Ready to jump-start your summer travels? Whether you want to lounge beachside, hike iconic trails, see world-famous works of art, or meander through medieval city centers, here are our picks for the ultimate May trip.
Looking for a Memorial Day trip or inspiration for a late spring break? May is the best time to take advantage of shoulder season in historic cities such as Stockholm, or if you prefer, to avoid rainy season and enjoy sunny days in Cuzco. Here are the 10 best places to travel.
May is good for: art history buffs, architecture aficionados
May in Madrid means rising temperatures, sunny days, and sweet shoulder season prices. Take advantage of the good weather by enjoying the city on foot.
Visit the expansive Plaza de Oriente, which is bordered by the Royal Palace (Palacio Real). The palace was built to outshine other European monarchies (with more than 3,400 rooms, it is the largest palace in Europe). Although the royal family lives elsewhere, this late baroque beauty features grand interiors (the king’s dressing room and royal pharmacy are standouts), and the palace grounds contain majestic gardens. The Royal Theatre is there too, and the square is especially striking at sunset. Don’t forget a stop at Madrid’s grand central square, Plaza Mayor, with its Castilian baroque brick-red facades and gray slate spires.
Madrid is one of the world’s top art capitals, a result of Spanish royals collecting masterpieces from the most venerable artists across Europe. Many of the biggest names are clustered in three museums, all of which are within walking distance of each other: the Museo del Prado (plenty of works by Velazquez and Goya), Museo Reina Sofia (home to Picasso’s sprawling Guernica), and the Museo Thyssen-Bornemisza (pieces spanning the 13th to 20th century). From February 27 to May 19, the latter showcases an exhibition by Indian artist and filmmaker Amar Kanwar.
Further afield, three UNESCO-designated sites lie within two hours of the city. The fantastical Alcázar of Segovia is the stuff of fairy tales and allegedly the inspiration for Disneyland’s castle. Then there’s Avila, known for its medieval city walls that form a fortress (you can walk on several sections). The walls encircle the highest concentration of Romanesque and Gothic churches per capita in Spain. Another nearby walled city, Toledo, teeters on a gorge above the River Tajo.
May is good for: audiophiles, rock stars at heart
The Twin Cities are too humble to brag about their vanguard art museums and James Beard Award–winning chefs, or the fact that their music scene is so cool it kept Prince here his whole life. Minneapolis is the larger, artsier city with a high-rise downtown. St. Paul is quieter and more historic, as befits the state capital. In May, go for the three-day Art-A-Whirl in Minneapolis’s gallery-laden Northeast neighborhood. It’s the largest open studio event in the United States, with more than 650 artists showing their wares, plus bands, beer, and food trucks fueling the rock ’n’ roll vibe.
While you’re there, check out First Avenue & 7th St. Entry, where native son Prince grooved in Purple Rain. It’s two venues in one: First Avenue is the midsize main room, a local rock institution with top-notch sound, while the wee Entry is where buzzy bands perform on a stage that’s a dive away from the crowd.
In the artsy Whittier neighborhood, Icehouse invites jazz, roots, and progressive hip-hop acts onto its cozy stage. Killer cocktails accompany the beats in the rustic wood and exposed-brick space. Meanwhile, Electric Fetus, the area’s top indie record shop, sits nearby and is great for flicking through vinyl stacks and getting the lowdown on concerts while you’re in town. St. Paul rocks, too, especially at Turf Club, a spirited little rock hall with live music nightly. It’s a vintage dive bar that also has a smaller lounge downstairs—if you can handle the creepy clown art.
May is good for: history buffs
The Swedish capital is made up of 14 islands linked by more than 50 bridges, and it is full of charms for people of all ages. May is one of the best months to go—temperatures are mild and days are long, but the high-season prices haven’t hit yet. If you arrive as early as May 1, you’ll experience May Day, when festivals and parades abound.
Get a sense of Stockholm’s medieval history by wandering the cobbled alleyways of the Old Town (Gamla Stan) and its many historical buildings and sites. Here, you'll find the Storkyrkan, the city’s main cathedral, and the Museum of Medieval Stockholm, which tells the city’s tale during the age of nobility and knights. Catch the pomp of the changing of the guard at the Royal Palace (12:15 p.m. on weekdays and 1:15 p.m. on Sundays).
A favorite city retreat is Hagaparken, a large royal park just north of the city center. It has lawns, lakes, and woodland, not to mention three regal residences and the Butterfly House with its 700 butterflies flitting about. A great end-point from a long walk is Koppartälten (the Copper Tents), three copper structures painted bright blue and gold that resemble something straight out of a Narnia novel. Constructed in 1787 and once used as royal stables, they were designed by King Gustav III’s theater architect. Today, one of the faux tents houses a café.
Another popular city center oasis is Djurgården, where you can experience rolling Swedish countryside a short bus ride away. Besides being a lovely place for locals to picnic and take summertime walks, the island is home to many historical sites and museums like the Abba Museum, the Spirits Museum (liquor, not ghosts), the maritime Vasa Museum, and more.
