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Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These are the siren songs that lure anyone with a yacht and a yearning to escape to the incomparable Caribbean Islands. Whether you're cruising through turquoise waters or lazing on powdery white beaches, the glamorous harbors and unknown coves of this area remain a hidden treasure.
Itineraries
2024 - Montreal to San Juan - 22 Days - Star PrideSelect
Destination: Caribbean
Departures: 10/12/24
Ports of Call: Starting in Montreal with stops in Quebec City, Gaspe, Cap aux Meules, Louisbourg, Halifax, Lunenburg, Bar Harbor, Portland, Boston, Hamilton, St. George, Gustavia, Basseterre, Virgin Gorda / Prickly Pear, San Juan
Duration: 22
2024 - Boston to San Juan - 11 Days - Star PrideSelect
Destination: Caribbean
Departures: 10/23/24
Ports of Call: Starting in Boston with stops in Hamilton, St. George, Gustavia, Basseterre, Virgin Gorda / Prickly Pear, San Juan
Duration: 11
2024 - San Juan to San Juan - 6 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/3/24
Ports of Call: Starting in San Juan with stops in Gustavia, Little Bay, St. Maarten, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 6
2024 - San Juan to San Juan - 13 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/3/24
Ports of Call: Starting in San Juan with stops in Gustavia, Little Bay, St. Maarten, 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 PrideSelect
Destination: Caribbean
Departures: 11/9/24
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, St. Maarten, St. Thomas, Gustavia, Little Bay, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14
2024 - San Juan to San Juan - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/9/24
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, St. Maarten
Duration: 7
2024 - San Juan to San Juan - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/16/24
Ports of Call: Starting in San Juan with stops in St. Thomas, Gustavia, Little Bay, St. Maarten, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 7
2024 - San Juan to San Juan - 14 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/16/24
Ports of Call: Starting in San Juan with stops in St. Thomas, Gustavia, Little Bay, St. Maarten, 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 PrideSelect
Destination: Caribbean
Departures: 11/23/24
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, St. Maarten, St. Thomas, Gustavia, Little Bay, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14
2024 - San Juan to San Juan - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/23/24
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, St. Maarten
Duration: 7
2024 - Bridgetown to Bridgetown - 10 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 11/27/24
Ports of Call: Starting in Bridgetown with stops in Little Bay, 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 PrideSelect
Destination: Caribbean
Departures: 11/30/24
Ports of Call: Starting in San Juan with stops in St. Thomas, Gustavia, Little Bay, St. Maarten, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 7
2024 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
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 SpiritSelect
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, Little Bay, Les Saintes, Roseau, Anse Mitan
Duration: 14
2024 - San Juan to Oranjestad - 14 Days - Star PrideSelect
Destination: Caribbean
Departures: 12/7/24
Ports of Call: Starting in San Juan with stops in St. Thomas, Gustavia, Little Bay, Roseau, Pigeon Island, St. George's, Bridgetown, Man-O-War Bay, Mayreau, Soufriere, Kralendijk, Willemstad, Oranjestad
Duration: 14
2024 - San Juan to Bridgetown - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 12/7/24
Ports of Call: Starting in San Juan with stops in St. Thomas, Gustavia, Little Bay, Roseau, Pigeon Island, St. George's, Bridgetown
Duration: 7
2024 - Bridgetown to Bridgetown - 14 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 12/14/24
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
2024 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 12/14/24
Ports of Call: Starting in Bridgetown with stops in Little Bay, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7
2024 - Bridgetown to Oranjestad - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 12/14/24
Ports of Call: Starting in Bridgetown with stops in Man-O-War Bay, Mayreau, Soufriere, Kralendijk, Willemstad, Oranjestad
Duration: 7
2024 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
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 SpiritSelect
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, Little Bay, Les Saintes, Roseau, Anse Mitan
Duration: 14
2024 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/21/24
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7
2024 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/21/24
Ports of Call: Starting in St. Maarten 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
2024 - Bridgetown to Bridgetown - 14 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 12/28/24
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
2024 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 12/28/24
Ports of Call: Starting in Bridgetown with stops in Little Bay, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7
2024 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/28/24
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7
2024 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/28/24
Ports of Call: Starting in St. Maarten 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 - 7 Days - Wind SpiritSelect
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 SpiritSelect
