7 Night - A Journey from San Juan to Miami
Starting in San Juan, Tortola / Road Town, St Johns AG, Antigua, Gustavia, Road Bay, Miami
2025 Sails: Dec 5, 2026: Feb 5, 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
2025 Sails: Dec 6, Dec 20, 2026: Jan 3, Jan 17, Jan 31, Feb 14, Feb 28, Mar 14, Nov 28, Dec 12, Dec 26, 2027: Jan 9, Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, More...

7 Night - Classic Caribbean
Starting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten
2025 Sails: Dec 7, Dec 21, 2026: Mar 21, 2027: Jan 23, Feb 6, Feb 20, Mar 6, Mar 20, More...

14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2025 Sails: Dec 7, 2027: Feb 6, Mar 6, More...

7 Night - Bridgetown to Bridgetown
Starting in Bridgetown, Castries, St Lucia, Fort-de-France, Gustavia, St Barthelemy, Roseau, St Georges, Bequia, Bridgetown
2025 Sails: Dec 8, More...

5 Night - San Juan / San Juan
Starting in San Juan, Virgin Gorda, Sandy Ground, Gustavia, St Thomas, San Juan
2025 Sails: Dec 10, More...

11 Night - A Sunny Break from Winter Blues
Starting in Philipsburg, Sail Through the Sir Francis Drake Channel, Great Harbour / Jost Van Dyke, The Bight Bay / Norman Island, North Sound / Virgin Gorda, Gustavia, Cabrits, Terre-De-Haut, Iles Des Saintes, Philipsburg
2025 Sails: Dec 10, More...

11 Night - Rendezvous of Two Windjammers
Starting in Philipsburg, North Sound / Virgin Gorda, The Bight Bay / Norman Island, Gustavia, Terre-De-Haut, Iles Des Saintes, Cabrits, Road Bay (Sandy Ground), Philipsburg
2025 Sails: Dec 11, More...

11 Night - Fort Lauderdale to Fort Lauderdale
Starting in Fort Lauderdale, Florida, San Juan, St John VI, Gustavia, St Barthelemy, St Kitts (Basseterre), Deshaies, Road Town, Tortola, Fort Lauderdale, Florida
2025 Sails: Dec 12, More...

7 Night - Caribbean Yachting Discovery
Starting in St Johns AG, Antigua, Barbuda, Antigua and Barbuda, Iles des Saintes, Guadeloupe, Deshaies, Guadeloupe, Gustavia, Saint Barthelemy, Virgin Gorda, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico
2025 Sails: Dec 13, 2026: Jan 10, Feb 7, More...