Make Your Next Trip Extraordinary

The Best Trips to Book in October: What to Lock In Now

by Brook Wilkinson | June 4, 2020




Knowing when to book a trip is as important as knowing when to take it. Certain destinations require just the right amount of lead time to ensure you still have your choice of accommodations, activities, and private guides. That’s why we run this monthly series showcasing the places you should be booking right now.

An extravagance of cherry blossoms, millions of wildebeest on the move, and spectacular glowing night skies: Some of the world’s greatest natural phenomena are approaching, and you’d better start planning now if you want to be there to experience it. Read on for these and other trips during the coming year that you’d be wise to book in October.

(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 Charming Christmas Markets

Christmas Market in Bolzano, Italy

Christmas Market in Bolzano, Italy.

For: November 2019 to January 2020

Six Christmas markets are held in Italy’s Alto Adige region during these months: The towns of Bolzano, Merano, Brunico, Vipiteno, Glorenza, and Bressanone each have their own specialty, from handcrafted wooden gifts to traditional alpine clothing to festive food and hot wine.

Why book in October? Unlike the Christmas markets in other parts of Europe, Alto Adige’s remain relatively under the radar, so it’s not too late to book a last-minute trip that will get you into the holiday spirit (and maybe help you cross a few people off your shopping list).

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China’s Yunnan Province: Cuisine and Culture

lunch at a local restaurant in Dali, Yunnan Province, China

The ingredients at a local lunch spot were so fresh because they were farmed nearby. Photo: Billie Cohen

For: December 2019

China’s capital of hippies and ham, Dali is known for its rich gastronomy and talented artisans; Trusted Travel Expert and Yunnan Province native Mei Zhang even wrote a book on the region’s long culinary history, Travels Through Dali With a Leg of Ham. In winter, Dali’s ham is given a salty rub and left to dry in elaborate smokehouses until it practically melts in your mouth. After eating your fill, you can visit nearby salt wells to witness a centuries-old process of salt harvesting (the seasoning has been a major contributor to China’s economy since at least the seventh century, and this area’s salt is widely revered). Dali’s also a bit of a hippie hideout, where you can view a surprising Chinese counterculture of dreadlocked youth selling handicrafts on the street, mixed among the local Naxi minority.

Why book in October? This is your last opportunity to find hotel space and a guide with access to the ethnic communities that will be preparing ham, sausages, and pickles for winter.

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Norway: Best Shot at the Northern Lights

Northern Lights, Finnmark, Norway

Northern Lights, Norway. Photo: Terje Rakke/Nordic Life –

For: December 2019 through March 2020

Winter is the best time to catch the northern lights, when the night sky glows with a rainbow of colors. Since snow is sure to be covering the ground during these months, you can spend your days dog- or reindeer-sledding, skiing, and snowshoeing. We can’t guarantee that you’ll see the aurora borealis, but every traveler we’ve sent to the little town of Alta in search of the phenomenon has witnessed it.

Why book in October? Before long, the best hotels and guides will be booked up—particularly over the Christmas season. Secure your spots now so that you won’t have to compromise a once-in-a-lifetime trip.

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Spring Break Diving/Snorkeling and Ski Trips

Aspen Skiing, Rockie Mountains

Skiing in Aspen. Photo: Parker Olsen.

For: March 2020

It may feel like the school year has only just begun, but now is the time to lock in plans for your family’s spring break travel, to both warm-weather destinations and cold.

Why book in October? Right now, you can still choose from a wide selection of accommodations in your chosen destination and reserve the best dive masters and ski instructors; if you wait until everyone else books, you might have to settle for lesser hotels and activities. Ski passes (which give you access to multiple resorts throughout the winter for a much lower price than individual lift tickets) are typically only available until mid-November.

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Morocco’s Most Beautiful Season

Flowers, High Atlas Mountains, Morocco

Flowers, High Atlas Mountains, Morocco

For: Mid-March to mid-May 2020

Spring is a prime time to visit Morocco, when the wildflowers are in bloom and Marrakech isn’t yet terribly hot. The valleys on the southern side of the High Atlas are green due to snow melt, and the gorgeous Ourika Valley is at its prettiest: all red rocks, green hills, and rushing river. Ourika is an easy day-trip from Marrakech, and you can stop at Setti Fatma village and hike to the waterfalls from there, or have a tagine lunch at one of the riverside restaurants.

Why book in October? Book at least four months in advance to have your pick of the most atmospheric riads and the savviest local guides.

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Japan’s Iconic Cherry Blossoms

women in kimonos look at cherry blossoms in Japan

Two young women in kimonos view the cherry blossoms at Koishikawa Korakuen Garden in Tokyo, Japan. Photo: Ben Simmons

For: April and May 2020

Springtime in Japan is the season of sakura, or cherry blossoms. Their sweet scent and beauty permeate the country, and the entire nation comes alive to celebrate hanami, or flower viewing, in colorful kimonos.

Why book in October? With both foreign and domestic travel at its peak during these months, you’ll need to plan well in advance to stay in the most atmospheric ryokans (particularly in Tokyo, Kanazawa, and Kyoto), and to hire the most well-connected guides.

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Italy’s Dolomites: A Summer Wonderland

landscape view of dolomites jagged mountains overlooking green fields and trees in Italy

The Dolomites are a breath-taking, jagged-peaked mountain range in the north of Italy. Photo: IC Bellagio

For: May through September 2020

Many associate an Italian vacation with culinary indulgence. In the Dolomites—a breath-taking, jagged-peaked mountain range in the north of the country—you can put all that carb-loading to work when you spend your days hiking and biking. But you don’t have to rough it: There are world-class resorts here (and chair lifts that let you skip the steepest sections), and even the backcountry rifugios serve delicious meals that will fuel your daily activities.

