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Cruise Dates

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October 2026

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Norwegian Bliss

Norwegian Cruise Line

Feb 1, 2027 - Feb 13, 2027 (12 Nights)

Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • St. Kitts • Philipsburg, St. Maarten • Manhattan

Average Starting Price

Feb 13, 2027 - Mar 14, 2027 (29 Nights)

Buenos Aires, Argentina • Buenos Aires, Argentina • Santos (Sao Paulo), Brazil • Ilha Grande, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Salvador da Bahia, Brazil • Recife, Brazil • Fortaleza, Brazil • Icoaraci (Belem), Brazil • Crossing the Equator • Devil's Island, France • Bridgetown, Barbados • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Fort Lauderdale

Average Starting Price

Jan 29, 2027 - Feb 6, 2027 (8 Nights)

San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Fort-De-France, Martinique • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

$1,352pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

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

San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Grenada • San Juan, Puerto Rico

Average Starting Price

Dec 19, 2026 - Dec 27, 2026 (8 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Bimini • Miami

Average Starting Price

$1,272pp

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!

Crystal Symphony

Crystal Cruises

Dec 13, 2026 - Dec 20, 2026 (7 Nights)

San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • St John's, Antigua • Marigot Bay, St. Martin, French West Indies • St. Thomas • Fort Lauderdale

Average Starting Price

$3,300pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Mar 21, 2027 - Mar 28, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Nov 18, 2026 - Nov 30, 2026 (12 Nights)

Miami • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • St John's, Antigua • Little Bay, Montserrat • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami

Average Starting Price

Dec 18, 2028 - Dec 28, 2028 (10 Nights)

Miami • San Juan, Puerto Rico • Road Bay, Anguilla • Little Bay, Montserrat • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami

Average Starting Price

36% OFF

Dec 11, 2027 - Dec 19, 2027 (8 Nights)

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

Average Starting Price

Jan 29, 2028 - Feb 5, 2028 (7 Nights)

Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

46% OFF

Jan 16, 2028 - Jan 23, 2028 (7 Nights)

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

Average Starting Price

$559pp

Jim's Onboard Credit

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