Caribbean

2024 - Montreal to San Juan - 22 days - Star Pride

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Destination: Caribbean
Departures: 10/12/24
Ports of Call: Starting in Montreal with stops in Quebec City, Gaspe, Cap aux Meules, Louisbourg, Halifax, Portland, Boston, Hamilton, St. George's, Gustavia, Basseterre, Virgin Gorda / Prickly Pear, San Juan
Duration: 22

2024 - Boston to San Juan - 11 days - Star Pride

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Destination: Caribbean
Departures: 10/23/24
Ports of Call: Starting in Boston with stops in Hamilton, St. George's, Gustavia, Basseterre, Virgin Gorda / Prickly Pear, San Juan
Duration: 11

2024 - San Juan to San Juan - 6 days - Star Pride

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Destination: Caribbean
Departures: 11/3/24
Ports of Call: Starting in San Juan with stops in Philipsburg, Charlestown, Gustavia, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 6

2024 - San Juan to San Juan - 13 days - Star Pride

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Destination: Caribbean
Departures: 11/3/24
Ports of Call: Starting in San Juan with stops in Philipsburg, Charlestown, Gustavia, Jost van Dyke, Virgin Gorda / Prickly Pear, St. George's, Bequia, Pigeon Island, Les Saintes
Duration: 13

2024 - San Juan to San Juan - 14 days - Star Pride

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Destination: Caribbean
Departures: 11/9/24
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, Philipsburg, St. Thomas, Gustavia, Basseterre, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14

2024 - San Juan to San Juan - 7 days - Star Pride

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Destination: Caribbean
Departures: 11/9/24
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, Philipsburg
Duration: 7

2024 - San Juan to San Juan - 7 days - Star Pride

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Destination: Caribbean
Departures: 11/16/24
Ports of Call: Starting in San Juan with stops in St. Thomas, Philipsburg, Gustavia, Basseterre, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 7

2024 - San Juan to San Juan - 14 days - Star Pride

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Destination: Caribbean
Departures: 11/16/24
Ports of Call: Starting in San Juan with stops in St. Thomas, Philipsburg, Gustavia, Basseterre, Jost van Dyke, Virgin Gorda / Prickly Pear, St. George's, Bequia, Pigeon Island, Les Saintes
Duration: 14

2024 - San Juan to San Juan - 14 days - Star Pride

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Destination: Caribbean
Departures: 11/23/24
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, Philipsburg, St. Thomas, Basseterre, Gustavia, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14

2024 - San Juan to San Juan - 7 days - Star Pride

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Destination: Caribbean
Departures: 11/23/24
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, Philipsburg
Duration: 7

2024 - Bridgetown to Bridgetown - 10 days - Wind Spirit

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Destination: Caribbean
Departures: 11/27/24
Ports of Call: Starting in Bridgetown with stops in Basseterre, Gustavia, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Les Saintes, Pigeon Island
Duration: 10

2024 - San Juan to San Juan - 7 days - Star Pride

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Destination: Caribbean
Departures: 11/30/24
Ports of Call: Starting in San Juan with stops in St. Thomas, Philipsburg, Basseterre, Gustavia, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 7

2024 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 12/7/24
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 7

2024 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 12/7/24
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia, Basseterre, Les Saintes, Roseau, Anse Mitan
Duration: 14

2024 - San Juan to Oranjestad - 14 days - Star Pride

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Destination: Caribbean
Departures: 12/7/24
Ports of Call: Starting in San Juan with stops in St. Thomas, Gustavia, Basseterre, Roseau, Pigeon Island, St. George's, Bridgetown, Man-O-War Bay, Mayreau, Soufriere, Willemstad, Oranjestad
Duration: 14

2024 - San Juan to Bridgetown - 7 days - Star Pride

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Destination: Caribbean
Departures: 12/7/24
Ports of Call: Starting in San Juan with stops in St. Thomas, Gustavia, Basseterre, Roseau, Pigeon Island, St. George's, Bridgetown
Duration: 7

2024 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 12/14/24
Ports of Call: Starting in Bridgetown with stops in Basseterre, Les Saintes, Roseau, Anse Mitan, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 14

2024 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 12/14/24
Ports of Call: Starting in Bridgetown with stops in Basseterre, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7

