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Beach Fun & Sun: A Remote Caribbean Getaway

Fares from

£2,879pp


Port to Port Philipsburg to Philipsburg
Departure date / Duration 14th February 2026, 7 nights
Yacht Name Wind Spirit
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Itinerary

Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in.Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from Windstar’s onboard Watersports Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar takes you to the secret beaches and invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.


Day to Day Itinerary

Date Country Port
Day 1 Sint Maarten (Dutch part) Philipsburg
Day 3 Anguilla Road Bay
Day 4 British Virgin Islands Sopers Hole, Tortola
Day 4 British Virgin Islands Great Harbour, Jost Van Dyke
Day 5 British Virgin Islands Great Harbour, Jost Van Dyke
Day 7 Saint Barthélemy Gustavia
Day 8 Sint Maarten (Dutch part) Philipsburg

Alternative Dates

Departing Arrives Price per person  
19th December 2026 from Philipsburg 26th December 2026 into Philipsburg from £ 2,212pp
2nd January 2027 from Philipsburg 9th January 2027 into Philipsburg from £ 1,913pp
16th January 2027 from Philipsburg 23rd January 2027 into Philipsburg from £ 2,137pp
30th January 2027 from Philipsburg 6th February 2027 into Philipsburg from £ 1,988pp
13th February 2027 from Philipsburg 20th February 2027 into Philipsburg from £ 2,063pp
27th February 2027 from Philipsburg 6th March 2027 into Philipsburg from £ 2,137pp
13th March 2027 from Philipsburg 20th March 2027 into Philipsburg from £ 1,988pp
28th March 2026 from Philipsburg 4th April 2026 into Philipsburg from £ 2,884pp
7th March 2026 from Philipsburg 14th March 2026 into Philipsburg from £ 2,585pp
4th January 2026 from Philipsburg 11th January 2026 into Philipsburg from £ 1,977pp
28th December 2025 from Philipsburg 4th January 2026 into Philipsburg from £ 3,631pp
14th December 2025 from Philipsburg 21st December 2025 into Philipsburg from £ 1,541pp
21st February 2026 from Philipsburg 28th February 2026 into Philipsburg from £ 3,103pp
31st January 2026 from Philipsburg 7th February 2026 into Philipsburg from £ 2,805pp
24th January 2026 from Philipsburg 31st January 2026 into Philipsburg from £ 2,656pp