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

Brook Wilkinson | May 1, 2017

If a sea or river cruise is in your 2018 travel plans, right now may well be a smart moment to book it. It’s true: If you want your choice of cabin and departure date, cruises to many destinations that are popular in May (Alaska, the Greek Islands) and to places where vessels are few (French Polynesia, France’s canals) need to be reserved a year in advance. Below, you’ll also find some ideas for upcoming festivals and feats of endurance that should be booked right now.

(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.)

Guadalajara’s Mariachi and Charreria Festival

a charro rodeos with a horse in Mexico's Charreria Festival guadalajara Mexico

A charro performs at Guadalajara’s Mariachi and Charreria Festival. Photo: Jalisco es Mexico

For: August and September

This festival in Mexico’s second-largest city celebrates many of the region’s trademarks: There are live performances by the finest mariachi bands from around the world, spectacles of the sport of charreria (a kind of Mexican rodeo event on horseback), and of course, there’s plenty of tequila produced in the neighboring distilleries.

Why book in May? Long considered a center of traditional culture, Guadalajara is an up-and-comer in the country’s burgeoning art scene, so hotel rooms and festival tickets have sold out in recent years; book now while both are still available.

Wendy recommends: Zachary Rabinor, Trusted Travel Expert for MexicoContact Zach through our site to be marked as a VIP and get the best possible trip.

England in Autumn

Buckland Manor, Cotswolds, England

Buckland Manor is one of the beautiful mansions in the Cotswolds, England. Photo: Jonathan Epstein/Celebrated Experiences

For: October and November

Few places are more charming and romantic than the English countryside during the fall, when the foliage is bright and colorful and the summer crowds have gone. It’s the perfect time to stroll between villages, go on drives along the winding roads, and while away an afternoon in front of a pub’s toasty fire. Plus, the restaurant menus are full of freshly harvested fruits and vegetables, plus lots of game, such as venison, duck, and pheasant.

Why book in May? Autumn is far less busy than the summer, but the beauty of the season is no longer a secret. Plan now for the fall so that you still have the best choice of accommodation at the finest countryside inns and stately homes, which have just a handful of rooms each.

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

Miao New Year Celebrations in China

For: October and November

Rich in colorful minority culture, China’s southwest province of Guizhou sparkles with the traditions of ethnic groups such as the Buyei Miao and Yi Miao. During October and November they will be preparing for their new year celebrations (Miao New Year falls on November 5th in 2017). Join the Miao people, adorned in their signature silver headdresses, as they gather provisions, arrange ancestor worship, visit neighboring villages, and play the Lusheng—a traditional musical instrument made from bamboo. You’ll be kindly welcomed into the community with rice wine and exotic feasts of local fare.

Why book in May? Still off the beaten path, Guizhou has only a few high-quality hotels and English-speaking guides; book now to ensure you get the best of the best.

Wendy recommends: Mei Zhang, Trusted Travel Expert for ChinaContact Mei through our site to be marked as a VIP and get the best possible trip.

Tasmania’s Overland Track

Cradle Mountain Huts Walk Tasmania

Tasmania’s six-day Overland Track takes you through a Wilderness World Heritage Area. Photo: Cradle Mountain Huts

For: November 2017 to March 2018

Tasmania’s iconic Overland Track is a six-day, 40-mile adventure through the heart of the island’s spectacular UNESCO-designated Wilderness World Heritage Area, past mountains and rainforest. You can go on your own, or join a guided trek and stay in private huts where three-course dinners are served, accompanied by Tasmanian wines.

Why book in May? Hiking permits during the busy summer season—particularly over school and Christmas holidays—are limited, and almost always sell out. Reserve your spot on the trail now, while permits for those most popular periods are still available.

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

Cruising the Mediterranean

For: May 2018

May is the sweet spot for a Mediterranean cruise: The weather is gorgeous, temperatures are ideal for sightseeing, and crowds are not as abundant as in summer, when kids are out of school and both overseas visitors and Europeans flock to the seashore.

Why book in May? Cruise-line incentives are generally the richest from May through October for the following year’s departures. Snag your preferred cabin at the best rate currently available, and don’t be too concerned about the price dropping or missing out on a last-minute deal: All cruise lines will fulfill a reimbursement request if the fare falls before you send in your final payment, as long as you didn’t book a nonrefundable rate.

Wendy recommends: Tom Baker, Trusted Travel Expert for Large, Affordable Ships and River Cruises. Contact Tom through our site to be marked as a VIP and get the best possible trip.

Cruising Alaska

Cascade Creek Trail, Thomas Bay, Tongass National Forest, Southeast Alaska

Cruise Alaska during the spring or fall and you’ll find a lot more than snow and ice. Photo: Lindlad Expeditons/David Vargas

For: May to September 2018

A cruise is the best way—indeed, the only way—to see some of Alaska’s most beautiful coastline. Look for one that encompasses both the Inside Passage (an archipelago of 10,000 islands in the Alaska Panhandle near British Columbia) and the Gulf of Alaska (the coastline farther north that gives you access to Alaska’s interior). The shoulder months of May and September see the lowest fares, as well as colorful wildflowers and fall foliage, respectively. The warmest and longest days are in June and July, when you’ll also see active, calving glaciers.

Why book in May? The season is short for Alaska cruises, so book at least a year in advance to reserve the cabin you want on the ship that’s right for you; if the price drops before your final payment, you can request a refund for the difference.

Wendy recommends: Tom Baker, Trusted Travel Expert for Alaska Cruises. Contact Tom through our site to be marked as a VIP and get the best possible trip.

A Freighter Cruise of French Polynesia

Hiva Oa Marquesas Islands French Polynesia

The Aranui 5’s route through the Marquesas Islands includes a stop at Hiva Oa, where you can walk a black-sand beach and see the most impressive collection of tika sculptures outside Easter Island.

For: May/June or September/October 2018

The Aranui 5 is a combination freighter/cruise ship that does a two-week trip from Papeete, Tahiti to the Marquesas Islands (see: How to Island-Hop Your Way Around French Polynesia). It’s one of the last such combination ships left in the world, giving travelers an overview of the region while resupplying local communities.

Why book in May? This cruise is so popular that it often sells out a year in advance; the balconied cabins go first. Book now for a spring or fall cruise next year.

Wendy recommends: Kleon Howe, Trusted Travel Expert for Tahiti, Bora Bora, and French Polynesia. Contact Kleon through our site to be marked as a VIP and get the best possible trip.

A French Canal Barge Trip

a canal barge cruise in france

Canal barge cruises move slowly, allowing for great up-close views of the French countryside. Photo: Barge Lady Cruises

For: June and September 2018

These two months are considered peak season for barge cruises along the canals of France, when the weather there is at its best. September is particularly popular in the wine regions, since that’s when the grape harvest takes place. Barges glide through the canals for a few hours each day, moving slowly enough that you can walk or bike alongside; passengers spend the other half of the day on guided excursions to local chateaux, markets, and villages. Canal barge cruising is a wonderful way to get to know a bit of France on an intimate level.

Why book in May? Barge vessels range in size from just four to 14 passengers, so there is very little inventory available. Itineraries during these most popular months often sell out a year or more in advance.

Wendy recommends: Ellen Sack, Trusted Travel Expert for European Canal Barge Trips. Contact Ellen 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, Twitter @wendyperrin, and Instagram @wendyperrin, and sign up for her weekly newsletter to stay in the know.

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