5 Days - Barefoot Break in the British Virgin Islands [Philipsburg, St. Maarten to Philip]
![5 Days - Barefoot Break in the British Virgin Islands [Philipsburg, St. Maarten to Philip]](/images/packages/extraimages/6744_14_5_day_bvi_sampler_12_2_2025 "5 Days - Barefoot Break in the British Virgin Islands [Philipsburg, St. Maarten to Philip]")
Starting from
$1,999*
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Ship: Wind Surf
Departure Date : Dec 02 2025
Itinerary
Day Philipsburg, Sint MaartenDepart 7:00 PM
"This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals�Marigot and Philipsburg�there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin. Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure�hiking, biking and zip lining�and amazing wildlife sightings in the sea, on land and in the sky."
"This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals�Marigot and Philipsburg�there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin. Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure�hiking, biking and zip lining�and amazing wildlife sightings in the sea, on land and in the sky."
Day Soper's Hole, Tortola, B.V.I. / Jost Van Dyke, Great Harbour, B.V.I.Arrive 8:00 AM, Depart 6:00 PM, Arrive 7:00PM
Arrive at the boardwalk of Pussers Landing and mingle with other yachtsmen in the utterly charming marina at Sopers Hole. Find a deserted stretch of beach to kick back and ponder this tiny ports rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime sunset Sail Away and cruise that glides along Sir Francis Drake Channel and on through The Narrows.
Jost Van Dyke, Great Harbour, B.V.I.
For an island comprised of a mere eight square miles, its amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, youll be ready for an evening drink on the beach where you can admire your Windstar ship aglow in the harbor.
Arrive at the boardwalk of Pussers Landing and mingle with other yachtsmen in the utterly charming marina at Sopers Hole. Find a deserted stretch of beach to kick back and ponder this tiny ports rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime sunset Sail Away and cruise that glides along Sir Francis Drake Channel and on through The Narrows.
Jost Van Dyke, Great Harbour, B.V.I.
For an island comprised of a mere eight square miles, its amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, youll be ready for an evening drink on the beach where you can admire your Windstar ship aglow in the harbor.
Day Jost Van Dyke, Great Harbour, B.V.I.Depart 10:00 PM
For an island comprised of a mere eight square miles, its amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, youll be ready for an evening drink on the beach where you can admire your Windstar ship aglow in the harbor.
For an island comprised of a mere eight square miles, its amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, youll be ready for an evening drink on the beach where you can admire your Windstar ship aglow in the harbor.
Day Virgin Gorda, Prickly Pear Beach, B.V.IArrive 8:00 AM, Depart 5:00 PM
A beautiful coral reef wavers just beneath you as your ship makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called The Baths, which form huge underground pools and caverns that youre free to explore.
A beautiful coral reef wavers just beneath you as your ship makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called The Baths, which form huge underground pools and caverns that youre free to explore.
Day Gustavia, Saint BarthelemyArrive 8:00 AM, Depart 10:00 PM
"St. Barts, a French territory in the Caribbean's Leeward Islands, is the ultimate jet-set beach destination. Its 14 pristine beaches are jewels set in sparkling waters, the cuisine is infused with a French flair and the scene is cosmopolitan chic. Other islands in the region might be casual and laid-back, but here the dress code is stylish caftans, oversize sunglasses and sky-high heels. And the preferred mode of transportation is the yacht. Gustavia, the capital and main port of St. Barts (also spelled St. Barths), embodies the island's international appeal. A former fishing village, it was named for King Gustav III of Swedenthe Swedes occupied the island in the early 19th century, leaving a legacy of names and sites. The town's winding streets are lined with high-end boutiques, excellent restaurants and plenty of bars where you can toast your visit with a glass of refreshing rosé. A handful of historic sites, including forts and a lighthouse, add to the attractions. "
"St. Barts, a French territory in the Caribbean's Leeward Islands, is the ultimate jet-set beach destination. Its 14 pristine beaches are jewels set in sparkling waters, the cuisine is infused with a French flair and the scene is cosmopolitan chic. Other islands in the region might be casual and laid-back, but here the dress code is stylish caftans, oversize sunglasses and sky-high heels. And the preferred mode of transportation is the yacht. Gustavia, the capital and main port of St. Barts (also spelled St. Barths), embodies the island's international appeal. A former fishing village, it was named for King Gustav III of Swedenthe Swedes occupied the island in the early 19th century, leaving a legacy of names and sites. The town's winding streets are lined with high-end boutiques, excellent restaurants and plenty of bars where you can toast your visit with a glass of refreshing rosé. A handful of historic sites, including forts and a lighthouse, add to the attractions. "
Day Philipsburg, Sint MaartenArrive 6:00 AM
"This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals�Marigot and Philipsburg�there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin. Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure�hiking, biking and zip lining�and amazing wildlife sightings in the sea, on land and in the sky."
"This Leeward island has been famously bisected into French and Dutch territories since 1648, and is referred to both as Saint Martin and Sint Maarten. In their respective capitals�Marigot and Philipsburg�there are ancient stone forts and candy-colored buildings lining winding streets. The Dutch side has a slightly larger population but is a bit smaller, at 34 square kilometers (13 square miles), versus the 53-square-kilometer (20-square-mile) Saint Martin. Named for its founder John Philips, Philipsburg, the capital of the Dutch side, has some excellent international art galleries, thumping discos and popular casinos. Farther afield are beautiful beaches and a seemingly endless array of nature conservancies. With them come extensive opportunities for adventure�hiking, biking and zip lining�and amazing wildlife sightings in the sea, on land and in the sky."
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