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Pirate Bays & Jet-Set Harbors Await – Caribbean Sailing Cruise

Pirate Bays & Jet-Set Harbors Await – Caribbean Sailing Cruise

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Description

Sail through the warm trade winds of the Lesser Antilles, beginning and ending in Philipsburg, St. Maarten. Experience the laid-back charm of Virgin Gorda and the Îles des Saintes, where beach bars and stunning coastal views await. Discover the unique tidal pools and grottoes of Virgin Gorda’s Baths, and immerse yourself in the glamorous atmosphere of St. Barths with its VIP beaches and high-end shopping. Martinique offers a taste of colonial elegance in the town of Saint-Pierre, set against the backdrop of a volcanic landscape. This journey blends relaxation with luxury and scenic exploration.

Trip Name
Pirate Bays & Jet-Set Harbors Await - Caribbean Sailing Cruise
Days
10
Overview
Vessel Type: Tall Ship (Sailing) Length: 109 metres Passenger Capacity: 64 Built / refurbished: 1931 / 2011 Sea Cloud is a ship with a soul, imbued by the original owners, Marjorie Merriweather Post and her husband E.F. Hutton in the 1930’s. The ship has played host to royalty, known service in wartime, and sailed the world over. She is a vessel of incomparable grace that harks back to the golden age of ship travel. Once you’ve been on Sea Cloud under full sail, you’ll begin your own love affair. Welcome aboard a legend Sea Cloud accommodates 58 guests in 28 outside cabins including two original owner’s suites that still feature original marble baths and fireplaces. At 360 feet she is an expansive ship with extensive public spaces on the top deck, where we luxuriate in deck chairs and watch the crew of 18 go aloft in the web of riggings to hand-set her 30 sails. Her dining room is hung with marine oil paintings of the period and accommodates all guests at once for a single seating. We’ll gather in the lounge each evening for Recap. Life aboard is a uniquely pleasing mix of elegance and informality—a return to the golden age of sailing in shorts and deck shoes. You’ll find all shipboard services impeccable.  Discover the romance of tall ship sailingExperience something many people don’t know exists in the 21st century—the romance of life under square sails. Discover the thrill of standing on deck as Sea Cloud gently glides through the water, her crew aloft in the riggings, running out and reefing sails. Settle in to your favorite areas on the top deck and bask in the incomparable experience of traveling aboard the finest tall ship to ever sail the seas. Lose yourself in an adventure that, in this day and age, is almost unimaginable. Please note deck and suite plans are indicative only and may vary slightly.

