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A Travel Editor's List of the 6 Best Places to Travel in May 2025

Spring fests, glorious gardens and urban buzz

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best places to travel in May: Toyko wisteria blossoms
Nobutoshi Akao / Getty Images

Whether you are daydreaming about a multi-generational trip or a weekend excursion with only one carry-on bag, if you're anything like me, right now you're just itching to get away. Whether filling that three-day Memorial Day weekend is priority number one or you're looking for an earlier May trip to beat the summer crowds, I've rounded up some of my favorite destinations to plan the ultimate spring escape. Throw on a pair of travel pants and join me at some of the best places to travel in May 2023.

WHY THE ‘BUFFER DAY’ IS THE SECRET TO A BETTER VACATION


How I Chose the Best Places to Travel in May 2025

To choose the best places to travel in May 2025, I looked toward the sun—because globally, traveling during the so-called "shoulder season" between winter's chill and summer's balmy temperatures can result in not only value, but more importantly activities to shake off winter gloom. I drew on my experience as an writer-editor at travel publications in knowing to avoid May's overly touristed Spring Break spots (sorry Cancun) but to enjoy more sophisticated spectacles, such as the blossoming gardens of Tokyo and the Kentucky Derby. Finally, I chose gorgeous destinations rich in culture—art in Santa Fe and San Miguel de Allende vies with the landscape for memorable beauty.

This Month, Don't Forget Your Real ID

After years of projected and unenforced deadlines mandating government-issued Real ID cards, the TSA has announced that starting Wednesday, May 7, 2025, every air traveler 18 years of age and older must have a REAL ID-compliant state-issued driver’s license or another acceptable form of ID to board a commercial aircraft. While passports will also be accepted, travel insiders are predicting potential airport delays and border snarls if travelers who are eligible for REAL IDs don't offer those up as identification.

best places to travel in may: indoor pool in Oslo, Norway
Sommerro Hotel

1. Oslo, Norway

May is a great time to visit Norway if you want to feel like a local—especially in Oslo, the country's capital. Weeks ahead of the summer crowds, there are flight deals on Norse Airways and Icelandair to be taken advantage of. You can enjoy a leisurely exploration of the city's urban offerings and natural wonders by walking around the Oslo Opera House, a glacier-like building that offers panoramic views of the city, plus an exciting array of opera, chamber concert, and ballet performances throughout the month. Conveniently located within the recently revitalized Bjørvika neighborhood, you'll find plenty more to do in the area, including top notch dining, boutique shopping, contemporary art galleries and the Munch Museum (where you can see all three variations of “The Scream.”)

If you want to immerse yourself in Nordic history, you can also partake in Viking rowboat rentals (so you can explore the sparkling waters of the fjord like an Old Norse traveler). When hunger strikes, stop by Ekspedisjonshallen, a beautiful all-day Art Deco eatery, or TAK OSLO, both of which are located at the glittering Sommerro hotel. The latter is an idyllic rooftop bar serving handcrafted cocktails with Japanese street food-inspired bites like smoked duck ramen and salmon sashimi. The trendy spot is set against an elegant backdrop inspired by Norwegian neo-romantic artist Harald Sohlberg’s lavender and emerald painting, “Moonlight in Nevlunghavn.”

best places to travel in may: Santa Fe, New Mexico
Inn of the Five Graces

2. Santa Fe, New Mexico

Santa Fe is one of those cities where you can always expect the unexpected, hence its nickname as “the City Different.” And come spring and summer, the town famous for its adobe architecture and kiva fireplaces comes alive with various festivals—and every day feels like its own art walk when you cruise down the famed Canyon Rd., which is lined with funky art galleries.

Check out traditional are at the Museum of Indian Arts & Culture, and make time for an immersive contemporary art experience at Meow Wolf, the interactive installation created by a coalition of artists in Santa Fe that now operates in seven cities nationwide. Also make time to browse Mountain Standard Time, a boutique housed in a former hotel suite at The Parador that sells stylish new and vintage knick-knacks for the home.

And while Santa Fe has long been known for its art, its spa scene should not be overlooked. Our absolute favorite for the environment alone is in town at the Inn of the Five Graces. This beautiful boutique hotel can only be described with two words: sensory overload. Filled with art, you enter the spa through an original adobe doorway where beautiful skylights, textiles sourced from Central and Southeast Asia, marble screens, fireplaces, mosaic tiling, shrines, large crystals, and hand-carved spa lockers create a totally unique (and ultra-relaxing) atmosphere. The spa plans to open a new outdoor area for outdoor relaxation and post-treatment soaks just in time for the warm weather, too. Outside of town, the spa at Bishop's Lodge is another favorite and offers a variety of vibrational treatments like sound baths, shamanic healing, and even astrology readings in a contemporary and peaceful setting, complete with an outdoor sauna.

3. San Miguel De Allende, Mexico

Experience the city's thriving craft cocktail scene at Bekeb and Luna Tapas Bar, which both happen to have rooftop seating, as well as Bovine and San Mezcal, where the emphasis is on everyone's favorite smoky spirit. With an ever-pleasant daily high of 84°F, May is also the ideal time to explore the enchanting colonial town's historic cobblestone streets and vibrant art scene.

