Where to Go: May

April 8th, 2021

May’s longer days and creeping sunshine signal the unofficial start to summer. And with the Memorial Day holiday, travelers are eager to pack their bags. Here are a few ideas to inspire your next trip.

Nantucket, MA

Just 30 miles off the coast of Cape Cod, Massachusetts, Nantucket is an idyllic island escape with miles of sandy beaches, centuries-old mansions, quaint shops and a classic small-town charm. With more than 50 percent of Nantucket under permanent conservation, much of the protected land is available for exploration. The island comes alive in spring, awash with color as more than three million daffodils bloom. Endless outdoor activities are on offer: biking, sailing, surfcasting, golfing and strolls to nearby lighthouses. Reunite with loved ones in a destination where families have vacationed for decades. Multi-generational families can opt for the one-, two- and three-bedroom residences or in-town lofts at White Elephant, conveniently located just steps from town with access to one of the only pools in town. The Woof Cottages at Nantucket Boat Basin also welcome four-legged family members, complete with a welcome basket of treats and a personalized pet tag. Local insider and pet concierge Bailey, the resident Black Lab/Brittany Spaniel mix, is available via email to share the best pet-friendly activities on island. For an intimate escape, The Wauwinet is an adults-only retreat situated between two private beaches, offering the feel of a private home and ambiance of storybook romance. Rates start at $175 per night at the Woof Cottages, $205 at The Wauwinet, and $715 for the White Elephant Residences.

JetBlue, United and American Airlines are launching direct service to the island beginning in May from east coast cities including Boston, New York, Newark, Washington D.C. and Charlotte. Travelers must complete the Massachusetts Travel Form and share proof of a negative Covid test taken within 72 hours of arrival.

Hamptons, NY

Memorial Day weekend signals the unofficial start of the Hamptons season. Visitors shouldn’t miss the latest exhibition at the Herzog and de Meruon-designed Parrish Art Museum. Affinities for Abstraction: Women Artists on Eastern Long Island, 1950-2020, will premiere on May 2 (through July 25) and is a freewheeling look at the work of 45 female artists who have called the Hamptons home, including Helen Frankenthaler, Grace Hartigan, Elaine de Kooning, and Lee Krasner. Across the street from the museum is the Hamptons’ first destination spa and wellness retreat, Shou Sugi Ban House. Embracing the wabi-sabi philosophy in both ethos and design, the property’s signature programing ranges from meditation to reiki to hikes on the beach. The just-launched Digital Detox is intended to redirect attention away from devices and back to the present moment, which is perhaps more necessary than ever. A Digital Detox Resource Guide will be on-hand to help guests tune into the innate wisdom of the mind, body and spirit. Oh and did we mention the plant-rich, hyper-seasonal meals are created by Noma co-founder Mads Refslund?

Water Mill is just 90 miles from NYC and can be accessed via car, Long Island Railroad, or the Hampton Jitney bus. Those flying into JFK, LaGuardia, or Islip/MacArthur Airports can take the Hampton Jitney to Southampton. New York just did away with its mandatory quarantine for out-of-state travelers.


Anguilla in May might be one of the island’s best-kept secrets. The weather is idyllic with low humidity and high temperatures. Having reopened to visitors in November, the island has been an appealing option for U.S. travelers with its very low Covid-19 cases (the island is currently CDC Level One). While guests must remain within their certified ‘vacation bubble’ for up to 14 days of their stay, the experience still checks all the boxes for a much-needed island escape. The vacation bubble concept includes a list of certified restaurants, activities and excursions that guests can experience outside of their pre-approved accommodations, like a round of golf, a glass-bottom boat ride or an offshore trip to the tiny island of Prickly Pear. And the best home base on the island is Cap Juluca, A Belmond Hotel, Anguilla. Set on Maundays Bay, the property lends itself to physical distancing, with standalone villas dotted along the pristine stretch of beach. Every room is beachfront, giving guests their very own slice of Caribbean Sea. The resort has launched a roster of daily programming, all available for private reservations, including wine classes, sunset sails, rum tastings, early-morning bird-watching, salt-scrub-making classes and more.

Visitors who require a negative Covid-19 test before returning home can do so with ease; Cap Juluca coordinates onsite testing to be administered in the comfort of guests’ own room. There are flights from the U.S. into Anguilla with connection through San Juan. Travelers can also fly into St. Martin and take a 25-minute boat ride to Anguilla. Those arriving via private jet can fly directly into Anguilla’s Clayton J. Lloyd International Airport (AXA).

Blue Mountains, Jamaica

The island’s beaches are just half the story. Meet Jamaica’s Blue Mountains – a range of steep peaks with tangled jungles and tropical rainforest shrouded perpetually by mist. On a clear day, from the 7,400-foot summit, one of the Caribbean’s highest vantage points, hikers can spot Cuba off to the north. The Blue Mountains were designated a UNESCO World Heritage site in 2015 due to its diverse flora and fauna, much of it endemic to Jamaica. Today, the mountains are as far as you can get from the hubbub of touristy beaches. There’s 200,000 acres to explore – including trails past coffee estates dating back to the 1700s and following in the footsteps of 18th-centrury British Sailors on their way from Kingston Harbor. There are roots in music too. Book a stay at Chris Blackwell’s Strawberry Hill, where the 12 cottages cling tightly to the mountainside and appear to be floating in the clouds. Blackwell founded Island Records in the 1960s, a label that went on to sign U2, The Cranberries and Cat Stevens. But in Jamaica, the music mogul is most famous for discovering Bob Marley and introducing reggae to the mainstream. It is well-known that Marley recuperated at Strawberry Hill following his 1976 assassination attempt in Kingston. Strawberry Hill can arrange full- and half-day guided hiking experiences with nightly rates starting at $280.

Direct service to Kingston airport is offered on American Airlines, Caribbean Airlines, Delta, JetBlue, Spirit and Air Canada from major cities including: Atlanta, Ft. Lauderdale/Miami, New York, Toronto. All international travelers must have a ‘travel authorization’ obtained before departure. Upon arrival into Jamaica, those 12 years of age and over are required to present a negative COVID-19 PCR or antigen test taken within 72 hours of entry.


Greece recently announced international tourists will be welcome beginning May 14. Perfect timing for booking a stay at the new Kalesma Mykonos, opening May 20. Kalesma brought together two Greek designers to create its authentically Cycladic look with a sleek, modern take: Studio Bonarchi and K-Studio (known for the new Mykonos airport and Scorpios Beach Club). Design details include Rick Owens furniture in the lobby, custom artwork in the 25 indoor/outdoor suites and two villas featuring pieces by Serbian artist Aleksander Vac and horsehair sconces, a nod to the mythical history of the area (Apollo was said to keep his horses here). The land has been in the owners’ family for over a century and the hotel will offer genuine insider knowledge of off-the-beaten-path sites while introducing a luxury experience that balances fun and privacy.

There are flights to Athens from several U.S. cities including New York, Chicago, and Philadelphia and AirTransat recently announced summer routes between Athens and both Montreal and Toronto. From Athens you can take a quick 40-minute flight to Mykonos or hop on a 2.5-hour high speed ferry. Travelers will need to show either proof of vaccine, proof of having antibodies or a negative PCR test.

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