11 Night - Masterpieces at Sea : Gems of the Leeward Islands
Starting in San Juan, Cruz Bay, St John VI, Gustavia, St Barthelemy, Basseterre, St Kitts, Falmouth Harbour, Antigua, Les Saintes, Guadeloupe, Rodney Bay, St Georges, Grenada, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan
2026 Sails: Oct 28, 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, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan
2026 Sails: Nov 8, 2027: Nov 8, 2028: Mar 13, More...

7 Night - San Juan & the Virgin Islands
Starting in San Juan, Cruz Bay, St John VI, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan
2026 Sails: Nov 15, 2027: Jan 10, Nov 1, Nov 15, 2028: Mar 20, More...

14 Night - Star Collector : Lovely Leewards
Starting in San Juan, Cruz Bay, St John VI, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, San Juan, St Georges, Grenada, Bequia, Mayreau, Les Saintes, Guadeloupe, Marigot Bay, San Juan
2026 Sails: Nov 15, 2027: Nov 1, Nov 15, 2028: Mar 20, More...

15 Night - Southern Caribbean in Depth
Starting in Miami, Florida, San Juan, Puerto Rico, Great Harbour, Jost van Dyke, British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Bridgetown, Barbados, Rodney Bay, Saint Lucia, Little Bay, Montserrat, St Johns AG, Antigua, Carambola Beach, Saint Kitts and Nevis, Spanish Town, Virgin Gorda, British Virgin Islands, Philipsburg, Sint Maarten
2026 Sails: Nov 20, More...

8 Night - Southern Caribbean Gems
Starting in Miami, Florida, San Juan, Puerto Rico, Great Harbour, Jost van Dyke, British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Port Elizabeth VC, Bequia, St Vincent and the Grenadines, Bridgetown, Barbados
2026 Sails: Nov 20, More...

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...

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...