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 - Treasure Islands
Starting in Philipsburg, St Maarten, Road Bay, Anguilla, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Gustavia, St Barts, Philipsburg, St Maarten
2026 Sails: Feb 28, Mar 14, Nov 28, Dec 12, 2027: Jan 9, 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...
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, 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...
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...
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 - Treasure IslandsStarting in Philipsburg, St Maarten, Road Bay, Anguilla, White Bay, Jost Van Dyke, Sopers Hole, Tortola, Sailing Sir Francis Drake Channel, The Bight / Norman Island, British Virgin Islands, Spanish Town, Virgin Gorda, Beach, Captains Best, British Virgin Islands, Basseterre, St Kitts (Morning), South Friars Bay, St Kitts, Gustavia, St Barts, Philipsburg, St Maarten
2026 Sails: Feb 28, Mar 14, Nov 28, Dec 12, 2027: Jan 9, More...
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...
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, 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...
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...