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The Best Places In the World to Visit In May

costa rica
Manuel Antonio National Park, Costa Rica | Manamana/Shutterstock
Manuel Antonio National Park, Costa Rica | Manamana/Shutterstock
Note: We know COVID-19 is impacting travel plans right now. For a little inspiration, we’ll continue to share stories from our favorite places around the world so you can keep daydreaming about your next adventure.

In less dire times, May is like the Friday before a three-day weekend. We’ve not technically arrived at summer, but every day, more of us embody a summer mentality -- making vacation plans, trying to cut out of work early, and generally enjoying the longer days and increased supply of sunshine after making it out of the dark chill of winter and early spring. It’s the widely acknowledged kickoff month for summer fun, when pools and amusement parks open and beach town parking lots start to fill up.

Travel is currently extremely inadvisable for Americans -- both for your own safety and for the safety of the people around you -- so depending how things develop over the next few weeks this particular spring might involve more daydreaming about what vacation plans we might be making for… next spring. But hey, now is the time to remind yourself you won’t be stuck inside forever.


Before summer truly hits its stride on the glorious beaches of Alabama’s Gulf Coast, there’s this little beach concert in Gulf Shores called the Hangout Music Festival the weekend before Memorial Day, which as of press time is still scheduled to take place. The closest thing to spring break you’ll acceptably be able to attend after college, this year’s lineup includes Billie Eilish, Lana Del Rey, Doja Cat, and Cage the Elephant. Even without the music, it’s an excuse to spend a weekend playing beach beer pong and partying with strangers at one of the best festivals of the year.

Memorial Day Weekend, head to Decatur for one of the state’s most popular events this time of year, the Alabama Jubilee Hot Air Balloon Classic. This is a good one for the kids -- aside from the dozens of hot air balloons, there’ll be a car show, a tractor show, arts and crafts, and food vendors.

MORE: While you're in Alabama, don't skip church… at this dive bar

Mount Kinabalu, Malaysia | Niti Thanomsri/


Care to trek up some mountains to the largest caves in the world to see the migration of wrinkle-lipped bats? Head to Mulu National Park, especially nice during May and the height of the dry season. If you’re into adrenaline adventure, take a four-day hike to the Pinnacles, a series of jagged rocks sticking up out of the jungle. Or take a short flight down to Mulu and see orangutans and proboscis monkeys, the latter in a park only accessible by boat.

Check out Sukau Greenview boat tours to get your fix -- if you’re lucky, you’ll catch some pygmy elephants, too. And don’t miss your chance to see orangutans up close (as opposed to through binoculars) at Sepilok Orangutan Sanctuary. Eat as much laksa as you physically can.

Prague, Czech Republic | Philip Clark Hill/Getty Images

Prague, Czech Republic

In addition to its jaw-dropping architecture and killer party scene, Prague is known for its many urban gardens. In May they shine their brightest, with flowers blooming at every turn, perfuming the city with the smell of lilac. Adding to the energy is the annual Spring Music Festival, a three-week celebration that includes concerts from jazz, rock, and classical artists at venues ranging from local theaters to the stately Smetana Hall.

Kick off the month by heading to the annual Festival of RosĂ© Wines at Prague Castle, then address the munchies you’ve worked up at one of Prague’s many excellent restaurants. And while you’re in the city that first week of May, you can avail yourself of the many Easter markets at places like Old Town Square, Wenceslas Square, and Saint George’s Basilica.

Costa Rica

May in Costa Rica is the beginning of “Green Season,” which is first and foremost a euphemism for “rainy season” but also just as much a euphemism for “discount season.” This time of year the jungle will be thick and lush, and sea turtles come ashore to nest at Tortuguero. Humpback whales migrate off the coast of the Osa Peninsula. The big-money tourists who come here from December to April drop off, and you’ll see hotel prices drop off with them.

Check out the thermal springs and waterfalls at Tabacon Thermal Resort, or enjoy an in-room hammock on the beach at the El Mangroove -- both are right near all the whitewater rafting, wildlife, and mangrove forests you could possibly expect from Costa Rica. If you don’t want to stay in hostels but cannot afford the Four Seasons, it makes for a nice mix of comfort and adventure. Mid-month, you might catch some of the Carrera de San Juan -- the country’s biggest marathon, stretching from Cartago to San Jose.

florida keys
Florida Keys, Florida | Bertl123/

The Florida Keys

This time of year the weather is still not oppressively humid, there’s less chance for rain, and the snowbirds have headed north -- leaving the islands pleasantly mild and empty. If you want to save some money, you can try the twin bed, build-your -own-room concept at the NYAH hotel. It’s easily the most fun you’ll ever have sleeping in bunk beds after age 9. And at the beginning of the month there is a, uh, Dolphin Rodeo -- food, drink, raffles, and live entertainment to kick off mahi-mahi fishing season.

Lots of festivals to choose from this month! Key Largo also hosts the Key Largo Original Music Festival, where songwriters and musicians perform intimate waterfront concerts across the island. Farther down in Key West, the Key West Songwriters Festival will have artists performing original works at venues all over the city.

