Where do you start when it comes to choosing the best islands to visit in May? The weather, local events, and the natural world all play a role, not to mention the diverse offerings of the islands themselves, which can obviously all be very different.
The pink sands of Bermuda, the volcanic beauty of Santorini, and the spring thaws of Alaska’s Revillagigedo all have their own unique charms – as does every other island in the world. The one thing that unites them, though, is that island life captures the imagination: a vision of escape, where life feels a little slower, the air a little fresher, and the sea always within reach.
With so many islands to explore then, how do you choose which one to visit? Here are some of the best islands to visit in May – destinations that promise unforgettable experiences, weather that is just right, and a taste of island life at its very best.
Sicily, Italy
Messina in Sicily, Italy
Italy’s largest island sits right at the “toe” of the country’s boot with its location at the convergence of the Mediterranean, Ionian, and Tyrrhenian Seas making it a crossroads of culture for thousands of years. That heady cultural mix – the Phoenicians, Greeks, Vandals, Roman, Arabs, Normans, and British all had spells here – combined with some truly incredible natural beauty makes it an ideal place to visit at any time of year.
Warming temperatures, wildflowers lining the streets and fields, and the air filled with citrus blossom all combine to make Sicily one of the best islands to visit in May.
In Messina, you can visit the world’s largest astronomical clock and the beautiful Norman-era Cathedral.
Catania in Sicily, Italy
Catania, meanwhile, is the gateway to Mount Etna, Europe’s most active volcano and an adventure-lover’s paradise. May is great for hiking the many lava trails and the visibility from the summit on a clear spring day is breathtaking.
Foodies will also love a trip here. Arancini – deep fried rice balls – is the regional specialty, while spring’s citrus harvest ensures dishes are packed with zesty flavors. May is also prime time for swordfish fishing in the Strait of Messina. Try it grilled, or in the local dish “Pasta alla Eoliana”.
Santorini, Greece
Fira in Santorini, Greece
If you’ve yearned for a trip to Greece after seeing images of whitewashed houses spilling over a cliff towards the sparkling Aegean, then it’s likely they were taken in Santorini – the poster child of the Greek islands.
Santorini’s beauty is legendary, providing images for countless magazine and brochure shots, the island towering above the sunken caldera of an active volcano, little sister Thirassia forming the opposite “rim” across the bay.
Oia in Santorini, Greece
Between them sit two lava islets, smoldering away in the sun to complete this iconic scene, overlooked from the caldera rim by capital Fira, upmarket Imerovigli, and the magical village of Oia.
Santorini’s beauty comes at a high price in high summer when the island is thronged with visitors – which is why May is such an ideal time to visit. The sun’s warmth is starting to heat up and everything’s open for the season, but it’s far from busy and much easier to explore.
While here, visit the ruins at Akrotiri to learn about the Minoans who once lived on the island, sample some local Assyrtiko white wine, and make sure to drink in those gorgeous views.
Iceland
Blue Lagoon, Iceland
Iceland is known for its dramatic landscapes: huge glaciers, towering volcanoes, raging waterfalls, and geothermal springs. Its position in the far reaches of the North Atlantic though means winter days are incredibly short, making it much harder to explore in natural light.
Come spring, the days are longer, temperatures milder, and crowds thinner – all of which combine to make it one of the best islands to visit in May. At this time of year, wildlife is also a major draw with puffins arriving along the coast to nest and whale watching season heading towards its summer peak.
Thingvellir National Park
Golden Circle tours around capital Reykjavik should be high on a list of must-dos. They feature Thingvellir National Park, where you can walk between the North American and Eurasian tectonic plates, the geothermal water eruptions of Geysir, and the powerful Gullfoss waterfall.
The Blue Lagoon – a geothermal spa – is another highlight, while in Iceland’s second largest city Akureyri, the magnificent botanical garden is coming into full bloom.
