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Panoramic view from Shirley Heights, Antigua, showing English Harbor and Caribbean landscape

Pirate Islands With A Yachtie Vibe

Philipsburg Roundtrip - Example 8 Day Cruise aboard Sea Cloud Spirit
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Board the Sea Cloud Spirit on this 8-day Caribbean cruise departing from Philipsburg, St. Maarten, where Dutch and French cultures meet near Great Bay Beach and the Boardwalk. You explore Gustavia in St. Barths with its colonial facades and elegant harbor, then St. John’s, Antigua, visiting Shirley Heights, Nelson’s Dockyard, and Betty’s Hope amid white-sand beaches and coral reefs. In the British Virgin Islands, you navigate the Sir Francis Drake Channel, discover Virgin Gorda’s granite boulders at The Baths, and anchor at White Bay and Great Harbor on Jost van Dyke. You finish with Norman Island, famed for pirate legends, before returning to Philipsburg.
A white beach swing over clear turquoise water on Norman IslandExplore the famous rock formations of the bathsExplore beautiful Jost van DykeGustavia Harbor in St. BarthsPanoramic view from Shirley Heights, Antigua, showing English Harbor and Caribbean landscape
Highlights
  • Stroll through Gustavia’s charming colonial streets
  • Take panoramic views from Shirley Heights in Antigua
  • Explore The Baths’ tidal pools and granite grottoes on Virgin Gorda’s beach
  • Cruise the scenic Sir Francis Drake Channel
  • Experience the Virgin Islands’ carefree beach, bar, and sailing lifestyle
Activity Level: Variable
Activity options vary depending on destination and operator. Activity level is determined by the range and intensity of activities you choose to participate in. Discuss with your Trip Planner which options are best for you.
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Full Itinerary

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Day 1: Philipsburg, St. Maarten | Embark

Embark in St. Maarten, an island split between Dutch and French territories. In Philipsburg, relax on the sandy Great Bay Beach and stroll along the Boardwalk with its restaurants. Explore the town’s shops and colorful streets just steps from the shore.

Day 2: Gustavia, St. Barthélemy

Visit St. Barths, a small Caribbean island known for its luxury and relaxed lifestyle. Walk through Gustavia’s streets with colonial buildings, browse the shops, or have a drink in the harbor’s bars and restaurants. The island is popular with travelers looking for a quiet, stylish getaway.

Day 3: At Sea

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 4: 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 5: North Sound, Virgin Gorda

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.

Day 6: North Sound, Virgin Gorda

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.

Sail through the Sir Francis Drake Channel

White Bay, Jost van Dyke
The Sir Francis Drake Channel, where swords 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.

Great Harbor, Jost van Dyke
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 7: 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 8: Philipsburg, St. Maarten | Disembark

  • 1 Breakfast
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.

Ship/Hotel

Sea Cloud Spirit

Sea Cloud Spirit
Sea Cloud Spirit Fitness Area
Sea Cloud Spirit Fitness Area

Dates & Prices

My Preferred Start Date

Per person starting at
$6,995 2-3 travelers
Superior single cabins, outside
Superior Single Stateroom
Superior Single Cabins (approx. 140 sq. ft.) are equipped with a built-in single bed, closet chair, and dressing table. The bathroom is equipped with a shower and golden fixtures. These are located on the Cabin Deck.
Superior cabins, outside
Superior
Superior stateroom (approx. 183 sq. ft.) is equipped with a California king bed (2 mattresses), seating with table, closet, seating with table, and dressing table. The spacious bathroom is equipped with a shower and golden fixtures. These cabins have portholes and are located on the Cabin Deck.
De luxe cabins, outside
Deluxe Stateroom
Deluxe Cabins (approx. 215 sq ft) are equipped with a California king bed, 71 in. x 79 in. (2 mattresses), a small comfortable sitting corner with a chair or couch and a table as well as a dressing table, bureau and wardrobe. The spacious bathroom is equipped with a sink, shower and WC. These cabins have portholes and are located on the Cabin Deck.
De luxe lido cabins, outside
Grand Stateroom
Grand Stateroom (approx. 194 sq. ft.) is equipped with a double bed (two single beds), closet, chair with table, dressing table, WiFi, TV, telephone, hair dryer, minibar, coffee machine, and safe. The spacious bathroom is equipped with a shower and golden fixtures. These cabins are located on the Lido Deck.
Junior suites with balcony
Junior Veranda Suite
Junior Veranda (approx. 237 sq. ft.to 65 sq. ft. including balcony) is located on the Veranda deck and offers a private balcony and twin arched windows. The cabins include a California king bed, walk-in closet, sofa, chair with table, dressing table, WiFi, TV, telephone, hair dryer, minibar, coffee machine, and safe. The bathroom is equipped with a shower, bathtub, and golden fixtures.
Suites with balcony
Veranda Suite
Veranda Suites are located on the Veranda Deck, approximately 301 sq. ft. of luxury living space with an 86 sq. ft. balcony. Features include a marble bathroom with shower, bathtub, and golden fixtures, along with a California king bed, walk-in closet, L-shaped sofa with full-sized fold-out bed, dressing table, WiFi, TV, telephone, hair dryer, minibar, coffee machine, and safe.

Notes

Rates are based on double occupancy. A limited number of cabins can be booked for individual use for an additional charge.
Included
  • 7 Breakfasts, 6 Lunches, 7 Dinners
  • 7 Nights Accommodations
  • Accommodations as listed
  • Ground transportation as listed
  • Activities as listed
  • Meals as listed
  • Access to a 24-7 Emergency line while traveling
  • Gratuities
  • Port Fees
  • Welcome and Farewell Cocktails   
  • Welcome champagne in the suite/stateroom
  • Daily fresh fruit basket in suite/stateroom
  • All coffee, tea specialties and soft drinks
  • Bottled water on the excursions
  • Fine wines from renowned winemakers
  • Open bar (except premium brands)
  • Beach barbecues in select destinations
  • Marina platform with use of water sports equipment such as snorkel gear, stand-up paddleboards, and towable tube (weather permitting)
  • Laundry service in suites
  • Curated moments
  • All meals including nightly 4-course menu and a 5-course gala dinner
  • WIFI: You can use your own laptop to access the Internet with an access code (WI-FI). Data volume of 10 GB is free of charge; additional data volume can be obtained from the reception desk at a charge.
  • One excursion in each port
Excluded
  • Travel Insurance
  • Personal Expenses
  • Flight costs (please request a quote)
  • Additional excursions during free time
  • Fuel and transportation surcharges (when applicable)

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The trip was terrific with great planning on your part. Most of the adventures were not mainstream and somewhat off the beaten path which made it especially enjoyable!! We felt taken care of and you all were readily available to respond to questions and issues. I would highly recommend your company and friends have already expressed interest based on our pictures and excitement.
Gale Cantor

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