Anguilla Cruises
Cruises that visit Caribbean: Anguilla
Related areas: Dog Island : Prickly Pear Cay : Road Bay : Sandy Ground
7 Night - St. Barths & Caribbean Gems Cruise
Starting in Charlotte Amalie, St Thomas, Fajardo Bay, White Bay, Jost van Dyke, Gustavia, Sandy Ground, St John VI (Cruz Bay), US Virgin Islands, Charlotte Amalie, St Thomas
2026 Sails: Dec 5, More...
21 Night - Star Collector : Hearty Ports & Rum Punches - a Transatlantic Crossing
Starting in Lisbon, St Johns AG, Philipsburg, St Maarten, Gustavia, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Philipsburg, St Maarten
2026 Sails: Dec 5, 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, Marigot, Saint Martin
2026 Sails: Dec 6, 2027: Jan 30, Feb 27, Mar 27, More...
14 Night - Discover the Pearls of the Caribbean
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, Marigot, Saint Martin, Marigot, Saint Martin, Anguilla, Virgin Gorda / Norman Island, British Virgin Islands, Norman Island / Jost van Dyke, British Virgin Islands, Anegada, British Virgin Islands, Saba, Bonaire, Saint Eustatius and Saba / Gustavia, Saint Barthelemy, Gustavia, Saint Barthelemy, Marigot, Saint Martin
2026 Sails: Dec 6, More...
14 Night - An Extended Journey Through Islands of Scenic Wonder & Coastal History
Starting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, Gustavia, San Juan, Road Bay, St Johns AG, Antigua, Basseterre, Grand Turk, Miami
2026 Sails: Dec 6, More...
9 Night - Pirates Islands and Sailors' Haunts
Starting in Philipsburg, Cabrits, Saint-Pierre, Soufriere, Terre-De-Haut, Iles Des Saintes, Charlestown, Nevis, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Dec 6, More...
14 Night - Leeward Island Jewels
Starting in Miami, Florida, San Juan, Puerto Rico, Spanish Town, Virgin Gorda, British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Fort-De-France, Martinique, Terre-de-Haut, Iles des Saintes, Guadeloupe, Little Bay, Montserrat, Road Bay, Anguilla, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Dec 6, More...
6 Night - Splendours of the Caribbean
Starting in San Juan, Puerto Rico, St John VI (Cruz Bay), US Virgin Islands, Nevis, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Gustavia, Saint Barthelemy, Prickly Pear Cays, Virgin Gorda, British Virgin Islands, Saint Thomas, US Virgin Islands
2026 Sails: Dec 7, More...
7 Night - History and Culture Visiting Caribbean Jewels
Starting in Pointe-a-Pitre, Les Saintes, Falmouth Bay, Charlestown, Nevis, Barbuda, Gustavia, Road Bay, Anguilla, Prickley Pear Cays, Marigot
2026 Sails: Dec 12, More...
7 Night - Cruising the Leeward Islands
Starting in Marigot, Saint Martin, Marigot, Saint Martin, Anguilla, Virgin Gorda / Norman Island, British Virgin Islands, Norman Island / Jost van Dyke, British Virgin Islands, Anegada, British Virgin Islands, Saba, Bonaire, Saint Eustatius and Saba / Gustavia, Saint Barthelemy, Gustavia, Saint Barthelemy, Marigot, Saint Martin
2026 Sails: Dec 13, 2027: Jan 9, Feb 6, Mar 6, Apr 3, 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 - St. Barths & Caribbean Gems CruiseStarting in Charlotte Amalie, St Thomas, Fajardo Bay, White Bay, Jost van Dyke, Gustavia, Sandy Ground, St John VI (Cruz Bay), US Virgin Islands, Charlotte Amalie, St Thomas
2026 Sails: Dec 5, More...
21 Night - Star Collector : Hearty Ports & Rum Punches - a Transatlantic CrossingStarting in Lisbon, St Johns AG, Philipsburg, St Maarten, Gustavia, Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Philipsburg, St Maarten
2026 Sails: Dec 5, 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, Marigot, Saint Martin
2026 Sails: Dec 6, 2027: Jan 30, Feb 27, Mar 27, More...
14 Night - Discover the Pearls of the CaribbeanStarting 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, Marigot, Saint Martin, Marigot, Saint Martin, Anguilla, Virgin Gorda / Norman Island, British Virgin Islands, Norman Island / Jost van Dyke, British Virgin Islands, Anegada, British Virgin Islands, Saba, Bonaire, Saint Eustatius and Saba / Gustavia, Saint Barthelemy, Gustavia, Saint Barthelemy, Marigot, Saint Martin
2026 Sails: Dec 6, More...
14 Night - An Extended Journey Through Islands of Scenic Wonder & Coastal HistoryStarting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, Gustavia, San Juan, Road Bay, St Johns AG, Antigua, Basseterre, Grand Turk, Miami
2026 Sails: Dec 6, More...
9 Night - Pirates Islands and Sailors' HauntsStarting in Philipsburg, Cabrits, Saint-Pierre, Soufriere, Terre-De-Haut, Iles Des Saintes, Charlestown, Nevis, Road Bay (Sandy Ground), Philipsburg
2026 Sails: Dec 6, More...
14 Night - Leeward Island JewelsStarting in Miami, Florida, San Juan, Puerto Rico, Spanish Town, Virgin Gorda, British Virgin Islands, Carambola Beach, Saint Kitts and Nevis, Roseau, Dominica, Fort-De-France, Martinique, Terre-de-Haut, Iles des Saintes, Guadeloupe, Little Bay, Montserrat, Road Bay, Anguilla, Great Harbour, Jost van Dyke, British Virgin Islands, Miami, Florida
2026 Sails: Dec 6, More...
6 Night - Splendours of the CaribbeanStarting in San Juan, Puerto Rico, St John VI (Cruz Bay), US Virgin Islands, Nevis, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Gustavia, Saint Barthelemy, Prickly Pear Cays, Virgin Gorda, British Virgin Islands, Saint Thomas, US Virgin Islands
2026 Sails: Dec 7, More...
7 Night - History and Culture Visiting Caribbean JewelsStarting in Pointe-a-Pitre, Les Saintes, Falmouth Bay, Charlestown, Nevis, Barbuda, Gustavia, Road Bay, Anguilla, Prickley Pear Cays, Marigot
2026 Sails: Dec 12, More...
7 Night - Cruising the Leeward IslandsStarting in Marigot, Saint Martin, Marigot, Saint Martin, Anguilla, Virgin Gorda / Norman Island, British Virgin Islands, Norman Island / Jost van Dyke, British Virgin Islands, Anegada, British Virgin Islands, Saba, Bonaire, Saint Eustatius and Saba / Gustavia, Saint Barthelemy, Gustavia, Saint Barthelemy, Marigot, Saint Martin
2026 Sails: Dec 13, 2027: Jan 9, Feb 6, Mar 6, Apr 3, More...