Bermuda
Jobson’s Cove, Bermuda
There are many reasons Bermuda is possibly the best island to visit in May – but one of the main ones is that May 23 is Bermuda Day. With colorful parades, dancing, and traditional gombey art performances, it marks the first day of the year when locals will take a dip in the ocean. You don’t have to wait for this official kick-off of summer to head to the beach, though.
By now, temperatures are reaching the low 80s, humidity is low, and the island’s famed pink sand beaches beckon. The capital, St. George is a highlight in May, too. A Unesco World Heritage Site, its cobbled streets are lined with colonial-era architecture accented by spring flowers.
Look out for landmarks such as St. Peter’s Church, the oldest Anglican church in the western hemisphere. The comfortable temperatures also make May a great month for outdoor exploration with the scenic paths of The Bermuda Railway Trail perfect for walking or cycling.
Jeju Island, South Korea
Hallasan in Jeju Island, South Korea
Known for its volcanic landscapes, lush greenery, and unique culture, Jeju Island sits off the southern coast of the Korean peninsula and is one of the country’s most popular visitor destinations. Another Unesco World Heritage Site, it is also home to Hallasan, an extinct volcano that is the country’s highest mountain.
Why is May such a good time to visit? Well, the weather is warm but not hot, and the landscape vibrant with bright azaleas and wildflowers. It’s also before the tourist season reaches its height, making it a good time to hike around the lower slopes of Hallasan. Elsewhere, there’s the world’s longest lava tube, and incredible waterfalls such as Cheonjiyeon and Jeongbang, swollen by spring rains.
St. Maarten
St. Maarten
St. Maarten is uniquely the smallest island in the world shared by two different nations: the Dutch side, Sint Maarten, and the French side, Saint-Martin. Set against the sparkling Caribbean and with some incredible beaches, the island is a great destination for a May vacation. This is the tail end of the high season, but it’s also before the more humid weather of summer arrives.
The result? Fewer crowds, lower prices, and fabulous conditions for both outdoor pursuits and water sports. Maho Beach – close to Princess Juliana International Airport – is both a great beach experience and the chance for unique photo ops as planes come in low over the sands on their final approach.
Orient Bay Beach on the French side is known for clear waters and some of the island’s best beach clubs. Philipsburg, the capital of the Dutch side, is known for its duty-free shopping. Pick up jewelry, electronics, and fashion, all at lower prices than at home.
Grand Cayman, Cayman Islands
Seven Mile Beach in Grand Cayman, Cayman Islands
The three Cayman Islands lying just south of Cuba are home to more than 100 different nationalities – a remarkable number given the country’s small size. At the start of May, they all come together to dance the days away at Carnival Batibano – a vibrant celebration of the islands’ multicultural make up. The bulk of celebrations take place in George Town, the country’s capital on Grand Cayman.
As with other Caribbean destinations, May also sees the final weeks of the dry season, making it ideal beach weather. Seven Mile Beach is a long stretch of sand just short of its name, but home to fabulous swimming, sunbathing, and water sports. Another attraction not to miss is Stingray City, where you can snorkel with southern stingrays in the wild.
Mykonos, Greece
Mykonos, Greece
If Santorini is the Greek islands’ poster child, Mykonos is its hedonistic sibling. Once a hippy community, its fame grew in the 1950s with the arrival of both Greek and Hollywood superstars who set the tone for the island’s glamorous future.
While there’s no doubt Mykonos is a blast in summer, visitors in May get to see its softer side. The island’s clubs, bars, and restaurants have all opened for summer, but the fun is yet to get into full swing. This quieter time reveals a different island. It’s one of whitewashed buildings, traditional windmills gently spinning in the breeze, and gorgeous beaches, almost empty before the summer hordes arrive.
Take time to explore those beaches, wander around the high-end boutiques in town, and settle down for the freshest of fish, looking out over the extremely romantic Little Venice waterfront.
