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

Brook Wilkinson | September 15, 2017

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.

Trees cloaked in butterflies, and spectacular glowing night skies: Two 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 nine 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.)

Mexico’s Monarch Butterflies

Monarch butterflies, Michoacán, Mexico

Monarch butterflies, Michoacán, Mexico. Photo: Scott Clark/Flickr

For: November through March

The Monarch butterflies arrive in Mexico on their annual southern migration in November, and they can be viewed at a biosphere reserve in the states of Michoacán and Mexico until March. It’s quite a sight to see, with up to one billion butterflies carpeting the forest. During the peak months of January and February, wildlife lovers can also see migrating gray whales in Baja California.

Why book in October? The hotel options are slim in this region, so it’s important to secure your room as soon as possible.

For a WOW trip, contact Mexico expert Zachary Rabinor via Wendy’s trip request form. You’ll be marked as a VIP and get a trip like this.

Cuisine and Culture in Dali, China

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

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.

For a WOW trip, contact China expert Mei Zhang via Wendy’s trip request form. You’ll be marked as a VIP and get a trip like this.

Norway’s Northern Lights

Northern Lights, Finnmark, Norway

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

For: December through March

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.

For a WOW trip, contact Norway expert Jan Sortland via Wendy’s trip request form. You’ll be marked as a VIP and get a trip like this.

Spring Break Diving/Snorkeling and Ski Trips

Aspen Skiing, Rockie Mountains

Skiing in Aspen. Photo: Parker Olsen.

For: March

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.

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

Spring in Cuba

The golden hour, a sunset over Havana, Cuba. Photo: Michael Petit

The golden hour, a sunset over Havana, Cuba. Photo: Michael Petit

For: March through May

With travel to Cuba exploding in popularity, finding a place to sleep on the island is becoming an increasingly difficult problem to solve. The most centrally located, top-rated hotels fill up far in advance. Spring is one of the best times to visit, before the summer heat (and hurricane season) hits.

Why book in October? Hotel space in Havana for next spring is already dwindling; if you plan ahead, you won’t be stuck in a shabby place on the outskirts of the city.

For a WOW trip, contact Cuba expert David Lee via Wendy’s trip request form. You’ll be marked as a VIP and get a trip like this.

Japan’s 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

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.

For a WOW trip, contact Japan expert Scott Gilman via Wendy’s trip request form. You’ll be marked as a VIP and get a trip like this.

Alaska Small-Ship Expedition Cruises

For: May through September

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.

For a WOW trip, contact Small-Ship Expedition Cruises expert Ashton Palmer via Wendy’s trip request form. You’ll be marked as a VIP and get a trip like this.

U.S. River Rafting Trips

river rafting Yampa river

River rafting trips are popular in summer; book early to get your top selection and good deals. Photo: OARS

For: May through September

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. Case in point: Wendy’s Trusted Travel Expert for river rafting vacations is offering an early-booking discount—typically around ten percent, though it varies by trip—to the first four people to sign up for trips on many of the country’s most stories waterways, including the Salmon, Colorado, and Green Rivers.

Why book in October? Since most people don’t start thinking about next summer’s travel until after the New Year, these discounts are still available on a number of trips, saving you as much as $300 per person.

For a WOW trip, contact River Rafting Vacations expert Mindy Gleason via Wendy’s trip request form. You’ll be marked as a VIP and get a trip like this.

Villas in Tuscany or Lake Como

For: Summer

Le Ripe villa, Tuscany, Italy

Le Ripe villa, Tuscany, Italy. Photo: Homebase Abroad

A villa in the Tuscan countryside or right on the shores of Lake Como is the stuff of many a traveler’s fantasy: a lovely stone farmhouse or an elegant estate, tastings at the winery down the road or day-trips into Milan, groups of family and friends sharing generous portions of fresh pasta around the dinner table. Long days and warm evenings make summer a lovely—but popular—time to book a villa stay.

Why book in October? The calendars of the best Italian villas in these iconic regions are quickly filling up; between mid-June and mid-July, there are already just a few houses left that sleep 14 or more people.

For a WOW trip, contact Italy Villa Vacations expert Mara Solomon via Wendy’s trip request form. You’ll be marked as a VIP and get a trip like this.

Sri Lanka’s Kandy Festival

An elephant procession for Kandy Esala Perahera, in Sri Lanka

A procession for Kandy Esala Perahera, in Sri Lanka. Photo: vasse nicolas,antoine/Flickr

For: August

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.

For a WOW trip, contact Sri Lanka expert Miguel Cunat via Wendy’s trip request form. You’ll be marked as a VIP and get a trip like this.

African 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

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 2017; 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.

For a WOW trip, contact East Africa experts Nina Wennersten and Dan Saperstein via Wendy’s trip request form. 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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