Road Bay Cruises
Cruises that visit Caribbean: Anguilla: Road Bay
7 Night - A Journey of Caribbean Celebrations & Island Wonders
Starting in San Juan, Basseterre, Tortola / Road Town, Gustavia, Road Bay, Miami
2026 Sails: Dec 20, More...
16 Night - Leeward Island Holiday
Starting in Miami, Florida, San Juan, Puerto Rico, Road Bay, Anguilla, Carambola Beach, Saint Kitts and Nevis, Marigot, St Martin, Terre-de-Haut, Iles des Saintes, Guadeloupe, Fort-De-France, Martinique, Rodney Bay, Saint Lucia, Roseau, Dominica, Little Bay, Montserrat, St Johns AG, Antigua, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Dec 20, More...
7 Night - Treasure Islands
Starting in Philipsburg, St Maarten, Gustavia, St Barts, 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, Road Bay, Anguilla, Philipsburg, St Maarten
2026 Sails: Dec 26, 2027: Mar 20, More...
14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Gustavia, St Barthelemy, Charlestown, Roseau, Dominica, Mayreau, Les Saintes, Guadeloupe, Basseterre, St Kitts, Philipsburg, St Maarten, Falmouth Harbour, Antigua, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Gustavia, St Barthelemy, Philipsburg, St Maarten
2026 Sails: Dec 26, More...
7 Night - Beach Fun & Sun : a Remote Caribbean Getaway
Starting in Philipsburg, St Maarten, Falmouth Harbour, Antigua, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Gustavia, St Barthelemy, Philipsburg, St Maarten
2027 Sails: Jan 2, Feb 13, Mar 13, Dec 5, 2028: Jan 30, Feb 27, More...
14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Falmouth Harbour, Antigua, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Gustavia, St Barthelemy, Philipsburg, St Maarten, Charlestown, Les Saintes, Guadeloupe, Mayreau, Roseau, Dominica, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten
2027 Sails: Jan 2, More...
14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Charlestown, Les Saintes, Guadeloupe, Mayreau, Roseau, Dominica, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Gustavia, St Barthelemy, Falmouth Harbour, Antigua, Philipsburg, St Maarten
2027 Sails: Jan 9, More...
7 Night - Caribbean Roundtrip from St Maarten (Philipsburg)
Starting in Philipsburg, Saint-Pierre, Soufriere, Cabrits, Charlestown, Nevis, Road Bay (Sandy Ground), Philipsburg
2027 Sails: Jan 11, Jan 25, More...
16 Night - An Extended Journey of Island Energy & Ocean Tranquillity
Starting in San Juan, St Maarten / Philipsburg, Terre-De-Haut, St Georges, Grenada, Castries, Puerto Plata, Dominican Republic, Miami, Charlotte Amalie (Saint Thomas), Road Bay, Saint-Pierre, Basseterre, St Maarten / Philipsburg, San Juan
2027 Sails: Jan 13, More...
14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Gustavia, St Barthelemy, Falmouth Harbour, Antigua, Philipsburg, St Maarten, Charlestown, Roseau, Dominica, Mayreau, Les Saintes, Guadeloupe, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten
2027 Sails: Jan 16, Jan 30, 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
7 Night - A Journey of Caribbean Celebrations & Island WondersStarting in San Juan, Basseterre, Tortola / Road Town, Gustavia, Road Bay, Miami
2026 Sails: Dec 20, More...
16 Night - Leeward Island HolidayStarting in Miami, Florida, San Juan, Puerto Rico, Road Bay, Anguilla, Carambola Beach, Saint Kitts and Nevis, Marigot, St Martin, Terre-de-Haut, Iles des Saintes, Guadeloupe, Fort-De-France, Martinique, Rodney Bay, Saint Lucia, Roseau, Dominica, Little Bay, Montserrat, St Johns AG, Antigua, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Dec 20, More...
7 Night - Treasure IslandsStarting in Philipsburg, St Maarten, Gustavia, St Barts, 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, Road Bay, Anguilla, Philipsburg, St Maarten
2026 Sails: Dec 26, 2027: Mar 20, More...
14 Night - Star Collector : Caribbean ExplorationsStarting in Philipsburg, St Maarten, Gustavia, St Barthelemy, Charlestown, Roseau, Dominica, Mayreau, Les Saintes, Guadeloupe, Basseterre, St Kitts, Philipsburg, St Maarten, Falmouth Harbour, Antigua, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Gustavia, St Barthelemy, Philipsburg, St Maarten
2026 Sails: Dec 26, More...
7 Night - Beach Fun & Sun : a Remote Caribbean GetawayStarting in Philipsburg, St Maarten, Falmouth Harbour, Antigua, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Gustavia, St Barthelemy, Philipsburg, St Maarten
2027 Sails: Jan 2, Feb 13, Mar 13, Dec 5, 2028: Jan 30, Feb 27, More...
14 Night - Star Collector : Caribbean ExplorationsStarting in Philipsburg, St Maarten, Falmouth Harbour, Antigua, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Gustavia, St Barthelemy, Philipsburg, St Maarten, Charlestown, Les Saintes, Guadeloupe, Mayreau, Roseau, Dominica, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten
2027 Sails: Jan 2, More...
14 Night - Star Collector : Caribbean ExplorationsStarting in Philipsburg, St Maarten, Charlestown, Les Saintes, Guadeloupe, Mayreau, Roseau, Dominica, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Gustavia, St Barthelemy, Falmouth Harbour, Antigua, Philipsburg, St Maarten
2027 Sails: Jan 9, More...
7 Night - Caribbean Roundtrip from St Maarten (Philipsburg)Starting in Philipsburg, Saint-Pierre, Soufriere, Cabrits, Charlestown, Nevis, Road Bay (Sandy Ground), Philipsburg
2027 Sails: Jan 11, Jan 25, More...
16 Night - An Extended Journey of Island Energy & Ocean TranquillityStarting in San Juan, St Maarten / Philipsburg, Terre-De-Haut, St Georges, Grenada, Castries, Puerto Plata, Dominican Republic, Miami, Charlotte Amalie (Saint Thomas), Road Bay, Saint-Pierre, Basseterre, St Maarten / Philipsburg, San Juan
2027 Sails: Jan 13, More...
14 Night - Star Collector : Caribbean ExplorationsStarting in Philipsburg, St Maarten, Road Bay, Anguilla, Sopers Hole, Tortola, Great Harbour, Jost Van Dyke, Virgin Gorda / Prickly Pear, Gustavia, St Barthelemy, Falmouth Harbour, Antigua, Philipsburg, St Maarten, Charlestown, Roseau, Dominica, Mayreau, Les Saintes, Guadeloupe, Basseterre, St Kitts, Gustavia, St Barthelemy, Philipsburg, St Maarten
2027 Sails: Jan 16, Jan 30, More...