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Cruises from Philipsburg, St. Maarten 2025/2026

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Sail Date Cruise Line Ship Destination Departs Length Price You Save Discounts
8 reviews
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7 night Treasure IslandsStar ClippersStar FlyerCaribbean - EasternPhilipsburgPhilipsburg7 NightsBasseterre, St. Kitts (morning) | Gustavia, St. Barts | Philipsburg, St. Maarten | Road Bay, Anguilla | Sopers Hole - Tortola, British Virgin Islands (BVI) | South Friars Bay - Beach, St. Kitts (afternoon) | Spanish Town - Virgin Gorda, British Virgin Islands (B.V.I) | White Bay, Jost van Dyke (B.V.I.)$1,870
Shipboard Credit Per Stateroom ($150)
Shipboard Credit Per Stateroom ($150)View ItineraryGet FREE Quote
25 reviews
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7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Feb 15 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg7 NightsGustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole$2,306
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
8 reviews
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7 night Leeward IslandsStar ClippersStar FlyerCaribbean - EasternPhilipsburgPhilipsburg7 NightsCabrits, Dominica | Charlestown, Nevis | Deshaies, Guadeloupe | Gustavia, St. Barts | Philipsburg, St. Maarten | Terre-de-Haut, Iles des Saintes$1,870
Shipboard Credit Per Stateroom ($150)
Shipboard Credit Per Stateroom ($150)View ItineraryGet FREE Quote
9 reviews
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7-day Yachtsman's CaribbeanSeabourn OvationCaribbeanPhilipsburgBridgetown7 NightsBridgetown, Barbados | Fort-De-France, Martinique | Grenada | Philipsburg, St. Maarten | Port Elizabeth, Bequia$4,818
Up To $500 Onboard Credit
Welcome Reception
Exclusive Amenity
Distinctive Host
*Distinctive Voyage
View ItineraryGet FREE Quote

