Road Bay Cruises
Cruises that visit Caribbean: Anguilla: Road Bay
28 Night - Star Collector : the Best of the Windward & Leeward Isles
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, Basseterre, Gustavia, St Johns AG, Les Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St Georges, Bridgetown, Bequia, Mayreau, Soufriere, Kralendijk, Willemstad AN, Oranjestad
2026 Sails: Jan 4, More...21 Night - Star Collector : a Lesser Antilles Odyssey
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, Basseterre, Gustavia, St Johns AG, Les Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St Georges, Bridgetown
2026 Sails: Jan 4, More...14 Night - Star Collector : Leeward & Windward Caribbean Havens
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, Basseterre, Gustavia, St Johns, Les Saintes, Roseau, Mayreau, Bridgetown
2026 Sails: Jan 4, More...
15 Night - An Extended Journey Through Caribbean Cinematic Paradise
Starting in 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, Little Bay, San Juan
2026 Sails: Jan 6, More...7 Night - A Journey from San Juan to Miami
Starting in San Juan, Gustavia, St Johns AG, Antigua, Tortola / Road Town, Road Bay, Miami
2026 Sails: Jan 6, More...
7 Night - History and Culture Visiting Caribbean Jewels
Starting in Pointe-a-Pitre, Les Saintes, Falmouth Bay, Barbuda, Charlestown, Nevis, Gustavia, Road Bay, Anguilla, Prickley Pear Cays, Marigot
2026 Sails: Jan 10, Feb 7, Mar 7, Apr 4, More...15 Night - An Extended Journey of Fabled Ports, Volcanic Isles and Soft Sands
Starting in Miami, St John VI (Cruz Bay), US Virgin Islands, Deshaies, St Georges, Grenada, Bridgetown, Little Bay, San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 13, More...14 Night - An Extended Journey Between Sophistication & Silky Sands
Starting in Bridgetown, Little Bay, San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown
2026 Sails: Jan 19, More...15 Night - An Extended Journey of Caribbean Inspiration and Island Beauty
Starting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan
2026 Sails: Jan 21, More...7 Night - A Journey from San Juan to Miami
Starting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 21, More...
Cruises that visit Caribbean: Anguilla: Road Bay
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28 Night - Star Collector : the Best of the Windward & Leeward IslesStarting 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, Basseterre, Gustavia, St Johns AG, Les Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St Georges, Bridgetown, Bequia, Mayreau, Soufriere, Kralendijk, Willemstad AN, Oranjestad
2026 Sails: Jan 4, More...
21 Night - Star Collector : a Lesser Antilles OdysseyStarting 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, Basseterre, Gustavia, St Johns AG, Les Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St Georges, Bridgetown
2026 Sails: Jan 4, More...
14 Night - Star Collector : Leeward & Windward Caribbean HavensStarting 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, Basseterre, Gustavia, St Johns, Les Saintes, Roseau, Mayreau, Bridgetown
2026 Sails: Jan 4, More...
15 Night - An Extended Journey Through Caribbean Cinematic ParadiseStarting in 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, Little Bay, San Juan
2026 Sails: Jan 6, More...
Deal link -> Special
7 Night - A Journey from San Juan to MiamiStarting in San Juan, Gustavia, St Johns AG, Antigua, Tortola / Road Town, Road Bay, Miami
2026 Sails: Jan 6, More...
7 Night - History and Culture Visiting Caribbean JewelsStarting in Pointe-a-Pitre, Les Saintes, Falmouth Bay, Barbuda, Charlestown, Nevis, Gustavia, Road Bay, Anguilla, Prickley Pear Cays, Marigot
2026 Sails: Jan 10, Feb 7, Mar 7, Apr 4, More...
15 Night - An Extended Journey of Fabled Ports, Volcanic Isles and Soft SandsStarting in Miami, St John VI (Cruz Bay), US Virgin Islands, Deshaies, St Georges, Grenada, Bridgetown, Little Bay, San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 13, More...
14 Night - An Extended Journey Between Sophistication & Silky SandsStarting in Bridgetown, Little Bay, San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown
2026 Sails: Jan 19, More...
15 Night - An Extended Journey of Caribbean Inspiration and Island BeautyStarting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan
2026 Sails: Jan 21, More...
Deal link -> Special
7 Night - A Journey from San Juan to MiamiStarting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 21, More...
