Luxury Luxury Anguilla Escape vacations

Luxury Anguilla Escape

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At a glance

? Don't forget that all of our itineraries are totally customized and so this is just an idea of what we can build for you.

Anguilla is one of the most exclusive destinations in the Caribbean. It’s a small island packed with luxury hotels and world-class beaches. As it’s so exclusive, Anguilla attracts far less tourism than some of the bigger islands so it has more of an untouched feel. Over the course of your stay, you’ll explore Anguilla’s local history and art scene, relax at top spa retreats, and take in the island’s natural beauty with time on the beach and at sea. An optional day trip to St. Maarten adds a mix of French and Dutch influences, with shopping, dining, and the famous Maho Beach experience before returning to Anguilla.

Anguilla is home to some of the most exclusive resorts in the Caribbean, and Cap Juluca, A Belmond Hotel and Four Seasons Resort Anguilla stand out as two of the island’s finest. Cap Juluca is a beachfront retreat set along the beach of Maundays Bay, where whitewashed Moorish-style villas offer direct beach access, private terraces, and direct ocean views. The resort is designed for seclusion and relaxation, with private cabanas, exceptional dining at Pimms, and a world-class spa, all just steps from the Caribbean Sea. In contrast, Four Seasons Anguilla is sophisticated and modern, set on the cliffs between Meads Bay and Barnes Bay, with a mix of elegant oceanfront rooms, private villas, and three infinity pools. Known for its contemporary design and upwardly mobile social scene, Four Seasons Anguilla gives you the full 5-star experience. Luxury and relaxation will shape any trip to Anguilla. It’s one of the best places in the Caribbean to unwind in style.

 

In detail

? Don't forget that most of our itineraries can be totally customized. Our expert team will be able to talk you through all the options.

Days 1–3: Arrival & Luxury Island Experiences

Land at Clayton J. Lloyd International Airport via private charter or a transfer from St. Maarten. A chauffeur will escort you to your five-star resort—perhaps the Four Seasons Resort Anguilla, Malliouhana, or the ultra-exclusive Cap Juluca, A Belmond Hotel. Spend your first afternoon unwinding on the pristine sands of Meads Bay Beach, where private cabanas, cocktails, and impeccable service set the tone for your stay. As the sun begins to set, head to the Sunset Lounge at Four Seasons for pre-dinner drinks before dinner.

Ease into your second day with a morning yoga session on the beach or a rejuvenating treatment at The Spa at Four Seasons. Later, venture to Shoal Bay East, widely considered Anguilla’s most breathtaking beach, where the calm Caribbean waters await. A long lunch at Tropical Sunset ensures you’re well-fed with fresh lobster and rum punch before an afternoon of pure relaxation back at your resort. As the evening sets in, slip into something elegant for a fine dining experience at Veya, a candlelit hideaway serving Caribbean fusion cuisine in a romantic treehouse-style setting.

Day three is all about adventure at a relaxed pace. Board a private luxury yacht for a day of sailing, snorkeling, and island-hopping. First stop: Prickly Pear Cays, a secluded offshore spot where crystal-clear waters and coral reefs offer the perfect snorkeling experience.

Days 1–3: Arrival & Luxury Island Experiences

Days 4–6: Exploring Anguilla

After breakfast, visit the Heritage Collection Museum, where a private guide will walk you through Anguilla’s past. Continue to Cheddie’s Carving Studio, where local artistry shines through in beautiful handcrafted sculptures. A stop at Rum & Reel for a premium rum-tasting session before heading to Blanchards Beach Shack for a casual gourmet lunch. Spend the afternoon unwinding by your resort’s infinity pool or opt for a private horseback ride along Cove Bay Beach.

Enjoy a spa morning at Zemi Thai House Spa, housed in a restored 300-year-old Thai teak house, where ancient wellness rituals are available. The afternoon is yours to enjoy at Rendezvous Bay, a stretch of soft sand ideal for unwinding in private beachfront cabanas while sipping on signature cocktails from the nearby Sunshine Shack. Come evening, let the romance of the island sweep over you with a private candlelit dinner on the beach, complete with a personal chef.

On the sixth day, set sail on a half-day catamaran excursion, stopping to explore nearby offshore cays and snorkel in hidden lagoons teeming with marine life. As dusk approaches, sip sundowners at The Cap Shack at Cap Juluca, a stylish beachfront bar, before heading to Ember, an open-fire grill restaurant where the island’s freshest seafood and prime cuts are cooked to perfection.

Days 4–6: Exploring Anguilla

Days 7–9: Private Villas, Hidden Beaches & Departure

Spend the morning at Little Bay, a small cove with breathtaking cliffs, perfect for a peaceful swim. A laid-back lunch at Elvis’ Beach Bar, famous for its fish tacos and rum punch. The afternoon is best spent unwinding at the beach. For dinner, experience Hibernia, an upscale yet intimate restaurant blending Caribbean and Asian cuisine with a great wine selection.

As your time in Anguilla nears its end, let the final full day be one of  leisure. Enjoy a long beachfront brunch at Celeste, where fresh tropical fruits, buttery pastries, and Champagne flow.

On departure day, enjoy a final dip in the infinity pool before a seamless private transfer whisks you to the airport. Whether by private charter or a first-class connection through St. Maarten, you’ll leave Anguilla in style.

Days 7–9: Private Villas, Hidden Beaches & Departure
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Further information

? Don't forget that most of our itineraries can be totally customized. Our expert team will be able to talk you through all the options.

Optional Island Hopping Excursion

A day trip from Anguilla to St. Maarten is just a short 20-minute ferry ride or 10-minute private charter flight away. Begin the day in style with a private yacht transfer over the Caribbean waters before docking at the port of Marigot, the chic French capital of the island. Stroll through its streets, stopping at Le Marché, a market filled with local crafts, spices, and fresh produce. Enjoy a gourmet French breakfast at La Croissanterie and try buttery pastries with rich coffee. Continue your journey to the Dutch side, where the cosmopolitan energy of Philipsburg offers designer shopping, beachfront bars, and a chance to experience the legendary Maho Beach, where planes fly overhead as they land at Princess Juliana Airport. For a more exclusive escape, unwind at Anse Marcel Beach, a cove tucked away from the crowds, or enjoy a long lunch at the Michelin-recommended L’Auberge Gourmande, serving refined French-Caribbean cuisine. As the sun begins to set, return to your yacht for a leisurely sail back to Anguilla.

Optional Island Hopping Excursion

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