Day 1: Arrive Anguilla — Meads Bay Sunset
Arrive via ferry from St. Martin or direct flight to Clayton J. Lloyd International Airport. Transfer to your boutique beachfront resort on Meads Bay, one of Anguilla’s most beautiful west-facing beaches. Afternoon at leisure: sink your toes into powdery white sand, swim in water so clear it defies description, and adjust to Anguilla’s famously relaxed pace. Sunset cocktails on the beach as the sky erupts in orange and pink. Welcome dinner at a beachfront restaurant—perhaps grilled crayfish at Blanchards or sunset tapas at Jacala. Overnight Meads Bay.
Day 2: Shoal Bay East — The World’s Most Beautiful Beach
Full day at Shoal Bay East, often voted among the world’s top beaches. This two-mile crescent of impossibly fine white sand meets water in shades of turquoise you never knew existed. Morning snorkeling among the vibrant coral reefs just offshore—expect to see angelfish, parrotfish, and rays. Lunch at one of the barefoot beach bars: Gwen’s Reggae Grill for jerk chicken, or Tropical Sunset for the famous crayfish sandwich. Afternoon snorkeling at the artificial reef created by the deliberately-sunk Spanish galleon replica El Buen Consejo. Return to Meads Bay for sunset. Overnight Meads Bay.
Day 3: Offshore Cays — Sandy Island & Prickly Pear
Morning boat excursion to Sandy Island, a tiny speck of sand and palm trees floating in the turquoise sea. When the tide rises, the island nearly disappears—you’ll have it mostly to yourself, with nothing but golden sand, crystal-clear water, and a small beach bar serving the best rum punch in the Caribbean. Excellent snorkeling on the surrounding reef. Continue to Prickly Pear Cay for lunch at the legendary Prickly Pear Island Restaurant—crayfish, grilled lobster, and fresh snapper with your toes in the sand. Afternoon swimming and snorkeling among the cay’s thriving marine life. Overnight Meads Bay.
Day 4: The Valley & Cultural Anguilla
Morning exploration of The Valley, Anguilla’s charming capital—more village than city. Visit the Anguilla National Museum housed in the Old Court House, telling the island’s story from Arawak settlement through the 1967 Revolution. See the Wallblake House (1787), one of the oldest plantation houses in the Caribbean. Browse the colorful Heritage Collection Museum and artisan galleries. Afternoon at Crocus Bay: kayak to Little Bay through dramatic cliffs teeming with seabirds, then swim and snorkel in this secluded cove only accessible by water. Sunset at Da’Vida’s on the water. Overnight Meads Bay.
Day 5: Rendezvous Bay & Maundays Bay
Morning at Rendezvous Bay, a spectacular two-mile sweep of sand with views of St. Martin’s mountains across the channel. Walk the entire length of the beach—you’ll rarely see more than a handful of other people. Afternoon at Maundays Bay on the south coast, another contender for Anguilla’s most beautiful strand. This protected bay offers the calmest swimming on the island. Visit the West End for sundowners at Elvis’s Beach Bar, a beloved local institution. Overnight Meads Bay.
Day 6: Scilly Cay & Island Point
Morning boat to Scilly Cay, a tiny private island off Island Harbour. The restaurant here serves legendary grilled lobster and crayfish in the most casual setting imaginable—a thatched-roof bar on a sand cay. Swim, snorkel, and soak in the easy Caribbean rhythms. Afternoon exploring Island Harbour, Anguilla’s fishing village, where brightly colored boats bob in the bay. Visit the Anguilla Arch, a natural limestone formation, and the Fountain Cavern, one of the island’s most important Arawak archaeological sites. Farewell dinner at a cliff-top restaurant overlooking the sea. Overnight Meads Bay.
Day 7: Final Morning & Departure
Final morning swim at your favorite beach. Transfer to the ferry or airport for your departure, carrying memories of the Caribbean’s most beautiful—and still wonderfully understated—island paradise.
