A Journey Through the Caribbean’s Most Captivating Contrasts
One sea, two styles. Which side of paradise are you on?
In the Caribbean, no two islands are quite alike, and that’s their appeal. Some offer barefoot luxury, others old-world charm, and some Champagne-fueled parties. When you charter a superyacht, you’re free to create the mood, whether that’s yoga at sunrise or dancing barefoot on the aft deck with a rum punch. Here, Northrop & Johnson’s charter experts break down four of the region’s most compelling island contrasts, each offering its own distinct rhythm, flavor and allure.
St. Barths or St. Lucia
A superyacht classic, St. Barths is the jewel of the French Caribbean. Effortlessly glamorous, the island is made for superyacht guests who appreciate a curated vibe and elevated energy. It’s this blend of chic sophistication and barefoot island living that has earned St. Barths a reputation as the Riviera of the Caribbean.
Chartering here means arriving in Gustavia Harbor and heading ashore to discover designer boutiques, before popping into Shellona or Nikki Beach for a rosé-fueled lunch. As the sun begins to set, it’s cocktails onboard, followed by dinner at Le Toiny or Bonito, and late-night people-watching at the Rémy Bar, Eden Roc.
If St. Barths is poised and chic, St. Lucia is raw and radiant. This Windward Island draws charterers to its untamed beauty, its twin volcanic peaks, rainforest slopes, tumbling waterfalls, and secluded coves. It’s an island for charterers seeking wellness with a wild edge. Start your day hiking the iconic Pitons or snorkeling in the protected waters off Anse Chastanet. Soak in the sulphur-rich springs, paddleboard beneath Petit Piton, or take a guided walk through the rainforest. Evenings are a quiet affair where guests can dine on the fresh catch-of-the-day onboard, or delight in local lobster and live music at a yachting crowd favorite, Sugar Beach.
Antigua or Anguilla
For those drawn to classic yachting culture, Antigua delivers. The island has long been a favorite among superyacht guests for its natural harbors, elegant beach clubs, and effortless mix of sailing heritage and luxury. With 365 beaches – one for every day of the year – and a yacht-friendly coastline of coves and sheltered anchorages, the island offers endless possibilities for cruising. Berth in Falmouth Harbour or Nelson’s Dockyard and head ashore to explore the island’s colonial past. The dockyard remains a visible symbol of England’s powerful navy, with Colonial naval buildings remaining intact. Lunch might mean grilled mahi at Catherine’s Café, followed by a quiet afternoon in the gardens of The Inn at English Harbour. Evenings bring cocktails at The Hut Little Jumby, or dinner onboard as the sun sets behind Shirley Heights.
Anguilla, meanwhile, is pure, understated beauty. With its footprint low and its beaches wide, it’s one of the Caribbean Leeward Islands’ most tranquil stops – no crowds, just white sands, turquoise waters, and a barefoot chic vibe. Anchor off Meads Bay or Little Bay and tender ashore to find beachfront grills serving just-caught lobster, or settle in for poolside cocktails at Belmond Cap Juluca. Paddleboard at sunrise, read for hours, and let the day drift by with a local rum and nothing on the agenda.
Nevis or Virgin Gorda
Nevis is the Caribbean at its most quietly refined – a historic island with substance. Drop anchor off Pinney’s Beach and tender ashore for an afternoon at the legendary Sunshine’s Beach Bar & Grill, or head inland to explore the island’s Colonial-era plantations, botanical gardens, and volcanic hot springs. History is layered into every experience here, from the birthplace of Alexander Hamilton to 18th-century sugar mills turned into elegant dining rooms. Take high tea at Montpelier Plantation & Beach, or simply enjoy the slow beauty of it all from the deck – lush hills rising behind you, golden beaches ahead, and a sense that time has stopped, just a little.
While Nevis leans into heritage, Virgin Gorda leans into effortless luxury with a barefoot edge. Part of the British Virgin Islands, it’s best known for The Baths – a stunning natural wonder of granite boulders, tide pools, and hidden caves that feels like nature’s own spa. Superyachts can drop anchor in the North Sound and tender ashore to Oil Nut Bay or the iconic Bitter End Yacht Club for a long lunch, a beachside cocktail, or a massage with a view. Days here move to island time – snorkeling over vibrant reefs, paddleboarding in sheltered bays, and dining barefoot under the stars. It’s laid back with a blend of easy charm and polished service.
Grenadines or Bahamas
A charter through the Grenadines is a lesson in slowing down. This scattering of islands stretching between St. Vincent and Grenada offers a sense of seclusion that’s increasingly rare in the Caribbean. Think anchorages with no one else in sight, mornings that begin with sunrise yoga on deck, and days spent gliding between coral reefs and desert island idylls.
Mustique brings understated glamour and quiet celebrity appeal, and invites a beach picnic or a long lunch at The Cotton House. Bequia has a sleepy charm, while the Tobago Cays deliver some of the best snorkeling in the region. The Grenadines are ideal for guests who want privacy, nature, and barefoot luxury.
By contrast, The Bahamas are made for easy days, shallow cruising, and waterborne fun. With hundreds of cays to explore, island-hopping here is effortless and scenic – from the buzzy beach clubs of Harbour Island to the crystal-clear waters and Instagram-famous pigs of the Exumas. There’s a sociability to chartering in The Bahamas. Days revolve around snorkel stops and sandbar lunches, while evenings bring sundowners on deck or dockside cocktails at places like Staniel Cay Yacht Club. It’s all about luxury with a splash of fun.
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