10 Best Places to Travel in May

Don’t wait for the summer rush—book a trip to one of these destinations before the crowds arrive.

Memorial Day might be the unofficial kickoff for summer, but why wait until then to take a vacation? There are plenty of reasons to squeeze in a trip before peak season starts, whether you want to see one of the world’s natural wonders in both its wet and dry states, or watch bears as they emerge from wintry hibernation. Here are our 10 best places to travel in May. Remember, though, that COVID-19 related regulations remain in place in many states and countries and are subject to change—always check updated mandates and requirements before booking any trip.

Memphis neighborhoods are evolving all the time, but the BBQ and live music remains timeless.

Memphis neighborhoods are evolving all the time, but the BBQ and live music remains timeless.

Photo by Heidi Kaden/Unsplash

Memphis, Tennessee

May is great for: lovers of ribs and rowdy music

Memphis has made strides in upgrading its slightly careworn downtown in recent times. Late last year, for example, it authorized a special tax at the iconic Peabody hotel to help bolster its coffers for a major improvement program. Beale Street, the city’s three-block entertainment hub, is also a focus of these efforts, with more money plowed into the nearby docking area for steamboats that first opened almost a decade ago.

This month, make an excuse to go check out the progress via Memphis in May, a month-long fest celebrating the two things for which the city is best known: barbecue and music. On the first weekend in May, there’s the Beale Street Music Festival—confirmed headliners include Foo Fighters and Lil Wayne, with more to be announced. Two weeks later, there’s the World Championship Barbecue Cooking Contest, temporarily relocated to the Fairgrounds in Liberty Park. Teams from all over the world compete to win $140,000 in prize money; why not apply to be a judge so you can sample everything?

Where to stay

If you want to stay 10 feet off of Beale (a la Marc Cohn), choose the new 227-key Hyatt; it’s the first and only hotel to have an address on that club- and bar-crammed road. Bonus: a couple of great waterfront F&B spots onsite.

Book now: Hyatt Centric Beale Street Memphis

How to get there: There’s a wide assortment of flights to MEM, including Frontier from Denver, Southwest from Atlanta, and Delta service from Minneapolis–St. Paul.

Early birds get the crowd-free worm at Cape Cod in May.

Early birds get the crowd-free worm at Cape Cod in May.

Photo by mamahoohooba/Shutterstock

Cape Cod, Massachusetts

May is great for: sporting a preppy sweater to watch a tony regatta

Forget high season, when the crowds swarm the roads and beaches of the Cape, and sneak in early, when the weather should be pleasant—think high 50s—and the vibe unruffled. Immerse yourself in the centuries-old history here via Maritime Days, four carefully crafted itineraries from the local Chamber of Commerce that offer a chance to guide yourself around the various landmarks (download them).

On Memorial Day weekend, it’s time for the annual Figawi race, a 50-year-old charity regatta (with associated parties) from Hyannis to Nantucket, a highlight of the social season here. Or you could browse the works of local creatives spotlit in Hyannis HyArts Artist Shanties, which kicks off on May 20 for the summer. Expect everything from painting and photography to rope work, much of it, of course, with more than a whiff of the ocean.

Where to stay

It only opened last month, but the Chapter House already has more than 300 years of history behind it: The historic inn was built in 1716 and has been lovingly overhauled as a 21-room boutique hotel. When the weather’s fine, the best place to dawdle is the huge lawn onsite.

Book now: Chapter House

How to get there: Boston-Logan is the closest airport, with service from all major airlines. It’s a 90-minute drive or so then to Cape Cod proper.

The Catskills offers much for New Yorkers (or anyone) to explore, including Wayside Cider.

The Catskills offers much for New Yorkers (or anyone) to explore, including Wayside Cider.

Photo by Michelle Heimerman

Catskills, New York

May is great for: a dollop of Mrs. Maisel–style nostalgia

Forget the Hamptons; the best countryside retreat close to New York City is less stuffy and far more affordable. The craggy region west of the Hudson River was historically a popular summer getaway site for everyday New Yorkers, and it reclaimed much of that cachet as the pandemic’s restrictions encouraged those same people to explore their backyard once again.

Head to Andes, an artsy cluster home to potter Stephanie Theado—she has an honesty store on her stoop when she’s shut—and Wayside Cider, with its enormous, linger-ready backyard, or stroll the winding, 11.5-mile trail around the enormous Ashokan Reservoir. For a jolt of urban life, check out rapidly gentrifying Kingston, on the water’s edge: the cluster of new stores and restaurants along Broadway and around Fair Street are both worth a detour.

Where to stay

Take a time warp back to the Mrs. Maisel–era heyday of the Catskills by booking an Airstream at the new AutoCamp Catskills, a brand new midcentury-modern-inflected resort just outside the town of Saugerties.

Book now: Autocamp Catskills

How to get there: Stewart is a handy access point for this slice of upstate New York, with service by both Frontier and Allegiant from the likes of Savannah, Georgia, and Orlando, Forida. Otherwise, fly into any NYC metro area airport and take the two-hour scenic drive north along the Hudson River.

