May is that splendid time of year when the sun plays peek-a-boo with the clouds a bit more confidently, and the flowers have finally decided that, yes, they will show off for a while. If you’ve been bitten by the travel bug (and honestly, who hasn’t been at some point?), May is your golden ticket to adventure.
It’s that magical time when the entire world seems to be on the cusp of something wonderful. From cities that buzz with festivals and events to serene landscapes where the only soundtrack is the gentle whisper of nature, the world is truly your oyster.
But where to jet off to, you ask?
Whether it’s the pulsing of busy streets, awash with color and life, or the tranquil allure of coastal towns where the ocean sings lullabies at sunset, May’s diverse palette offers something for every traveler.
Here are the 10 best places to travel in May.
Tuscany, Italy
Tuscany in May is absolutely enchanting, offering a perfect blend of delightful weather and vibrant landscapes that make it a prime destination for travelers.
Imagine wandering through rolling hills, draped in the fresh, green hues of spring, with wildflowers adding splashes of color as far as the eye can see. The temperate climate is ideal for exploring picturesque villages, historic vineyards, and awe-inspiring art cities like Florence and Siena without the sweltering heat or crowds of peak tourist season.
Related: Everyone is going to Sicily — try these 7 underrated places in Italy instead
May also brings a sense of renewal and celebration to the region, with numerous local festivals and events that showcase Tuscany’s rich culture, exquisite cuisine and world-renowned wines. It’s a time when you can truly immerse yourself in the authentic Tuscan lifestyle, making memories that last a lifetime.
TPG tip: Toscana Resort Castelfalfi just reopened this spring after a mega two-year renovation, with brand-new villas, a new 22-seat restaurant in its medieval castle and a brand-new partnership in its spa with Thai wellness brand RAKsa. You can book rooms for around $1,000 or 66,666 Chase Ultimate Rewards points per night.
Charleston, West Virginia
Heading to Charleston, West Virginia, in May? You’re in for a real treat! From May 24 to 26, the city comes alive with the Vandalia Gathering, a festival that’s all about celebrating traditional Appalachian dance, music and crafts.
Imagine spending your days immersed in the rich cultural heritage of West Virginia, tapping your feet to the rhythm of fiddles, banjos, mandolins and guitars. And when night falls, the State Theater lights up with concerts by some of the most talented traditional Appalachian musicians. It’s not just about the music and dance, though. You’ll also get to try some incredibly delicious food that will leave you wanting more.
And if you’re up for more adventure, take a short drive to America’s newest national park — New River Gorge National Park and Preserve. About an hour from Charleston, this park is a paradise for outdoor enthusiasts, offering hiking, biking, rock climbing, camping and world-class whitewater rafting, all set against the stunning backdrop of West Virginia’s natural beauty. And the best part? There’s no entry fee.
TPG tip: Charleston has your choice of national chains, like the Four Points by Sheraton Charleston (available from $114 or 15,500 Marriott Bonvoy points per night) and more. But if you’re looking for a unique stay, try a night at the Brass Pineapple Bed and Breakfast. The cozy inn offers guest rooms (from $209) with private bathrooms and is furnished with pristine Victorian antiques.
Related: The 17 best hotels in Charleston, from historic inns to modern stays
Scottish Highlands, Scotland
Oh, the Scottish Highlands in spring — what a spectacle! Picture yourself, kilt donned, golf club in hand, embarking on an adventure that takes you back to the 15th century.
Yes, that’s right. Golf, a sport born in Scotland, still thrives here, especially during the Kilted Open, which takes place May 17-19. This isn’t just any golf tournament; it’s a celebration of Scottish heritage, complete with kilts, team spirit and a competitive edge for the most creatively named team.
The venue? None other than the historic Braemar Golf Club, nestled in the breathtaking Cairngorms National Park, dating back to 1902. Here, amid the watchful eyes of golden eagles and stags, players get to experience golf in its most majestic setting. And this year introduces an even more exclusive twist — the chance to play on the royal grounds of Balmoral Castle, a privilege previously unheard of for golf enthusiasts.
