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Go on a dream trip: These are the best places to visit in May

Where should you vacation in May?

Nantucket lighthouse and daffodils
ruthiejmiller / Unsplash

May is easily my favorite month of the year. Winter is finally in the rearview mirror, April showers have done their job, and now — cue the sunshine and blooming flowers — the world is coming alive again. It’s that perfect in-between season where everything just feels lighter and brighter.

It also happens to be one of the best times to travel. Summer crowds haven’t arrived yet, kids are still in school, and the weather is amazing. Warm but not sweltering, cool but not freezing. From international travel adventures to dreamy weekend getaways, May is packed with incredible destinations just waiting to be explored. These are our best places to visit in May — where will you go first?

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Our favorite May destinations around the world

Plane taking off with ocean in the background
Oleksandr P / Pexels

May isn’t the most popular month to travel. But maybe it should be. Summer months bring dense crowds and high costs. Winter ski trips can bring the same, along with a corresponding chill. But May makes things easy with its refreshing mood, sparse travelers, and palatable pricing.

Picking a May destination is like perusing a color palette, with various shades to suit your fancy. Maybe you need a place to unwind by the ocean, take in the salty air, and enjoy fresh seafood. Or if you want to get closer to nature, going on safari in pristine wilderness could be the ticket. Either way, we’ve got something for you.

Nantucket, Massachusetts

Lighthouse in Nantucket, Massachusetts
Rusty Watson / Unsplash

During May in Nantucket, you’ll have mile after mile of coastline to yourself, letting you soak in the ocean air in peace. Three million blooming daffodils capture the springtime feeling, and temps in the mid-50s to mid-60s are just right for relaxing. 

Then there’s the food. Visit local markets like Nantucket Seafoods or Glidden’s Island Seafood, and pick from fresh lobster, Nantucket Bay scallops, oysters, and much, much more. Or, check out the Nantucket Wine & Food Festival from May 14-18, with a curated selection from local artisans and chefs. 

Zambia, Africa

Elephant playing in river, Zambia
Nicole Olwagen / Unsplash

In our changing world, truly unspoiled places become more and more scarce. That can be especially true with regard to wildlife, with animals in zoos replacing those in their natural habitat. But Zambia lets you get up close and personal with elephants, lions, zebras, rhinos, and more.

With the Emerald Season ending, May is the perfect time to go on safari, providing mellow weather on long days and ideal lighting for vivid photographs. Besides that, Victoria Falls along the Zambezi River provides a stunning natural sight.

Louisville, Kentucky

Horses racing in the Kentucky Derby
Kentucky Derby Official Website

The Kentucky Derby lasts around two minutes. During that span, there’s unmatched tension and excitement as thoroughbreds strain and race toward the finish line. But the competition isn’t the only attraction on derby day. The track at Churchill Downs becomes a cultural hub with a vibrant atmosphere, celebratory mood, and unique Kentucky fare.

Try a mint julep cocktail — composed of whiskey, sugar, water, and mint — while you take in the festive hats worn by race attendees. Get up close with magnificent horses, whose athleticism and power are a sight to behold. Then, when the starting gate opens, get ready for two minutes like you’ve never experienced.

Sicily, Italy

Ancient ruins in Sicily, Italy
Simon Maage / Unsplash

Italy is an epicenter of history, culture, art, and cuisine. Sicily offers that and more. Just off the toe of Italy’s boot, the island has warm Mediterranean waters, an active volcano, and fascinating ruins. Of course, there’s cuisine options in abundance, from Arancini — deep-fried Risotto rice balls — to Caponata — a salad containing eggplant, capers, olives, and more.

We’d visit the Mount Etna volcano for its continual eruptions that date back 500,000 years. After that, we’d take in Sicily’s ancient ruins, like those found in Agrigento and Selinunte. To cap things off, we’d explore Catania’s street food vendors for a mix of textures and flavors.

Yellowstone National Park

Grand Prismatic Spring, Yellowstone National Park
Ledain / Pixabay

As spring takes shape and nature awakens, what better place to visit than this national gem? Toward the end of May, the park’s mostly open, letting you explore trails and attractions and bask in the pure environment. Since temps hover in the mid-50s, it’s neither cold nor hot, and you can savor the season’s spirit of renewal.

We’d venture to the Grand Prismatic Overlook Trail, then look for Bison in Lamar Valley. At Yellowstone Lake — 20 miles long and 14 miles wide, at 7,500 feet elevation — we’d hop in a kayak and take it all in. Then we’d set up camp and settle in for stargazing. 

Lisbon, Portugal

Lisbon, Portugal
Amanda Teague / The Manual

Lisbon is easily one of the best places to visit in May, and here’s why: The weather is just right. Summers in Portugal can get incredibly hot (we’re talking high 90s), which is great when you’re lounging at the beach but not so fun when you’re hiking up one of the city’s infamous hills. But in May? Expect comfortable temperatures in the high 60s to mid-70s, perfect for wandering the colorful streets without melting.

Start your day with a flaky, custardy pastel de nata from Manteigaria (arguably the best in the city), then hop on the iconic Tram 28 for a scenic ride through Lisbon’s charming neighborhoods. Explore the district of Alfama, where you can admire hand-painted azulejos (tiles), and end the night with a soulful fado performance at a cozy tavern. If you’re up for a little adventure, take a day trip to Sintra, a fairy-tale town filled with castles, or soak up the sun in Cascais, a coastal town just a short train ride away.

Travel in May: Easy on the wallet and good for the soul

Zambia sunset in Africa
Birger Strahl / Unsplash

For a mix of pleasure, thrift, and peace, traveling in May is hard to beat. You have pleasant weather that encourages relaxation. Light crowds and low prices let you enjoy on a budget. Nature’s bounty is on full display. These destinations offer a little of everything, whether you’re after natural wonders or a rich cultural experience. Whichever you choose, you’re in for a memorable trip. Happy exploring.

Mark Reif
Mark Reif is a storyteller focused on the intersection of outdoor culture, travel, and design. From the peaks of Banff to the…
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