2024 - Bridgetown to Oranjestad - 7 days - Star Pride

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Destination: Caribbean
Departures: 12/14/24
Ports of Call: Starting in Bridgetown with stops in Man-O-War Bay, Mayreau, Soufriere, St. George's, Willemstad, Oranjestad
Duration: 7

2024 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 12/21/24
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 7

2024 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 12/21/24
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia, St. John's, Roseau, Anse Mitan
Duration: 14

2024 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 12/21/24
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7

2024 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 12/21/24
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia, Falmouth Harbour, Road Bay, Jost van Dyke, Virgin Gorda / Prickly Pear, Soper's Hole
Duration: 14

2024 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 12/28/24
Ports of Call: Starting in Bridgetown with stops in St. John's, Roseau, Castries, Anse Mitan, Pigeon Island, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 14

2024 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 12/28/24
Ports of Call: Starting in Bridgetown with stops in St. John's, Roseau, Castries, Anse Mitan, Pigeon Island
Duration: 7

2024 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 12/28/24
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Jost van Dyke, Virgin Gorda / Prickly Pear, Soper's Hole, Gustavia
Duration: 7

2024 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 12/28/24
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Jost van Dyke, Virgin Gorda / Prickly Pear, Soper's Hole, Gustavia, Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre
Duration: 14

2025 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 1/4/25
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 7

2025 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 1/4/25
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia, Basseterre, Les Saintes, Roseau, Anse Mitan
Duration: 14

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 1/4/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 1/4/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, Falmouth Harbour, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Road Bay
Duration: 14

2025 - Oranjestad to Bridgetown - 7 days - Star Pride

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Destination: Caribbean
Departures: 1/4/25
Ports of Call: Starting in Oranjestad with stops in Willemstad, St. George's, Soufriere, Mayreau, Man-O-War Bay, Bridgetown
Duration: 7

2025 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 1/11/25
Ports of Call: Starting in Bridgetown with stops in Basseterre, Les Saintes, Roseau, Anse Mitan, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 14

2025 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 1/11/25
Ports of Call: Starting in Bridgetown with stops in Basseterre, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 1/11/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Gustavia, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Road Bay
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 1/11/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Gustavia, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Road Bay, Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre
Duration: 14

2025 - Bridgetown to Oranjestad - 7 days - Star Pride

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Destination: Caribbean
Departures: 1/11/25
Ports of Call: Starting in Bridgetown with stops in Man-O-War Bay, Mayreau, Soufriere, Willemstad, Kralendijk, Oranjestad
Duration: 7

2025 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 1/18/25
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 7

2025 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 1/18/25
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia, St. John's, Roseau, Les Saintes, Anse Mitan
Duration: 14

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 1/18/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 1/18/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14

2025 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 1/25/25
Ports of Call: Starting in Bridgetown with stops in St. John's, Roseau, Les Saintes, Anse Mitan, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 14

2025 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 1/25/25
Ports of Call: Starting in Bridgetown with stops in St. John's, Roseau, Les Saintes, Anse Mitan, Pigeon Island
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 1/25/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7

2025 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 2/1/25
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 7

2025 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 2/1/25
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia, Basseterre, Les Saintes, Roseau, Anse Mitan
Duration: 14

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 2/1/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 2/1/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre
Duration: 14

2025 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 2/8/25
Ports of Call: Starting in Bridgetown with stops in Basseterre, Les Saintes, Roseau, Anse Mitan, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 14

2025 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 2/8/25
Ports of Call: Starting in Bridgetown with stops in Basseterre, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 2/8/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 2/8/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia, Falmouth Harbour, Jost van Dyke, Virgin Gorda / Prickly Pear, Soper's Hole, Road Bay
Duration: 14

2025 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 2/15/25
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 2/15/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Jost van Dyke, Virgin Gorda / Prickly Pear, Soper's Hole, Gustavia, Road Bay
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 2/15/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Jost van Dyke, Virgin Gorda / Prickly Pear, Soper's Hole, Gustavia, Road Bay, Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre
Duration: 14

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 2/22/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7

2025 - Bridgetown to Oranjestad - 7 days - Star Pride

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Destination: Caribbean
Departures: 2/22/25
Ports of Call: Starting in Bridgetown with stops in Man-O-War Bay, Mayreau, Soufriere, St. George's, Willemstad, Oranjestad
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 2/22/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia, Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 3/1/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 3/8/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 3/8/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre
Duration: 14

