Anguilla Cruises
Cruises that visit Caribbean: Anguilla
Related areas: Dog Island : Prickly Pear Cay : Road Bay : Sandy Ground
8 Night - Sun, Sea, and Serenity
Starting in Philipsburg, Gustavia, Cabrits, Terre-De-Haut, Iles Des Saintes, Saint-Pierre, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Feb 27, Mar 26, More...
7 Night - Eastern Caribbean with St. Barths
Starting in Marigot, Saint Martin, Prickly Pear Cays, Anguilla, Charlestown / Cades Bay, Saint Kitts and Nevis, Gustavia, Saint Barthelemy, Falmouth Bay, English Harbour, Antigua and Barbuda, Iles des Saintes, Guadeloupe, Soufriere, Saint Lucia, Bridgetown, Barbados
2026 Sails: Feb 28, More...
7 Night - British Islands Discovery Cruise
Starting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Prickly Pear, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, Sandy Ground, Gustavia, Philipsburg, Charlotte Amalie, St Thomas
2026 Sails: Feb 28, More...
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), Gibraltar, 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 - 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...
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...
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
8 Night - Sun, Sea, and SerenityStarting in Philipsburg, Gustavia, Cabrits, Terre-De-Haut, Iles Des Saintes, Saint-Pierre, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Feb 27, Mar 26, More...
7 Night - Eastern Caribbean with St. BarthsStarting in Marigot, Saint Martin, Prickly Pear Cays, Anguilla, Charlestown / Cades Bay, Saint Kitts and Nevis, Gustavia, Saint Barthelemy, Falmouth Bay, English Harbour, Antigua and Barbuda, Iles des Saintes, Guadeloupe, Soufriere, Saint Lucia, Bridgetown, Barbados
2026 Sails: Feb 28, More...
7 Night - British Islands Discovery CruiseStarting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Prickly Pear, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, Sandy Ground, Gustavia, Philipsburg, Charlotte Amalie, St Thomas
2026 Sails: Feb 28, More...
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...
Deal link -> Special
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), Gibraltar, Barcelona
2026 Sails: Mar 2, More...
Deal link -> Special
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 - 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
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...