Anguilla Barefoot Luxury & Beach Bliss — 6 Days 33 Beaches Discovery

Tour Overview

Itinerary Highlights

Day 1: Arrival in Anguilla — Meads Bay Sunset & Welcome Dinner

Arrive in Anguilla via ferry from St. Martin (a scenic 25-minute crossing) or direct flight to Clayton J. Lloyd International Airport. Your private driver meets you with a signature Anguillian rum punch — the island’s official welcome drink — and transfers you along coastal roads to your luxury beachfront resort on Meads Bay. As you arrive, the view stops you in your tracks: a mile of perfect white sand curving into impossibly turquoise water, with the silhouette of St. Martin on the distant horizon. After settling into your ocean-view suite with private terrace, take your first barefoot walk along Meads Bay — this is Anguilla, where shoes are optional and the sand is so fine it squeaks underfoot. At sunset, the beach transforms as the sky explodes in shades of pink, orange, and gold behind the neighboring island. Welcome dinner at Blanchards Beach Shack, an Anguillian institution founded by American expats whose story of leaving everything behind to open a restaurant on this tiny island became a bestselling book. Overnight at your Meads Bay resort.

Day 2: Shoal Bay East — The World’s Best Beach

After a leisurely breakfast overlooking the sea, drive across the island to Shoal Bay East, the 2-mile stretch of white sand consistently ranked among the world’s top beaches by Travel + Leisure, Conde Nast Traveler, and TripAdvisor. The water here displays an almost artificial spectrum of blues — pale aquamarine near shore deepening to electric turquoise and cobalt at the reef line. Settle onto loungers at one of the beach bars that dot the shore, where you can alternate between swimming in the crystal-clear water, snorkeling the vibrant reef that runs parallel to the beach, and enjoying fresh cocktails delivered to your lounger. Lunch at Gwen’s Reggae Grill, a beloved beachside institution serving jerk chicken, grilled lobster, and strong rum punches to the soundtrack of Bob Marley — the essence of laid-back Anguillan spirit. In the afternoon, explore the remnants of an old sea salt industry at Road Bay, and visit the tiny Wallblake House (1787), the oldest building on the island and a rare surviving plantation house with intact slave quarters that tell a more complete story of Anguilla’s history. Return to Meads Bay for another legendary sunset. Dinner tonight at Jacala, where French-trained chef Alain Laurent serves exquisite French-Caribbean cuisine at tables set directly on the sand under swaying coconut palms.

Day 3: Private Boat Expedition — Prickly Pear, Sandy Island & Offshore Cays

Today is your private boat expedition day to Anguilla’s offshore treasures. After breakfast, board your private motor yacht at the resort’s dock and set course for Prickly Pear Cays, a pair of uninhabited islands 8 miles northwest of Anguilla. These cays sit atop a vast submerged reef system offering some of the best snorkeling in the Eastern Caribbean — the visibility here often exceeds 30 meters (100 feet), revealing gardens of elkhorn coral, sea fans, and schools of blue tangs, snappers, and parrotfish. Your crew will grill fresh-caught lobster and fish right on the boat’s deck while you swim, snorkel, or simply float in the warm Caribbean water. Continue to Sandy Island, a tiny palm-fringed sandbar that appears at low tide — there’s nothing here but white sand, turquoise water, and a single rustic restaurant serving grilled seafood and rum punches. This is the Anguilla of postcards and daydreams: wade through knee-deep water to your private picnic spot on the sandbar’s tip, where you can look in every direction and see only sea and sky. As you sail back to Meads Bay in the late afternoon, keep watch for dolphins that frequently play in the boat’s wake. Return to your resort with the evening at leisure — your concierge can arrange a casual dinner at a local roadside BBQ stand for some of the island’s best authentic cooking.

Day 4: Rendezvous Bay, The Valley & Artisan Trail

Spend the morning at Rendezvous Bay, a spectacular 2-mile crescent of beach offering postcard-perfect views of St. Martin across the channel. The calm, shallow waters here extend for hundreds of meters — perfect for a long walking wade where the water never rises above your waist. Visit the mid-point of the bay where the legendary Dune Preserve, banker turned reggae musician Bankie Banx’s driftwood-built beach bar, once stood as one of the world’s most famous beach bars. Continue to The Valley, Anguilla’s diminutive capital — more a sleepy village than a city, with brightly painted government buildings and the charming St. Gerard’s Catholic Church with its distinctive stone facade. Visit the Anguilla Tourist Board’s artisan shop for locally made sea salt, hot sauces, and handcrafted jewelry, then explore the island’s burgeoning street art scene — colorful murals by local artists adorn walls throughout The Valley, celebrating Anguillian heritage, sea life, and island culture. Lunch at Falcon’s Nest, the island’s beloved roti shop where you’ll taste authentic Anguillian home cooking. In the afternoon, visit the historic salt ponds between Road Bay and Sandy Ground, where salt was harvested for export until the 1980s, and learn about this industry that once dominated island life. Return to your resort for sunset and dinner at Straw Hat, an elegant over-water restaurant on Meads Bay’s northern end known for its seafood and signature frozen mojitos.

