Road Bay Cruises
Cruises that visit Caribbean: Anguilla: Road Bay
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...
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: Jan 24, More...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
2026 Sails: Jan 28, More...7 Night - Beach Fun & Sun : a Remote Caribbean Getaway
Starting in Philipsburg, St Maarten, St Johns, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Jan 31, More...10 Night - An Extended Journey Into the Caribbean's Most Desirable Shores
Starting in Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan, Tortola / Road Town, St Johns AG, Antigua, Gustavia, Road Bay, Miami
2026 Sails: Feb 2, More...15 Night - A Grand Journey Through Caribbean Serenity and Tropical Treasures
Starting in San Juan, Tortola / Road Town, St Johns AG, Antigua, Gustavia, Road Bay, Miami, Puerto Plata, Dominican Republic, Roseau, Bridgetown, Deshaies, St John VI (Cruz Bay), US Virgin Islands, San Juan
2026 Sails: Feb 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
2026 Sails: Feb 5, More...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...
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...
Cruises that visit Caribbean: Anguilla: Road Bay
Click on a cruise ship itinerary that visits Road Bay (below) and select a sail date to receive competing cruise quotes. To search all cruise itineraries (not just Road Bay), please visit: Cruise Search or try our Virtual Cruise Advisor™.
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...
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: Jan 24, More...
15 Night - An Extended Journey Into the Tropical Enchantment of Caribbean SplendourStarting 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
2026 Sails: Jan 28, More...
7 Night - Beach Fun & Sun : a Remote Caribbean GetawayStarting in Philipsburg, St Maarten, St Johns, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Jan 31, More...
10 Night - An Extended Journey Into the Caribbean's Most Desirable ShoresStarting in Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan, Tortola / Road Town, St Johns AG, Antigua, Gustavia, Road Bay, Miami
2026 Sails: Feb 2, More...
15 Night - A Grand Journey Through Caribbean Serenity and Tropical TreasuresStarting in San Juan, Tortola / Road Town, St Johns AG, Antigua, Gustavia, Road Bay, Miami, Puerto Plata, Dominican Republic, Roseau, Bridgetown, Deshaies, St John VI (Cruz Bay), US Virgin Islands, San Juan
2026 Sails: Feb 5, More...
Deal link -> Special
7 Night - A Journey from San Juan to MiamiStarting in San Juan, Tortola / Road Town, St Johns AG, Antigua, Gustavia, Road Bay, Miami
2026 Sails: Feb 5, More...
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...
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...