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9 reviews
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14-day Caribbean Gems In DepthSeabourn OvationCaribbeanPhilipsburgPhilipsburg14 NightsAntigua | Bridgetown, Barbados | Fort-De-France, Martinique | Grenada | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | Port Elizabeth, Bequia | St. Lucia$8,677
Up To $1000 Onboard Credit
Welcome Reception
Exclusive Amenity
Distinctive Host
*Distinctive Voyage
View ItineraryGet FREE Quote
25 reviews
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7 night Caribbean (Classic Caribbean (Feb 22 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg7 NightsBasseterre | Charlestown | Gustavia | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Roseau$2,611
Up To $300 Onboard Credit
 View ItineraryGet FREE Quote
8 reviews
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7 night Treasure IslandsStar ClippersStar FlyerCaribbean - EasternPhilipsburgPhilipsburg7 NightsBasseterre, St. Kitts (morning) | Gustavia, St. Barts | Philipsburg, St. Maarten | Road Bay, Anguilla | Sopers Hole - Tortola, British Virgin Islands (BVI) | South Friars Bay - Beach, St. Kitts (afternoon) | Spanish Town - Virgin Gorda, British Virgin Islands (B.V.I) | White Bay, Jost van Dyke (B.V.I.)$1,870
Shipboard Credit Per Stateroom ($150)
Shipboard Credit Per Stateroom ($150)View ItineraryGet FREE Quote
1 reviews
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7 night Caribbean (Philipsburg to Marigot)PonantLe PonantCaribbeanPhilipsburgMarigot7 NightsBeef Island | Jost Van Dyke | Marigot | Norman Island | Philipsburg | Virgin Gorda$8,710
Up To $1000 Onboard Credit
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25 reviews
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7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Mar 1 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg7 NightsGustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole$2,377
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
8 reviews
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7 night Leeward IslandsStar ClippersStar FlyerCaribbean - EasternPhilipsburgPhilipsburg7 NightsCabrits, Dominica | Charlestown, Nevis | Deshaies, Guadeloupe | Gustavia, St. Barts | Philipsburg, St. Maarten | Terre-de-Haut, Iles des Saintes$1,870
Shipboard Credit Per Stateroom ($150)
Shipboard Credit Per Stateroom ($150)View ItineraryGet FREE Quote
9 reviews
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7-day Yachtsman's CaribbeanSeabourn OvationCaribbeanPhilipsburgBridgetown7 NightsBridgetown, Barbados | Fort-De-France, Martinique | Grenada | Philipsburg, St. Maarten | Port Elizabeth, Bequia$4,818
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)View ItineraryGet FREE Quote
9 reviews
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19-day Yachtsman's Caribbean & Atlantic PassageSeabourn OvationCaribbeanPhilipsburgLisbon19 NightsBridgetown, Barbados | Fort-De-France, Martinique | Grenada | Lisbon, Portugal | Madeira, Portugal | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Saint Pierre et Miquelon, France$8,690
Up To $1000 Onboard Credit
Welcome Reception
Exclusive Amenity
Distinctive Host
*Distinctive Voyage
View ItineraryGet FREE Quote
2 reviews
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8 night Marigot to San JuanSeaDream Yacht ClubSeaDream IICaribbeanPhilipsburgSan Juan del Sur8 NightsCharlestown, Nevis, St. Kitts & Nevis | Cruz Bay, St. John, U.S.V.I. | Gustavia, St. Barths, F.W.I. | Norman Island, B. V. I. | Philipsburg, Sint Maarten, Dutch Caribbean | San Juan, Puerto Rico | Sandy Ground, Anguilla, B.W.I. | Spanish Town, Virgin Gorda, B. V. I. | White Bay, Jost van Dyke, B. V. I.$6,679
Up To $750 Onboard Credit
Onboard Credit!
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25 reviews
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14 night Star Collector Voyages (Caribbean Explorations (Mar 8 2025))WindstarWind SurfCaribbean - SouthernPhilipsburgPhilipsburg14 NightsBasseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Road Bay | Roseau | Soper's Hole$5,619
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
25 reviews
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6 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway (Mar 8 2025))WindstarWind SurfCaribbeanPhilipsburgPhilipsburg6 NightsFalmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | Road Bay | Soper's Hole$2,306
Up To $250 Onboard Credit
Onboard Credit!
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8 reviews
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7 night Treasure IslandsStar ClippersStar FlyerCaribbean - EasternPhilipsburgPhilipsburg7 NightsBasseterre, St. Kitts (morning) | Gustavia, St. Barts | Philipsburg, St. Maarten | Road Bay, Anguilla | Sopers Hole - Tortola, British Virgin Islands (BVI) | South Friars Bay - Beach, St. Kitts (afternoon) | Spanish Town - Virgin Gorda, British Virgin Islands (B.V.I) | White Bay, Jost van Dyke (B.V.I.)$1,870
Shipboard Credit Per Stateroom ($150)
Shipboard Credit Per Stateroom ($150)View ItineraryGet FREE Quote
Itinerary Map/Ship Image7 night Philipsburg to BridgetownSeaDream Yacht ClubSeaDream ICaribbeanPhilipsburgBridgetown7 NightsBridgetown, Barbados, Barbados | Deshaies, Guadeloupe, F.W.I. | Gustavia, St. Barths, F.W.I. | Mayreau, St. Vincent and the Grenadines | Philipsburg, Sint Maarten, Dutch Caribbean | Rodney Bay, Saint Lucia | Sandy Ground, Anguilla, B.W.I. | Soufriere Bay, Saint Lucia | Terre De Haut, Îles des Saintes, Guadeloupe, F.W.I.$5,719
Up To $750 Onboard Credit
Onboard Credit!
View ItineraryGet FREE Quote
25 reviews
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14 night Star Collector Voyages (Caribbean Explorations (Mar 15 2025))WindstarWind SurfCaribbean - SouthernPhilipsburgPhilipsburg14 NightsBasseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Road Bay | Roseau | Soper's Hole$6,919
Shipboard Credit Per Person ($150)
Shipboard Credit Per Person ($150)View ItineraryGet FREE Quote
25 reviews
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7 night Caribbean (Classic Caribbean (Mar 15 2025))WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg7 NightsBasseterre | Charlestown | Gustavia | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Roseau$2,771
Up To $300 Onboard Credit
Welcome Reception
Exclusive Amenity
Distinctive Host
*Distinctive Voyage
View ItineraryGet FREE Quote
8 reviews
Itinerary Map/Ship Image
7 night Leeward IslandsStar ClippersStar FlyerCaribbean - EasternPhilipsburgPhilipsburg7 NightsCabrits, Dominica | Charlestown, Nevis | Deshaies, Guadeloupe | Gustavia, St. Barts | Philipsburg, St. Maarten | Terre-de-Haut, Iles des Saintes$1,870
Shipboard Credit Per Stateroom ($150)
Shipboard Credit Per Stateroom ($150)View ItineraryGet FREE Quote

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