14 Night - Leeward Island Jewels
Starting in Miami, Florida, San Juan, Puerto Rico, Road Bay, Anguilla, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Fort-De-France, Martinique, Little Bay, Montserrat, Terre-de-Haut, Iles des Saintes, Guadeloupe, Spanish Town, Virgin Gorda, British Virgin Islands, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Nov 22, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, St Georges, Grenada, Bequia, Mayreau, Les Saintes, Guadeloupe, Marigot Bay, San Juan, Cruz Bay, St John VI, Gustavia, St Barthelemy, Basseterre, St Kitts, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan
2026 Sails: Nov 22, More...

9 Night - The Americas & Caribbean
Starting in Fort Lauderdale, Nassau (Paradise Island), Samana, San Juan, Jost Van Dyke, British Virgin Islands, Oranjestad, Aruba, Cartagena CO
2026 Sails: Nov 23, More...

19 Night - The Americas & Caribbean
Starting in Fort Lauderdale, Nassau (Paradise Island), Samana, San Juan, Jost Van Dyke, British Virgin Islands, Oranjestad, Aruba, Cartagena CO, Willemstad AN, Kralendijk, Oranjestad, Aruba, Santa Marta, Panama Canal Transit, Fuerte Amador (Panama City), Puntarenas
2026 Sails: Nov 23, More...

28 Night - The Americas & Caribbean
Starting in Fort Lauderdale, Nassau (Paradise Island), Samana, San Juan, Jost Van Dyke, British Virgin Islands, Oranjestad, Aruba, Cartagena CO, Willemstad AN, Kralendijk, Oranjestad, Aruba, Santa Marta, Panama Canal Transit, Fuerte Amador (Panama City), Puntarenas, Playa Flamingo, Acajutla, Zihuatanejo, Manzanillo, Puerto Vallarta, San Diego
2026 Sails: Nov 23, More...

5 Night - The Americas & Caribbean
Starting in San Juan, Jost Van Dyke, British Virgin Islands, Oranjestad, Aruba, Cartagena CO
2026 Sails: Nov 27, More...

7 Night - Treasure Islands
Starting in Philipsburg, St Maarten, Road Bay, Anguilla, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Gustavia, St Barts, Philipsburg, St Maarten
2026 Sails: Nov 28, Dec 12, 2027: Jan 9, 2028: Jan 22, More...

7 Night - A Tall Ship's Dream Destination
Starting in Philipsburg, St Johns AG, Antigua, Gustavia, North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, White Bay, Jost Van Dyke, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, Philipsburg
2026 Sails: Nov 29, More...

7 Night - San Juan & the Virgin Islands
Starting in San Juan, Cruz Bay, St John VI, Gustavia, St Barthelemy, Basseterre, St Kitts, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan
2026 Sails: Nov 29, Dec 13, Dec 27, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, Cruz Bay, St John VI, Gustavia, St Barthelemy, Basseterre, St Kitts, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan, St Georges, Grenada, Bequia, Mayreau, Deshaies, Marigot Bay, San Juan
2026 Sails: Nov 29, Dec 13, Dec 27, More...