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 3/15/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 3/15/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia, Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14

2025 - Oranjestad to Bridgetown - 7 days - Star Pride

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Destination: Caribbean
Departures: 3/15/25
Ports of Call: Starting in Oranjestad with stops in Willemstad, Kralendijk, Soufriere, Mayreau, Man-O-War Bay, Bridgetown
Duration: 7

2025 - Colon to Bridgetown - 11 days - Wind Star

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Destination: Caribbean
Departures: 3/15/25
Ports of Call: Starting in Colon with stops in Cartagena, Santa Marta, Oranjestad, Willemstad, St. George's, Mayreau, Bridgetown
Duration: 11

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 3/22/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7

2025 - Bridgetown to Bridgetown - 7 days - Star Pride

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Destination: Caribbean
Departures: 3/29/25
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Anse Mitan, Mayreau, St. George's, Bequia
Duration: 7

2025 - New York City to San Juan - 7 days - Star Pride

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Destination: Caribbean
Departures: 10/19/25
Ports of Call: Starting in New York with stops in St. George's, San Juan
Duration: 7

2025 - San Juan to San Juan - 7 days - Star Pride

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Destination: Caribbean
Departures: 10/26/25
Ports of Call: Starting in San Juan with stops in Cruz Bay, Basseterre, Gustavia, Philipsburg, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 7

2025 - San Juan to San Juan - 7 days - Star Pride

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Destination: Caribbean
Departures: 11/2/25
Ports of Call: Starting in San Juan with stops in Cruz Bay, Basseterre, Gustavia, Philipsburg, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 7

2025 - San Juan to San Juan - 14 days - Star Pride

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Destination: Caribbean
Departures: 11/2/25
Ports of Call: Starting in San Juan with stops in Cruz Bay, Basseterre, Gustavia, Philipsburg, Jost van Dyke, Virgin Gorda / Prickly Pear, St. George's, Bequia, Pigeon Island, Les Saintes, Marigot
Duration: 14

2025 - San Juan to San Juan - 7 days - Star Pride

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Destination: Caribbean
Departures: 11/9/25
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, Marigot
Duration: 7

2025 - San Juan to San Juan - 14 days - Star Pride

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Destination: Caribbean
Departures: 11/9/25
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, Marigot, Cruz Bay, Basseterre, Gustavia, Philipsburg, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14

2025 - San Juan to San Juan - 7 days - Star Pride

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Destination: Caribbean
Departures: 11/16/25
Ports of Call: Starting in San Juan with stops in Cruz Bay, Basseterre, Gustavia, Philipsburg, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 7

2025 - San Juan to San Juan - 14 days - Star Pride

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Destination: Caribbean
Departures: 11/16/25
Ports of Call: Starting in San Juan with stops in Cruz Bay, Basseterre, Gustavia, Philipsburg, Jost van Dyke, Virgin Gorda / Prickly Pear, St. George's, Bequia, Pigeon Island, Les Saintes, Marigot
Duration: 14

2025 - Bridgetown to Colon - 11 days - Wind Spirit

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Destination: Caribbean
Departures: 11/18/25
Ports of Call: Starting in Bridgetown with stops in Bequia, Mayreau, St. George's, Kralendijk, Willemstad, Oranjestad, Cartagena, Colon
Duration: 11

2025 - San Juan to San Juan - 7 days - Star Pride

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Destination: Caribbean
Departures: 11/23/25
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, Marigot
Duration: 7

2025 - San Juan to San Juan - 14 days - Star Pride

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Destination: Caribbean
Departures: 11/23/25
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, Marigot, Cruz Bay, Gustavia, Basseterre, Philipsburg, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14

2025 - San Juan to San Juan - 7 days - Star Pride

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Destination: Caribbean
Departures: 11/30/25
Ports of Call: Starting in San Juan with stops in Cruz Bay, Gustavia, Basseterre, Philipsburg, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 5 days - Wind Surf

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Destination: Caribbean
Departures: 12/2/25
Ports of Call: Starting in Philipsburg with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 5

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 12 days - Wind Surf

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Destination: Caribbean
Departures: 12/2/25
Ports of Call: Starting in Philipsburg with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre
Duration: 12

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 12/7/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 12/7/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 12/14/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 12/14/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre
Duration: 14

