Star Collector: Leeward & Windward Caribbean Havens

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 4×4 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.
Day | Description | View All |
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Day 1 |
St. Maarten |
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Day 2 |
Jost Van Dyke, Great Harbour |
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Day 2 |
Soper's Hole |
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Day 3 |
Jost Van Dyke, Great Harbour |
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Day 3 |
Virgin Gorda |
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Day 4 |
Virgin Gorda |
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Day 5 |
Road Bay |
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Day 6 |
Gustavia |
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Day 7 |
Falmouth Harbour |
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Day 8 |
St. Maarten |
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Day 9 |
Basseterre |
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Day 10 |
Gustavia |
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Day 11 |
Little Bay |
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Day 12 |
Les Saintes |
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Day 13 |
Roseau |
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Day 14 |
Pigeon Island |
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Day 15 |
Bridgetown |
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