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, Little Bay, Les Saintes, Roseau, Anse Mitan
Duration: 14
2025 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/4/25
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/4/25
Ports of Call: Starting in St. Maarten 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 PrideSelect
Destination: Caribbean
Departures: 1/4/25
Ports of Call: Starting in Oranjestad with stops in Willemstad, Kralendijk, Soufriere, Mayreau, Man-O-War Bay, Bridgetown
Duration: 7
2025 - Bridgetown to Bridgetown - 14 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 1/11/25
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
2025 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 1/11/25
Ports of Call: Starting in Bridgetown with stops in Little Bay, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7
2025 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/11/25
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/11/25
Ports of Call: Starting in St. Maarten 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 Oranjestad - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 1/11/25
Ports of Call: Starting in Bridgetown with stops in Man-O-War Bay, Mayreau, Soufriere, Kralendijk, Willemstad, Oranjestad
Duration: 7
2025 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
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 SpiritSelect
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, Little Bay, Les Saintes, Roseau, Anse Mitan
Duration: 14
2025 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/18/25
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7
2025 - Bridgetown to Bridgetown - 14 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 1/25/25
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
2025 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 1/25/25
Ports of Call: Starting in Bridgetown with stops in Little Bay, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7
2025 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/25/25
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/25/25
Ports of Call: Starting in St. Maarten 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 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
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 SpiritSelect
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, Little Bay, Les Saintes, Roseau, Anse Mitan
Duration: 14
2025 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 2/1/25
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 2/1/25
Ports of Call: Starting in St. Maarten 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 SpiritSelect
Destination: Caribbean
Departures: 2/8/25
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
2025 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 2/8/25
Ports of Call: Starting in Bridgetown with stops in Little Bay, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7
2025 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 2/8/25
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 2/8/25
Ports of Call: Starting in St. Maarten 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 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
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 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 2/15/25
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 2/15/25
Ports of Call: Starting in St. Maarten 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 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 2/22/25
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7
2025 - Bridgetown to Oranjestad - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 2/22/25
Ports of Call: Starting in Bridgetown with stops in Man-O-War Bay, Mayreau, Soufriere, Kralendijk, Willemstad, Oranjestad
Duration: 7
2025 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/1/25
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/1/25
Ports of Call: Starting in St. Maarten 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 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/8/25
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/8/25
Ports of Call: Starting in St. Maarten 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 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/15/25
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre, Gustavia
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/15/25
Ports of Call: Starting in St. Maarten 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 PrideSelect
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 StarSelect
Destination: Caribbean
Departures: 3/15/25
Ports of Call: Starting in Colon with stops in Cartagena, Santa Marta, Oranjestad, Willemstad, Kralendijk, St. George's, Mayreau, Bridgetown
Duration: 11
2025 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/22/25
Ports of Call: Starting in St. Maarten 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 PrideSelect
Destination: Caribbean
Departures: 3/22/25
Ports of Call: Starting in Bridgetown with stops in Little Bay, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7
2025 - Bridgetown to Bridgetown - 7 Days - Star PrideSelect
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 - Montreal to San Juan - 22 Days - Star PrideSelect
Destination: Caribbean
Departures: 10/7/25
Ports of Call: Starting in Montreal with stops in Quebec City, Gaspe, Cap aux Meules, Louisbourg, Halifax, Lunenburg, Bar Harbor, Portland, Boston, Hamilton, St. George, Gustavia, Basseterre, Virgin Gorda / Prickly Pear, San Juan
Duration: 22
2025 - Boston to San Juan - 11 Days - Star PrideSelect
Destination: Caribbean
Departures: 10/18/25
