Anguilla Cruises
Cruises that visit Caribbean: Anguilla
Related areas: Dog Island : Prickly Pear Cay : Road Bay : Sandy Ground
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 - British & French Islands Discovery Cruise
Starting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Prickly Pear, Gustavia, Sandy Ground, South Friars Bay, Spanish Town, Virgin Gorda, Peter Island, San Juan
2026 Sails: Mar 7, 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...
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...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 - Eastern Caribbean with St. Barths
Starting in Bridgetown, Barbados, Soufriere, Saint Lucia, Iles des Saintes, Guadeloupe, Falmouth Harbour, Antigua and Barbuda, Charlestown / Cades Bay, Saint Kitts and Nevis, Gustavia, Saint Barthelemy, Prickly Pear Cays, Anguilla, Marigot, Saint Martin
2026 Sails: Mar 14, Mar 28, More...7 Night - Reverie Under Sail in the Heart of the Lesser Antilles
Starting in Marigot, Sandy Island, Anguilla, Virgin Gorda, Cooper Island, Norman Island, Jost Van Dyke, Beef Island, Dog Island, Anguilla, Philipsburg
2026 Sails: Mar 14, 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...
7 Night - Windward & Leeward Islands Cruise
Starting in Charlotte Amalie, St Thomas, Prickly Pear, Sandy Ground, Gustavia, Falmouth Bay, Terre De Haut, Iles des Saintes, Le Marin, Bridgetown, Barbados
2026 Sails: Mar 15, 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
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 - British & French Islands Discovery CruiseStarting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Prickly Pear, Gustavia, Sandy Ground, South Friars Bay, Spanish Town, Virgin Gorda, Peter Island, San Juan
2026 Sails: Mar 7, 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...
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...
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...
7 Night - Eastern Caribbean with St. BarthsStarting in Bridgetown, Barbados, Soufriere, Saint Lucia, Iles des Saintes, Guadeloupe, Falmouth Harbour, Antigua and Barbuda, Charlestown / Cades Bay, Saint Kitts and Nevis, Gustavia, Saint Barthelemy, Prickly Pear Cays, Anguilla, Marigot, Saint Martin
2026 Sails: Mar 14, Mar 28, More...
7 Night - Reverie Under Sail in the Heart of the Lesser AntillesStarting in Marigot, Sandy Island, Anguilla, Virgin Gorda, Cooper Island, Norman Island, Jost Van Dyke, Beef Island, Dog Island, Anguilla, Philipsburg
2026 Sails: Mar 14, 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...
7 Night - Windward & Leeward Islands CruiseStarting in Charlotte Amalie, St Thomas, Prickly Pear, Sandy Ground, Gustavia, Falmouth Bay, Terre De Haut, Iles des Saintes, Le Marin, Bridgetown, Barbados
2026 Sails: Mar 15, More...
