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Anguilla Luxury Travel: A Sample Itinerary

Days 1 - 3

Your dual-island adventure begins in Anguilla's pristine paradise before exploring St. Kitts' volcanic heritage and Nevis' colonial charm.

Day one welcomes you to Shoal Bay East, consistently ranked among the world's finest beaches with two miles of powdery coral sand. The beach bar sunset tradition dates back to the 1980s when Anguilla first opened to tourism after decades as a quiet fishing island. Your second day combines Heritage Museum visits chronicling the journey to British Overseas Territory status in 1980 with swimming at Little Bay's cliff-sheltered waters once used by smugglers during Prohibition. Day three offers glass-bottom kayaking to Sandy Island and snorkeling coral gardens protected since marine conservation began in the 1990s, before flying to St. Kitts in the evening.

Days 4 - 7

Days four through seven explore St. Kitts' sugar plantation history and volcanic landscapes with Nevis' colonial elegance.

Your fourth day begins in Basseterre, St. Kitts' capital since 1627, exploring Independence Square where slave auctions once occurred, now a peaceful park surrounded by Georgian architecture. Ride the scenic railway built in 1912 to transport sugar cane, offering panoramic views of abandoned plantation estates. Day five ascends Mount Liamuiga, St. Kitts' dormant volcano at 3,792 feet, hiking through rainforest to the crater lake, or relaxing at peninsula beaches with luxury resort amenities. Your sixth day takes the ferry to Nevis, birthplace of Alexander Hamilton in 1755, exploring Charlestown's well-preserved colonial buildings and the Museum of Nevis History. Day seven balances Nevis Botanical Gardens' tropical beauty with afternoon spa treatments at historic plantation inns, some dating to the 17th century sugar boom.

Days 8 - 12

Your final stretch returns to Anguilla for beachfront bliss and cultural immersion before departure.

Day eight flies back to Anguilla for Road Bay rum tasting and beach BBQ featuring fresh lobster, embracing the island's fishing heritage dating to the 18th century. Day nine sails to Prickly Pear Cays for snorkeling in Marine Park waters established in 1999, followed by complete beach relaxation on uninhabited islands. Your tenth day offers wellness experiences with morning yoga and sea salt spa treatments, plus Caribbean fusion dining reflecting African, British, and French influences. Day eleven features private catamaran cruising with dolphin spotting, or horseback riding on beaches where wild horses once roamed freely. Day twelve concludes with oceanfront brunch and farewell swimming at Rendezvous Bay, carrying memories of two destinations showcasing both pristine natural beauty and rich colonial heritage spanning centuries of Caribbean history.

BEST TIME

TAILORED TRIPS

from £2500 pp, per night

Shoal Bay - Sandy Island - Meads Bay - Scilly Cay

Days 1 - 3

A Journey Through Two Islands

Days 4 - 7

History Unveiled

Days 8 - 12

Beachfront Bliss

Trip Highlights

Begin in Anguilla, unwinding on Shoal Bay East’s world-famous sands, exploring cliff-sheltered coves, and discovering the island’s transformation from quiet fishing village to boutique beach haven.

Enjoy marine adventures, from glass-bottom kayaking and snorkeling coral gardens near Sandy Island to rum tastings and BBQs that honor Anguilla’s seafaring heritage.

Dive into St. Kitts’ history, with scenic rail rides past old sugar plantations, hikes up Mount Liamuiga’s volcanic slopes, and Georgian-era architecture in Basseterre’s colonial center.

Experience Nevis’ colonial charm, visiting Alexander Hamilton’s birthplace, tranquil botanical gardens, and plantation inns turned luxury retreats on the island known for its understated elegance.

End with island indulgence, returning to Anguilla for yoga, salt spa treatments, sailing to uninhabited islets, and dolphin-spotting cruises—all framed by centuries of Caribbean cultural fusion.

Day 1

The Valley introduces Anguilla's understated luxury and pristine beaches, where this low-lying coral island maintains Caribbean authenticity without mass tourism.

Your first day explores The Valley, Anguilla's modest capital where traditional Caribbean architecture and local markets reflect the island's commitment to sustainable tourism development. With no high-rise hotels or cruise ship ports, Anguilla has preserved its character as a peaceful retreat where 15,000 residents maintain fishing and farming traditions alongside boutique hospitality that attracts discerning travelers seeking authentic Caribbean experiences.

Days 2 - 4

Days two through four showcase Anguilla's world-renowned beaches and maritime culture, from powdery white sands to boat excursions that reveal hidden coves.

Day two spends time at Shoal Bay East, consistently ranked among the world's best beaches for its 2-mile stretch of brilliant white sand and turquoise waters protected by coral reefs. The beach's pristine condition reflects Anguilla's environmental protection policies that limit development while preserving natural beauty.

Your third day explores secluded beaches accessible only by boat, where private coves and snorkeling sites remain largely undisturbed, demonstrating how Anguilla's small size (16 miles long, 3 miles wide) creates intimate connections with pristine marine environments. Day four visits heritage sites including the Anguilla Archaeological and Historical Society museum, where artifacts reveal 4,000 years of habitation from Arawak peoples through colonial periods to modern independence movements.