Whale-watching and a new exhibition at the aquarium make for a great May in Monterey.

Whale-watching and a new exhibition at the aquarium make for a great May in Monterey.

Photo by Chase Dekker/Shutterstock

Monterey, California

May is great for: whales and penguins

Whaling helped build the town of what’s now Monterey in the times of early European settlement, a license to print money from the ocean. Thankfully, it’s now forbidden to hunt those animals, but the oceans still teem with them, especially this month when migration seasons overlap, filling the bay with killer, humpback, and blue whales. They’re particularly drawn to the waters here thanks to the namesake, one-mile-deep submarine canyon, which keeps the temperatures chilly.

Book an excursion to go spotting with marine biologist Nancy Black, or if you’d rather experience the ocean without risk of seasickness, opt instead for the Monterey Bay Aquarium, one of the world’s best marine conservation showcases with enormous floor-to-ceiling windows on many tanks. Into the Deep, a new exhibit, opens in April. Don’t miss the de facto mascots of the site, a colony of African penguins, who are fed with much fanfare every morning.

Where to stay

The Spindrift Inn is a handy luxury perch right on the water at Cannery Row, and the modern building is designed to evoke the Gold Rush–era heyday.

Book now: The Spindrift Inn

How to get there: It’s a two-hour drive south of San Francisco to this other bay area; fly into SFO via all major carriers.

Temperatures are just right for backpacking in Peru at this time of year.

Temperatures are just right for backpacking in Peru at this time of year.

Photo by NiarKrad/Shutterstock.

Sacred Valley, Peru

May is great for: just-right conditions to roam the entire region

The weather hits the Goldilocks Zone this month in Peru—just right for just about everything. The dry season of the Andean Zone begins, ideal for roaming the Sacred Valley, that iconic Inca stronghold that’s home to Machu Picchu, among others. Try the Salkantay Trek as a less well-trod alternative to the Inca Trail. Greenery is still ample, and paths are clear and less treacherous. Even better, temps remain warm but less oppressive than a few weeks earlier. Lima, on the coastal desert strip, will hover in the 60s; it will be transformed by Noche en Blanco, a series of parties and events inspired by Europe’s White Nights in the Miraflores district as well as the Fiesta de la Cruces on May 3, a Catholic legacy inspired by Saint Helena and her veneration of the true cross.

Where to stay

The ecolodge Las Qolqas is a glamping-style resort with safari-inspired tents, set right in the Sacred Valley. Expect floor-to-ceiling windows to maximize your views.

Book now: Las Qolqas

How to get there: There are direct flights to Lima from Miami, Atlanta, and New York–JFK.

Hit up the Evan Williams Bourbon Experience on Whiskey Row in Louisville.

Hit up the Evan Williams Bourbon Experience on Whiskey Row in Louisville.

Photo by Rosemarie Mosteller/Shutterstock

Louisville, Kentucky

May is great for: big hats, big bets, and big cocktails

Who wouldn’t want an excuse to dress up, place a few bets, and glug a few juleps for the Derby on the first Saturday this month? Arrive a few days early and you can take part in the festival that is its local warm-up act: There are parades and wacky races (beds and steamboats both) as part of the schedule. If you miss that weekend, it’s still worth a trip to check out the Kentucky Bourbon Trail, which provides itineraries for 19 small craft distilleries or 18 big-name ones; visitors can get a passport stamp to show that they’ve visited (and opportunities for prizes).

In downtown, the elixir bubbles forth from gleaming copper stills at the Evan Williams Bourbon Experience. Family-friendly exhibits take you back to 1783, when bourbon making began, while production tours show how it’s done today. A few blocks away, elegant Angel’s Envy offers tours and tastings of its slightly sweet, port-cask-finished whiskey.

Where to stay

The aptly-named Hotel Distil is a chic, 205-room property right on Whiskey Row, still home to some of the top-notch local liquor makers like Angel’s Envy. Whether drowning your sorrows or celebrating a win, you can safely stagger home.

Book now: Hotel Distil

How to get there: Try the brand new low-cost carrier Breeze, which has flights to Louisville from New York–Islip, Hartford, Connecticut, and Tampa, Florida, among others.

Bolivia's Salar de Uyuni salt flat is a once-in-a-lifetime place to visit and photograph.

Bolivia’s Salar de Uyuni salt flat is a once-in-a-lifetime place to visit and photograph.

Photo by Jam Travels/Shutterstock

Bolivia’s salt flats

May is great for: the best of both worlds at a world-renowned site

The 4,000-square-mile salt plain at Salar de Uyuni is the remnant of an ancient lake that dried up millions of years ago. May—the tail end of the wet season and the beginning of the dry season—is an ideal month to visit: The flats are more accessible, and thanks to the mix of sunny and rainy days, travelers may be able to see the salt flats both dry and when they are flooded, which creates the surreal mirror effect captured in countless photos. (Remember to bring sunglasses—the brightness of the reflection on the salt is unpleasant unless your eyes are shielded.)

