24 reviews | Mar 08, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Mar 08, 2025 | Windstar | Star Pride | World Cruise | Balboa | Bridgetown | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Panama Canal | San Blas | Santa Marta | Soufriere | Willemstad | $4,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
2 reviews | Mar 27, 2025 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 14 Nights | Bora Bora | Fakarava | Moorea | Motu Mahaea (Tahaa) | Omoa, Fatu Hiva, Marquesas | Papeete | Rangiroa | $7,599 Up To $1000 Onboard Credit | | Suite! |
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24 reviews | Mar 29, 2025 | Windstar | Wind Surf | Europe | Philipsburg | Lisbon | 14 Nights | Lisbon | Ponta Delgada | St. Maarten | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Apr 20, 2025 | Windstar | Wind Star | Mediterranean | Barcelona | Athens (Piraeus) | 14 Nights | Athens, Greece | Barcelona | Bastia | Calvi | Gythion | Mahon | Messina (Taormina) | Monemvasia | Palma de Mallorca | Ponza | Portoferraio | Rome | Sorrento | $5,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
2 reviews | Jun 19, 2025 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 14 Nights | Bora Bora | Fakarava | Moorea | Motu Mahaea (Tahaa) | Omoa, Fatu Hiva, Marquesas | Papeete | Rangiroa | $7,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Sep 01, 2025 | Windstar | Star Pride | USA - New England | Reykjavik | Montreal | 14 Nights | Bonne Bay / Woody Point | Havre St. Pierre | Montreal | Nanortalik | Narsaq | Prince Christian Sound | Qaqortoq | Quebec City | Reykjavik | St. Anthony | $6,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
2 reviews | Sep 18, 2025 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 14 Nights | Bora Bora | Fakarava | Moorea | Motu Mahaea (Tahaa) | Omoa, Fatu Hiva, Marquesas | Papeete | Rangiroa | $7,599 Up To $1000 Onboard Credit | | Suite! |
11 reviews | Oct 11, 2025 | Windstar | Wind Spirit | Mediterranean | Athens (Piraeus) | Barcelona | 14 Nights | Athens, Greece | Barcelona | Bastia | Calvi | Gythion | Mahon | Messina (Taormina) | Monemvasia | Palma de Mallorca | Ponza | Portoferraio | Rome | Sorrento | $4,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Oct 19, 2025 | Windstar | Wind Star | Mediterranean | Athens (Piraeus) | Barcelona | 14 Nights | Athens, Greece | Barcelona | Bastia | Calvi | Gythion | Mahon | Messina (Taormina) | Monemvasia | Palma de Mallorca | Ponza | Portoferraio | Rome | Sorrento | $4,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Nov 04, 2025 | Windstar | Wind Spirit | Transatlantic | Lisbon | Bridgetown | 14 Nights | Bridgetown | Lisbon | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 07, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
5 reviews | Dec 13, 2025 | Windstar | Star Legend | Caribbean | Malaga | Rome | 14 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | | Suite! |
24 reviews | Dec 14, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 21, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $4,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Bridgetown | 14 Nights | Basseterre | Bridgetown | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 11, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Gustavia | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | St. Maarten | $3,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 18, 2026 | Windstar | Wind Surf | Caribbean | Bridgetown | Oranjestad | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Soufriere | St. George's | Willemstad | $4,099 Up To $500 Onboard Credit | | |
11 reviews | Jan 31, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |