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Road Bay Cruises

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™.

Road Bay
Cruise Specials

Explora Journeys, EXPLORA II
EXPLORA II Cruises15 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...
Windstar Cruises, Wind Surf
Wind Surf Cruise Ship7 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...
Explora Journeys, EXPLORA II
EXPLORA II Cruises15 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...
EXPLORA II Cruises7 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...
Windstar Cruises, Wind Surf
Wind Surf Cruise Ship7 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...
Windstar Cruises, Wind Surf
Wind Surf Cruise Ship14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, 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 21, More...
Windstar Cruises, Wind Surf
Wind Surf Cruise Ship21 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...
Windstar Cruises, Wind Surf
Wind Surf Cruise Ship7 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...
Explora Journeys, EXPLORA I
EXPLORA I Cruises27 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...
EXPLORA III Cruises14 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...

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Road Bay Cruises