Where to Go in May: 20 Great Spots for a Shoulder Season Trip

April 29, 2016 by

Asia, Australia & the Pacific, Europe, Festivals & Events, Middle East & Africa, North America, Places to Go, South & Central America, Things to Do, Top Travel Destinations, Travel Advice & Inspiration

Get ready for May travel!

Get ready for May travel!

Whether you’ve had enough of the April showers and need a travel respite, or you’re trying to hit the tail end of the shoulder season or just itching to add a new stamp to your passport, May is an excellent month to hit the road. Almost no matter where you’re headed, the month has that desirable not-too-hot-and-not-too-cold weather, and it’s also a time for some pretty big festivals. Here are some ideas for where to go in May.


China is an enormous country, so it’s hard to make travel generalizations but – on the whole – May is an excellent month in which to visit China. It captures all the things we love about shoulder seasons – the weather is downright perfect, with mostly warm weather in between the cold and rainy winter and oppressively humid summers, and the high summer season crowds haven’t arrived yet. As an added bonus, the spring flowers make every scene a photo op.

Book a 9-day China Highlights Tour to the see the best of the country.


You might associate June with the start of summer, but in many ways summer gets going in Chicago in May. If the weather permits, Chicago’s beaches open in May (over Memorial Day weekend), and the Crown Fountain in Millennium Park is turned on. Water may not be the relief in May that it will be in Chicago by August, but it’s definitely a sign of a city looking forward to sunnier weather. And by May, it’s generally warm enough to enjoy being on the top deck of a boat for the Chicago Architecture River Cruise.

Tuscany, Italy

Relax in picturesque Tuscany this May

Relax in picturesque Tuscany this May.

Is there a bad time to go to Tuscany? Probably not. But May offers not only the high probability of summer-like weather but also a chance to experience a local festival that’s been going on for centuries. On May 15th, St Ubaldo’s feast day, plan to be in the town of Gubbio for the Corsa dei Ceri (Race of the Candles), when three teams of local men race through the town and up the hill, each carrying a 600 pound statue of St Ubaldo. The unwieldy wooden statues replaced wax candles in the 16th century. Spectators line the race route – it’s one of Tuscany’s most popular medieval festivals.

Madrid, Spain

There’s something about a city in the midst of a celebration that just makes you want to stay forever. Madrid in May is that kind of city, with enough festivals on the calendar you may wonder how the locals get anything done. Perhaps the best of the bunch is the San Isidro festival, which takes over the city for a week in mid-May, honoring its patron saint with music, markets, food, religious processions, traditional costumes and more.

Mediterranean Islands

Touring the islands of the Mediterranean in May means enjoying reliably warm weather without having to endure blistering heat or humidity. You’ve got plenty of choices, too. There’s the Med’s largest island, Sicily, within spitting distance of Italy while remaining culturally unique from the rest of the country. There’s Cyprus, the third largest island in the Mediterranean just off the coast of Turkey, with strong ties to both Greek and Turkish culture depending on where you go on the island. And then there’s little Malta, between Sicily and Libya, a historically important spot for both military and religious reasons with nine UNESCO World Heritage Sites.

Mexico City, Mexico

In most places, the coming of summer means sun – but in Mexico City, it can often mean rain. The spring, then, is one of the best times to visit, even if it’s consequently also one of the most popular times. It’s not just the near-perfect weather that draws crowds to Mexico City in May, however – it’s also Cinco de Mayo. The festival isn’t the major holiday in Mexico that Americans seem to think it is based on celebrations north of the border, but it’s still a national holiday throughout Mexico.

Rio de Janeiro, Brazil

May's a great time to hit the beach in Rio.

May’s a great time to hit the beach in Rio.

When does everyone say is the time to be in Rio? During Carnival, of course, which is in February or March. Which is why going to Rio de Janeiro in May is for contrarians – and budget travelers – only. May comes after the hottest summer weather finally leaves, and prices tend to go down after Easter (which is sometimes as late as April). You’ll still have to deal with humidity, but that’s what taking a dip in the ocean is for.

Southeastern United States

Given the drenching humidity of summer in places like Georgia and South Carolina, spring travel to the area makes a lot of sense. In addition to the fine weather and southern hospitality, you can bask in music at the Atlanta Jazz Festival (one of the country’s top jazz festivals) or check out the Spoleto Festival USA (one of the top arts festivals in the world) in Charleston. Complete your culture tour of the southeastern states with a Midnight in the Garden of Good and Evil Walking Tour of Savannah.

New York City, USA

It’s hard to imagine a slow travel season in New York City, arguably the greatest city on earth. But even with a full schedule of summer events and festivals in NYC, summer may not be the best time to visit simply because of the often extreme heat and humidity; the concrete jungle leaves few places to cool down. Plan your visit for May when the weather is usually warm, and the bulk of the summer crowds are still at home. A trip now means you can also visit the new 9/11 Memorial Museum, which opened in 2014.

