If you’re looking to travel in May, read on for destinations and resorts offering a range of late-spring travel experiences. Choose from city stays to nature-forward escapes and relaxed shoulder-season getaways.
Hyatt Regency Maui Resort & Spa
May is an especially enticing time to visit Maui as Hyatt Regency Maui Resort and Spa welcomes back its popular Nashville Nights songwriter series. Running monthly from April through September, the open-air concert series brings acclaimed country artists to the resort’s Halona Kai Lawn, offering intimate evening performances set against Ka‘anapali Beach. In May, guests can catch a blending of live music, oceanfront ambiance, and Southern-inspired food and drinks, making it an especially appealing cultural highlight during Maui’s shoulder season. The calendar of events includes:
May 23 — A country singer-songwriter from Knoxville, Tennessee who first gained national attention as the runner-up on The Voice Season 9 as part of Blake Shelton’s team. Since The Voice, the singer has released a full-length album, Can’t Hide Country (2023), and an EP, Memory Lane (2025), performed at the Grand Ole Opry multiple times, toured with major artists, and signed to RECORDS/Sony Music Nashville.
InterContinental New York Barclay
InterContinental New York Barclay’s Journey to 100 is a year-long centennial program marking the hotel’s approach to its 100th anniversary in 2026. Rather than centering the milestone around a single celebratory event, the initiative unfolds across 2026 through a structured series of historically grounded experiences that reflect the decades shaping the hotel’s identity since its opening in 1926.
In May 2026, the program turned its focus to the 1960s. Throughout the month, The Parlour will serve 1960s themed menus that reflect the formality, classical technique, and international influence that defined luxury hotel dining during the era. Offerings include Eggs Benedict at breakfast, Poached Pike Quenelles for lunch and dinner, and the Harvey Wallbanger at the bar, creating a cohesive snapshot of mid-century dining and social ritual at the Barclay. Together, these elements reinforce how each decade within Journey to 100 is distinctly expressed through the hotel’s evolving culinary narrative.
InterContinental Dominica Cabrits Resort & Spa
As the Dominica Jazz ’n Creole Festival marks its 15th edition, Dominica steps further into the spotlight as a destination where music, heritage, and community converge in a way that feels both genuine and alive. Over the past decade and a half, the festival has evolved into one of the island’s most defining cultural moments, reflecting a steady commitment to creative expression rooted in place rather than spectacle. Held on May 3, 2026, the event takes place at Fort Shirley, set within Cabrits National Park, where the historic waterfront setting creates a direct link between Dominica’s past and present and shapes how the festival is experienced.
Jazz ’n Creole distinguishes itself through both its format and philosophy. Designed as a day-into-evening celebration, the festival emphasizes accessibility and inclusivity, welcoming families, multigenerational audiences, locals, and visitors alike. This intentional pacing fosters a relaxed, communal atmosphere, encouraging audiences to linger with the music, the food, and one another. Musically, the programming explores the dialogue between jazz and Creole culture, highlighting how global jazz traditions intersect with Dominica’s rhythms, languages, and musical heritage to create performances that feel organic, expressive, and deeply connected to place.
For travelers attending the festival, InterContinental Dominica Cabrits Resort & Spa offers a natural place to stay. Located within Cabrits National Park and just moments from Fort Shirley, the resort allows guests to experience Jazz ’n Creole while remaining immersed in the same landscape that frames the event. Set between rainforest-covered hills and the Caribbean Sea, the resort provides a refined yet grounded base for the weekend, pairing contemporary comfort with a strong sense of location, and enabling visitors to move seamlessly between festival programming and quiet moments of rest, reflection, and exploration.
Six Senses Laamu
May is prime surf season in Laamu Atoll, one of the Maldives’ most untouched and culturally rich regions, and Six Senses Laamu is offering a Learn to Surf experience. The only surf resort in the entire Laamu Atoll, Six Senses Laamu sits directly beside the atoll’s most consistent swells and vibrant marine ecosystem, offering unparalleled access to surf breaks, snorkel sites, and year-round marine life.
Offered through May 2026, the Learn to Surf experience includes three one-on-one lessons with a Tropicsurf teacher, daily breakfast and dinner for two, and a 60-minute rejuvenating massage at the Six Senses Spa for two people. The program offers a seamless introduction to surfing, allowing guests to build confidence and technique under the guidance of seasoned professionals in one of the Maldives’ most sought-after surf settings.
Rates start at $2,500+ per night, with the offer applicable for a minimum five-night stay. To book, please contact reservations-maldives@sixsenses.com.
Vakkaru Maldives
May is a quietly magical time to experience the Maldives, marking the start of stingray season as these graceful creatures begin gathering around the atolls. It also signals the beginning of the shoulder season, when the islands feel calmer and less crowded, yet conditions remain ideal. Warm waters and excellent visibility make May especially well suited for snorkeling, diving, and lagoon exploration, while brief tropical showers tend to be refreshing rather than disruptive. For travelers seeking standout wildlife encounters, uncrowded beaches, and strong value, May strikes the perfect balance between peak season and summer.
Located in the Baa Atoll UNESCO Biosphere Reserve, Vakkaru Maldives offers exceptional access to the region’s renowned marine life during this time of year. The resort’s Splash Dive & Water Sports Center leads guided snorkeling on the house reef, seasonal manta and stingray encounters, and marine biologist–led excursions highlighting coral gardens, turtles, and vibrant reef fish. Beyond the water, guests can enjoy sunset cruises, dolphin quests, kayaking, private yacht charters, and a coral adoption program. Set on a lush private island with 113 Beach and Overwater Villas, Vakkaru pairs these experiences with world-class dining, an overwater Ayurveda-focused spa, and thoughtfully designed offerings for all ages, making it an ideal May escape for ocean lovers.