Days 5 - 6

Your final days embrace island exclusivity and peaceful departure preparations, epitomizing Anguilla's appeal as a tranquil Caribbean sanctuary.

Day five explores Scilly Cay, a private island where day trips include fresh lobster prepared beachside, representing the personalized service and unspoiled settings that define Anguillian hospitality. Your sixth day concludes at Meads Bay, where calm waters and powder-soft sand provide final moments of Caribbean perfection before departure from an island that has successfully balanced tourism development with environmental and cultural preservation.

BEST TIME

TAILORED TRIPS

from £2500 pp, per night

Discover The Valley

Day 1

The Valley

Days 2 - 4

Secluded Beaches

Days 5 - 6

Day Trips to Remember

Trip Highlights

Stroll through The Valley, Anguilla’s quiet capital, where low-rise charm and local markets reflect a commitment to sustainable, small-scale tourism.

Sink your feet into Shoal Bay East’s flawless white sands, consistently ranked among the world’s best beaches and protected by coral reefs and strict environmental policies.

Boat to hidden coves and snorkeling spots, where Anguilla’s compact size reveals secluded beaches and marine life in pristine, crowd-free waters.

Trace 4,000 years of island history at heritage sites and the Archaeological Museum, uncovering stories from Indigenous Arawak culture to colonial rule and modern self-governance.

Dine beachside on Scilly Cay and unwind at Meads Bay, experiencing Anguilla’s signature blend of barefoot luxury, personal hospitality, and Caribbean serenity.

Best Luxury Hotels in Anguilla: Conte's Seasonal Picks for 2025

Four Seasons Resort and Residences

Barnes Bay and Meads Bay, Anguilla

Four Seasons Resort and Residences Anguilla is an exceptional beachfront resort offering a luxurious Caribbean escape. Situated on the pristine sands of Barnes Bay and Meads Bay, the resort features spacious rooms, suites, and private residences, all with stunning ocean views. Guests can enjoy world-class dining, unwind at the spa, or take part in water activities, including snorkeling and paddle-boarding.

With its impeccable service and elegant surroundings, Four Seasons Anguilla provides the perfect balance of relaxation, adventure, and luxury, making it one of the top destinations for travellers seeking the best of the Caribbean.

Aerial view of a modern house with a pool, featuring a father and child enjoying water play under a sunny sky surrounded by lush greenery.

A serene beachfront swing bed under a modern architectural structure, overlooking turquoise waters and a distant sailboat.

A stylish restaurant with elegant tables overlooking the ocean, bathed in warm sunset light through large windows.

Aerial view of a modern resort by the turquoise sea, showcasing white buildings and lush greenery along the coastline.

Malliouhana

Meads Bay, Anguilla

Malliouhana, a Member of Small Luxury Hotels of the World, is a glamorous beachfront resort on Anguilla, offering a refined blend of Caribbean elegance and modern luxury. Set on the stunning shores of Meads Bay, the resort provides spacious rooms, suites, and private villas, all featuring beautiful ocean views and contemporary design.

Guests can indulge in gourmet cuisine, relax by the infinity pool, or enjoy various water activities. With its elegant ambiance and exceptional service, Malliouhana offers an unforgettable escape for those seeking luxury, tranquility, and world-class amenities in one of the Caribbean’s most beautiful destinations.

A luxurious white villa with a pool, surrounded by lush greenery and hills under a bright blue sky, perfect for relaxation.

A luxurious seaside view featuring a poolside with lounge chairs, turquoise waters, and a catamaran sailing in the distance.

A beautifully set outdoor dining table with string lights overlooking the ocean at sunset, surrounded by lush greenery.

Luxurious bathroom with a freestanding tub, glass shower, and modern fixtures, featuring natural light and a relaxing design.

Cap Juluca

Maundays Bay, Anguilla

Cap Juluca, A Belmond Hotel, is an renowned beachfront resort on the stunning southernmost shores of Anguilla, offering an unparalleled luxury experience. Known for its Moorish-inspired architecture, Cap Juluca provides a collection of 68 beachfront rooms, suites, and villas, all offering breathtaking views of the Caribbean Sea.

The resort features four beautiful restaurants, a full-service Guerlain spa, and a range of activities, including water sports and golf. With its laid-back elegance and personalised service, Cap Juluca is the perfect destination for those seeking a luxurious and serene getaway in one of the Caribbean’s most exclusive locations.

A serene dining area at Cap Juluca Hotel, Anguilla, with a table set for two, framed by arched columns and overlooking a sparkling blue waterfront.

A beautifully plated dish with vegetables and garnishes on a white plate, set on a wooden table with colorful pottery and utensils.

Bright hotel room featuring a cozy sofa, dining area, and beach view through large glass doors, with modern decor and natural light.

A serene beach scene in Anguilla with sun loungers, umbrellas, and a clear pool beside turquoise waters and a boat in the distance.