Day 5: Little Bay, Crocus Bay & Sea-to-Table Cooking Experience

Start the morning with a journey to Little Bay, one of the Caribbean’s most dramatically beautiful hidden beaches — accessible only by boat or by climbing down a rope from the cliff top. Your boat captain will drop you on this tiny cove enclosed by 50-foot limestone cliffs, where the water is impossibly clear and pelicans dive for their breakfast just offshore. Spend some of the morning snorkeling among the cliffs where parrotfish, butterflyfish, and occasional sea turtles inhabit the rocky crevices. Continue by boat to Crocus Bay, a peaceful stretch of beach popular with locals for its calm waters and relaxed vibe. Here you’ll find Da’Vida, a beachfront restaurant where you’ll participate in a sea-to-table cooking experience — start by meeting the local fishermen returning with the morning’s catch, select your fish or lobster, and then join the chef in the open-air kitchen to learn the techniques behind Anguilla’s legendary seafood dishes. Prepare and enjoy your own lunch as your reward. In the afternoon, visit Katouche Bay, a wild and remote beach where fossilized coral cliffs reveal the island’s geological history and natural caves offer the adventurous a glimpse of Anguilla underground. The day’s final stop is Barnes Bay, an elegant crescent of sand that serves as the eastern bookend to Meads Bay — quiet, refined, and the perfect spot for your last Anguillian sunset. Farewell dinner at Veya, the island’s most acclaimed fine dining restaurant hidden in a tropical garden, where Chef Carrie Bogar creates a magical ‘Omakase-style’ dinner menu that changes daily based on what fishermen and farmers deliver that morning.

Day 6: Morning Swim & Departure

Wake up to the sound of gentle waves on your final morning in paradise. Take one last swim in the crystal-clear water of Meads Bay as the morning sun warms the sand, then enjoy a final breakfast on your terrace overlooking the sea. Pack a bag of Anguillian sea salt and local hot sauce from the resort’s boutique — the flavors that will remind you of this island long after you’ve returned home. Your driver transfers you to the ferry terminal or airport for your departure. As Anguilla recedes in the distance — that flat, coral-limestone island with its halo of white beaches and turquoise water — you’ll understand why those who discover Anguilla return again and again. Unlike its flashier Caribbean neighbors, Anguilla’s luxury is quiet, confident, and genuinely welcoming. Your tour concludes upon arrival at your connecting hub.

Included

• 5 nights at a luxury beachfront boutique resort on Meads Bay (ocean-view suite with private terrace)
• Daily breakfast at the resort
• Private full-day motor yacht expedition to Prickly Pear Cays and Sandy Island with gourmet BBQ lunch (Day 3)
• Half-day boat excursion to Little Bay and Crocus Bay (Day 5)
• Sea-to-table cooking experience with lunch at Da’Vida (Day 5)
• Welcome dinner at Blanchards Beach Shack
• Farewell dinner at Veya Restaurant (Day 5)
• All land transportation on Anguilla in private vehicle with driver
• Airport/ferry arrival and departure transfers with welcome rum punch
• Snorkeling equipment for all boat excursions
• English-speaking local guide throughout

Excluded

• International flights to/from St. Martin or Anguilla
• Ferry between St. Martin and Anguilla (~$60 per person round trip)
• Lunches on Days 1, 2, and 4 (except where specified)
• Dinners on Days 3 and 4 (wide range of excellent beachfront restaurants available)
• Alcoholic beverages at restaurants (except welcome rum punch and two included dinners)
• Travel insurance (mandatory)
• Tips and gratuities for guides, boat crew, and drivers
• Spa services at resort
• Personal purchases and souvenirs

Why Choose This Tour

• Visit Shoal Bay East — consistently voted one of the world’s top 5 beaches by Travel + Leisure, Conde Nast Traveler
• 33 pristine white sand beaches on a tiny 16-mile island — more beaches per square mile than almost anywhere on Earth
• Private motor yacht expedition to Prickly Pear and Sandy Island — your own lobster grill on a deserted sandbar
• Sea-to-table cooking experience with local chef — choose your catch and learn to prepare it
• Recognized as the “Culinary Capital of the Caribbean” — more top-quality restaurants per capita than many major cities
• No crowds, no cruise ships, no high-rise hotels — Anguilla’s intentional underdevelopment is its greatest luxury
• Two fine dining dinners included: Blanchards Beach Shack and Veya (ranked best restaurant in the Caribbean by multiple publications)
• Genuine Caribbean charm — locals greet you by name by day two; this is authentic island hospitality
• Perfect for couples and honeymooners seeking romance, privacy, and uncrowded perfection
• Discover the Caribbean as it was 50 years ago — before mass tourism discovered the rest of the islands