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Peregrine Travel Centre

Across A Sea Of Idyllic Islands – Caribbean Islands Sailing from Philipsburg

Across A Sea Of Idyllic Islands – Caribbean Islands Sailing from Philipsburg

From EUR €4,155

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Description

This sailing voyage through the British Virgin Islands and the northern Lesser Antilles combines relaxed island life with elegant passages under full sail. Departing from Philipsburg, the route threads through the sheltered waters of the Sir Francis Drake Channel, calling at Virgin Gorda, Jost van Dyke, and Norman Island, where turquoise bays, granite formations, and laid-back beach culture define the experience. Days under sail offer unhurried time at sea before the journey continues to Antigua and glamorous St. Barthélemy, known for its French flair, stylish harbour, and vibrant social scene. The itinerary balances scenic sailing, distinctive island cultures, and classic Caribbean anchorages, returning to St. Maarten after a week shaped by wind, sea, and sunshine.
Some departures may have slightly modified itineraries. Please confirm the itinerary with an Expedition Specialist.

Trip Name
Across A Sea Of Idyllic Islands - Caribbean Islands Sailing from Philipsburg
Days
8
Overview
Vessel Type: Tall Ship (Sailing) Length: 105 metres Passenger Capacity: 88 Built: 2001 Sea Cloud II is a romantic tall ship that masterfully blends the elegance of classic sailing with the comfort and convenience of modern luxury. Inspired by her legendary predecessor from the 1930s, this three-masted barque is fitted with 23 sails and is hand-sailed whenever possible, adding a sense of theatre and tradition to every voyage. With 44 cabins accommodating just 88 guests, the atmosphere aboard remains intimate and relaxed, while the interiors evoke the charm of a bygone era—polished wood, sweeping staircases, and vintage nautical style—all paired with the contemporary standards of a premium expedition ship. Guests aboard Sea Cloud II enjoy spacious decks for sun-soaked sailing days, al fresco dining on the Lido Deck, and a wellness area featuring a sauna, massage therapy, and fitness facilities. The ship’s welcoming indoor spaces include an elegant dining room and a comfortable lounge for evening Recaps hosted by expert field staff such as historians and photo instructors. Meals focus on locally sourced ingredients and regional cuisine, served in an informal yet refined setting. With an open Bridge policy and wide, accessible passageways, Sea Cloud II invites guests not just to relax, but to immerse themselves fully in the experience of life under sail.

Itinerary



Day 1 - Day 1 Philipsburg, St. Maarten
Dutch 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 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 3 - Day 3 North Sound, Virgin Gorda & Great Harbour, Jost van Dyke
Explorers 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.The Sir Francis Drake Channel, where swords were once crossed, is now one of the most beautiful sailing spots. Jost van Dyke, the smallest of the main islands in the British Virgin Islands, is a mountainous volcanic object of beauty with fewer than 300 inhabitants. One of them, Foxy, has been mixing his cocktails since 1968 and the bar of the same name enjoys a legendary reputation as perhaps the most famous beach bar in the Lesser Antilles. The island's past is less reputable – it was named by a Dutch pirate. The island gives its most beautiful treasures to all who visit – fine sand, green palm trees, colorful beach bars and the luminous blue of the sea.
Day 4 - Day 4 Norman Island, British Virgin Islands
It 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 5 - Day 5 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 6 - Day 6 St. John’s, Antigua
St John’s is the capital of this small island in the Antilles, a former British colony. From Shirley Heights in the south you have a fantastic view over the English harbor and Nelson's Dockyard, an old restored shipyard named after the Admiral. Visit Betty's Hope, a restored sugar mill where "white gold" would have been processed during the island's bitter past. Now sweet black pineapples grow in the gentle rolling landscape around Boggy Peak. The coast is lined with bays and lagoons, dazzling white palm-filled beaches – one for every day of the year – and an almost unbroken coral reef.
Day 7 - Day 7 Gustavia, St. Barthélemy
St. 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 8 - Day 8 Philipsburg, St. Maarten
Dutch 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 9 - Please note:
Itineraries are subject to change. 

