Anguilla Cruises
Cruises that visit Caribbean: Anguilla
Related areas: Dog Island : Prickly Pear Cay : Road Bay : Sandy Ground
15 Night - An Extended Journey Through Caribbean Cinematic Paradise
Starting in San Juan, Gustavia, St Johns AG, Antigua, Tortola / Road Town, Road Bay, Miami, St John VI (Cruz Bay), US Virgin Islands, Deshaies, St Georges, Grenada, Bridgetown, Little Bay, San Juan
2026 Sails: Jan 6, More...7 Night - A Journey from San Juan to Miami
Starting in San Juan, Gustavia, St Johns AG, Antigua, Tortola / Road Town, Road Bay, Miami
2026 Sails: Jan 6, More...
7 Night - History and Culture Visiting Caribbean Jewels
Starting in Pointe-a-Pitre, Les Saintes, Falmouth Bay, Barbuda, Charlestown, Nevis, Gustavia, Road Bay, Anguilla, Prickley Pear Cays, Marigot
2026 Sails: Jan 10, Feb 7, Mar 7, Apr 4, More...
10 Night - the Best of the Secluded Caribbean Cruise
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Prickly Pear, Sandy Ground, Gustavia, Philipsburg, Terre De Haut, Iles des Saintes, Port Elizabeth VC, Bequia, Tobago Cays, Bridgetown, Barbados
2026 Sails: Jan 10, More...
7 Night - St. Barths & Caribbean Gems Cruise
Starting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Prickly Pear, Sandy Ground, Gustavia, South Friars Bay, Falmouth Bay, Philipsburg
2026 Sails: Jan 11, More...15 Night - An Extended Journey of Fabled Ports, Volcanic Isles and Soft Sands
Starting in Miami, St John VI (Cruz Bay), US Virgin Islands, Deshaies, St Georges, Grenada, Bridgetown, Little Bay, San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 13, More...7 Night - Reverie Under Sail in the Heart of the Lesser Antilles
Starting in Marigot, Sandy Island, Anguilla, Virgin Gorda, Norman Island, Cooper Island, Beef Island, Jost Van Dyke, Beef Island, Dog Island, Anguilla, Philipsburg
2026 Sails: Jan 17, Feb 14, Mar 14, More...14 Night - An Extended Journey Between Sophistication & Silky Sands
Starting in Bridgetown, Little Bay, San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown
2026 Sails: Jan 19, More...15 Night - An Extended Journey of Caribbean Inspiration and Island Beauty
Starting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan
2026 Sails: Jan 21, More...7 Night - A Journey from San Juan to Miami
Starting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 21, More...
Cruises that visit Caribbean: Anguilla
Click on a cruise ship itinerary that visits Anguilla (below) and select a sail date to receive competing cruise quotes. To search all cruise itineraries (not just Anguilla), please visit: Cruise Search or try our Virtual Cruise Advisor™.
Related areas: Dog Island : Prickly Pear Cay : Road Bay : Sandy Ground
Deal link -> Special
15 Night - An Extended Journey Through Caribbean Cinematic ParadiseStarting in San Juan, Gustavia, St Johns AG, Antigua, Tortola / Road Town, Road Bay, Miami, St John VI (Cruz Bay), US Virgin Islands, Deshaies, St Georges, Grenada, Bridgetown, Little Bay, San Juan
2026 Sails: Jan 6, More...
7 Night - A Journey from San Juan to MiamiStarting in San Juan, Gustavia, St Johns AG, Antigua, Tortola / Road Town, Road Bay, Miami
2026 Sails: Jan 6, More...
7 Night - History and Culture Visiting Caribbean JewelsStarting in Pointe-a-Pitre, Les Saintes, Falmouth Bay, Barbuda, Charlestown, Nevis, Gustavia, Road Bay, Anguilla, Prickley Pear Cays, Marigot
2026 Sails: Jan 10, Feb 7, Mar 7, Apr 4, More...
10 Night - the Best of the Secluded Caribbean CruiseStarting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Prickly Pear, Sandy Ground, Gustavia, Philipsburg, Terre De Haut, Iles des Saintes, Port Elizabeth VC, Bequia, Tobago Cays, Bridgetown, Barbados
2026 Sails: Jan 10, More...
7 Night - St. Barths & Caribbean Gems CruiseStarting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Prickly Pear, Sandy Ground, Gustavia, South Friars Bay, Falmouth Bay, Philipsburg
2026 Sails: Jan 11, More...
Deal link -> Special
15 Night - An Extended Journey of Fabled Ports, Volcanic Isles and Soft SandsStarting in Miami, St John VI (Cruz Bay), US Virgin Islands, Deshaies, St Georges, Grenada, Bridgetown, Little Bay, San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 13, More...
7 Night - Reverie Under Sail in the Heart of the Lesser AntillesStarting in Marigot, Sandy Island, Anguilla, Virgin Gorda, Norman Island, Cooper Island, Beef Island, Jost Van Dyke, Beef Island, Dog Island, Anguilla, Philipsburg
2026 Sails: Jan 17, Feb 14, Mar 14, More...
14 Night - An Extended Journey Between Sophistication & Silky SandsStarting in Bridgetown, Little Bay, San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown
2026 Sails: Jan 19, More...
Deal link -> Special
15 Night - An Extended Journey of Caribbean Inspiration and Island BeautyStarting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami, Charlotte Amalie (Saint Thomas), Terre-De-Haut, Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan
2026 Sails: Jan 21, More...
Deal link -> Special
7 Night - A Journey from San Juan to MiamiStarting in San Juan, Gustavia, Tortola / Road Town, St Johns AG, Antigua, Road Bay, Miami
2026 Sails: Jan 21, More...
