wilkinson | September 1, 2016

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.)


Water Festival in Siem Reap Cambodia

Water Festival in Siem Reap. Photo: Ploy Photography

For: November

The Water Festival 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.

Sydney, 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 2017.

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

Corcovado National Park, Costa Rica

Corcovado National Park, Costa Rica. Photo courtesy GreenSpot.

For: December 2016 through March 2017

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.


Dormition Abbey at Sundown, Jerusalem, Israel

Dormition Abbey at sundown, Jerusalem, Israel. Photo by Noam Chen.

For: December 2016 and March 2017

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.

Venice, Italy

Photo: armelle76/Pixabay

Photo: armelle76/Pixabay

For: February 2017

Carnevale is the high point in Venice’s social calendar, a masked extravaganza where elegance and style come together in transgression. In 2017, it will happen from February 18 to 28. 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.


Vintage cars in Old Havana, Cuba. Photo: Michael Petit

Vintage cars in Old Havana, Cuba. Photo: Michael Petit

For: February to April 2017

Thanks to the warming of relations between the U.S. and Cuba and the announcement of commercial airline routes, the floodgates have opened for Americans traveling to this Caribbean time capsule. Savvy explorers should not miss its appealing blend of frozen-in-time history, architecture, live music, and nightlife.

Why book in September? There aren’t nearly enough hotel rooms to satisfy the demand, so you 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 even considering traveling next winter or spring, 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.


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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