Road Bay Cruises
Cruises that visit Caribbean: Anguilla: Road Bay
17 Night - An Extended Journey Into Tropical Utopia, Coral Wonders & Blissful Beaches
Starting in San Juan, Oranjestad, Willemstad AN, Kralendijk, Bridgetown, Terre-De-Haut, St Maarten / Philipsburg, Jost Van Dyke, San Juan, St Johns AG, Antigua, Road Bay, Spanish Town (Virgin Gorda), Charlotte Amalie (Saint Thomas), Miami
2026 Sails: Feb 20, More...
7 Night - Beach Fun & Sun : a Remote Caribbean Getaway
Starting in Philipsburg, St Maarten, St Johns, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Feb 21, More...
22 Night - Star Collector : a Lesser Antilles Odyssey
Starting in Philipsburg, St Maarten, St Johns AG, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten, Basseterre, Gustavia, Falmouth Harbour, Les Saintes, Roseau, Mayreau, Bridgetown, Basseterre, St Johns AG, Les Saintes, Roseau, Mayreau, Anse Mitan, Bridgetown
2026 Sails: Feb 21, More...
14 Night - Star Collector : Leeward & Windward Caribbean Havens
Starting in Philipsburg, St Maarten, St Johns, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten, Basseterre, Gustavia, Falmouth Harbour, Les Saintes, Roseau, Mayreau, Bridgetown
2026 Sails: Feb 21, More...
8 Night - Sun, Sea, and Serenity
Starting in Philipsburg, Gustavia, Cabrits, Terre-De-Haut, Iles Des Saintes, Saint-Pierre, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Feb 27, Mar 26, 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
2026 Sails: Feb 28, Mar 14, Nov 28, Dec 12, 2027: Jan 9, More...
7 Night - A Journey Into Tropical Utopia & Spanish Legacy with Art Deco Flair
Starting in San Juan, St Johns AG, Antigua, Road Bay, Spanish Town (Virgin Gorda), Charlotte Amalie (Saint Thomas), Miami
2026 Sails: Mar 2, More...
23 Night - A Grand Journey of Lively Latin Flair, Modern Marvels & Coastal Charm
Starting in San Juan, St Johns AG, Antigua, Road Bay, Spanish Town (Virgin Gorda), Charlotte Amalie (Saint Thomas), Miami, San Juan, St Maarten / Philipsburg, Santa Cruz de Tenerife, Arrecife (Lanzarote), Tangier, Barcelona
2026 Sails: Mar 2, More...
15 Night - An Extended Journey Through Spectacular Nature and Historic Wonders
Starting in San Juan, St Georges, Grenada, Bequia, Bridgetown, Fort-de-France, Martinique, Gustavia, Basseterre, San Juan, Road Bay, St Johns AG, Antigua, St Maarten / Philipsburg, Spanish Town (Virgin Gorda), Miami
2026 Sails: Mar 3, More...
7 Night - History and Culture Visiting Caribbean Jewels
Starting in Pointe-a-Pitre, Les Saintes, Falmouth Bay, Barbuda, Charlestown, Nevis, Gustavia, Prickley Pear Cays, Road Bay, Anguilla, Marigot
2026 Sails: Mar 7, Apr 4, 2027: Jan 9, More...
Cruises that visit Caribbean: Anguilla: Road Bay
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17 Night - An Extended Journey Into Tropical Utopia, Coral Wonders & Blissful BeachesStarting in San Juan, Oranjestad, Willemstad AN, Kralendijk, Bridgetown, Terre-De-Haut, St Maarten / Philipsburg, Jost Van Dyke, San Juan, St Johns AG, Antigua, Road Bay, Spanish Town (Virgin Gorda), Charlotte Amalie (Saint Thomas), Miami
2026 Sails: Feb 20, More...
7 Night - Beach Fun & Sun : a Remote Caribbean GetawayStarting in Philipsburg, St Maarten, St Johns, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Feb 21, More...
22 Night - Star Collector : a Lesser Antilles OdysseyStarting in Philipsburg, St Maarten, St Johns AG, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten, Basseterre, Gustavia, Falmouth Harbour, Les Saintes, Roseau, Mayreau, Bridgetown, Basseterre, St Johns AG, Les Saintes, Roseau, Mayreau, Anse Mitan, Bridgetown
2026 Sails: Feb 21, More...
14 Night - Star Collector : Leeward & Windward Caribbean HavensStarting in Philipsburg, St Maarten, St Johns, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten, Basseterre, Gustavia, Falmouth Harbour, Les Saintes, Roseau, Mayreau, Bridgetown
2026 Sails: Feb 21, More...
8 Night - Sun, Sea, and SerenityStarting in Philipsburg, Gustavia, Cabrits, Terre-De-Haut, Iles Des Saintes, Saint-Pierre, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Feb 27, Mar 26, More...
7 Night - Treasure IslandsStarting 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
2026 Sails: Feb 28, Mar 14, Nov 28, Dec 12, 2027: Jan 9, More...
7 Night - A Journey Into Tropical Utopia & Spanish Legacy with Art Deco FlairStarting in San Juan, St Johns AG, Antigua, Road Bay, Spanish Town (Virgin Gorda), Charlotte Amalie (Saint Thomas), Miami
2026 Sails: Mar 2, More...
23 Night - A Grand Journey of Lively Latin Flair, Modern Marvels & Coastal CharmStarting in San Juan, St Johns AG, Antigua, Road Bay, Spanish Town (Virgin Gorda), Charlotte Amalie (Saint Thomas), Miami, San Juan, St Maarten / Philipsburg, Santa Cruz de Tenerife, Arrecife (Lanzarote), Tangier, Barcelona
2026 Sails: Mar 2, More...
15 Night - An Extended Journey Through Spectacular Nature and Historic WondersStarting in San Juan, St Georges, Grenada, Bequia, Bridgetown, Fort-de-France, Martinique, Gustavia, Basseterre, San Juan, Road Bay, St Johns AG, Antigua, St Maarten / Philipsburg, Spanish Town (Virgin Gorda), Miami
2026 Sails: Mar 3, More...
7 Night - History and Culture Visiting Caribbean JewelsStarting in Pointe-a-Pitre, Les Saintes, Falmouth Bay, Barbuda, Charlestown, Nevis, Gustavia, Prickley Pear Cays, Road Bay, Anguilla, Marigot
2026 Sails: Mar 7, Apr 4, 2027: Jan 9, More...