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 12/21/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 7

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 12/21/25
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14

2025 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 12/28/25
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 1/4/26
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7

2026 - Philipsburg, St. Maarten to Bridgetown - 21 days - Wind Surf

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Destination: Caribbean
Departures: 1/4/26
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Basseterre, St. John's, Les Saintes, Pigeon Island, Kingstown, Bridgetown, Anse Mitan, Castries, Bequia, Mayreau, St. George's
Duration: 21

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 55 days - Wind Surf

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Destination: Caribbean
Departures: 1/4/26
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Basseterre, St. John's, Les Saintes, Pigeon Island, Kingstown, Bridgetown, Anse Mitan, Castries, Bequia, Mayreau, St. George's, Man-O-War Bay, Soufriere, Kralendijk, Willemstad, Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon, Isla San Andres , Roatan, Belize City, Costa Maya, Cozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana
Duration: 55

2026 - Philipsburg, St. Maarten to Bridgetown - 14 days - Wind Surf

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Destination: Caribbean
Departures: 1/4/26
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Basseterre, St. John's, Les Saintes, Pigeon Island, Kingstown, Bridgetown
Duration: 14

2026 - Philipsburg, St. Maarten to Oranjestad - 28 days - Wind Surf

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Destination: Caribbean
Departures: 1/4/26
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Basseterre, St. John's, Les Saintes, Pigeon Island, Kingstown, Bridgetown, Anse Mitan, Castries, Bequia, Mayreau, St. George's, Man-O-War Bay, Soufriere, Kralendijk, Willemstad, Oranjestad
Duration: 28

2026 - Philipsburg, St. Maarten to Bridgetown - 7 days - Wind Surf

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Destination: Caribbean
Departures: 1/11/26
Ports of Call: Starting in Philipsburg with stops in Basseterre, Gustavia, St. John's, Les Saintes, Pigeon Island, Kingstown, Bridgetown
Duration: 7

2026 - Philipsburg, St. Maarten to Bridgetown - 14 days - Wind Surf

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Destination: Caribbean
Departures: 1/11/26
Ports of Call: Starting in Philipsburg with stops in Basseterre, Gustavia, St. John's, Les Saintes, Pigeon Island, Kingstown, Bridgetown, Anse Mitan, Castries, Bequia, Mayreau, St. George's
Duration: 14

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 10 days - Wind Spirit

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Destination: Caribbean
Departures: 1/14/26
Ports of Call: Starting in Philipsburg with stops in Basseterre, Roseau, Castries, Bequia, St. George's, Mayreau, Anse Mitan, Les Saintes, Gustavia
Duration: 10

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 17 days - Wind Spirit

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Destination: Caribbean
Departures: 1/14/26
Ports of Call: Starting in Philipsburg with stops in Basseterre, Roseau, Castries, Bequia, St. George's, Mayreau, Anse Mitan, Les Saintes, Gustavia, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Road Bay, Falmouth Harbour
Duration: 17

2026 - Bridgetown to Bridgetown - 7 days - Wind Surf

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Destination: Caribbean
Departures: 1/18/26
Ports of Call: Starting in Bridgetown with stops in Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St. George's
Duration: 7

2026 - Bridgetown to Oranjestad - 14 days - Wind Surf

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Destination: Caribbean
Departures: 1/18/26
Ports of Call: Starting in Bridgetown with stops in Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St. George's, Man-O-War Bay, Soufriere, Kralendijk, Willemstad, Oranjestad
Duration: 14

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 1/24/26
Ports of Call: Starting in Philipsburg with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour
Duration: 7

2026 - Bridgetown to Oranjestad - 7 days - Wind Surf

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Destination: Caribbean
Departures: 1/25/26
Ports of Call: Starting in Bridgetown with stops in Man-O-War Bay, Mayreau, Soufriere, Kralendijk, Willemstad, Oranjestad
Duration: 7

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 1/31/26
Ports of Call: Starting in Philipsburg with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour
Duration: 7

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 1/31/26
Ports of Call: Starting in Philipsburg with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour, Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre
Duration: 14

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 2/7/26
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 7

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 2/7/26
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Road Bay, Falmouth Harbour
Duration: 14