Ports of Call: Starting in Boston with stops in Hamilton, 5658, Gustavia, Basseterre, Virgin Gorda / Prickly Pear, San Juan
Duration: 11
2025 - San Juan to San Juan - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/1/25
Ports of Call: Starting in San Juan with stops in St. John, St. Maarten, Basseterre, Gustavia, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 7
2025 - San Juan to San Juan - 14 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/1/25
Ports of Call: Starting in San Juan with stops in St. John, St. Maarten, Basseterre, Gustavia, Jost van Dyke, Virgin Gorda / Prickly Pear, St. George's, Bequia, Pigeon Island, Les Saintes
Duration: 14
2025 - San Juan to San Juan - 14 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/8/25
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, St. Maarten, St. John, Basseterre, Gustavia, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14
2025 - San Juan to San Juan - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/8/25
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, St. Maarten
Duration: 7
2025 - San Juan to San Juan - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/15/25
Ports of Call: Starting in San Juan with stops in St. John, St. Maarten, Basseterre, Gustavia, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 7
2025 - San Juan to San Juan - 14 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/15/25
Ports of Call: Starting in San Juan with stops in St. John, St. Maarten, Basseterre, Gustavia, Jost van Dyke, Virgin Gorda / Prickly Pear, St. George's, Bequia, Pigeon Island, Les Saintes
Duration: 14
2025 - San Juan to San Juan - 14 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/22/25
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, St. Maarten, St. John, Basseterre, Gustavia, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 14
2025 - San Juan to San Juan - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/22/25
Ports of Call: Starting in San Juan with stops in St. George's, Bequia, Pigeon Island, Les Saintes, St. Maarten
Duration: 7
2025 - San Juan to San Juan - 7 Days - Star PrideSelect
Destination: Caribbean
Departures: 11/29/25
Ports of Call: Starting in San Juan with stops in St. John, St. Maarten, Basseterre, Gustavia, Jost van Dyke, Virgin Gorda / Prickly Pear
Duration: 7
2025 - St. Maarten to St. Maarten - 5 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/2/25
Ports of Call: Starting in St. Maarten with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 5
2025 - St. Maarten to St. Maarten - 12 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/2/25
Ports of Call: Starting in St. Maarten with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Charlestown, Roseau, Pigeon Island, Les Saintes, Basseterre
Duration: 12
2025 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/7/25
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/7/25
Ports of Call: Starting in St. Maarten 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 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/14/25
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/14/25
Ports of Call: Starting in St. Maarten 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 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/21/25
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 7
2025 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/21/25
Ports of Call: Starting in St. Maarten 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 - Colon to Bridgetown - 11 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 12/27/25
Ports of Call: Starting in Colon with stops in Cartagena, Santa Marta, Oranjestad, Willemstad, Kralendijk, St. George's, Mayreau, Bridgetown
Duration: 11
2025 - Colon to St. Maarten - 18 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 12/27/25
Ports of Call: Starting in Colon with stops in Cartagena, Santa Marta, Oranjestad, Willemstad, Kralendijk, St. George's, Mayreau, Bridgetown, Roseau, Pigeon Island, Les Saintes, Little Bay, Gustavia, Basseterre, St. Maarten
Duration: 18
2025 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 12/28/25
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7
2026 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/4/26
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7
2026 - St. Maarten to Bridgetown - 21 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/4/26
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Basseterre, Little Bay, Deshaies, Roseau, Pigeon Island, Bridgetown, Anse Mitan, Castries, Bequia, Mayreau, St. George's
Duration: 21
2026 - St. Maarten to St. Maarten - 55 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/4/26
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Basseterre, Little Bay, Deshaies, Roseau, Pigeon Island, 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 - St. Maarten to Bridgetown - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/4/26
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Basseterre, Little Bay, Deshaies, Roseau, Pigeon Island, Bridgetown
Duration: 14
2026 - St. Maarten to Oranjestad - 28 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/4/26
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Basseterre, Little Bay, Deshaies, Roseau, Pigeon Island, Bridgetown, Anse Mitan, Castries, Bequia, Mayreau, St. George's, Man-O-War Bay, Soufriere, Kralendijk, Willemstad, Oranjestad
Duration: 28
2026 - Bridgetown to St. Maarten - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 1/7/26
Ports of Call: Starting in Bridgetown with stops in Roseau, Pigeon Island, Les Saintes, Little Bay, Gustavia, Basseterre, St. Maarten
Duration: 7
2026 - St. Maarten to Bridgetown - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/11/26
