STAR COLLECTOR: LEEWARD & WINDWARD CARIBBEAN HAVENS on Wind Surf
Photo Credit: Roger Paperno
Little ports, remote reaches and sincere island pleasures exclusive to small-ship cruising beckon during this two-week exploration of the Caribbean’s Windward and Leeward Islands. Take the wheel of a 4x4 buggy and follow dirt roads along the rural outskirts of Falmouth Harbour on Antigua. Sail from Gustavia to remote Colombier Bay and swim or sunbathe among anchored mega yachts prior to elegant snacks and cocktails. Stroll amid brightly painted shops and beach boutiques along the palm-lined shores of Soper’s Hole in Tortola, or relax and sip sweet, rum-flavored cocktails at a waterfront café. Sit back in airy rattan furniture as you ride a refurbished railcar along a century-old narrow-gauge railway on St. Kitts. Take an ATV tour along deserted roads and abandoned villages near Foxes Bay and hear memories of life before the Montserrat Volcano eruption. Scan the horizon for breaching whales as your catamaran captain and crew sail into former whaling waters off Dominica.
About Wind Surf
About Windstar Cruises
THE WORLD'S BEST SMALL SHIP CRUISE LINE
NO ONE ELSE GOES SO FAR TO GET TRAVELERS SO CLOSE …
You’re closer to secluded coves, tiny villages, misty fjords. To ancient ruins, medieval alleyways, quaint marinas. To unspoiled beaches, unfamiliar cultures, undiscovered atolls. To enlivening your curiosity and awakening your sense of wonder. You’re closer than ever to the kind of authentic and unforgettable experiences that you travel to find in the first ...
NO ONE ELSE GOES SO FAR TO GET TRAVELERS SO CLOSE …
You’re closer to secluded coves, tiny villages, misty fjords. To ancient ruins, medieval alleyways, quaint marinas. To unspoiled beaches, unfamiliar cultures, undiscovered atolls. To enlivening your curiosity and awakening your sense of wonder. You’re closer than ever to the kind of authentic and unforgettable experiences that you travel to find in the first ...
Jan 04, 2026 through
Jan 18, 2026
Dec 29, 2025
7:00 PM
Category b
Inside
Outside
Balcony
Suite
8404911
|
Itinerary
Day | Port | Arrive | Depart |
---|---|---|---|
1 | Philipsburg, St. Maarten | 7:00 PM | |
2 | Falmouth Harbour | 8:00 AM | 6:00 PM |
3 | Road Bay | 8:00 AM | 6:00 PM |
4 | Jost Van Dyke, Great Harbour | 7:00 PM | |
4 | Soper's Hole | 8:00 AM | 6:00 PM |
5 | Jost Van Dyke, Great Harbour | 10:00 PM | |
6 | Virgin Gorda / Prickly Pear, British Virgin Islands | 8:00 AM | 5:00 PM |
7 | Gustavia | 8:00 AM | 10:00 PM |
8 | Philipsburg, St. Maarten | 6:00 AM | 7:00 PM |
9 | Basseterre | 7:00 AM | 10:00 PM |
10 | Little Bay | 8:00 AM | 6:00 PM |
11 | Gustavia | 8:00 AM | 11:00 PM |
12 | Deshaies | 12:30 AM | 10:00 PM |
13 | Roseau | 8:00 AM | 5:00 PM |
14 | Pigeon Island | 7:00 AM | 4:00 PM |
15 | Bridgetown | 5:00 AM |