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Cruise Dates

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October 2026

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Norwegian Pearl

Norwegian Cruise Line

Feb 20, 2027 - Mar 2, 2027 (10 Nights)

Philadelphia • Tortola • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia

Average Starting Price

Feb 5, 2028 - Feb 15, 2028 (10 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

Dec 5, 2027 - Dec 12, 2027 (7 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados

Average Starting Price

Feb 6, 2027 - Feb 13, 2027 (7 Nights)

San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

36% OFF

Nov 27, 2027 - Dec 5, 2027 (8 Nights)

Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida

Average Starting Price

$964pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Jan 30, 2027 - Feb 6, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Jan 3, 2027 - Jan 10, 2027 (7 Nights)

Miami • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami

Average Starting Price

9% OFF

Dec 29, 2027 - Jan 8, 2028 (10 Nights)

San Juan, Puerto Rico • Marigot Bay, St. Martin, French West Indies • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Cap Cana (Punta Cana), Dominican Republic • Montego Bay, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale

Average Starting Price

$5,380pp

Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Norwegian Prima

Norwegian Cruise Line

Mar 14, 2027 - Mar 21, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Thomas • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico

Average Starting Price

46% OFF

Jan 2, 2028 - Jan 9, 2028 (7 Nights)

Miami • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Miami

Average Starting Price

Dec 10, 2026 - Dec 20, 2026 (10 Nights)

Miami • St. John • Philipsburg, St. Maarten • St. Kitts • Les Saintes, F.W.I. • Fort-De-France, Martinique • Little Bay, Montserrat • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Dec 6, 2026 - Dec 20, 2026 (14 Nights)

Miami • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Terre de Haut, Guadeloupe • Little Bay, Montserrat • Road Bay, Anguilla • Great Harbor Jost Van Dyke, British Virgin Islands • Miami

Average Starting Price

$7,153pp

Jim's Onboard Credit

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