Best Places to Travel in May

It’s been a while since we’ve planned a solid vacation, but the world is slowly but surely starting to open up again to vaccinated travelers. And the timing is perfect, as May is one of our favorite times to roam the world. The weather is usually ideal no matter where you go, and the crowds are much thinner than during the summer months. Plus, its position between spring break and summer vacation means you’re probably itching for a nice bonus trip—especially after 2020. But where to go? Whether you want to experience some of America’s best, under-the-radar cities, soak up the sun in Mykonos, or even squeeze in a safari in Zambia, these are the 11 best places to travel in May, all of which will be open to U.S. travelers by next month. 

While the CDC has said that vaccinated Americans can begin traveling again, you should still check entry requirements at each state you’re visiting and what your home state guidelines are when you return. If you’re comfortable traveling overseas, make sure to check the CDC guidelines on your destination. Remember, as well, to update your travel insurance, ensuring that the coverage you have will apply during the pandemic, whether it’s a standalone policy or insurance that’s bundled with one of many travel-focused credit cards. And if you’re not quite ready to travel yet, bookmark this list for a potential getaway next year.

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission. Additional reporting by Mark Ellwood.

  • The Wauwinet Nantucket
    Courtesy The Wauwinet

    Nantucket, Massachusetts

    So much more than just a summer town, Nantucket is a beauty in every season. But there’s extra incentive to visit in May, and not just to beat the summer influx of tourists: JetBlue, United, and American Airlines are launching direct service to the island throughout the month from east coast cities including Boston, New York, Newark, Washington D.C. and Charlotte. (Although there’s still something to be said about the relaxed ferry ride from Martha’s Vineyard.) Plus, Nantucket becomes extra beautiful in late-April/early-May when more than three million daffodils blossom on the island. While you’re not out biking, sailing, or strolling to nearby lighthouses, you better be eating seafood. Try the oysters at Cru (open for the season in May) or Atlantic halibut at upscale Dune for some unforgettable meals. To wind down at the end of a busy day, you can’t do much better than The Wauwinet. The five-star hotel (and 2020 Gold List winner) is tucked away on the far northeastern side of the island, meaning the only crowds you’ll run into are fellow guests and friendly staff members.

     
  • Saguaro National Park Arizona
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    Tucson, Arizona

    Arizona is less than ideal during the sweltering summer months, but it’s one of the country’s best places to travel in May. Tucson is a buzzing town well worth spending a long weekend in, thanks in large part to its incredible food scene. It was designated a City of Gastronomy by UNESCO in 2015, and made headlines when the hot dogs at El Güero Canelo won a James Beard Award in 2018. Downtown is just a 20-minute drive from Saguaro National Park, where you can spot the country’s largest cacti (some reach 50 feet) and wildflowers during the spring months. You don’t want to miss any of those blooms or sunsets, so try to set up camp as close to the park as you can. Articles director Stephanie Wu swears by Posada by the Joshua Tree House, a Southwestern-inspired five-room home available on Airbnb. It’s so beautiful, you could get away with planning the entire trip around your stay there.

     
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  • Machu Picchu
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    Machu Picchu

    May marks the beginning of dry season in Peru, which makes it the perfect time to see the endpoint of the Inca Trail in its greenest glory. As an added bonus, visiting Machu Picchu in May helps you avoid the heaviest crowds of June, July, and August. This is one of those trips that you typically have to plan a year in advance, which means your 2022 has the potential to be pretty epic. Make sure to carve out some time to explore the city of Cusco, which most people use as a starting point for their Machu Picchu visit. (They’re about two hours apart by train.) The Andean city oozes colonial charm, from its cobblestone roads to the Baroque architecture of its churches.

     
     
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  • Holland Michigan
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    Holland, Michigan

    If you’re sad about missing tulip season in the Netherlands this year, consider planning a visit to Holland, Michigan. The appropriately named town (and great day trip from Chicago) is filled with old-fashioned windmills, re-envisioned Germanic villages, dainty gardens, and—best of all—millions of tulips. Try to time your visit to the town’s annual Tulip Town Festival, held this year from May 1–9. The festival celebrates Holland’s rich Dutch history with a Dutch market and costume exhibit, carnival, and flower-themed events like flower arranging lessons and yoga in the tulips. Book a room at Castle in the Country, a Victorian inn with a wrap-around porch and secluded location that lends itself perfectly to stargazing.

     
  • Kensh Psarou Mykonos
    Andreas Bekas

    Mykonos, Greece

    Greece recently announced international tourists will be welcome beginning May 14, and we have our eyes set right on Mykonos. (From Athens you can take a quick 40-minute flight to Mykonos or hop on a 2.5-hour high speed ferry.) The island has warm weather and thinner crowds than during the summer months, plus a few new hotels that we’re particularly excited about. Just southeast of Mykonos town, Kenshō Psarou had its first full season in 2019, with 31 individually designed rooms and a stunning four-bedroom villa. The hotel sat on the back burner in 2020, but is back with a few new additions in the works throughout this year. Also on our radars is the new Kalesma Mykonos, opening May 20. Be one of the first to experience the five-star hotel’s whitewashed, Cycladic look and panoramic views of the Aegean Sea.

