The 20 Best Places to Travel in May

Trek through the beautiful wilds of this luscious green and biologically diverse landscape, come face to face with pygmy elephants and orangutans. Hike up mountain peaks, through jungles, or explore the world’s largest caves. Borneo offers glimpses of a landscape most of us only access with our best imagination. May is a great time to go as it’s the middle of its dry season.

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Nicknamed “The City of a Hundred Spires,” this capital is steeped in culture from several key eras. Walk the pedestrian Charles Bridge, built in 1402, visit its famed Old Town Square (and enjoy one of its many delicious local eats and brews), take in the Gothic churches or basque in the shadows of Baroque buildings. Don't miss the hourly show put on by the city’s famed Astronomical clock. May is a fantastic time to go particularly, as the whole city comes a-bloom, filling its many urban gardens with fragrant blossoms and budding magnolia trees. May is host to the Spring Music Festival, the Festival of Rose Wines (in a castle, no less). Yes, please. Prague is also city projected to increase in popularity in 2019.

The Cayman Islands offer up equal parts party and relaxation. May brings the long-standing carnival tradition of many Caribbean islands to the Caymans, with a flavour unique to Grand Cayman. Known as Batabano, the parade winds down through George Town, and is full of masquerade bands, colourful costumes, high-energy calypso and soca music, and dancing to boot. To switch gears and shift to a slower pace, you can check out Seven Mile Beach or scuba dive by the Kittiwake - an old submarine.

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Not too far from Greece, Italy follows the same tourism seasonality. The southern coastal city of Naples is great especially, with the average daily temperature hovering at about 25°C. The weather significantly improves in the second half of the month, with fewer days of rain as well. Renown for being the birthplace of pizza, you will find yourself at the foot of Mount Vesuvius - a volcano that completely decimated (and preserved) the town of Pompeii and its residents in 79 AD. With so much history, you need not look far for somewhere to go. Venture to the city’s cathedral, Duomo di San Gennaro, and take in the frescoes, but first, start the day off by taking in the bay-side views with an espresso in hand.

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Memphis in May is a month long festival that encompasses the city’s most notable annual events, nestled alongside the Big Missus (or The Mighty Mississippi, if you will). That’s merely one reason to go this time of year. Another? Well, if you like barbecue (and smoked meat), May also brings one of the world’s largest barbecue competitions - the World Championship Barbecue Cooking Contest. Rumor has it, if the wind blows just right, you’ll be able to smell the aromas throughout the city. The weather is warm in the day, and cool in the evenings, so you'll want to dress accordingly. Historically, the spot is significant for a variety of reasons, including its role in the Civil Rights movement, and serving as the fertile delta that birthed Blues Music. This legacy lives on, and great music is always just around the corner. Case in point: don’t miss the Beale Street Music Festival, which always promises to serve up a good time. Plus? Memphis is also one of 20 less expensive U.S. holiday destinations.

The start of the country’s “green season” (a creative take on the region’s “rainy season”), Costa Rica is nevertheless not-to-be-missed and worth the wetter weather during the month of May. It is when you can still catch many dry breaks, and when much of the rain is relegated to evenings and short, heavy spurts. Take a hike to the tip to see Lake Arenal where you can windsurf, zip-line through the jungle, or visit the breathtaking blues of Rio Celeste. To unwind from the day, soak in the region's naturally occurring hot springs. See if you can spot the red-eyed tree frog, the shy yellow eyelash viper, or the sassy coati (cousin of the raccoon). This is a country that promises adventure and delivers it in spades.

Like the region and want to continue exploring? Check out these 20 lesser-known Central American gems.

Porto, so named for the fortified wine the region is known for, is becoming more and more popular as the word gets out. However, it is still less crowded than some of the other areas of Portugal. May is a great time to go because it’s warm without being too hot. You’ll find the friendly smiles, and welcoming hospitality equal to the delicious seafood and beautiful beaches. Speaking of which, there are many to choose from all along the coast. If you fancy yourself a fan of the Harry Potter series, make sure to visit Libraria Lello. It is recognized as one of the most beautiful bookshops and thought to have inspired J.K. Rowling.

