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...

14 Night - Star Collector : Caribbean Explorations
Starting in 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, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten
2025 Sails: Dec 14, 2026: Mar 14, 2027: Feb 13, Mar 13, More...

7 Night - Beach Fun & Sun : a Remote Caribbean Getaway
Starting in 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 14, 2026: Jan 4, 2027: Jan 2, Feb 13, Mar 13, More...

14 Night - An Extended Journey of Caribbean Festivities and West Indies Coastal Wonders
Starting in Miami, Ocean Cay, Charlotte Amalie (Saint Thomas), Spanish Town (Virgin Gorda), Marigot, San Juan, Road Bay, St John VI (Cruz Bay), US Virgin Islands, New Year Fireworks Sju, Puerto Plata, Dominican Republic, Key West, Miami
2025 Sails: Dec 22, More...

15 Night - An Extended Journey Into Shimmering New Dawns and Caribbean Secrets
Starting in Miami, New Year Fireworks Sju, Jost Van Dyke, Deshaies, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan, Gustavia, St Johns AG, Antigua, Tortola / Road Town, Road Bay, Miami
2025 Sails: Dec 29, More...

17 Night - An Extended Journey of Fireworks, Fiestas and Spectacular Shores
Starting in San Juan, Road Bay, St John VI (Cruz Bay), US Virgin Islands, New Year Fireworks Sju, Puerto Plata, Dominican Republic, Key West, Miami, San Andres Island, Colon, Bocas del Toro, Puerto Limon, George Town, Grand Cayman, Miami
2025 Sails: Dec 29, More...

7 Night - A Journey Savy New Years Celebrations and Caribbean Conviviality
Starting in San Juan, Road Bay, St John VI (Cruz Bay), US Virgin Islands, New Year Fireworks Sju, Puerto Plata, Dominican Republic, Key West, Miami
2025 Sails: Dec 29, More...

16 Night - An Extended Journey Between Idyllic & Volcanic Isles
Starting in Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan, Gustavia, St Johns AG, Antigua, Tortola / Road Town, Road Bay, Miami, St John VI (Cruz Bay), US Virgin Islands, Deshaies, St Georges, Grenada, Bridgetown
2026 Sails: Jan 3, More...

8 Night - Caribbean Roundtrip from St Maarten (Philipsburg)
Starting in Philipsburg, Saint-Pierre, Soufriere, Cabrits, Charlestown, Nevis, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Jan 4, Jan 18, More...

10 Night - Sublime Southern Caribbean
Starting in Bridgetown, Mayreau, Roseau, Anse Mitan, Charlestown, Basseterre, St Johns, Falmouth Harbour, Gustavia, Road Bay, Philipsburg, St Maarten
2026 Sails: Jan 4, More...