Itinerary



Day 1 - Day 1 Philipsburg, St. Maarten
Departure 7:00 pmDutch in the south, French in the north – on St. Maarten you will find an unusual piece of Europe in the middle of the Caribbean. Because of the natural salt deposits, the Dutch West India Company once claimed the island for itself and – according to legend – divided the island up in 1648 after a drinking competition with the French. In the colorful port city of Philipsburg, a day at the beach can be perfectly combined with a stroll through town: From the fine sandy Great Bay Beach it is only a stone's throw to the Boardwalk with its restaurants and to the boutiques of the small city center.
Day 2 - Day 2 North Sound, Virgin Gorda
Arrival 1:00 pm, Departure 11:00 pmExplorers once used to cross swords in the Sir Francis Drake Channel. Nowadays the sea around the British Virgin Islands is one of the world's best sailing areas. Heavenly bays, gorgeous beaches, idyllic anchoring spots, smart yacht clubs and charming little beach bars make the island a popular haunt for sailors. On Virgin Gorda, once called "The Fat Virgin" by Columbus due to its shape, you can find "The Baths", one of nature's most beautiful oddities, in the National Park. Ground to a sphere and polished to a shine, the huge granite formations on the beach and in the water create a multi-branched labyrinth of giant boulders.
Day 3 - Day 3 Norman Island/British Virgin Islands
Arrival 8:00 am, Departure 6:00 pmIt almost seems as if no other career choice than pirate was possible in the 17th and 18th centuries in the British Virgin Islands. Jost van Dyke, Blackbeard, Francis Drake – they all went on the prowl in the Dream Territory during the golden age of privateering. Norman Island was named after the pirate captain Norman, who allegedly hid his treasures here, and inspired Robert Louis Stevenson to write his adventure novel “Treasure Island”. If you dig a little in the fine sand on the uninhabited private island today, you probably won’t discover any gold coins, but you will discover an equally valuable treasure: deep, Caribbean relaxation.
Day 4 - Day 4 Gustavia, St. Barthélemy
Arrival 4:00 pmSt. Barthélemy, affectionately known as St. Barths by most, already had many "owners" before the Lesser Antilles were acquired by France in 1877. When the first estate was acquired by the banker David Rockefeller in 1957, the island's future was finally sealed. It became a refuge for the international jet set and an elegant holiday paradise for many Hollywood stars. For over 40 years, St. Barths has cultivated a luxurious lifestyle with a Caribbean laissez-faire approach. You can stroll through the charming main town of Gustavia, whose beautifully restored houses and colonial facades look out over the sea with its elegant superyachts, browse in the shops for precious items, or enjoy a sundowner in the picturesque harbor surrounded by clusters of high class bars and restaurants.
Day 5 - Day 5 Gustavia, St. Barthélemy
Departure 11:00 pmSt. Barthélemy, affectionately known as St. Barths by most, already had many "owners" before the Lesser Antilles were acquired by France in 1877. When the first estate was acquired by the banker David Rockefeller in 1957, the island's future was finally sealed. It became a refuge for the international jet set and an elegant holiday paradise for many Hollywood stars. For over 40 years, St. Barths has cultivated a luxurious lifestyle with a Caribbean laissez-faire approach. You can stroll through the charming main town of Gustavia, whose beautifully restored houses and colonial facades look out over the sea with its elegant superyachts, browse in the shops for precious items, or enjoy a sundowner in the picturesque harbor surrounded by clusters of high class bars and restaurants.
Day 6 - Day 6 Day under full sails
Climbing the rigging, untying ropes, setting sails – today is all about sailing. Time to lean back and relax in the deck chair and watch the passionate crew hoisting the sails by hand.
Day 7 - Day 7 Saint-Pierre, Martinique
Arrival 8:00 am, Departure 1:30 pmThe 'Paris of the Islands,' the 'Pearl of the Antilles,' or the 'Venice of the Tropics' – Saint-Pierre in the northwest of the French dream island Martinique has always inspired romantic comparisons. Founded in 1635, the city at the foot of the volcanic mountain Pelée flourished due to sugar and slave trade, becoming the economic and cultural center of the island. Prosperity continued until 1902 when Pelée erupted, destroying Saint-Pierre and burying 30,000 people under lava, embers, and ash. Today, the coastal town is officially classified as a 'City of Art and History': In addition to the ruins of the theater and the old church, the intricate buildings of the Chamber of Commerce and the cathedral are worth a visit.
Day 8 - Day 8 Terre-de-Haut, Îles des Saintes
Arrival 8:00 am, Departure 1:00 pmÎles des Saintes is a small archipelago that was disputed for a long time until it finally became French in 1816. In the charming main town of Terre-de-Haut, take a delightful stroll along the waterside promenade. Boutiques, cafés, bars and restaurants invite you to browse and spend some time here. The savoir vivre takes place against a backdrop lit up in all the pastel shades of the Caribbean. Fort Napoleon is set high above the bay and your climb up to it is rewarded by a spectacular panoramic view. On the other side of the island, the Plage de Pompierre invites you to enjoy a dip in the sea and sunbathe on the beach.
Day 9 - Day 9 Road Bay/Anguilla
Arrival 2:00 pm, Departure 7:00 pmAnguilla is one of the Leeward Islands in the Lesser Antilles, a British Overseas Territory that also includes several small, uninhabited coral islands. This small island is host to more than 30 superb beaches protected by coral reefs. Enjoy the turquoise blue sea and white sandy beaches of Road Bay as you swim against a backdrop of palm trees.
Day 10 - Day 10 Philipsburg, St. Maarten
Arrival 8:00 amDutch in the south, French in the north – on St. Maarten you will find an unusual piece of Europe in the middle of the Caribbean. Because of the natural salt deposits, the Dutch West India Company once claimed the island for itself and – according to legend – divided the island up in 1648 after a drinking competition with the French. In the colorful port city of Philipsburg, a day at the beach can be perfectly combined with a stroll through town: From the fine sandy Great Bay Beach it is only a stone's throw to the Boardwalk with its restaurants and to the boutiques of the small city center.
Day 11 - Please note:
Itineraries are subject to change.

Trip Dates

StartEndPrice FromRoom Type
02-03-202511-03-2025Array Array4,985GTY Double Cabin. From
02-03-202511-03-2025Array Array5,665Category 5. From
02-03-202511-03-2025Array Array6,655Category 4. From
02-03-202511-03-2025Array Array7,645Category 3. From
02-03-202511-03-2025Array Array8,285Category 2. From
02-03-202511-03-2025Array Array8,725Category 1. From
02-03-202511-03-2025Array Array10,045Category C. From
02-03-202511-03-2025Array Array10,695Category B. From
02-03-202511-03-2025Array Array11,445Category A. From
11-03-202520-03-2025Array Array5,665Category 5. From
11-03-202520-03-2025Array Array6,655Category 4. From
11-03-202520-03-2025Array Array7,645Category 3. From
11-03-202520-03-2025Array Array8,285Category 2. From
11-03-202520-03-2025Array Array8,725Category 1. From
11-03-202520-03-2025Array Array10,045Category C. From
11-03-202520-03-2025Array Array10,695Category B. From
11-03-202520-03-2025Array Array11,445Category A. From
11-03-202520-03-2025Array Array0Bucket Regatta Departure
11-03-202520-03-2025Array Array4,985GTY Double Cabin. From

Inclusions

    • Where the Yachties Meet: Check out the laid-back beach bars of Virgin Gorda and the Îles des Saintes.
    • The Baths: Float in Virgin Gorda’s tidal pools and grottoes, formed from granite boulders on a picturesque beach.
    • Celeb-Packed Paradise: St. Barths calls to all A-listers with VIP beaches, high-end shopping, and luxe private parties.
    • At the Foot of the Volcano: Martinique charms with its colonial town of Saint-Pierre.

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