Road Bay Cruises
Cruises that visit Caribbean: Anguilla: Road Bay
21 Night - Star Collector : Spectacular Transatlantic Journey : Caribbean to the Azores
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, Ponta Delgada, Lisbon
2026 Sails: Mar 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: Mar 28, More...
27 Night - A Grand Journey of Colourful Moroccan Shores & Idyllic Caribbean Scenery
Starting in Barcelona, Alicante, Lisbon, Casablanca, Tangier, Malaga, Spain, Motril, Barcelona, Cadiz, Funchal (Madeira), St Johns AG, Antigua, Road Bay, San Juan, Miami
2026 Sails: Oct 21, More...
14 Night - An Extended Journey of Maritime Soul & Island Zest
Starting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami
2026 Sails: Oct 25, More...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...
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™.
21 Night - Star Collector : Spectacular Transatlantic Journey : Caribbean to the AzoresStarting 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, Ponta Delgada, Lisbon
2026 Sails: Mar 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: Mar 28, More...
27 Night - A Grand Journey of Colourful Moroccan Shores & Idyllic Caribbean SceneryStarting in Barcelona, Alicante, Lisbon, Casablanca, Tangier, Malaga, Spain, Motril, Barcelona, Cadiz, Funchal (Madeira), St Johns AG, Antigua, Road Bay, San Juan, Miami
2026 Sails: Oct 21, More...
14 Night - An Extended Journey of Maritime Soul & Island ZestStarting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami
2026 Sails: Oct 25, More...
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...
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...