Vienna, Austria

Vienna is an ideal destination in the shoulder seasons, including May, for all the reasons you’d expect – the weather is fairly mild, crowds are smaller and prices are lower. You’re likely to experience some rainy days in May, though, so bring an umbrella or just plan to duck into a cafe for a snack.

Tokyo, Japan

Visit Tokyo in May and avoid the height of crowds and heat.

Visit Tokyo in May and avoid the height of crowds and heat.

The crush of summer crowds in Tokyo combined with intense heat and humidity gives you a good excuse to visit the metropolis in May instead. The famous cherry blossoms will have already bloomed earlier in the spring, but the city is still awash in floral color and temperatures are simply warm – not overbearing.

Bali, Indonesia

In Bali, where the temperatures remain consistent year-round, it’s not a question of visiting in the warm or the cool season – it’s a question of visiting in the wet or dry season. The dry season begins in April, so May can be an excellent time to go. You’ll be able to enjoy all of the outdoor activities Bali has to offer without being slowed by brutal humidity. May is also part of the high tourist season, however, so be sure to plan ahead, budget for higher prices on things like hotel rooms and brace yourself for crowds.

Niagara Falls

Unlike some famous waterfalls around the world, there isn’t exactly a slow season at Niagara Falls. That means you can target your trip around weather and prices rather than the falls themselves. In May, you’ll get the first somewhat warm weather of the season, and all the tours and activities that closed up shop for winter will be open again. You’ll probably still want to bundle up a bit, however, especially on the viewing platforms where you’re bound to get wet.

If you’re visiting NYC, you can take a day trip to Niagara and get there fast on a private plane.

Machu Picchu, Peru

Explore Machu Picchu with a couple of llama friends!

Explore Machu Picchu with a couple of llama friends!

May is autumn in Peru, and it’s one of the shoulder seasons when savvy travelers plan treks to Machu Picchu. The weather is warm – although you’ll still want to bring layers to put on after sundown – and the high season tourist rates haven’t kicked in yet. You won’t have the ancient Incan city to yourself, but you’re far more likely to find quiet moments in May than you would in June through September.

Learn about how to pick your perfect Machu Picchu trek.


In the Bahamas, May marks the start of the rainy season and June the start of the hurricane season. So why visit in May? Because average rain levels are half of what they’ll be in June, the weather is still usually warm and wonderful and, since it’s the island’s off-season, you’ll get better deals and face smaller crowds. By waiting until May, you’re also avoiding the brief (but very noisy) spring break season in March and April.

Istanbul, Turkey

Istanbul at night

Istanbul at night

The tourist season in Istanbul begins in earnest in June, but crowds start to descend in May as the weather warms up. Hotel prices may not be at their peak yet, but you’ll still get better deals if you book a few months in advance. Note that May 19th is a national holiday in Turkey – it’s Atatürk, Youth and Sports Day – with parades, dances and sporting events held in honor of Atatürk and the start of the Turkish War of Independence.

Prague, Czech Republic

Prague may be yet another European city with its high tourist season in the summer, but May in Prague feels a bit like one long festival. Prague Spring is an international classical music festival that runs through the month. The Prague Food Festival lasts three days and highlights the best of Czech cuisine. And in the latter half of May you can imbibe at the Czech Beer Festival, which also includes Czech food and music.

Learn more about Czech beer in Prague.

Napa and Sonoma, USA

The fall harvest season is certainly a delicious time to visit Napa and Sonoma, but head for these historic California wine regions in May and you’re treated to vineyards with grapes still hanging on the vines. The weather is typically lovely in May, and of course there’s plenty of wine to taste. Keep in mind that May is the start of the high season, so book in advance for the best deals and know that you won’t be the only tourist around.


Pretty Porto makes a great shoulder season getaway.

Pretty Porto makes a great shoulder season getaway.

Portugal, like much of the rest of Europe, is at its best in the spring and fall, when the weather is warm (but not too hot) and crowds and prices are manageable. While a place like Porto along the northern coast can be ideal starting in May and running straight through to September, the city of Lisbon is best avoided in the hotter summers if at all possible. So if you’re visiting both parts of the country, May is an excellent time to do that.


Vietnam in May is lovely if a bit schizophrenic, with different weather patterns dominating different parts of the country. The northern parts of Vietnam can be extremely hot and humid in May, while the south tends to be hot and dry. The central part of the coast is often wet and a bit cooler in May. Depending on where you go, May in Vietnam can be a bargain or smack in the middle of high season, so choose your adventure.

Jessica Spiegel

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