Famous for winter activities at the nearby Jackson Hole, and the Grand Teton and Yellowstone national parks, this is the spot for you if you enjoy exploring the wilder side of spring. Wildflowers are in bloom and the rest of the wildlife is waking up from hibernation as well. Because it’s the shoulder season, rates are more affordable and there is still plenty going on to connect you to this unique destination. Jackson embraces its western heritage with Old West Days festival, which features stage coach rides, a brewfest, and the start of the Jackson Hole Rodeo.

Spain, like Greece or Italy, is also emerging from its semi-slumber. Enjoy tapas and sangria al fresco with friends in one of the many outdoor restaurants on La Rambla and trendy El Raval. Barcelona is a very pedestrian-friendly city, and if you’re able to, take its streets by foot; its lovely details are easily overlooked in a faster mode of transit. The temperature is typically around 25°C, and will allow for a dip in the sea, at the nearby Barceloneta Beach. Explore the other-worldly Park Guell, Casa Batllo or Gaudi’s other masterpieces (do not miss Sagrada Familia). Also, do yourself a favour, and order a paella at the waterfront restaurant, Xiringuito Escriba. You’ll savour the atmosphere as much as the fresh seafood. If you find yourself in the city at the end of the month, don’t miss the Ciutat Flamenco Festival. After all, when in Barcelona...

May is the perfect sweet spot between the time just after most of the snowbirds have left, and just before the weather gets too humid. The region has a unique flavour of a rustic, laid-back, beach-shack vibe, but in a way that still reminds you that you’re in the United States. There is lots to do, taste, see and hear, and the crystal blue waters don’t hurt the eyes either. May brings two music festivals - the Key Largo Original Music Festival and the Key West Songwriters Festival, found a little further south. Both will get you intimate, smaller-scale performances and expose you to new talent. Don’t miss the train tracks to nowhere (literally); the Overseas Railroad that had an extension to the Middle Keys ends partway across the turquoise blues. Constructed and operated at the start of the last century, its use came to a halt when the Labour Day Hurricane - a Category 5 spinner - destroyed it in 1935. Also, if you happen to be a fan of the Netflix drama “Bloodline”, be sure to check out the Moorings Village and Spa and stay at the gorgeous Blue Charlotte House that serves as the setting for the Rayburn homestead.

As with the other Nordic countries, the cold weather starts easing its grip on Sweden, and its citizens kick things off with a double-holiday no less: Walpurgis Night (April 30) and May Day (May 1). There are parades, music, bonfires, and other festivities. Swedes more generally embrace the socializing culture of many European nations (and beyond), and even have a name for the tradition of taking a coffee and cake break with friends (fika). Stockholm is a great place to visit if you’re a history buff or a fan of the show “Vikings”. Visit the Royal Palace (yes, the Swedes have a monarchy) and the city’s “old town” -- Gamla Stan. It dates back to the 1200s, and provides a scenic medieval atmosphere where you can take in local cafes, restaurants and boutiques. Explore Skansen, the oldest outdoor museum in the world, or the Vasa Museum, which holds an early 17th century Swedish battleship, that sunk on its maiden voyage and was recovered in 1961.

This genteel city is recognized for the key park bench scene in “Forrest Gump,” shot in Chippewa Square. Its fragrant streets, and high walkability encourage visitors to take a leisurely stroll, and get the most out of the city. Don’t miss visiting the gorgeous Forsyth Park, with its moss draped oak trees, and the iconic fountain. Established in 1733, there is a lot of historic architecture to take in but plenty of great restaurants and bars to choose from as well.

Travelling to this bucket list city is always great when it’s on a budget. Given that it too, like its Nordic continental neighbour, is in the midst of its shoulder season, it means you’re getting reasonable prices and smaller crowds to check out top tourist locales. At the same time, certain attractions are becoming more accessible. For example, The Buckingham Palace Changing of the Guard is back on a daily routine, and is a treat to see at least once in a lifetime. Another Royals-related event taking place in late May is the RHS Chelsea Flower Show; this year Kate Middleton collaborated with landscape architects to bring attention to the benefits of nature. Other Members of the Royal family also attend the show.