Ports of Call: Starting in St. Maarten with stops in Basseterre, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown
Duration: 7
2026 - St. Maarten to Bridgetown - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 1/11/26
Ports of Call: Starting in St. Maarten with stops in Basseterre, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown, Anse Mitan, Castries, Bequia, Mayreau, St. George's
Duration: 14
2026 - St. Maarten to St. Maarten - 10 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 1/14/26
Ports of Call: Starting in St. Maarten with stops in Little Bay, Roseau, Castries, Mayreau, St. George's, Bequia, Anse Mitan, Les Saintes, Gustavia
Duration: 10
2026 - St. Maarten to St. Maarten - 17 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 1/14/26
Ports of Call: Starting in St. Maarten with stops in Little Bay, Roseau, Castries, Mayreau, St. George's, Bequia, 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 SurfSelect
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 SurfSelect
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 - St. Maarten to St. Maarten - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 1/24/26
Ports of Call: Starting in St. Maarten with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour
Duration: 7
2026 - St. Maarten to St. Maarten - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 1/31/26
Ports of Call: Starting in St. Maarten with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour
Duration: 7
2026 - St. Maarten to St. Maarten - 14 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 1/31/26
Ports of Call: Starting in St. Maarten 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 - St. Maarten to St. Maarten - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 2/7/26
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 7
2026 - St. Maarten to St. Maarten - 14 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 2/7/26
Ports of Call: Starting in St. Maarten 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 St. Maarten - 19 Days - Wind SurfSelect
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, St. Maarten
Duration: 19
2026 - St. Maarten to St. Maarten - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 2/14/26
Ports of Call: Starting in St. Maarten with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour
Duration: 7
2026 - Cozumel to St. Maarten - 18 Days - Wind SurfSelect
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, St. Maarten, Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 18
2026 - Cozumel to St. Maarten - 11 Days - Wind SurfSelect
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, St. Maarten
Duration: 11
2026 - St. Maarten to St. Maarten - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 2/21/26
Ports of Call: Starting in St. Maarten with stops in Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour
Duration: 7
2026 - St. Maarten to Bridgetown - 21 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 2/21/26
Ports of Call: Starting in St. Maarten 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 - St. Maarten to Bridgetown - 14 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 2/21/26
Ports of Call: Starting in St. Maarten 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 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 2/28/26
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 7
2026 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 2/28/26
Ports of Call: Starting in St. Maarten 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
2026 - St. Maarten to Bridgetown - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 2/28/26
Ports of Call: Starting in St. Maarten with stops in Basseterre, Gustavia, Little Bay, Les Saintes, Roseau, Pigeon Island, Bridgetown
Duration: 7
2026 - St. Maarten to Bridgetown - 14 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 2/28/26
Ports of Call: Starting in St. Maarten with stops in Basseterre, Gustavia, Little Bay, Les Saintes, Roseau, Pigeon Island, Bridgetown, Anse Mitan
Duration: 14
2026 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/7/26
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7
2026 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
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 SpiritSelect
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 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/14/26
Ports of Call: Starting in St. Maarten with stops in Falmouth Harbour, Road Bay, Soper's Hole, Jost van Dyke, Virgin Gorda / Prickly Pear, Gustavia
Duration: 7
2026 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/14/26
Ports of Call: Starting in St. Maarten 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
2026 - Bridgetown to Bridgetown - 14 Days - Wind SpiritSelect
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, Little Bay, Les Saintes, Roseau, Anse Mitan
Duration: 14
2026 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
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 - St. Maarten to St. Maarten - 7 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/21/26
Ports of Call: Starting in St. Maarten with stops in Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre
Duration: 7
2026 - St. Maarten to St. Maarten - 14 Days - Wind SurfSelect
Destination: Caribbean
Departures: 3/21/26
Ports of Call: Starting in St. Maarten 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
2026 - Bridgetown to Bridgetown - 7 Days - Wind SpiritSelect
Destination: Caribbean
Departures: 3/21/26
Ports of Call: Starting in Bridgetown with stops in Little Bay, Les Saintes, Roseau, Anse Mitan, Pigeon Island
Duration: 7
   
 

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