Wander amongst the colorful buildings and stately mansions as you admire its architecture, or take a guided walking tour, evening food tour, or archeological tour to dive deeper into San Miguel de Allende’s rich history. La Parroquia de San Miguel Arcángel, a stunning neo-Gothic cathedral, should be top of your list, and we’d also recommend the famous Fabrica la Aurora art and design center, home to various galleries and artist studios that exude this region’s bohemian spirit. If you're not afraid of heights and open to a more unique experience, GetYourGuide also offers a hot air balloon ride over the surrounding and very picturesque countryside, where breathtaking views of the city and surrounding hills are guaranteed.

4. Louisville, Kentucky

Home of bourbon, baseball, bluegrass and the Kentucky Derby, Kentucky's largest city—which sits on the Ohio River—has been called one of the friendliest cities in the country. Pro tip: Spend a perfect weekend day in town by filling up on Southern staples at The Porch before popping into Woodford Reserve's distillery for a tour and tasting. Served in a gold-plated glass, the revered bourbon brand will also be serving a special $1,000 Mint Julep at the Kentucky Derby this year, with more details to be released soon, in case you want to ball out at the big event. It is Louisville's big draw come May, filled with extravagant hats, fancy dresses and ice-cold drinks at the iconic Thoroughbred track Churchill Downs. Now in its 147th year, the thrilling event is said to be the greatest two minutes in sports. During the rest of May, when the Derby crowds have cleared out, you can enjoy Louisville's other famed cocktail, the old-fashioned, on Whiskey Row. Evan Williams Bourbon Experience, Angel's Envy, Jim Beam Urban Stillhouse and the Peerless are just a few of our favorite distilleries in this thriving part of downtown.

best places to travel in may: man on paddle board in glassy lake in Indianapolis, Indiana
Visit Indy

5. Indianapolis, Indiana

Indianapolis should top your list if you're a sports enthusiast looking for an action-packed destination this May. The city offers a month-long celebration of the iconic Indy 500, attracting nearly half a million visitors with red-carpet experiences, concerts, tailgating and more—but that's not all there is to get revved up about. Bring your best pair of kicks and test your limits at the Indy Mini, one of the largest half marathons in the country. Runners are treated to a picturesque exploration of downtown Indianapolis, culminating with the unique opportunity to run on the Indianapolis Motor Speedway track and across the hallowed Yard of Bricks. The city's recently undertaken several exciting redevelopment projects, including a revitalization of the stunning White River (which now offers over 50 paddleboards, kayaks, and canoes for group or self-guided tours) and the addition of the Bicentennial Unity Plaza at Gainbridge Fieldhouse, where visitors and locals can enjoy a plethora of community recreation spaces on NBA and WNBA-star turf. For the adventure seeker, there's no shortage of things to do and see in this classic American city—or traditional eats for that matter, especially the Hoosier favorite pork tenderloin sandwich, best experienced at the old English-style pub The Aristocrat on College Ave where the meat is pounded out just thin enough to hang over the edge of the bun for a tasty, tender meal. 

best places to travel in may: wisteria at Ashikaga in Tokyo, Japan
Japan National Tourism Organization

6. Tokyo, Japan

After Golden Week (the week from 29 April to May 6 containing multiple Japanese holidays), Japan's charming roadside gardens and scenic flower parks boast a delightful profusion of azaleas, wisteria and tulips, providing uninterrupted enjoyment of Japan's natural beauty. Ashikaga Flower Park's Great Wisteria Festival, located outside of Tokyo, is breathtaking, with radiant 160-year-old blooming wisteria trees illuminated at night, creating an ethereal effect. In May, the city’s lively Sanja Festival is an excellent choice for those seeking a more electrifying cultural experience, culminating in a dynamic display of stately parades, magnificent mikoshi shrines (sacred religious palanquins believed to transport deities) and generous servings of sake to keep the festivities going strong. You will also want to attend the Tokyo Sumo Tournaments, as expert Japanese Rikishi compete for the coveted title of Yokozuna. At the same time, spectators sip sake and sample yakitori in a stadium. Speaking of food, you'll find no shortage of classic and innovative Japanese fare around the city. Try unagi (barbecued freshwater eel) and other street food-style seafood skewers like squid and clam at Nisshin Tasuke, or for a more upscale dining experience, you can try to reserve a table at the frequently booked-up DEN, which offers exquisitely prepared seasonal plates in a stylish, modern atmosphere.



Freelance PureWow Editor

Dan Koday is a travel and lifestyle writer and editor with 15+ years experience creating content for your favorite websites, print publications and brands. As a native to the NYC metropolitan area, Dan is an expert on all things Gotham, but likes to get out of town, too. After a recent trip to Antarctica, he's officially traveled to all four corners of the globe. 

dana dickey

Senior Editor

  • Writes about fashion, wellness, relationships and travel
  • Oversees all LA/California content and is the go-to source for where to eat, stay and unwind on the west coast
  • Studied journalism at the University of Florida

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