Where to stay

Kachi Lodge is a partnership between Swiss outfitter Amazing Escapes and the Indigenous Jirira community. It’s the first permanent luxury lodge here and a highly sustainable camp, located at the foot of the Tunupa volcano, with six solar-powered geodesic domes with wood-pellet stoves, bay windows, and incinerating toilets. Reclaimed wood furniture, traditional bayeta textiles, and artwork from Gastón Ugalde (considered the Andean Andy Warhol) decorate the lodge.

Book now: Kachi Lodge

How to get there: Uyuni is the nearest town to this natural wonder; book a day tour at one of the agencies in Plaza Arce. There are regular connections for the hour-long flight from La Paz to Uyuni; reach La Paz from the United States on Latam and Avianca, among others.

The grizzlies come out of hibernation around about now.

The grizzlies come out of hibernation around about now.

Photo by Don Laidlaw/Shutterstock

British Columbia’s coast

May is great for: getting up close (well, close enough) with the grizzlies

Come to this far-flung corner of the Canadian west coast this month for peak bear viewing. Almost 20 years ago, Khutseymateen Grizzly Bear Sanctuary was the first area to be specifically protected for grizzlies and their habitat; it’s within the traditional territory of the Tsimshian nation. This month, after a long winter hibernation, you can watch them graze on the sedge grass, and romp within it, often with cubs in tow.

A tour through the park includes a water safari–style adventure sailing on shallow waters in a 24-foot boat, which allows you to safely (and respectfully) truly get close to the bears for around six hours each day. There’s also an orientation that shares the culture and history of the Indigenous peoples who lived here before Europeans arrived.

Where to stay

For maximum nature viewing, book one of the six floating bedrooms at Khutz Lodge, a glamping-style setup with a wood-fired sauna and outdoor firepit (but shared bathrooms).

Book now: Khutz Lodge

How to get there: You’ll need to take a seaplane the final leg to this sanctuary after arriving at Prince Rupert airport (YPR), which has regular service to Vancouver on Air Canada, a trip that takes about two hours.

United just started flying nonstop to Naples from the East Coast again.

United just started flying nonstop to Naples from the East Coast again.

Photo by BAHDANOVICH ALENA/Shutterstock


May is great for: mozzarella fiends and monument buffs

Maggio dei Monumenti is the festival in May where historic palaces, homes, and galleries usually off-limits to public view become accessible for one month each year. Also, don’t miss the Complesso Monumentale dei Girolamini, a gallery filled with baroque Old Masters, and look everywhere for exquisite examples of locally made Capodimonte porcelain, which was a backbone of its artistic output for centuries.

There’s a vibrant contemporary scene, too, thanks to the likes of London-based gallery Thomas Dane, which recently opened a permanent satellite here. And, of course, no visit to Naples would be complete without an extensive tasting of the delicacy it deeded to the world: pizza. Among the countless woodfired ovens here two standouts include di Matteo, regularly named the world’s best, and Port’Alba, which has a plausible claim to be the oldest such joint in the world.

Where to stay

Think of the Atelier Inès Arts & Suites hotel as not just a crash pad but also a temple—in this case, to the work of the Neapolitan artist and sculptor Annibale Oste. There are six art-crammed rooms, as well as a workshop where his son Vincenzo schools guests, and others, in jewelry-making and interior design.

Book now: Atelier Inès Arts & Suites

How to get there: United has reinstated its seasonal nonstop service from EWR to Naples, once daily—a boon for East Coasters.


May is great for: near-silent safaris without the roar of a 4x4

The summer rains, which drench the area between October and April, have just started receding, so the floodwaters in the Okavango Delta reach their peak around now. That maximizes the reach of any water safari weaving its way through lagoons and channels that simmer in the bright sunlight.

Botswana is an ideal spot to ditch a 4x4 and instead scull through the channels on a mokoro, or traditional canoe; the chance to see insects and flowers up close and enjoy the bush in near-silence rather than damped by a car motor, is unmissable. There will likely be large game to see, too, including elephants and hippos. Always plan a safari with a little support from a seasoned operator like Mavros, the travel offshoot of the decades-old African jeweler.

Where to stay

Little Sable on the Khwai Private Reserve has eight tents, each with an outdoor shower and a viewing deck across the grasslands.

Book now: Little Sable

How to get there: Both Air Botswana and Emirates offer international connections into the country’s capital, Maun; it’s a short charter plane ride from there up into the delta.

This article was originally published in 2019 and has been updated several times, mostly recently in March 2022, with new information.

British-born, New York–based Mark Ellwood has lived out of a suitcase for most of his life. He is editor-at-large for luxury bible Robb Report and columnist for Bloomberg Luxury. Recent stories have led him to hang out with China’s trendsetters in Chengdu and learn fireside raps from cowboy poets in Wyoming.