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Everything taken care of, End to End.
This Itinerary Begins
With You
At Conte, no two itineraries are the same. Share what matters to you when you travel - your preferences and pace - and we’ll craft a journey that reflects you completely. Thoughtfully designed, expertly delivered, and entirely yours.
ANGUILLA
Itinerary Overview
Days 1 - 3
A Journey Through Two Islands
Days 4 - 7
BEST TIME
BEST TIME
TAILORED TRIPS
BEST TIME
Days 8 - 12
Beachfront Bliss
History Unveiled
Highlights of Your Journey
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.
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.
Day 1
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 2 - 4
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 5 - 6
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.
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.
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 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.
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.
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.
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 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.
Best Luxury Hotels in Anguilla: Conte's Seasonal Picks for 2025
Aurora Anguilla Merrywing Beach
Merrywing Bay, Anguilla
Aurora Anguilla stretches across 300 acres on the island of Anguilla, including a beachfront enclave at Merrywing Bay. The Merrywing Beach accommodations range from ocean‑view suites to private‑home‑style estate villas, all designed with comfort and elegance. Many rooms feature generous terraces or balconies, and the suites offer amenities like rainfall showers, spa‑style bathrooms, and open living spaces - perfect for families or couples looking for a relaxed Caribbean stay.
Beyond the rooms, Aurora Anguilla Merrywing Beach offers a full luxury‑resort experience. Guests enjoy beach and pool access, a water park and entertainment park, multiple restaurants and bars (including beachside dining at Breezes and fine dining at Sole di Mare), a spa, a signature 18‑hole golf course, and a variety of activities from sailing and snorkeling to pickleball and cave tours.
Quintessence Hotel
Long Bay Beach, Anguilla
Quintessence Hotel, often nicknamed “The Q” or “The Tropical Grand Mansion.”, is a luxurious mansion house hotel perched above the white sands of Long Bay Beach, with just nine suites and villas. Each villa feels like a private residence, with handcrafted furnishings, marble bathrooms, Hästens beds, and original Haitian artwork throughout.
Guests enjoy an infinity pool, a spa, tennis, a yoga pavilion, and 24‑hour butler and concierge service. Culinary offerings centre on the elegant restaurant Julians, serving French‑Caribbean “island soul food,” complemented by an award‑winning Tuscan‑style wine cellar.
ÀNI Anguilla
Little Bay Beach, Anguilla
ÀNI Anguilla is a completely private, all‑inclusive property perched on cliffs above Little Bay Beach on Anguilla’s northern coast. The property features two elegant villas, North and South, spanning 10 suites and guest rooms, and can host up to 20 guests - with rates starting from 6 suites up to the full 10, ÀNI Anguilla offers a unique, exclusive buyout property amongst some of the world's most beautiful beaches.
Your stay includes full‑board dining, free‑flowing drinks, daily spa treatments, and access to wellness, fitness and leisure amenities including a gym, tennis court, private pools, and hot tubs. Guests enjoy a range of curated experiences - from sunset cruises, night kayaking, paddle‑boarding, snorkeling and guided cycling or walking tours to cooking and cocktail‑mixology classes, kids’ activities, and even private movie‑nights under the stars.
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.
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.
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.