TPG tip: Fife Arms is the quintessential hotel for a Highlands stay and costs about $406 per night.
Maryland
If you’re plotting a May getaway, Maryland beckons with its famed Chesapeake Bay crabs, casting a spell on seafood lovers. As Capri Cafaro — TV host and creator of “America the Bountiful,” a new food and travel series airing on PBS member stations nationwide — eloquently puts it, “May is the perfect time to visit Maryland as it’s prime time for its famous Chesapeake Bay crabs.”
Imagine journeying to the Eastern Shore, where the essence of summer unfolds early. At Big Owl’s Tiki Bar, a grapefruit crush in hand marks the beginning of relaxation. At the same time, a bushel of crabs at Fisherman’s Inn Crab Deck in Kent Narrows invites you to indulge in the quintessential Maryland experience.
Alternatively, Annapolis presents a more subdued charm for those seeking tranquility. Meander through its historic cobblestone streets, soaking in the state capital’s rich heritage. Cafaro recommends a culinary tour that includes “crabcakes at the historic Middleton Tavern, diving into crab dip at Buddy’s Crab and Ribs, or taking a water taxi to explore the harborfront area.”
TPG tip: Book a room at Fairfield Inn & Suites for around $140 or 21,000 Marriott Bonvoy points per night.
Barcelona
Barcelona in May is an absolute delight, offering the perfect day (“un día perfecto”) with fewer crowds, gentle weather and days that stretch on invitingly.
Imagine meandering through the enchanting streets of the Gothic Quarter with ease, capturing the awe-inspiring beauty of Sagrada Familia without the summer crowds, or savoring the city’s finest tapas without the wait.
For those who revel in music, Primavera Sound kicks off May 30, featuring an impressive lineup, including Lana Del Rey, SZA and Charli XCX.
Transport to this mesmerizing city is becoming even more accessible. United Airlines is set to bridge San Francisco and Barcelona with a daily flight starting in May. American Airlines will introduce a direct flight from Dallas-Fort Worth in June, making the journey to Barcelona’s wonders more convenient than ever.
TPG tip: Almanac Barcelona is available for around $867 or 57,800 Chase Ultimate Rewards points per night.
Galapagos Islands, Ecuador
The Galapagos is pure magic for anyone who loves getting up close with wildlife. Imagine swimming alongside tropical fish, bumping flippers with penguins or chilling with sea lions on the beach. And let’s not forget the tortoises that look like they’ve stepped right out of prehistory, those comical blue-footed boobies doing their dance and iguanas sunbathing like they own the place.
May is the time to be there, especially if you’re into the whole David Attenborough scene. You’ll catch the blue-footed boobies in their flirtatious glory — it’s their mating season. Plus, it’s the last call for the warm season, so the water is just perfect. Think crystal-clear views of the underwater world, which is pretty much unbeatable.
Related: My first cruise to the Galapagos: The good, the bad and the absolutely adorable
TPG tip: And if you’re wondering how to make the most of it, check out what Geographic Expeditions has going on. It offers cozy group trips — seven, nine and 10 days long. You get to snorkel, glide through mangroves on Zodiac charters and have naturalists fill your brain with cool facts about everything you’re seeing. It’s like stepping into a documentary.
Memphis
May transforms the Tennessee city into a vibrant hub of culture and cuisine, thanks to the Memphis in May International Festival. This monthlong celebration kicks off with the World Championship Barbecue Cooking Contest from May 15 to 18 at Liberty Park. It’s one of the nation’s most esteemed, attracting pitmasters globally to showcase their culinary prowess. Visitors can get a taste of the action with general admission, or for a more immersive experience, opt for the Kingsford Tour of Champions or BBQ Alley.
But the festivities don’t end there. On May 25, the streets of downtown Memphis come alive with the Great American River Run. Starting on the iconic Beale Street and winding past cherished city landmarks, it offers a unique perspective of Memphis, whether you’re running, walking or cheering on participants.
