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Eastern Caribbean Cruise Specials

We've gathered all of the Eastern Caribbean 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 Eastern Caribbean cruises) to receive multiple custom cruise options to compare, please visit our Cruise Search page.

All Cruise Specials


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Holland America, Zuiderdam
Discount
Zuiderdam11 Nights Eastern Caribbean Cruise: Windward & Leeward Islands $846 pp
11 Night - Eastern Caribbean : Windward & Leeward Islands - Starting in Miami, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Fort-De-France, Martinique, Roseau, Dominica, Basseterre, St Kitts and Nevis, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Miami, Florida
2026 Sails: Oct 31 Get a Quote
Holland America, Zuiderdam
Family
Zuiderdam11 Nights Eastern Caribbean Cruise from $883 pp
11 Night - Eastern Caribbean : Windward & Leeward Islands - Starting in Miami, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Fort-De-France, Martinique, Roseau, Dominica, Basseterre, St Kitts and Nevis, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Miami, Florida
2026 Sails: Oct 31 Get a Quote
Explora Journeys, EXPLORA III
Discount
EXPLORA III7 NT A Journey Through Beguiling Caribbean & Lush Landscapes from $8320pp
7 Night - A Journey Through Beguiling Caribbean Coastlines & Lush Landscapes - Starting in Miami, Providenciales, Puerto Plata, Dominican Republic, La Romana, Jost Van Dyke, Gustavia, San Juan
2026 Sails: Nov 8 Get a Quote
Explora Journeys, EXPLORA III
Discount
EXPLORA III14 NT A Journey Of Blissful Escapes & Shoreline Splendour from $12825 pp
14 Night - An Extended Journey of Blissful Escapes & Shoreline Splendour - Starting in Miami, Providenciales, Puerto Plata, Dominican Republic, La Romana, Jost Van Dyke, Gustavia, San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami
2026 Sails: Nov 8 Get a Quote
Holland America, Rotterdam
Discount
Rotterdam11 Nights Eastern Caribbean Cruise from $978 pp
11 Night - Eastern Caribbean : Windward & Leeward Islands - Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Roseau, Dominica, Castries, Saint Lucia, Basseterre, St Kitts and Nevis, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida
2026 Sails: Nov 10, Dec 1 Get a Quote
Holland America, Rotterdam
Discount
Rotterdam11 Nights Eastern Caribbean Cruise from $997 pp
11 Night - Eastern Caribbean : Windward & Leeward Islands - Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Roseau, Dominica, Castries, Saint Lucia, Basseterre, St Kitts and Nevis, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida
2026 Sails: Nov 10, Dec 1 Get a Quote
Holland America, Rotterdam
Discount
Rotterdam11 Night Eastern Caribbean Cruise: Windward & Leeward Islands $957 pp plus
11 Night - Eastern Caribbean : Windward & Leeward Islands - Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Roseau, Dominica, Castries, Saint Lucia, Basseterre, St Kitts and Nevis, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida
2026 Sails: Nov 10, Dec 1 Get a Quote
Holland America, Rotterdam
Family
Rotterdam21 Nights Eastern & Western Caribbean Cruise from $1581 pp
21 Night - Eastern & Western Caribbean : Leeward Islands & Mexico - Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Roseau, Dominica, Castries, Saint Lucia, Basseterre, St Kitts and Nevis, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida, RelaxAway, Half Moon Cay, Bahamas, Falmouth, Jamaica, Mahogany Bay, Roatan, Honduras, Belize City, Belize, Costa Maya, Mexico, Cozumel, Mexico, Fort Lauderdale, Florida
2026 Sails: Nov 10 Get a Quote
Holland America, Eurodam
Discount
Eurodam14 Night Western & Eastern Caribbean Cruise: Mexico & Bahamas $987 pp
14 Night - Western & Eastern Caribbean : Mexico & Bahamas - Starting in Fort Lauderdale, Florida, RelaxAway, Half Moon Cay, Bahamas, Ocho Rios, Jamaica, Georgetown, Cayman Islands, Cozumel, Mexico, Fort Lauderdale, Florida, RelaxAway, Half Moon Cay, Bahamas, Amber Cove, Dominican Republic, Grand Turk, Turks and Caicos, Key West, Florida, Fort Lauderdale, Florida
2026 Sails: Nov 14 Get a Quote
Explora Journeys, EXPLORA III
Family
EXPLORA III7 NT A Journey Of Blissful Escapes & Island Splendour from $4200 pp
7 Night - A Journey of Blissful Escapes & Island Splendour - Starting in San Juan, Road Bay, St Johns AG, Antigua, Frederiksted, Saint Croix, Isla Catalina, Puerto Plata, Dominican Republic, Miami
2026 Sails: Nov 15 Get a Quote

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Eastern Caribbean Cruise Specials