May is one of the best times to visit the islands of the United States. The weather is warm, the crowds are smaller, and the scenery is breathtaking. It’s the perfect month for a relaxing break or an action-packed adventure.
From tropical beaches to hidden nature spots and vibrant local culture, the U.S. islands offer something for everyone, no matter what kind of vacation you’re after.
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Tropical Paradise: Maui, Hawaii
In May, Maui offers the perfect balance of warm temperatures and less rainfall compared to other months. Explore the famous Road to Hana, snorkel in Molokini Crater, or unwind on Ka’anapali Beach. The island’s lush landscapes are in full bloom, making it a great time for hiking in Haleakalā National Park.
Plus, the Maui Onion Festival typically takes place in May, celebrating the island’s sweet and mild onions with cooking competitions and tastings. For surfers, Honolua Bay offers excellent waves in late spring, while the Maui Arts & Cultural Center hosts outdoor performances.
Cultural Haven: Puerto Rico
May marks the tail end of Puerto Rico’s dry season, making it an excellent time to explore both the vibrant city of San Juan and the lush interior. Visit El Yunque National Forest, stroll through Old San Juan’s colorful streets, and savor local dishes like mofongo.
Vieques Island, just off the mainland, is home to the bioluminescent Mosquito Bay, where the waters glow at night. Additionally, the Ponce Carnival often falls in early May, with parades, masks, and vibrant dance performances celebrating Puerto Rican heritage.
Northeast Charm: Martha’s Vineyard, Massachusetts
By May, Martha’s Vineyard comes alive with spring blossoms and fewer tourists compared to the peak summer months. Enjoy scenic bike rides through charming towns like Edgartown and Vineyard Haven. Visit local farms for fresh produce or relax on the sandy shores of South Beach.
The island’s fishing charters also kick off in May, perfect for anglers seeking striped bass. Don’t miss the Vineyard Artisans Festival, showcasing handmade crafts and local artistry, which typically begins its season in late spring.
Coastal Adventure: San Juan Islands, Washington
Located off the coast of Washington State, the San Juan Islands boast mild weather and blooming wildflowers in May. Kayak through the serene waters in search of orcas, or hike Mount Constitution on Orcas Island for panoramic views. The charming town of Friday Harbor offers art galleries, seafood eateries, and the Whale Museum, celebrating the region’s marine life.
In addition, May is prime time for birdwatching, with bald eagles and migratory species often spotted throughout the islands.
Southern Gem: Key West, Florida
In May, Key West is sunny, warm, and not yet overwhelmed by summer vacationers. Visit Ernest Hemingway’s Home, enjoy the Sunset Celebration at Mallory Square, and snorkel the coral reefs of Dry Tortugas National Park.
The annual Key West Songwriters Festival also takes place in May, attracting musicians from across the country. For a more laid-back experience, explore the scenic Overseas Highway or take a day trip to the neighboring island of Bahia Honda.
Rustic Beauty: Catalina Island, California
Just 35 kilometers or 22 miles off the coast of Los Angeles, Catalina Island offers a tranquil retreat in May before the summer crowds arrive. Take a glass-bottom boat tour to view underwater life or explore the quaint streets of Avalon.
Hike the Trans-Catalina Trail for a more rugged adventure, and spot bison grazing in the island’s interior. The island also hosts the annual Catalina Island Rugby Festival, drawing teams from across the region for a weekend of sports and festivities.
Practical Tips for Island Travel in May
- Check ferry schedules: Some islands have limited ferry services in early May before the high season begins.
- Prepare for variable weather: Even on tropical islands, evenings can be cool or breezy.
- Book activities in advance: Popular tours, like snorkeling in Maui or whale watching in the San Juan Islands, can fill up quickly.
- Embrace local events: From food festivals in Hawaii to cultural celebrations in Puerto Rico, May often brings unique island festivities.
- Respect local wildlife: On islands known for unique species, such as the wild horses of Vieques or the bison of Catalina, always follow guidelines to keep a safe distance.