May is good for: fashionistas, bargain hunters
Over 140 languages are spoken on the streets of Canada’s largest city (pop.: 2.7 million). Toronto is a patchwork of historic neighborhoods and multicultural enclaves, with a downtown sporting the country’s tallest skyscrapers. In May, when weather is mild, festivals begin to populate the monthly calendar in earnest (Canadian Music Week and Hot Docs International Documentary Festival, for starters). Spring is a great time to add to your closet, too, and Toronto is a top-notch place for shopping.
Toronto’s Queen Street has quirky antique shops at its west end, plenty of boutiques on the east side, and is packed with edgy independent designer brands in between. Abutting Queen Street is King Street West, which includes the city’s Fashion District. Toronto’s vibrant Kensington Market is a must-visit, too, especially on Pedestrian Sunday, the last Sunday of every month from May to October. Visitors will find the streets blocked off for a wild array of music, art, and vendors.
You might also want to check out the Gerrard India Bazaar, the biggest South Asian market in North America. Neon-lit signs, candy-colored shopfronts, and the smell of rich curry make this a great place for feasting your way through the night. Meanwhile, the long-standing Dr. Flea’s Flea Market in Etobicoke and the Leslieville Summer Flea Market are great for finding secondhand and upcycled goods, rare antiques, and other well-loved, but gently used, items.
May is good for: sea lovers, whale watchers
Located on California’s central coast about a two-hour drive from San Francisco, Monterey Bay spans 40 miles from Santa Cruz in the north to Pacific Grove; it is teeming with sea creatures, thanks in part to Monterey Canyon, a submarine canyon descending 6,000 feet below sea level. Visitors can witness the migration of different whales year-round, but in May there are opportunities to spot killer, humpback, and blue whales, which migrate through December. Music lovers can also appreciate the increasingly popular California Roots Music & Arts Festival, held over Memorial Day weekend.
Ranked among the world’s greatest marine museums, Monterey Bay Aquarium is the area’s main tourist draw and welcomes 2 million guests a year. Floor-to-ceiling glass viewing walls allow visitors full views of underwater ecosystems, like the Kelp Forest (where leopard sharks roam) and Open Sea (home to sea turtles and huge schools of sardines). Morning feedings of the African penguin colony and the always-playful sea otters are crowd-pleasing delights.
Active travelers of all levels will find a suitable land or sea adventure in Monterey. To truly immerse yourself in the local lifestyle, grab a kayak, get out on the ocean, and watch the clouds and coastline drift by. Gliding across the waters of Monterey Bay in near silence can be a humbling and serene experience, or it can turn into a bucket-list encounter with playful schools of dolphins or breaching whales. Migrating blue and humpback whales feed on fish in the bay in the summer as they journey back north to Alaska, so don’t be shocked by a giant shadow swimming underneath your kayak.
May is good for: booze hounds, equestrians of all levels
The Kentucky Derby captures international headlines on the first Saturday in May, with mint juleps, elaborate hats, and edge-of-your-seat horse racing, but it’s the Kentucky Derby Festival that puts on the real show. Although there are events as early as November, the festival ramps up during the two weeks prior to the Derby, and pretty much anything goes: a steamboat race, hot air balloon chase, marathon, and concerts with big-name acts.
The horse race isn’t the only reason to visit Kentucky in May. Cocktail connoisseurs will appreciate the city’s reputation as the center of the bourbon-making universe, with most of the world’s supply coming from the city and its surroundings. 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.
To visit the big-name distilleries like Jim Beam and Maker’s Mark, you’ll have to road-trip into the surrounding countryside. Kentucky’s Bourbon Trail links the distilleries, plus others in the region. The trail takes you to 11 distilleries where you can get a passport stamp to show that you’ve visited (you get your passport at your first distillery stop)—and earns you a free T-shirt (or whatever prize is on offer at that time). If you decide to take the full trail tour, plan on at least four days to visit all 11 distilleries.
May is good for: art history fans, Francophiles
It would take a lifetime to experience all of Paris’s landmark buildings, world-class restaurants, and masterpiece-filled museums. But you can scratch the surface with a trip in May, a shoulder season month that sees lower hotel rates, fewer crowds, and plenty of daylight for sightseeing. Remember to pack or buy an umbrella, in case of May showers.
The City of Light truly has something for everyone. Love art? Aesthetes could spend a whole day with Mona Lisa and Venus de Milo at the Louvre, or gaping at works by Kandinsky and Pollock at the Centre Pompidou. Cinephiles may catch an art house film at the opulent La Pagode or a ballet at the Opera Palais Garnier. Stroll along the Rue d’Auverbilliers in the 19th arrondissement for the longest mural in Paris, and stop (often) for an espresso and croissant—or glass of wine—at the city’s countless cafés (check out the art deco Café de Flore, where early 20th-century writers and philosophers hobnobbed). Get a reservation at one of Paris’s 100+ Michelin-starred restaurants for an unforgettable meal. Pick up a vintage souvenir or two at the enormous Marché aux Puces de Saint-Ouen, where more than 1,500 vendors hawk their wares across four markets, or go high-end and splurge at Dior.