Revillagigedo Island, Alaska
Tongass National Forest, Alaska
Revillagigedo Island sits on Alaska’s Inside Passage, offering visitors a rich blend of fishing, logging, and Native heritage, allied with a stunning natural landscape of dramatic fjords backed by the Tongass National Forest. It’s one of the best islands to visit in May thanks to the milder temperatures that really bring this lush landscape to life.
In Alaska in May, waterfalls gush with water from melted snows, the trees have their plushest foliage, and wildlife is active, with bears fattening up after a long winter of hibernation.
The Creek in Ketchikan, Alaska
Bald eagles and seals can readily be spotted along the shores, while it’s also the beginning of the spring salmon run. The island’s capital, Ketchikan, was built as a frontier town around Ketchikan Creek where the salmon swim upstream to spawn. The Creek is also home to Creek Street, an historic boardwalk that was once the town’s red-light district, but now houses galleries, restaurants, and cafés.
Find time while exploring Ketchikan to visit the Totem Heritage Center and learn about the fascinating culture of indigenous tribes the Tlingit, Haida, and Tsimshian. Dining out here is a must, too. Seafood is a treat thanks to the abundance of salmon, while halibut and Dungeness crab feature highly on many menus.
Santa Cruz, Galápagos
Santa Cruz, Galápagos
The Galápagos are famously one of the most biodiverse destinations on the planet and in May, they come to life, quite literally. For May in the Galapagos is baby season – a great time to see sea lion pups, as well as hatchlings of marine and land iguanas.
May also brings the wet and warm season to an end, with temperatures hitting the mid-80s. The seas are also notably calm, making for excellent snorkeling and wildlife viewing conditions to outlying islands.
Charles Darwin Research Center in Santa Cruz, Galápagos
The main island of Santa Cruz is the hub of a tour here. Home to the Charles Darwin Research Station, it’s a great spot to get an insight into the islands’ biodiversity. Make sure to pack a swimsuit, too. Tortuga Bay is one of Santa Cruz’s most picturesque beaches. Its white sands stretch for more than a mile and are home to a variety of wildlife, including iguanas, pelicans, and crabs. Snorkel over the reefs here and you could spot white-tipped reef sharks and rays.
Oahu, Hawaii
Oahu, Hawaii
Known as “The Gathering Place”, the Hawaiian island of Oahu is the kind of place you’ll readily recommend to friends and family because it caters to almost everyone. Vibrant city life, iconic beaches, historic sites, and lush natural landscapes can all be found here.
May is an ideal time to visit: temperatures are warm, the summer rush yet to begin, the ocean is calm and clear, and the landscapes more verdant than ever. Iconic Waikiki Beach is a prime spot to visit especially for novice surfers, paddle boarders, and swimmers, while Hanauma Bay offers great snorkeling conditions.
Hikers will love the many trails too – especially the Diamond Head Crater hike with its summit views over capital Honolulu and the Pacific. There’s fabulous food in Hawaii too, with poke – seasoned raw fish – and kalua pork local dishes you should try. May is also mango season, and this sweetest of fruits features prominently in desserts and drinks.
Key West, Florida
Duval Street in Key West, Florida
May is a fabulous time to visit Key West, the southernmost island in the Florida Keys, just 90 miles north of Cuba. The island has all the usual spring draws of warm weather without the crowds, but adds in a host of festive fun too. May usually kicks off with the annual Key West Songwriters Festival, said to be the largest such event of its kind.
Singer-songwriters from around the world gather here to play intimate gigs. The festival then links into Cinco de Mayo, which is celebrated here with all kinds of parties, many of which involve some excellent margaritas.
Outside of these main events, there’s always something going on thanks to the island’s strong artistic and literary heritage. Head down Duval Street with its Cuban and Caribbean influences, take in the Ernest Hemingway Home and Museum, or simply sit back and relax on one of the amazing beaches.
Key West, Florida
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