Road Bay Cruises
Cruises that visit Caribbean: Anguilla: Road Bay
16 Night - A Grand Journey of Lively Culture & Stunning Beaches
Starting in Barcelona, Cadiz, Funchal (Madeira), St Johns AG, Antigua, Road Bay, San Juan, Miami
2026 Sails: Nov 1, More...24 Night - A Grand Journey of Vibrant Cultures, Mayan Marvels & Idyllic Beaches
Starting in Barcelona, Cadiz, Funchal (Madeira), St Johns AG, Antigua, Road Bay, San Juan, Miami, Merida (Progreso), Roatan Island, Belize City, Ocean Cay, Miami
2026 Sails: Nov 1, More...
7 Night - A Journey Into Caribbean Exploration & Island Delights
Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami
2026 Sails: Nov 1, More...14 Night - An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines
Starting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami, Providenciales, Puerto Plata, Dominican Republic, La Romana, Jost Van Dyke, Gustavia, San Juan
2026 Sails: Nov 1, More...14 Night - An Extended Journey of Blissful Escapes & Shoreline Splendour
Starting in Miami, Providenciales, Puerto Plata, Dominican Republic, La Romana, Jost Van Dyke, Gustavia, San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami
2026 Sails: Nov 8, More...7 Night - A Journey of Blissful Escapes & Island Splendour
Starting in San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami
2026 Sails: Nov 15, More...14 Night - An Extended Journey of Tropical Harmony & Natural Wonders
Starting in San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan
2026 Sails: Nov 15, More...
14 Night - Leeward Island Jewels
Starting in Miami, Florida, San Juan, Puerto Rico, Road Bay, Anguilla, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Fort-De-France, Martinique, Terre-de-Haut, Iles des Saintes, Guadeloupe, Little Bay, Montserrat, Spanish Town, Virgin Gorda, British Virgin Islands, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Nov 22, More...
21 Night - Star Collector : Hearty Ports & Rum Punches - a Transatlantic Crossing
Starting in Lisbon, St Johns AG, Philipsburg, St Maarten, Gustavia, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Philipsburg, St Maarten
2026 Sails: Dec 5, More...14 Night - An Extended Journey Through Islands of Scenic Wonder & Coastal History
Starting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, Gustavia, San Juan, Road Bay, St Johns AG, Antigua, Basseterre, Grand Turk, Miami
2026 Sails: Dec 6, 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™.
Deal link -> Special
16 Night - A Grand Journey of Lively Culture & Stunning BeachesStarting in Barcelona, Cadiz, Funchal (Madeira), St Johns AG, Antigua, Road Bay, San Juan, Miami
2026 Sails: Nov 1, More...
24 Night - A Grand Journey of Vibrant Cultures, Mayan Marvels & Idyllic BeachesStarting in Barcelona, Cadiz, Funchal (Madeira), St Johns AG, Antigua, Road Bay, San Juan, Miami, Merida (Progreso), Roatan Island, Belize City, Ocean Cay, Miami
2026 Sails: Nov 1, More...
Deal link -> Special
7 Night - A Journey Into Caribbean Exploration & Island DelightsStarting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami
2026 Sails: Nov 1, More...
14 Night - An Extended Journey Into Island Delights, Hidden Coves & Chic CoastlinesStarting in San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami, Providenciales, Puerto Plata, Dominican Republic, La Romana, Jost Van Dyke, Gustavia, San Juan
2026 Sails: Nov 1, More...
14 Night - An Extended Journey of Blissful Escapes & Shoreline SplendourStarting in Miami, Providenciales, Puerto Plata, Dominican Republic, La Romana, Jost Van Dyke, Gustavia, San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami
2026 Sails: Nov 8, More...
7 Night - A Journey of Blissful Escapes & Island SplendourStarting in San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami
2026 Sails: Nov 15, More...
14 Night - An Extended Journey of Tropical Harmony & Natural WondersStarting in San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan
2026 Sails: Nov 15, More...
14 Night - Leeward Island JewelsStarting in Miami, Florida, San Juan, Puerto Rico, Road Bay, Anguilla, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Fort-De-France, Martinique, Terre-de-Haut, Iles des Saintes, Guadeloupe, Little Bay, Montserrat, Spanish Town, Virgin Gorda, British Virgin Islands, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Nov 22, More...
21 Night - Star Collector : Hearty Ports & Rum Punches - a Transatlantic CrossingStarting in Lisbon, St Johns AG, Philipsburg, St Maarten, Gustavia, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Philipsburg, St Maarten
2026 Sails: Dec 5, More...
14 Night - An Extended Journey Through Islands of Scenic Wonder & Coastal HistoryStarting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, Gustavia, San Juan, Road Bay, St Johns AG, Antigua, Basseterre, Grand Turk, Miami
2026 Sails: Dec 6, More...