MORE: Key West is actually one of our favorite Caribbean beaches

The Cayman Islands

Cayman Islands

Carnival is a big tradition on almost every Caribbean island, but the biggest and most-accessible to Americans is Batabano, the epic parade that winds through George Town on Grand Cayman. It’s not calm, but if dressing in almost nothing and dancing your way down the road by Seven Mile Beach for an afternoon is your idea of a vacation, this is the trip for you.

If you feel like doing any actual relaxing, Cayman is also the culinary capital of the Caribbean. The scuba diving here is also among the best in the region, highlighted by Kittiwake -- a wreck made from an old submarine rescue vessel sunk just off of Seven Mile Beach.

Downtown Louisville, Kentucky | f11photo/

Louisville, Kentucky

It's no secret the Kentucky Derby is the only thing a lot of people can tell you about Louisville. This is a bummer, because you should most definitely take some time to check out other stuff Louisville has to offer. Try some of the legendary restaurants in the city, or head to NuLu, where newer spots like Galaxie and Royals Hot Chicken make it one of the best food neighborhoods in the South.

Then there’s the nearby Kentucky Bourbon Trail (and the more under-the-radar Kentucky Craft Bourbon Trail) holding nearly a dozen distilleries -- Jim Beam, Makers Mark, Evan Williams. If you want to keep the drinking within city limits, you’ll find plenty of fantastic bars here as well -- start at the quintessentially divey Back Door, or mix it up by going for cocktails downtown at Meta.

Porto, Portugal

Porto is rapidly becoming popular with American tourists, but it’s not yet clogged with them the way Lisbon often is. May happens to be one of the best times of year in which to visit -- the flowers are blooming and the sea breeze is cooling. Head to this coastal city for some of the best seafood you’ll have in your life -- if you’ve never tried tripe, now is your time. Rent a car and hit up some of the many, many secret beaches up and down the coast. Or check out Livraria Lello, the library that inspired the Harry Potter books.

Try all three varieties of Porto’s most celebrated export, um, Port. A river cruise down the Douro River Valley that culminates in port-tasting is the preferable way to do this. Ruby and tawny may be the best-known varieties, but sit on a veranda drinking white Port, or a white Port and tonic, and see what you’ve been missing.

MORE: What to see and do in Porto, Portugal

st croix
Frederiksted Beach, Saint Croix | Wolfso/

US Virgin Islands

The US Virgin Islands have done a hell of a job rebuilding from hurricanes Irma and Maria. The historic district on St. Thomas has long since gotten back up and running, with more open restaurants and beaches than you could ever hope to visit. Head to St. Croix and walk through historic Christiansted on an island food tour that lets you enjoy your doubles and fruit popsicles while you look at the turquoise water beyond.

St. Croix’s Buck Island, a national monument with one of the most spectacular beaches in the world, got a whole new beach when Irma took out a bunch of trees along the island’s northwestern corner and dumped a load of sand on it. Even regular visitors to the island don’t necessarily know about it. Enjoy all this before the summer humidity kicks in for real.

MORE: After the storms, St. John is still a perfect destination

Greenville, South Carolina | Cvandyke/Shutterstock

Greenville, South Carolina

May is a fun time in Greenville. Well over 100 pop-up art galleries appear downtown for the extremely popular annual festival Artisphere, where the artists range from dancers and musicians to glass blowers and chefs (The event has been rescheduled for August this year, but next May should be back in full swing). Beyond that, May in Greenville offers you free live music on Main Street each Thursday and Friday and movies in the park and concerts on the river every Wednesday evening. In between, you can hop on the free trolley and explore the city’s restaurants and theaters, or hit its famously lush hiking and biking trails. It’s lovely outside right now.

MORE: Greenville has a solid beer scene!

Couch. The one in your living room. | Albina Glisic/Shutterstock

BONUS: Couch, Your Living Room

Look, the thing about May 2020, specifically, is that we are almost certainly not supposed to be going anywhere. The place you’re gonna be spending May 2020 is home, so now is the time to get really acquainted with it. Do you have a fire escape you rarely sit on? Go sit on it! Do you have a garage with one of those ceiling trap doors you pull down with a string! Go pull! Does the Wifi still catch in your attic? Find out! Have you assessed what materials you have on hand for making either indoor or outdoor forts? This is the time! Do you have a crawl space leading off from that unfinished part of the basement? Do you fit? Crawl into it my friend! You can use your newfound personal space to daydream about a much more luxurious trip when it's safe to do so.

Planning a trip for a different time of year? Check out our monthly travel recommendations for the best places to travel in January, February, March, April, June, July, August, September, October, November, and December

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Matt Meltzer is a contributing writer to Thrillist. Follow him on Instagram @meltrez1.
Kastalia Medrano is Thrillist's Travel Writer. You can send her travel tips at, and Venmo tips at @kastaliamedrano.
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