Trip Dates

StartEndPrice FromRoom Type
29-11-202606-12-2026EUR €4,870Category E: Superior Cabins, Outside. From
29-11-202606-12-2026EUR €5,720Category D: De Luxe Cabins, Outside. From
29-11-202606-12-2026EUR €5,950Category F: Superior Single Cabins, Outside. From
29-11-202606-12-2026EUR €6,570Category C: De Luxe Lido Cabins, Outside. From
29-11-202606-12-2026EUR €7,760Category B: Junior Suites With Balcony. From
29-11-202606-12-2026EUR €8,780Category A: Suites With Balcony. From
14-12-202621-12-2026EUR €7,760Category B: Junior Suites With Balcony. From
14-12-202621-12-2026EUR €8,780Category A: Suites With Balcony. From
14-12-202621-12-2026EUR €4,870Category E: Superior Cabins, Outside. From
14-12-202621-12-2026EUR €5,720Category D: De Luxe Cabins, Outside. From
14-12-202621-12-2026EUR €5,950Category F: Superior Single Cabins, Outside. From
14-12-202621-12-2026EUR €6,570Category C: De Luxe Lido Cabins, Outside. From
04-01-202711-01-2027EUR €4,580Category E: Superior Cabins, Outside. From
04-01-202711-01-2027EUR €5,380Category D: De Luxe Cabins, Outside. From
04-01-202711-01-2027EUR €5,600Category F: Superior Single Cabins, Outside. From
04-01-202711-01-2027EUR €6,180Category C: De Luxe Lido Cabins, Outside. From
04-01-202711-01-2027EUR €7,300Category B: Junior Suites With Balcony. From
04-01-202711-01-2027EUR €8,260Category A: Suites With Balcony. From
18-01-202725-01-2027EUR €4,870Category E: Superior Cabins, Outside. From
18-01-202725-01-2027EUR €5,720Category D: De Luxe Cabins, Outside. From
18-01-202725-01-2027EUR €5,950Category F: Superior Single Cabins, Outside. From
18-01-202725-01-2027EUR €6,570Category C: De Luxe Lido Cabins, Outside. From
18-01-202725-01-2027EUR €7,760Category B: Junior Suites With Balcony. From
18-01-202725-01-2027EUR €8,780Category A: Suites With Balcony. From
05-12-202712-12-2027EUR €4,752Category E: Superior Cabins, Outside. From
05-12-202712-12-2027EUR €5,474Category D: De Luxe Cabins, Outside. From
05-12-202712-12-2027EUR €5,831Category F: Superior Single Cabins, Outside. From
05-12-202712-12-2027EUR €6,248Category C: De Luxe Lido Cabins, Outside. From
05-12-202712-12-2027EUR €7,378Category B: Junior Suites With Balcony. From
05-12-202712-12-2027EUR €8,492Category A: Suites With Balcony. From
27-03-202803-04-2028EUR €4,155Category F Upper/Lower Beds. From
27-03-202803-04-2028EUR €4,905Category E. From
27-03-202803-04-2028EUR €5,595Category D. From
27-03-202803-04-2028EUR €5,830Category C. From
27-03-202803-04-2028EUR €6,425Category B. From
27-03-202803-04-2028EUR €7,380Category A. From

Inclusions

    • French Flair, Dutch Charm: See cultures come together in inspiring ways on the shared island of St. Maarten.
    • Celeb-Packed Paradise: St. Barths calls all A-listers with VIP beaches, high-end shopping, and luxe private parties.
    • The Baths: Float in Virgin Gorda’s tidal pools and grottoes, formed from granite boulders on a picturesque beach.
    • It’s a Yachtie Life: Indulge in the Virgin Islands’ carefree customs of beach, bar, and sea.

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