Barefoot Break in the British Virgin Islands

From $2,450 per person

6 days

Ship: Wind Surf

Barefoot Break in the British Virgin Islands
Windstar Cruises

The British Virgin Islands is known as the yachting capital of the Caribbean and this five-day escape shows you why. Come with us to charming islands with a laid-back attitude, places where you can still find incredible natural beauty, and colonial towns that effortlessly blend Dutch, French, and Caribbean cultures. Explore 17<sup>th</sup> century forts and duty-free shopping on St. Maarten and St. Bart. Go snorkeling or take a Jeep off-roading on mountainous Tortola. Visit the Baths on Virgin Gorda &ndash; a series of granite boulders sculpted by the sea into incredible natural pools and grottoes. And spend the night on Jost Van Dyke, enjoying the island long after the day-trippers leave &ndash; your own private paradise with postcard-pretty crescent beaches, quirky beach bars, and the famous effervescent sea water of the Bubbly Pool.

Journey Summary

  • Day 1 - Dec. 2, 2025, Tue. - Philipsburg, St. Maarten
  • Day 2 - Dec. 3, 2025, Wed. - Soper's Hole
  • Day 3 - Dec. 4, 2025, Thu. - Jost Van Dyke, Great Harbour
  • Day 4 - Dec. 5, 2025, Fri. - Jost Van Dyke, Great Harbour
  • Day 5 - Dec. 6, 2025, Sat. - Virgin Gorda / Prickly Pear, British Virgin Islands
  • Day 6 - Dec. 7, 2025, Sun. - Gustavia

Detailed Itinerary

Day-by-day description of your cruise and cruise activities.

Day 1 - December 02, 2025

Philipsburg, St. Maarten

Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.

Day 2 - December 03, 2025

Soper's Hole

Arrive at the boardwalk of Pusser&rsquo;s Landing and mingle with other yachtsmen in the utterly charming marina at Soper&rsquo;s Hole. Find a deserted stretch of beach to kick back and ponder this tiny port&rsquo;s rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away.&nbsp;

Day 3 - December 04, 2025

Jost Van Dyke, Great Harbour

For an island comprised of a mere eight square miles, it&rsquo;s 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 &nbsp;Drake Waterway. After all that, you&rsquo;ll be ready for an evening drink on the beach &mdash; where you can admire your Windstar ship aglow in the harbor.

Day 4 - December 05, 2025

Jost Van Dyke, Great Harbour

For an island comprised of a mere eight square miles, it&rsquo;s 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 &nbsp;Drake Waterway. After all that, you&rsquo;ll be ready for an evening drink on the beach &mdash; where you can admire your Windstar ship aglow in the harbor.

Day 5 - December 06, 2025

Virgin Gorda / Prickly Pear, British Virgin Islands

<ul>
<li><strong>The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Although uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called &ldquo;The Baths,&rdquo; which form huge underground pools and caverns.</strong></li>
</ul>
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<strong>Please note: only guests with shore excursions booked through Windstar can be tendered to Gun Creek.</strong>

Day 6 - December 07, 2025

Gustavia

Affectionately known as St. Barts, the Caribbean&rsquo;s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island&rsquo;s signature ti punch as kite surfers fly by.

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Dec 02, 2025

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