Anguilla Cruises
Cruises that visit Caribbean: Anguilla
Related areas: Dog Island : Prickly Pear Cay : Road Bay : Sandy Ground
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...
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...14 Night - Star Collector : Caribbean Explorations
Starting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten, St Johns, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 21, More...
7 Night - Best of British Virgin Islands & St. Barths Cruise
Starting in Charlotte Amalie, St Thomas, Sandy Ground, Gustavia, Philipsburg, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, White Bay, Jost van Dyke, St John VI (Cruz Bay), US Virgin Islands, Charlotte Amalie, St Thomas
2026 Sails: Mar 28, More...21 Night - Star Collector : Spectacular Transatlantic Journey : Caribbean to the Azores
Starting in Philipsburg, St Maarten, St Johns, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten, Ponta Delgada, Lisbon
2026 Sails: Mar 28, More...7 Night - Beach Fun & Sun : a Remote Caribbean Getaway
Starting in Philipsburg, St Maarten, St Johns, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 28, More...
27 Night - A Grand Journey of Colourful Moroccan Shores & Idyllic Caribbean Scenery
Starting in Barcelona, Alicante, Lisbon, Casablanca, Tangier, Malaga, Spain, Motril, Barcelona, Cadiz, Funchal (Madeira), St Johns AG, Antigua, Road Bay, San Juan, Miami
2026 Sails: Oct 21, More...
14 Night - An Extended Journey of Maritime Soul & Island Zest
Starting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami
2026 Sails: Oct 25, More...16 Night - A Grand Journey of Lively Culture & Stunning Beaches
Starting in Barcelona, Cadiz, Funchal (Madeira), St Johns AG, Antigua, Road Bay, San Juan, Miami
2026 Sails: Nov 1, 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
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...
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...
14 Night - Star Collector : Caribbean ExplorationsStarting in Philipsburg, St Maarten, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg, St Maarten, St Johns, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 21, More...
7 Night - Best of British Virgin Islands & St. Barths CruiseStarting in Charlotte Amalie, St Thomas, Sandy Ground, Gustavia, Philipsburg, Spanish Town, Virgin Gorda, Trellis Bay, Beef Island, White Bay, Jost van Dyke, St John VI (Cruz Bay), US Virgin Islands, Charlotte Amalie, St Thomas
2026 Sails: Mar 28, More...
21 Night - Star Collector : Spectacular Transatlantic Journey : Caribbean to the AzoresStarting in Philipsburg, St Maarten, St Johns, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten, Ponta Delgada, Lisbon
2026 Sails: Mar 28, More...
7 Night - Beach Fun & Sun : a Remote Caribbean GetawayStarting in Philipsburg, St Maarten, St Johns, Road Bay, Sopers Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St Maarten
2026 Sails: Mar 28, More...
27 Night - A Grand Journey of Colourful Moroccan Shores & Idyllic Caribbean SceneryStarting in Barcelona, Alicante, Lisbon, Casablanca, Tangier, Malaga, Spain, Motril, Barcelona, Cadiz, Funchal (Madeira), St Johns AG, Antigua, Road Bay, San Juan, Miami
2026 Sails: Oct 21, More...
Deal link -> Special
14 Night - An Extended Journey of Maritime Soul & Island ZestStarting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, St Maarten / Philipsburg, San Juan, Tortola / Road Town, Basseterre, Gustavia, Road Bay, Miami
2026 Sails: Oct 25, More...
Deal link -> Special
16 Night - A Grand Journey of Lively Culture & Stunning BeachesStarting in Barcelona, Cadiz, Funchal (Madeira), St Johns AG, Antigua, Road Bay, San Juan, Miami
2026 Sails: Nov 1, More...
