Top 10 destinations to explore in May

May ushers in a delightful season when the sun starts to shine through the clouds more boldly, and flowers burst into bloom, eager to impress. If wanderlust has struck you (and let's be real, who hasn't felt that urge?), May is your perfect opportunity for adventure.

It's a captivating period when the world appears poised for something extraordinary. From vibrant cities filled with festivals to tranquil landscapes where nature's soft murmurs prevail, the globe is truly yours to discover.

But where should you escape to, you wonder?

Whether it's the lively energy of bustling streets teeming with color or the peaceful charm of coastal towns where the ocean hums soothing melodies at sunset, May offers a rich variety for every traveler.

Discover the 10 top destinations to explore in May.

Tuscany, Italy

May in Tuscany is truly magical, showcasing a perfect harmony of pleasant weather and lively scenery, making it an ideal spot for travelers.

Picture yourself strolling through undulating hills adorned in the fresh, vibrant greens of spring, with wildflowers painting the landscape in brilliant colors. The mild climate invites exploration of charming villages, historic vineyards, and stunning art cities like Florence and Siena, all without the oppressive heat or crowds typical of the peak tourist months.

May ushers in a season of renewal and festivity across the region, with a multitude of local festivals and events that highlight Tuscany's rich heritage, delectable cuisine, and celebrated wines. It's an opportunity to fully embrace the authentic Tuscan way of life, creating memories that will last a lifetime.

TPG tip: Toscana Resort Castelfalfi has just reopened this spring following an extensive two-year renovation, featuring brand-new villas, a newly added 22-seat restaurant in its medieval castle, and an exciting collaboration with Thai wellness brand RAKsa at its spa. Rooms can be booked for around $1,000 or 66,666 Chase Ultimate Rewards points per night.

Charleston, West Virginia

Planning a trip to Charleston, West Virginia, in May? You're in for a delightful experience! From May 24 to 26, the city bursts into life with the Vandalia Gathering, a festival dedicated to celebrating traditional Appalachian dance, music, and crafts.

Imagine spending your days immersed in the vibrant cultural heritage of West Virginia, swaying to the melodies of fiddles, banjos, mandolins, and guitars. As night falls, the State Theater lights up with performances from some of the finest traditional Appalachian musicians. But it’s not just about music and dance; you'll also get to savor incredibly delicious food that will leave you craving more.

For those seeking more adventure, take a short drive to America's newest national park — New River Gorge National Park and Preserve. Located about an hour from Charleston, this park is a haven for outdoor lovers, offering hiking, biking, rock climbing, camping, and world-class whitewater rafting, all set against the breathtaking backdrop of West Virginia's natural beauty. And the best part? There’s no entrance fee.

TPG tip: Charleston features a variety of national chains, like the Four Points by Sheraton Charleston (rooms starting at $114 or 15,500 Marriott Bonvoy points per night). If you prefer a unique experience, consider a stay at the Brass Pineapple Bed and Breakfast. This charming inn offers guest rooms (from $209) with private baths, beautifully adorned with pristine Victorian antiques.

Scottish Highlands, Scotland

Ah, the Scottish Highlands in spring — what a sight to behold! Imagine yourself, kilt swaying, golf club ready, embarking on an adventure that transports you to the 15th century.

Indeed! Golf, a sport that originated in Scotland, continues to flourish here, especially during the Kilted Open, scheduled for May 17-19. This isn’t just any golf tournament; it’s a jubilant celebration of Scottish culture, featuring kilts, team camaraderie, and a competitive spirit for the most creatively named teams.

The venue? The historic Braemar Golf Club, nestled within the stunning Cairngorms National Park, established in 1902. Here, under the watchful gaze of golden eagles and majestic stags, players can enjoy golf in its most spectacular setting. This year offers an exclusive twist — the opportunity to play on the royal grounds of Balmoral Castle, a privilege previously unimaginable for golf lovers.

TPG tip: Fife Arms is the ideal hotel for a Highlands getaway, with rates around $406 per night.

Maryland

If you’re planning a May escape, Maryland calls to you with its renowned Chesapeake Bay crabs, captivating seafood aficionados. As Capri Cafaro — TV host and creator of "America the Bountiful," a new food and travel series on PBS — beautifully states, "May is the ideal time to visit Maryland, as it's peak season for its famous Chesapeake Bay crabs."

Envision heading to the Eastern Shore, where the spirit of summer arrives early. At Big Owl's Tiki Bar, a refreshing grapefruit crush signals the start of your relaxation. Meanwhile, a bushel of crabs at Fisherman's Inn Crab Deck in Kent Narrows invites you to experience the quintessential Maryland delight.

Alternatively, Annapolis offers a quieter allure for those in search of peace. Stroll through its historic cobblestone streets, absorbing the rich heritage of the state capital. Cafaro suggests a culinary tour featuring "crabcakes at the iconic Middleton Tavern, savoring crab dip at Buddy's Crab and Ribs, or taking a water taxi to explore the charming harborfront area."

TPG tip: Consider booking a room at Fairfield Inn & Suites for approximately $140 or 21,000 Marriott Bonvoy points per night.

Barcelona

May in Barcelona is truly enchanting, presenting an ideal day ("un día perfecto") with lighter crowds, mild weather, and lengthening days that beckon exploration.

Picture yourself wandering through the captivating streets of the Gothic Quarter at your leisure, marveling at the stunning Sagrada Familia without the summer throngs, or indulging in the city's best tapas without the hassle of waiting.

