Road Bay Cruises
Cruises that visit Caribbean: Anguilla: Road Bay
14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Deshaies, Basseterre, Gustavia, Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Feb 28, 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...7 Night - Beach Fun & Sun : a Remote Caribbean Getaway
Starting in Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 7, More...15 Night - An Extended Journey of Paradise Beauty and Colourful Shores
Starting in San Juan, Road Bay, St Johns AG, Antigua, St Maarten / Philipsburg, Spanish Town (Virgin Gorda), Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan
2026 Sails: Mar 11, More...7 Night - A Journey from San Juan to Miami
Starting in San Juan, Road Bay, St Johns AG, Antigua, St Maarten / Philipsburg, Spanish Town (Virgin Gorda), Miami
2026 Sails: Mar 11, More...14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 14, 2027: Feb 13, Mar 13, More...7 Night - James Beard Foundation : Beach Fun & Sun : a Remote Caribbean Getaway
Starting in Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 14, 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™.
14 Night - Star Collector : Caribbean ExplorationsStarting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Deshaies, Basseterre, Gustavia, Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Feb 28, More...
Deal link -> Special
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...
7 Night - Beach Fun & Sun : a Remote Caribbean GetawayStarting in Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Virgin Gorda / Prickly Pear, British Virgin Islands, Sopers Hole, Jost Van Dyke, Great Harbour, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 7, More...
15 Night - An Extended Journey of Paradise Beauty and Colourful ShoresStarting in San Juan, Road Bay, St Johns AG, Antigua, St Maarten / Philipsburg, Spanish Town (Virgin Gorda), Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan
2026 Sails: Mar 11, More...
Deal link -> Special
7 Night - A Journey from San Juan to MiamiStarting in San Juan, Road Bay, St Johns AG, Antigua, St Maarten / Philipsburg, Spanish Town (Virgin Gorda), Miami
2026 Sails: Mar 11, More...
14 Night - Star Collector : Caribbean ExplorationsStarting in Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 14, 2027: Feb 13, Mar 13, More...
7 Night - James Beard Foundation : Beach Fun & Sun : a Remote Caribbean GetawayStarting in Philipsburg, St Maarten, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 14, More...
