Anguilla Cruises
Cruises that visit Caribbean: Anguilla
Related areas: Dog Island : Prickly Pear Cay : Road Bay : Sandy Ground
7 Night - Vibes of the Virgin Islands
Starting in Saint Thomas, US Virgin Islands, St John VI, US Virgin Islands, Virgin Gorda / Norman Island, British Virgin Islands, Norman Island, British Virgin Islands, Sandy Ground, Anguilla / Philipsburg, Sint Maarten, Saint Martin, Philipsburg, Sint Maarten (Saint Martin) Gustavia, Saint Barthelemy, Gustavia, Saint Barthelemy, Saint Thomas, US Virgin Islands
2026 Sails: Dec 13, Dec 20, Dec 27, 2027: Jan 16, Jan 30, Feb 20, Feb 27, Mar 6, Mar 27, More...
14 Night - An Extended Journey of Island Calm & Coastal Retreats
Starting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan, Basseterre, Tortola / Road Town, Gustavia, Road Bay, Miami
2026 Sails: Dec 13, More...
7 Night - A Journey Through Caribbean Gems & Multi-Coloured Coasts
Starting in San Juan, Road Bay, St Johns AG, Antigua, Basseterre, Grand Turk, Miami
2026 Sails: Dec 13, More...
15 Night - An Extended Journey Through Wild Beauty and Tropical Festivities
Starting in San Juan, Road Bay, St Johns AG, Antigua, Basseterre, Grand Turk, Miami, Ocho Rios, Jamaica, Isla Catalina, Jost Van Dyke, St Maarten / Philipsburg, Charlotte Amalie (Saint Thomas), San Juan
2026 Sails: Dec 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, Marigot
2026 Sails: Dec 19, More...
8 Night - Caribbean Celebration I Cruise
Starting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Norman Island, Leverick Bay, Virgin Gorda, Prickly Pear, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, Marigot, Sandy Ground, Gustavia, Charlotte Amalie, St Thomas
2026 Sails: Dec 19, More...
8 Night - Caribbean Celebration Ii Cruise
Starting in San Juan, Gustavia, Sandy Ground, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, Leverick Bay, Virgin Gorda, Cane Garden Bay, Tortola, Norman Island, White Bay, Jost van Dyke, San Juan
2026 Sails: Dec 19, More...
14 Night - Star Collector : Caribbean Explorations
Starting in 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, Gustavia, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Philipsburg, St Maarten
2026 Sails: Dec 19, More...
7 Night - Beach Fun & Sun : a Remote Caribbean Getaway
Starting in 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 19, More...
7 Night - Eastern Caribbean with St. Barths
Starting in Marigot, Saint Martin, Marigot, Saint Martin / Prickly Pear Cays, Anguilla / Gustavia, Saint Barthelemy, Gustavia, Saint Barthelemy, Charlestown, Saint Kitts and Nevis / Cades Bay, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Iles des Saintes, Guadeloupe, Soufriere, Saint Lucia, Bridgetown, Barbados
2026 Sails: Dec 20, 2027: Jan 16, Feb 13, Mar 13, 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 - Vibes of the Virgin IslandsStarting in Saint Thomas, US Virgin Islands, St John VI, US Virgin Islands, Virgin Gorda / Norman Island, British Virgin Islands, Norman Island, British Virgin Islands, Sandy Ground, Anguilla / Philipsburg, Sint Maarten, Saint Martin, Philipsburg, Sint Maarten (Saint Martin) Gustavia, Saint Barthelemy, Gustavia, Saint Barthelemy, Saint Thomas, US Virgin Islands
2026 Sails: Dec 13, Dec 20, Dec 27, 2027: Jan 16, Jan 30, Feb 20, Feb 27, Mar 6, Mar 27, More...
14 Night - An Extended Journey of Island Calm & Coastal RetreatsStarting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan, Basseterre, Tortola / Road Town, Gustavia, Road Bay, Miami
2026 Sails: Dec 13, More...
Deal link -> Special
7 Night - A Journey Through Caribbean Gems & Multi-Coloured CoastsStarting in San Juan, Road Bay, St Johns AG, Antigua, Basseterre, Grand Turk, Miami
2026 Sails: Dec 13, More...
15 Night - An Extended Journey Through Wild Beauty and Tropical FestivitiesStarting in San Juan, Road Bay, St Johns AG, Antigua, Basseterre, Grand Turk, Miami, Ocho Rios, Jamaica, Isla Catalina, Jost Van Dyke, St Maarten / Philipsburg, Charlotte Amalie (Saint Thomas), San Juan
2026 Sails: Dec 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, Marigot
2026 Sails: Dec 19, More...
8 Night - Caribbean Celebration I CruiseStarting in Charlotte Amalie, St Thomas, St John VI (Cruz Bay), US Virgin Islands, Norman Island, Leverick Bay, Virgin Gorda, Prickly Pear, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, Marigot, Sandy Ground, Gustavia, Charlotte Amalie, St Thomas
2026 Sails: Dec 19, More...
8 Night - Caribbean Celebration Ii CruiseStarting in San Juan, Gustavia, Sandy Ground, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, Leverick Bay, Virgin Gorda, Cane Garden Bay, Tortola, Norman Island, White Bay, Jost van Dyke, San Juan
2026 Sails: Dec 19, More...
14 Night - Star Collector : Caribbean ExplorationsStarting in 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, Gustavia, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Philipsburg, St Maarten
2026 Sails: Dec 19, More...
7 Night - Beach Fun & Sun : a Remote Caribbean GetawayStarting in 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 19, More...
7 Night - Eastern Caribbean with St. BarthsStarting in Marigot, Saint Martin, Marigot, Saint Martin / Prickly Pear Cays, Anguilla / Gustavia, Saint Barthelemy, Gustavia, Saint Barthelemy, Charlestown, Saint Kitts and Nevis / Cades Bay, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Iles des Saintes, Guadeloupe, Soufriere, Saint Lucia, Bridgetown, Barbados
2026 Sails: Dec 20, 2027: Jan 16, Feb 13, Mar 13, More...