2026 - Colon to Philipsburg, St. Maarten - 19 days - Wind Surf

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Destination: Caribbean
Departures: 2/9/26
Ports of Call: Starting in Colon with stops in Bocas Del Toro, Isla San Andres , Roatan, Belize City, Costa Maya, Cozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Jost van Dyke, Virgin Gorda / Prickly Pear, Philipsburg
Duration: 19

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 2/14/26
Ports of Call: Starting in Philipsburg with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour
Duration: 7

2026 - Cozumel to Philipsburg, St. Maarten - 18 days - Wind Surf

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Destination: Caribbean
Departures: 2/17/26
Ports of Call: Starting in Cozumel with stops in Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Jost van Dyke, Virgin Gorda / Prickly Pear, Philipsburg, Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 18

2026 - Cozumel to Philipsburg, St. Maarten - 11 days - Wind Surf

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Destination: Caribbean
Departures: 2/17/26
Ports of Call: Starting in Cozumel with stops in Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Jost van Dyke, Virgin Gorda / Prickly Pear, Philipsburg
Duration: 11

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 2/21/26
Ports of Call: Starting in Philipsburg with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour
Duration: 7

2026 - Philipsburg, St. Maarten to Bridgetown - 21 days - Wind Spirit

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Destination: Caribbean
Departures: 2/21/26
Ports of Call: Starting in Philipsburg with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour, Basseterre, Little Bay, Les Saintes, Roseau, Pigeon Island, Bridgetown, Anse Mitan
Duration: 21

2026 - Philipsburg, St. Maarten to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 2/21/26
Ports of Call: Starting in Philipsburg with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour, Basseterre, Little Bay, Les Saintes, Roseau, Pigeon Island, Bridgetown
Duration: 14

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 2/28/26
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 7

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 2/28/26
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, Falmouth Harbour, Road Bay, Virgin Gorda / Prickly Pear, Soper's Hole, Jost van Dyke
Duration: 14

2026 - Philipsburg, St. Maarten to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 2/28/26
Ports of Call: Starting in Philipsburg with stops in Basseterre, Gustavia, Little Bay, Les Saintes, Roseau, Pigeon Island, Bridgetown
Duration: 7

2026 - Philipsburg, St. Maarten to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 2/28/26
Ports of Call: Starting in Philipsburg with stops in Basseterre, Gustavia, Little Bay, Les Saintes, Roseau, Pigeon Island, Bridgetown, Anse Mitan
Duration: 14

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 3/7/26
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Virgin Gorda / Prickly Pear, Soper's Hole, Jost van Dyke, Gustavia
Duration: 7

2026 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 3/7/26
Ports of Call: Starting in Bridgetown with stops in Little Bay, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7

2026 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 3/7/26
Ports of Call: Starting in Bridgetown with stops in Little Bay, Les Saintes, Roseau, Anse Mitan, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 14

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 3/14/26
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 3/14/26
Ports of Call: Starting in Philipsburg with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre
Duration: 14

2026 - Bridgetown to Bridgetown - 14 days - Wind Spirit

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Destination: Caribbean
Departures: 3/14/26
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia, Basseterre, Les Saintes, Roseau, Anse Mitan
Duration: 14

2026 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 3/14/26
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 7

2026 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 3/14/26
Ports of Call: Starting in Bridgetown with stops in Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St. George's, Bequia
Duration: 7

2026 - Oranjestad to Bridgetown - 7 days - Star Pride

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Destination: Caribbean
Departures: 3/15/26
Ports of Call: Starting in Oranjestad with stops in Willemstad, Kralendijk, Soufriere, Mayreau, Man-O-War Bay, Bridgetown
Duration: 7

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 3/21/26
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia
Duration: 7

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 14 days - Wind Surf

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Destination: Caribbean
Departures: 3/21/26
Ports of Call: Starting in Philipsburg with stops in Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, St. John's, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14

2026 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 3/21/26
Ports of Call: Starting in Bridgetown with stops in Basseterre, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7

2026 - Bridgetown to Bridgetown - 7 days - Wind Spirit

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Destination: Caribbean
Departures: 3/21/26
Ports of Call: Starting in Bridgetown with stops in Basseterre, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7

2026 - Philipsburg, St. Maarten to Philipsburg, St. Maarten - 7 days - Wind Surf

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Destination: Caribbean
Departures: 3/28/26
Ports of Call: Starting in Philipsburg with stops in St. John's, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7