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: Nov 22, 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...

9 Night - Caribbean Flair Away from the Everyday
Starting in Philipsburg, Terre-De-Haut, Iles Des Saintes, Soufriere, Chatham Bay / Union Island, Port Elizabeth VC / Bequia, Cabrits, Philipsburg
2025 Sails: Nov 26, More...

7 Night - Leeward Islands
Starting in Philipsburg, St Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles Des Saintes, Cabrits, Dominica, Terre-De-Haut, Iles Des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St Barts, Philipsburg, St Maarten
2025 Sails: Nov 29, Dec 13, Dec 27, 2026: Jan 10, Jan 24, Feb 7, Feb 21, Mar 7, More...

5 Night - Barefoot Break in the British Virgin Islands
Starting in Philipsburg, St Maarten, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2025 Sails: Dec 2, More...

12 Night - Star Collector : Ivory Beaches & Sapphire Seas of the Caribbean
Starting in Philipsburg, St Maarten, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten
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...

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...

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...