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Anguilla Cruise Specials

We've gathered all of the Anguilla cruise specials ordered by sail date. Click on a special and select a sail date to get a single cruise quote from the cruise agency that posted that particular special. To search through all cruise itineraries (not just Anguilla cruises) to receive multiple custom cruise options to compare, please visit our Cruise Search page.

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Explora Journeys, EXPLORA I
Family
EXPLORA I Cruises10 NT A Journey into the Caribbean’s Most Desirable Shores from $6745 pp
10 Night - An Extended Journey Into the Caribbean's Most Desirable Shores - Starting in Bridgetown, Fort-de-France, Martinique, Basseterre, San Juan, Tortola / Road Town, St Johns AG, Antigua, Gustavia, Road Bay, Miami
2026 Sails: Feb 2 Get a Quote
Explora Journeys, EXPLORA I
Family
EXPLORA I Cruises15 NT A Journey through Sun-kissed Wonders & Island Rhythms from $7770 pp
15 Night - A Grand Journey Through Caribbean Serenity and Tropical Treasures - Starting in San Juan, Tortola / Road Town, St Johns AG, Antigua, Gustavia, Road Bay, Miami, Puerto Plata, Dominican Republic, Roseau, Bridgetown, Deshaies, St John VI (Cruz Bay), US Virgin Islands, San Juan
2026 Sails: Feb 5 Get a Quote
Explora Journeys, EXPLORA I
Family
EXPLORA I Cruises17 NT A Journey into Tropical Utopia,Coral Wonders& Beaches from $8160 pp
17 Night - An Extended Journey Into Tropical Utopia, Coral Wonders & Blissful Beaches - Starting in San Juan, Oranjestad, Willemstad AN, Kralendijk, Bridgetown, Terre-De-Haut, St Maarten / Philipsburg, Jost Van Dyke, San Juan, St Johns AG, Antigua, Road Bay, Spanish Town (Virgin Gorda), Charlotte Amalie (Saint Thomas), Miami
2026 Sails: Feb 20 Get a Quote
Explora Journeys, EXPLORA I
Family
EXPLORA I Cruises23 NT A Journey of Lively Latin Flair,Modern Marvels &Coastals from $8970pp
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 Get a Quote
Explora Journeys, EXPLORA I
Family
EXPLORA I Cruises7 Nights A Journey into Tropical Utopia & Art Deco Flair from $3570 pp
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 Get a Quote
Explora Journeys, EXPLORA II
Family
EXPLORA II Cruises15 NT A Journey Through Spectacular Nature&Historic Wonders from $7,400 pp
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 Get a Quote
Explora Journeys, EXPLORA II
Discount
EXPLORA II Cruises7 Night A Journey to Antillean Isles and Sublime Sunsets from $3895 pp
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 Get a Quote
Explora Journeys, EXPLORA II
Family
EXPLORA II Cruises7 NT A Journey to Antillean Isles and Sublime Sunsets from $3,915 pp
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 Get a Quote
Explora Journeys, EXPLORA II
Family
EXPLORA II Cruises15 NT An Extended Journey Of Paradise Beauty&Colourful Shoresfrom $8,285 pp
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 Get a Quote
Explora Journeys, EXPLORA III
Discount
EXPLORA III Cruises14 NT An Extended Journey Of Maritime Soul & Island Zest from $8170 pp
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 Get a Quote

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Anguilla Cruise Specials