It’s no secret among those in the travel industry that vacationing during shoulder season is the economic, environmental, and exciting alternative to overcrowded summer travel. Escape to these dreamy island getaways this shoulder season.
Nantucket, Massachusetts
Nantucket might be one of summer’s buzziest destinations, but springtime on the island offers the same coastal charm with far fewer crowds. April and May on the island are epitomized by a delightful blend of charm, renewal, and coastal elegance, and perfectly embodied by Greydon House. Originally a sea captain's home, this boutique property features nautical themes and refined design, creating a welcoming atmosphere that feels like a retreat. Spring’s shoulder season transforms Nantucket into a vibrant haven, with blooming daffodils and quiet streets that allow visitors to experience the island’s beauty without the summer crowds. Greydon House remains open year-round, providing thoughtful programming and personalized service, making it an ideal base for exploring the island during the shoulder season. Guests can enjoy activities such as leisurely hikes along Nantucket’s trails, visits to iconic lighthouses like Brant Point and Sankaty Head, or simply strolling through the cobblestone streets adorned with spring flowers. Dining at Via Mare, Greydon House's Venetian-inspired restaurant, is another highlight.
Spring on Nantucket also brings seasonal events such as the annual Daffodil Festival (April 24 - 27), which sees the island celebrate renewal with antique car parades, flower shows, and an abundance of family-friendly activities. Whether you’re seeking relaxation or exploration, Nantucket in spring—especially with a stay at Greydon House—promises an enchanting getaway filled with seasonal charm and community spirit.
Dorado Beach, Puerto Rico (pictured)
Escape to Dorado Beach, a Ritz- Carlton Reserve, for the ultimate peaceful retreat in Puerto Rico, especially as the shoulder season approaches this May through June. This time of year offers fewer crowds making it the ideal moment to enjoy the island’s natural beauty and luxury at its finest. With the estate’s serene beachfront setting, reimagined suites, and personalized service from Embajadors, the resort offers the ideal getaway. Guests can savor seasonal dining at COA, indulge in oceanfront fusion cuisine at Posi+tivo Sand Bar, or Italian-inspired dishes at Flor de Sal. The award-winning Spa Botánico provides nature-infused treatments in tranquil, treetop pavilions, and the Naturalist Program allows guests of all ages to engage with Puerto Rico’s culture and wildlife, from exploring coral reefs to learning about the island’s famous coqui frogs. Visiting during shoulder season allows guests to avoid the hustle of the busy season, all while enjoying the island’s perfect weather and the estate’s abundance of amenities and activities.
Grand Cayman, Cayman Islands
May is an ideal time to visit Grand Cayman, offering a perfect balance of affordability, fewer crowds, and exceptional experiences. As the shoulder season begins, travelers can enjoy direct or one-stop flights from major U.S. cities like New York, Miami, and Los Angeles for as low as $325, paired with reduced accommodation rates. This quieter period allows for more intimate exploration of iconic attractions such as Seven Mile Beach, Stingray City, and Rum Point, where pristine weather and water visibility exceeding 100 feet create optimal conditions for snorkeling and scuba diving among thriving coral reefs and marine life. Early turtle nesting season also begins in May, offering opportunities to spot Green, Hawksbill, Loggerhead, and Leatherback species. Culinary and social scenes shine during this time, with Grand Cayman emerging as a Caribbean dining hotspot. Bonny Moon Beach Club on Seven Mile Beach exemplifies the island’s vibrant energy, hosting full moon parties, tarot readings, and communal gatherings over fresh sushi, ceviche, and seasonal dishes. Nearby, Ms. Piper’s Kitchen + Garden blends global influences with local flavors, serving creative wood-fired fare like Gochujang-glazed Korean Ribs and Grilled Banoffee Pie in a whimsical, story-driven setting. With warm temperatures, minimal rainfall, and a lively yet relaxed atmosphere, May provides an unparalleled opportunity to experience Grand Cayman’s natural beauty and cultural vitality without the high-season crowds.