Memphis in May also serves as a cultural exchange, honoring a different country each year. France is in the spotlight this year, with various speakers, artists, and celebrities appearing at events designed to foster connections between Memphis residents and visitors, and French culture.
TPG tip: Stay at Hyatt Centric Beale Street Memphis for around $259 or 12,000 World of Hyatt points per night.
Greenville, South Carolina
If you’re looking for a place that’s buzzing with life, especially in spring, you’ve got to check out Greenville, South Carolina. You can stroll down quaint tree-lined Main Street, popping into more than 120 locally owned eateries and boutiques, and catch a ride on the free trolley that meanders through this mile-and-a-half stretch of pure charm.
Come Wednesday nights, the city has this cool tradition where everyone gathers for movies in the park at dusk. It’s free and outdoors — the perfect way to spend a balmy evening. And if you’re into music, you’re in luck because Thursday and Friday nights here mean free outdoor concerts. Picture this: a gentle South Carolina breeze, your favorite tunes floating in the air, surrounded by a community of music lovers.
For art lovers, Greenville shines during Mother’s Day weekend with Artisphere. Main Street transforms into a vibrant gallery with artists from around the globe showcasing their work, as well as live art demos and performances that light up the city.
If you’re around in late May, check out Gallabrae, the Scottish Games held Memorial Day weekend. It’s a full-on celebration of Scottish culture with games, dance and music that’s a blast for families or anyone looking to have a good time.
TPG tip: Book a room at the Holiday Inn Express & Suites Greenville-Downtown for $154 or 32,000 IHG One Rewards points per night.
Grand Junction, Colorado
If you’re eyeing a trip in May, Grand Junction, Colorado, should be high on your list, and here’s why: wild horse foals, just days old, playing under the vast Colorado sky in the Little Book Cliffs.
This spot is one of only four herd management areas in the state where you can see wild horses living freely, echoing the American West’s vibrant history. These aren’t just any horses; they’re the descendants of those owned by Native Americans, Spanish explorers, ranchers and even the U.S. Cavalry.
Heading to the Little Book Cliffs is an absolute must-do for horse lovers or anyone captivated by nature’s unspoiled beauty. With such a genetically diverse herd, you’re in for a treat — you could spot everything from palominos to paints and maybe even a curly. Plus, the nearby orchards are a sight for sore eyes, with their cherry and peach blossoms in full bloom.
TPG tip: Stay at the Hotel Maverick, built against Grand Junction’s sprawling red rock canyons on the campus of Colorado Mesa University, for around $209 or 13,933 Chase Ultimate Rewards points per night.
Sao Paulo, Brazil
Considered one of the best times to visit, May in Sao Paulo hits that sweet spot of its shoulder season, where the climate is just right — warm but not too hot, and the rainy days take a backseat.
This is when the city truly comes alive, hosting some of its most anticipated events. There’s ILTM Latin America from May 7-10, a premier gathering that puts the spotlight on luxury travel trends and destinations from around the globe.
Then, as mid-May rolls around, the city gears up for Virada Cultural, a 24-hour marathon May 18 and 19 that transforms Sao Paulo into a vibrant tableau of its rich cultural tapestry. From electrifying dance performances to captivating theater shows, it’s a nonstop celebration of the arts that showcases the city’s dynamic spirit.
TPG tip: Centrally located in the heart of the vibrant city near the lively Avenida Paulista, Rosewood Sao Paulo — available for $673 or 44,866 Chase Ultimate Rewards points per night — is a respite in the bustling city.
Related reading:
- Key travel tips you need to know — whether you’re a beginner or expert traveler
- The best travel credit cards
- Where to go in 2024: The 16 best places to travel
- 6 real-life strategies you can use when your flight is canceled or delayed
- 8 of the best credit cards for general travel purchases
- 13 must-have items the TPG team can’t travel without