Dreaming of hiking the iconic Inca trail of Machu Picchu? May is one of the best months to take on this Andean adventure, sans the crowds. The rainy season is over but because it’s still so early in the season, you still get the deep greens that make these views so breathtaking. May temperatures are relatively temperate, and hover around 10°C at night, so you’ll want to plan your essentials accordingly. This trip does require extensive planning, in part due to permit requirements, and these can take several months to get, so keep that in mind.

If Cannes is a destination on your must-visit list, May is a great time to go. Located on France’s Cote d’Azur, this southern coastal city swells to nearly three times its size for the Cannes Film Festival. While normally, travel advice cautions against visiting destinations during peak season or popular events, if you’re a film buff or a celeb fiend (this is a safe space - no judgement), you’ll want to take in the city in all its glitzy lustre. In its 72nd year, the 12-day event will be held from May 14 - 25, and brings stars, red carpet events and a festive atmosphere that celebrates storytelling.

Safer than its beautiful neighbour, Namibia, Botswana is a land-locked country that is just to the north of South Africa (the two share a border). May kicks off the region’s dry season and that means warm days and cool nights for those less acclimatized to the region. Botswana sets out to protect about 40 percent of its wildlife and so, it offers great opportunities to see The Big Five in their natural habitat (the elephant, lion, cape buffalo, rhino and leopard). The Chobe National Park is a good start, and it has plenty of options for lodging (from camping to luxury abodes). The sunsets alone make the trip worthwhile.

Like other countries that experience shoulder season, Greece is a good bet for the usual reasons. However, with it being further south than some of the other places mentioned on this list, the weather gets warmer sooner. There is still a gamble when it comes to perfect beach conditions (if that’s your priority, stick to the summer months), but the region still gets a good amount of sun for the month of May, and you’ll benefit from fewer crowds at the most popular spots. The month is also when the locale starts to open up after the much slower winter months, so the prices are more appealing as well. In Santorini, you’ll want to do a boat tour (try for sunset) to take in the contrasting red-stone beauty of the island and the white cycladic architecture of the villages. Don’t miss Oia - arguably the island’s most beautiful village - and Pyrgos, an old town that has twisting pathways and old churches.

Because Hawaii experiences heaviest rains in its “winter” season, it is a great place to visit in May. When it does rain, it’s typically only at night. The temperatures also start to shift upwards, and typically average in the mid- to high-20s. While other off-season months may limit your choice of islands to visit, May’s weather makes each of them a worthy destination (we highly recommend the low-key Kauai for its preternatural beauty). That said, if you’re planning to visit the mountains or check out the volcanoes, you will need a light jacket and long pants. In terms of prices, avoid the first week of May (it’s a Japanese week-long holiday, which brings an influx of tourists), and Memorial Day weekend. Fees tend to increase with incoming long-weekend vacationers from the mainland here as well. If you do happen to find yourself here during these three days, don’t miss the Lantern Floating Festival.

The country’s metropolitan capital blends skyscrapers, a high-tech subway system, street markets, and tradition in a beautiful way. You can visit Gyeongbokgung Palace (which formerly housed 7,000 rooms), the Jogyesa Temple and its ancient trees, or the otherworldly futurist Dongdaemun Design Plaza. May is a particularly great time to visit as the whole country celebrates the Lotus Lantern Festival. The festival celebrates the birth of Buddha, and the whole city turns out in droves to illuminate one of the city’s busiest streets.

You don’t have to go far to enjoy the best the month of May has to offer. With much of Canada embracing the Victoria Day long weekend, there is plenty to do and see. Case in point: Kaslo May Days, in the Kootenay Rockies. This tradition has been revived every Victoria Day long weekend since 1892 on the shores of Kootenay Lake, close to the Purcell Mountain Range. There are helicopter tours, delicious food, vintage cars, music, and a competition awarding North America’s fittest Logger Sport athletes. There is axe throwing, log rolling, springboard chopping, and tree climbing. You’ll find yourself looking forward to the other long weekends that are just around the corner.

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