Why book in October? The Dolomites’ winter season picks up in November, at which point it can be hard to pin down the best guides (who are all out skiing and snowshoeing). Better to start planning now, when things are relatively quiet and the local businesses have time to think about next summer.

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Alaska Small-Ship Expedition Cruises

Alaskan brown bear sow and its cub at Brooks Falls in katmai National Park, Alaska

An Alaskan brown bear sow and its cub at Brooks Falls in Katmai National Park, Alaska. Photo: Shutterstock

For: May through September 2020

Alaska’s cruise season runs from mid-April to late September, and each part of the short season offers different highlights. May sees fewer visitors, the arrival of migrating humpback whales (typically late in the month), and bears foraging along the shoreline at dusk and dawn. May and June have the most days of sunshine, and you’ll find beautiful wildflowers abloom in June and July. Humpback whales, orcas, sea otters, bald eagles, and sea lion colonies can be seen throughout most of the season. The smaller ships, which carry fewer than 100 passengers, get you 10 to 15 yards from bears, moose, glaciers, and waterfalls. Days are dictated not by a port-to-port schedule, but by seizing the best opportunities for wildlife watching, hiking, and kayaking.

Why book in October? For these cruises, the most popular cabin categories and departure dates typically sell out before Thanksgiving.

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U.S. River Rafting Trips

white water rafting boat in river of Gates of Lodore Colorado

Rafting the Gates of Lodore, in Colorado. Photo: Josh Miller

For: May through September 2020

Rafting trips are popular come summer, but if you have the smarts to book now, you’ll not only secure spots on some of the country’s most beautiful rivers, you’ll have access to deals that will disappear by the time everyone else starts shopping.

Why book in October? Since most people don’t start thinking about next summer’s travel until after the New Year, discounts may be available on a number of trips.

Ask about a river rafting trip

Ask Wendy to find the right travel specialist for your needs and to plan the best possible trip. You’ll be marked as a VIP and get a trip like this.

Italian Villas for a Family Reunion in Tuscany or Lake Como

Villa di Torno, Lake Como

Dining outdoors at Villa di Torno, Lake Como. Photo courtesy Homebase Abroad.

For: June through August 2020

Renting a house to live like a local in Tuscany or the Amalfi Coast has become intensely popular, and few villas in either region fit groups of 14 or more travelers. If you’re set on a waterfront property on the Amalfi Coast—which we strongly recommend, so that you can come and go by boat to avoid the slow-moving road traffic—your options are even more limited. Many of the houses represented by Mara Solomon (our Trusted Travel Expert who specializes in Italian estate rentals of four bedrooms or more) come with a private cook to prepare your group’s meals—because where’s the fun in preparing dinner for 20?—and have recently seen upgrades from their owners.

Why book in October? The calendars of the best Italian villas in these iconic regions are quickly filling up—particularly for mid-June to mid-July, when families want to get away together before the kids head to summer camp.

Ask about a villa vacation in Italy

You’ll be marked as a VIP and get a trip like this. Smaller families or groups needing smaller homes and less elaborate arrangements should Ask Wendy instead.

Tanzania’s Hidden Gem

safari tourists in a jeep watching elephants pass in Tanzania

The Chem Chem Reserve is strategically located between two of the country’s crown jewels—Lake Manyara and Tarangire National Park. Photo: Chem Chem Safari Lodge

For: June to October 2020

Northern Tanzania is home to the stuff safari dreams are made of: herds of zebra, wildebeest, and giraffe stretching to the horizon; Maasai warriors displaying their bush skills; elephants basking in a riverine mud bath. The Chem Chem Reserve is strategically located between two of the country’s crown jewels—Lake Manyara and Tarangire National Park—and the three Chem Chem properties there offer an array of experiences without an overabundance of tourists. What’s more, the owners’ commitment to conservation and community development means that lions aren’t preying on herders’ livestock, and women are getting the support they need to start small businesses.

Why book in October? For this month only, our Trusted Travel Expert can save you 15% on any stay at Chem Chem Lodge, Little Chem Chem, and Forest Chem Chem between June and October 2020—but only if you contact her via

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Sri Lanka’s Best Festival

people dancing in traditional costumes at the Kandy Festival in Sri Lanka

Sri Lanka’s Kandy Festival. Photo: Sri Lanka in Style

For: August 2020

Sri Lanka’s largest and most popular festival (particularly with children) is the Kandy Esala Perahera, an annual celebration where religion, tradition, and the arts come together to pay homage to the sacred tooth relic of the Lord Buddha, which has been housed in the country since the fourth century. These ten days of striking processions feature scores of glittering elephants, fire breathers, and thousands of dancers, culminating on the full moon day when the relic is paraded through the streets of Kandy.

Why book in October? Some of Kandy’s hotels have rooms with views of the perahera; these generally sell out around November. Almost all of the hotels in town sell out by Christmas.

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Africa’s Peak Time for Safaris

great migration, wildebeest, mara river, masai mara Kenya

The great migration wildebeest crossing the Mara River, Masai Mara, Kenya. Photo: Hippo Creek Safaris

For: September 2020

September is glorious in South Africa: The winter chill has left, spring is on its way, and the grasses have been eaten down, leaving the animals in full view. It’s also the best time to see the annual migration in East Africa—the ultimate wildlife spectacle, where more than a million wildebeest and other animals pass through Kenya’s Masai Mara Game Reserve.

Why book in October? It’s already difficult to find space at safari lodges and camps for August; by next month, it’s likely that the best places will be full for September as well. Most airlines release award seats about 11 months in advance, so right now you have the best chance of redeeming miles for next year’s flights.

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