Take advantage of the spring weather: Grab picnic items at one of the food markets such as Marché Bastille, and take your snacks to the banks of the Seine. Or grab a crème glacée (ice cream) and people-watch from the green chairs in the Jardin du Luxembourg. Above all, enjoy the magic of Paris while it’s still relatively crowd-free.
May is great for: adventurous spirits, hikers
The Andean city of Cuzco was once the heart of the Inca Empire. Situated 11,000 feet above sea level, this UNESCO World Heritage site is one of the most visited cities in Peru. Although May is winter in the Southern Hemisphere, it’s also the beginning of the dry season and hasn’t quite hit high season for crowds yet. The area is the gateway to the Sacred Valley and stunning swaths of the Amazon Basin, as well as Machu Picchu.
Set in a remote, achingly beautiful corner of the Andes—all emerald peaks, snaking mists, endemic orchids, and meandering llamas—the most famous Inca citadel has the rare power to induce one of life’s pinch-me moments. To work around the crowds, consider a hiking adventure that puts you at the ruins before daybreak. The classic Inca Trail takes you from the outskirts of Ollantaytambo to Machu Picchu’s Sun Gate over the course of three nights and four days. Though the trek isn’t easy—the Inca era was clearly the golden age of comically steep mountain staircases—there’s an embarrassment of riches along the way: the ever-shifting terrain, microclimates, flora, fauna, and plenty of Instagram-worthy views (hello, snowcapped Vilcanota Range), to say nothing of the Inca ruins sprinkled throughout.
Other amazing ruins to see include the terraced circles at Moray, believed to be an agricultural complex (but no one knows for sure); the stronghold at Ollantaytambo, which served as the base for the Incas’ Spanish resistance; and the underrated house complexes at Winay Wayna along the Inca Trail. All are near Machu Picchu, although some are harder to get to than others.
May is good for: gourmands
Tokyo is captivating year-round. Go starting in mid-May to avoid the “Golden Week” high season for Japanese tourists; you’ll also avoid the very humid summer months. If you’re there from May 17-19, check out the Sanja Festival, one of Tokyo’s largest traditional shrine festivals, with dances, games, food, music, and parades. With more Michelin stars than anywhere else in the world, Tokyo is a city where you’ll find plenty of places to celebrate a special occasion (or just have a really nice meal). Kick off your fine-dining food tour with sushi—years of tradition and fantastic ingredients make it a must.
The three-starred Sukiyabashi Jiro is worth every star, with owner Jiro Ono still overseeing the making of each bite-sized masterpiece. The omakase tasting menu (around 20 pieces) is the best way to go. A little more low-key is Sushi Sho, although getting a bite of the action here is a challenge. Chef Keiji Nakazawa’s tiny restaurant serves only 10 pre-reserved diners a sushi and sake feast every night. Otherwise, try your luck with the 20 first-come-first-served lunchtime sets a day.
Prefer street food? Start with ikayaki, grilled whole squid on a stick, which is loved by Instagrammers and foodies alike. Head to the Tsukiji Fish Market to sample the best in the city. Another photogenic option is taiyaki, fish-shaped cakes filled with savory or sweet concoctions, although the original anko (red bean paste) is still the best. Taiyaki Wakaba near Yotsuya station is one of the best places to sample taiyaki.
If you can handle the line wrapped around the corner, head to Satiu Steak House to sample menchikatsu, deep-fried beef or pork. Mochi lovers should look out for the similar dango, rice flour dumplings that bear a striking resemblance to their better-known cousins.
Trinidad & Tobago
May is great for: aquaphiles
May is the end of the dry season in Trinidad & Tobago, meaning you might get better prices toward the end of the month (although the later you go, the higher the risk of rain). You’ll also avoid the influx of North American travelers who tend to come during winter and Carnival (occurring in March 2019).
Both Trinidad and Tobago have plenty of offshore reefs for marine explorations. If you want to dive with sharks, you’ve come to the right place. A wide variety of the toothy ocean sharks inhabit some of the top dive sites, mostly located around the island of Tobago. Scuba divers may see hammerheads, dolphins, and tarpon that come here to feed, when they’re drift diving with the Guiana current. On Trinidad, the best dive sites are in the northwestern part of the island, off the Chaguaramas Peninsula.
The shallow reefs around Tobago allow for off-the-beach snorkeling in the area around Store Bay and Arnos Vale. The Kariwak Reef is a closed reef near Store Bay Beach with angel fish, stingrays, and other reef fish like the sneaky, tubular trumpet fish that like to camouflage themselves in the vertical coral.
Trinidad has some beautiful beaches, notably Maracas Bay, where the surf conditions are ideal for body surfing or bodyboarding. Try water sports such as wake surfing, wake skating, and water-jet powered fly boarding with Liquid Adrenalin. Tobago’s Pigeon Point Beach—consistently ranked among the best beaches in the world—has companies such as Radical Sports and offers lessons for windsurfing and kiteboarding. To see beautiful bioluminescence, go to Bon Accord Lagoon. It’s best during a new moon (this year that means May 4) when conditions are dark enough to fully appreciate the captivating light emitted by the glowing inhabitants in the shallow waters.