15 Night - An Extended Journey Into the Tropical Enchantment of Caribbean Splendour
Starting in Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan, Tortola / Road Town, St Johns AG, Antigua, Gustavia, Road Bay, Miami
2025 Sails: Nov 27, 2026: Jan 28, More...

19 Night - An Extended Journey of Wild Grace
Starting in Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan, Tortola / Road Town, St Johns AG, Antigua, Gustavia, Road Bay, Miami, La Romana, San Juan, Basseterre, Les Trois-Ilets, Bequia, Kingstown, Bridgetown
2025 Sails: Dec 2, More...

8 Night - Pirate Islands and Sailors' Haunts
Starting in Philipsburg, Gustavia, Road Bay (Sandy Ground), North Sound / Virgin Gorda, Sail Through the Sir Francis Drake Channel, Great Harbour / Jost Van Dyke, White Bay, Jost Van Dyke, Philipsburg
2025 Sails: Dec 4, More...

16 Night - An Extended Journey of Bewitching Caribbean Gems
Starting in San Juan, Tortola / Road Town, St Johns AG, Antigua, Gustavia, Road Bay, Miami, La Romana, San Juan, Basseterre, Les Trois-Ilets, Bequia, Kingstown, Bridgetown
2025 Sails: Dec 5, More...

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...

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, Dec 21, 2027: Feb 6, Mar 6, 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 - 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...

6 Night - San Juan / San Juan
Starting in San Juan, Portsmouth DM, Falmouth Harbour, Antigua, Sandy Ground, Virgin Gorda, San Juan
2025 Sails: Dec 12, More...