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10-night Ocean Crossing Cruise
Apr 5, 2025 Aboard Star Pride Bridgetown (Barbados), Santa Cruz de TenerifeBridgetown (Barbados), Santa Cruz de Tenerife Optional Promotions:EXCLUSIVEpricing from:$1,9235-night Barefoot Break in the British Virgin Islands
Dec 2, 2025 Aboard Wind Surf St. Maarten (Philipsburg), Sopers Hole, Tortola,...St. Maarten (Philipsburg), Sopers Hole, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda ,... Optional Promotions:EXCLUSIVEpricing from:$2,1507-night Southern Spain Winter Escapes Cruise
Nov 21, 2025 Aboard Star Legend Barcelona, Barcelona, Palma de Mallorca,...Barcelona, Barcelona, Palma de Mallorca, Valencia, Cartagena (Spain), Gibraltar, Malaga, Malaga Optional Promotions:EXCLUSIVEpricing from:$2,2427-night San Juan & The Virgin Islands Cruise
Oct 26, 2025 Aboard Star Pride San Juan, Cruz Bay, St. John, Basseterre, St....San Juan, Cruz Bay, St. John, Basseterre, St. Kitts, Gustavia, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda ... Optional Promotions:EXCLUSIVEpricing from:$2,2717-night Bermuda Bliss Cruise
Oct 19, 2025 Aboard Star Pride New York City, St. George's, Bermuda, St....New York City, St. George's, Bermuda, St. George's, Bermuda, San Juan Optional Promotions:EXCLUSIVEpricing from:$2,4267-night Mediterranean Island Mosaic Cruise
Oct 26, 2025 Aboard Wind Star Rome (Civitavecchia), Portoferraio, Elba, Bastia,...Rome (Civitavecchia), Portoferraio, Elba, Bastia, Calvi, Mahon, Palma de Mallorca, Barcelona Optional Promotions:EXCLUSIVEpricing from:$2,4337-night Southern Spain Winter Escapes Cruise
Nov 7, 2025 Aboard Star Legend Barcelona, Palma de Mallorca, Valencia, Cartagena...Barcelona, Palma de Mallorca, Valencia, Cartagena (Spain), Cartagena (Spain), Gibraltar, Malaga, Malaga Optional Promotions:EXCLUSIVEpricing from:$2,4427-night Beach Fun & Sun: A Remote Caribbean Getaway
Dec 14, 2025 Aboard Wind Surf St. Maarten (Philipsburg), Falmouth Harbour,...St. Maarten (Philipsburg), Falmouth Harbour, Antigua, Road Bay, Sopers Hole, Tortola, Jost Van Dyke, Jost Van Dyke,... Optional Promotions:EXCLUSIVEpricing from:$2,4676-night The Spanish Main: Rise Of The New World Cruise
Dec 7, 2025 Aboard Star Pride San Juan, Santo Domingo, Cartagena (Colombia),...San Juan, Santo Domingo, Cartagena (Colombia), Cartagena (Colombia), San Blas Islands, Colon (Panama) Optional Promotions:EXCLUSIVEpricing from:$2,5357-night Beach Fun & Sun: A Remote Caribbean Getaway
Jan 4, 2026 Aboard Wind Surf St. Maarten (Philipsburg), Falmouth Harbour,...St. Maarten (Philipsburg), Falmouth Harbour, Antigua, Road Bay, Sopers Hole, Tortola, Jost Van Dyke, Jost Van Dyke,... Optional Promotions:EXCLUSIVEpricing from:$2,6107-night Enchanting Colombia And Panamanian Islands Cruise
Dec 13, 2025 Aboard Wind Spirit Colon (Panama), San Blas Islands, Cartagena...Colon (Panama), San Blas Islands, Cartagena (Colombia), Cartagena (Colombia), Santa Marta, Oranjestad, Aruba Optional Promotions:EXCLUSIVEpricing from:$2,61514-night Ocean Crossings
Nov 4, 2025 Aboard Wind Spirit Lisbon, Bridgetown (Barbados)Lisbon, Bridgetown (Barbados) Optional Promotions:EXCLUSIVEpricing from:$2,6257-night San Juan & The Virgin Islands Cruise
Nov 9, 2025 Aboard Star Pride San Juan, St. George's, Grenada, Bequia,...San Juan, St. George's, Grenada, Bequia, Grenadines, Pigeon Island, St. Lucia, Iles des Saintes, Marigot, St. Martin,... Optional Promotions:EXCLUSIVEpricing from:$2,6307-night San Juan & The Virgin Islands Cruise
Nov 23, 2025 Aboard Star Pride San Juan, St. George's, Grenada, Bequia,...San Juan, St. George's, Grenada, Bequia, Grenadines, Pigeon Island, St. Lucia, Iles des Saintes, Marigot, St. Martin,... Optional Promotions:EXCLUSIVEpricing from:$2,6307-night Lush & Lovely Island of the Lesser Antilles
Jan 11, 2026 Aboard Wind Surf St. Maarten (Philipsburg), Basseterre, St. Kitts,...St. Maarten (Philipsburg), Basseterre, St. Kitts, Little Bay, Gustavia, Deshaies, Guadeloupe, Roseau, Dominica, Pigeon... Optional Promotions:EXCLUSIVEpricing from:$2,6367-night Beach Fun & Sun: A Remote Caribbean Getway
Jan 24, 2026 Aboard Wind Spirit St. Maarten (Philipsburg), Sopers Hole, Tortola,...St. Maarten (Philipsburg), Sopers Hole, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda ,... Optional Promotions:EXCLUSIVEpricing from:$2,6607-night San Juan & The Virgin Islands Cruise
Nov 30, 2025 Aboard Star Pride San Juan, Cruz Bay, St. John, Gustavia,...San Juan, Cruz Bay, St. John, Gustavia, Basseterre, St. Kitts, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda ... Optional Promotions:EXCLUSIVEpricing from:$2,6627-night San Juan & The Virgin Islands Cruise
Nov 16, 2025 Aboard Star Pride San Juan, Cruz Bay, St. John, Basseterre, St....San Juan, Cruz Bay, St. John, Basseterre, St. Kitts, Gustavia, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda ... Optional Promotions:EXCLUSIVEpricing from:$2,6627-night Jewels of the Windward Islands
Jan 18, 2026 Aboard Wind Surf Bridgetown (Barbados), Anse Mitan, Castries,...Bridgetown (Barbados), Anse Mitan, Castries, Pigeon Island, St. Lucia, Pigeon Island, St. Lucia, Bequia, Grenadines,... Optional Promotions:EXCLUSIVEpricing from:$2,7227-night Classic Caribbean
Dec 21, 2025 Aboard Wind Surf St. Maarten (Philipsburg), Charlestown, Roseau,...St. Maarten (Philipsburg), Charlestown, Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Gustavia,... Optional Promotions:EXCLUSIVEpricing from:$2,751
showing 1 - 20 of 400 matching results
Terms and Conditions: New bookings only. May not be combinable with certain fares, amenities, and/or promotions. Other restrictions may apply. Fares/rates are per person, based on double occupancy for select sail and travel dates; are capacity controlled and subject to availability at time booking and may be pulled without notice. We reserve the right to correct errors. Information and pricing is subject to change without notice. While we do our very best to ensure that information and pricing appearing in this website is complete and accurate, we cannot be responsible for incomplete and inaccurate representations, which may or may not be under our control. In the event of a pricing error, misrepresentation or omission, we reserve the right to adjust the pricing or make any other corrections.