     
  • Annapolis Maryland
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    Maryland Coast

    The charming towns and countryside of the Chesapeake Bay are just as glorious as New England in the springtime—and not just because you get to fill up on Maryland blue crab sprinkled with Old Bay. Stop by the small town of St. Michaels, where maritime life looms large at its namesake museum and gorgeous harbor. When it comes to accommodations, go with the 78-room Inn at Perry Cabin, a postcard-pretty hotel dating to the Colonial era. If you’d rather go a little more city-centric, spend a long weekend in Annapolis. The capital city is particularly travel-worthy in May, with a farmers’ market open every Sunday, notable concerts, and even a Mother’s Day cruise around the city on May 9.

     
  • Kentucky Derby Louisville
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    Louisville, Kentucky

    You haven’t experienced true day drinking until you’re sipping on a mint julep at Churchill Downs, home of the Kentucky Derby. Held on Saturday, May 1 this year, the iconic horse race is a great excuse to spend a long weekend in Louisville (and break out your biggest hat)—just note that, due the pandemic, reserved seats have been limited to 40–50 percent capacity as of writing, and general admission tickets have yet to be released. Once there, you should, of course, prioritize spending time at Churchill Downs, where you can visit the Kentucky Derby museum, sip cocktails, and enjoy some fine dining at one of the venue’s many restaurants and lounges. Book a room at 21c Museum Hotel—a regular favorite in our Readers’ Choice Awards—for the exposed brick walls, art exhibits, and a bar that has more than 120 bottles of Kentucky bourbon.

     
  • Puebla Mexico
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    Puebla, Mexico

    While Cinco de Mayo is more of an excuse for Americans to drink margaritas than an actual Mexican celebration, Puebla is one town that actually does go all out for the holiday. The country’s fourth-largest city was the site of the 1862 battle that Cinco de Mayo marks, and residents honor the date with parades, fireworks, and military reenactments. But Puebla is so much more than one highlighted day on the calendar. The city is known for its delicious food (it’s the birthplace of mole, gorditas, and cemita sandwiches), shops that will leave you filling a second suitcase with souvenirs, and a colorful village feel that provides endless photo opportunities. When it comes to hotels, we’ve been in love with Azul Talavera (formerly Rosewood Puebla) ever since it opened in 2017. Aside from its impeccable design and spacious rooms, the property has the best rooftop in the city, where you can sip a watermelon martini while gazing out over the smoking volcano Popocatépetl.

     
  • Mauna Kea Hawaii
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    Mauna Kea, Hawaii

    Astrotourism seems to become more and more popular with each passing year, with travelers planning trips and booking accommodations specifically catered to viewing the night sky. One of the world’s best stargazing spots is Mauna Kea on Hawaii’s Big Island, a 13,803-foot peak that’s an easy drive from the city of Hilo. The dormant volcano has a world-famous observatory near its summit, from which you can see the Milky Way, bands of Jupiter, and most of the stars in both the Northern and Southern Hemispheres. This year, we’re particularly eager to visit the site in May—specifically May 26, to witness the first total lunar eclipse since early 2019. 

     
  • Zambia
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    Zambia

    Zambia is a popular safari destination, with 30 percent of the country allocated as national parkland. The country (which is now open to American travelers) also has the Zambezi River which flows into Victoria Falls, one of the world’s most jaw-dropping waterfalls. These natural sites are primed for a socially distanced vacation in May, which marks the end of Emerald Season, the time of year when the bush is green, the weather is not too hot, and the light is perfect for photographing wildlife. Book your safari trip with boutique tour operator The Bushcamp Company, which operates six camps in the southern parts of South Luangwa National Park. Each camp is worth staying at, but this year you should look toward the recently renovated Chindeni Bushcamp, with four simple-yet-comfortable canvas tents that channel the frontier days of safari travel.

     
  • Greenville SC
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    Greenville, South Carolina

    Voted one of the best cities in the U.S. in this year’s Readers’ Choice Awards, Greenville is a great South Carolina alternative to more tourist-heavy Charleston and Hilton Head Island. Visit during May for some of the city’s best annual festivals and events, like the Saturday Market; Sound Check, a weekly (and currently socially distanced) outdoor concert series every Wednesday night; and Artisphere, a popular art festival held this year from May 7–9. The spring season is also ideal for exploring the outdoors, and Greenville is especially primed for hiking and biking, thanks to its proximity to five state parks and the Blue Ridge Mountains. And you’re going to need to stretch your legs a bit after filling up at one of the 100+ locally owned restaurants in the downtown area. Come sundown, recharge at the brand new AC Hotel on Main Street, which features works from more than 100 local artists, plus five new food and drink concepts opening in May.

    Source: cntraveler.com