For music lovers, Primavera Sound begins on May 30, boasting a stellar lineup featuring Lana Del Rey, SZA, and Charli XCX.

Access to this enchanting city is getting even easier. United Airlines will launch a daily flight connecting San Francisco and Barcelona starting in May, while American Airlines is set to offer a direct route from Dallas-Fort Worth in June, making it simpler than ever to explore Barcelona's delights.

TPG tip: Stay at Almanac Barcelona for approximately $867 or 57,800 Chase Ultimate Rewards points per night.

Galapagos Islands, Ecuador

The Galapagos is a dream come true for wildlife enthusiasts. Picture yourself swimming with vibrant tropical fish, playfully nudging penguins, or lounging with sea lions on the beach. Don't forget the ancient tortoises that seem to have emerged from a prehistoric tale, the entertaining blue-footed boobies strutting their stuff, and the iguanas basking in the sun like they're royalty.

May is the ideal month to visit, especially for fans of the David Attenborough vibe. You'll witness the blue-footed boobies in all their flirty glory during their mating season. Plus, it's the final stretch of warm weather, making the waters perfect. Imagine crystal-clear views of the underwater wonders—it's simply unmatched.

TPG tip: If you're looking to maximize your experience, consider what Geographic Expeditions offers. They provide comfortable group trips lasting seven, nine, or ten days, featuring snorkeling, Zodiac tours through mangroves, and knowledgeable naturalists who share fascinating insights about your surroundings. It's like living in a nature documentary.

Memphis 

May turns Tennessee's Memphis into a lively epicenter of culture and cuisine, thanks to the Memphis in May International Festival. This month-long celebration kicks off with the World Championship Barbecue Cooking Contest from May 15 to 18 at Liberty Park. It's one of the country's most prestigious events, drawing pitmasters from around the globe to display their culinary skills. Visitors can savor the experience with general admission, or for a deeper dive, choose the Kingsford Tour of Champions or BBQ Alley.

The celebrations continue beyond that. On May 25, downtown Memphis buzzes with excitement during the Great American River Run. Kicking off on the legendary Beale Street and meandering past beloved city landmarks, this event provides a distinctive view of Memphis, whether you're running, walking, or cheering from the sidelines.

Memphis in May also acts as a cultural exchange, spotlighting a different country each year. This time, France takes center stage, featuring various speakers, artists, and celebrities at events aimed at bridging connections between Memphis locals and French culture.

TPG tip: Consider booking a stay at Hyatt Centric Beale Street Memphis for approximately $259 or 12,000 World of Hyatt points per night.

Greenville, South Carolina

If you're searching for a lively destination, especially in spring, Greenville, South Carolina is a must-visit. Wander down the charming, tree-lined Main Street, explore over 120 locally-owned restaurants and shops, and hop on the free trolley that glides along this delightful mile-and-a-half stretch.

On Wednesday nights, the city embraces a wonderful tradition where everyone gathers for movies in the park at twilight. It's a free outdoor event — an ideal way to enjoy a warm evening. And if you're a music fan, you're in for a treat as Thursday and Friday nights bring free outdoor concerts. Imagine a gentle South Carolina breeze, your favorite melodies in the air, surrounded by fellow music enthusiasts.

Art lovers will find Greenville particularly vibrant during Mother's Day weekend with Artisphere. Main Street transforms into a lively gallery, featuring artists from around the world displaying their creations, along with live art demonstrations and performances that bring the city to life.

If you're around in late May, don't miss Gallabrae, the Scottish Games taking place over Memorial Day weekend. This festive celebration of Scottish culture includes games, dance, and music, making it a fantastic experience for families and anyone seeking a good time.

TPG tip: Reserve 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 planning a trip in May, Grand Junction, Colorado, deserves a top spot on your itinerary, and here’s why: witness wild horse foals, just days old, frolicking beneath the expansive Colorado sky in the Little Book Cliffs.

This location is one of just four herd management areas in the state where wild horses roam freely, reflecting the rich tapestry of the American West’s history. These horses are descendants of those once owned by Native Americans, Spanish explorers, ranchers, and even the U.S. Cavalry.

A visit to the Little Book Cliffs is a must for horse enthusiasts or anyone enchanted by nature’s untouched beauty. With a genetically diverse herd, you might encounter everything from palominos to paints, and even a curly. Additionally, the nearby orchards offer a stunning view, with cherry and peach blossoms in full bloom.

TPG tip: Consider a stay at Hotel Maverick, nestled against Grand Junction's majestic red rock canyons on the campus of Colorado Mesa University, for approximately $209 or 13,933 Chase Ultimate Rewards points per night.

Sao Paulo, Brazil

May is often regarded as one of the prime times to visit Sao Paulo, striking the perfect balance of shoulder season with pleasantly warm weather and minimal rain.

During this vibrant month, the city buzzes with energy, hosting some of its most exciting events. Notably, ILTM Latin America takes place from May 7-10, showcasing luxury travel trends and destinations from around the world.

As mid-May approaches, Sao Paulo prepares for Virada Cultural, a thrilling 24-hour event on May 18 and 19 that transforms the city into a lively showcase of its rich cultural heritage. From dazzling dance acts to mesmerizing theater performances, this nonstop celebration highlights the vibrant spirit of the city.

TPG tip: Nestled in the heart of the bustling city near the lively Avenida Paulista, Rosewood Sao Paulo offers a tranquil escape for $673 or 44,866 Chase Ultimate Rewards points per night.