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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 Serenity

Crystal Cruises

Oct 12, 2027 - Dec 22, 2027 (71 Nights)

New York, New York • Royal Naval Dockyard, Bermuda • Royal Naval Dockyard, Bermuda • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • San Juan, Puerto Rico • St. Kitts • Castries, St. Lucia • Scarborough (Tobago), Trinidad and Tobago • Devil's Island, France • Fortaleza, Brazil • Maceio, Brazil • Salvador da Bahia, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Ilhabela, Brazil • Balneario Camboriu, Brazil • Montevideo, Uruguay • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina • Punta del Este, Uruguay • Puerto Madryn, Argentina • Port Stanley, Falkland Islands • Ushuaia, Argentina • Punta Arenas, Chile • Punta Arenas, Chile • Chilean Fjords Cruising • Chilean Fjords Cruising • Laguna San Rafael, Chile • Chacabuco, Chile • Castro, Chile • Puerto Montt, Chile • Valparaíso, Chile • Valparaíso, Chile • Bahia CoQuimbo, Chile • Iquique, Chile • General San Martin, Peru • Lima, Peru • Salaverry (Trujillo), Peru • Guayaquil, Ecuador • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Limon, Costa Rica • Roatan Island, Honduras • Santo Tomas de Castilla, Guatemala • Belize City • Cozumel • Cozumel • Progreso, Mexico • Fort Lauderdale

Average Starting Price

Nov 5, 2027 - Nov 13, 2027 (8 Nights)

Miami • Providenciales, Turks and Caicos Islands • Gustavia, St. Barts • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • St. John • San Juan, Puerto Rico

Average Starting Price

Dec 12, 2027 - Dec 22, 2027 (10 Nights)

Port Canaveral (Orlando), Florida • San Juan, Puerto Rico • St. Kitts • St. Lucia • Philipsburg, St. Maarten • St. Thomas • Port Canaveral (Orlando), Florida

Average Starting Price

Dec 19, 2027 - Dec 26, 2027 (7 Nights)

Fort Lauderdale • Samana, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

$1,284pp

Jim's Onboard Credit

30% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Mar 30, 2027 - Apr 9, 2027 (10 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Gustavia, St. Barts • Philipsburg, St. Maarten • St. Thomas • La Romana, Dominican Republic • Nassau • Miami

Average Starting Price

Nov 12, 2027 - Nov 22, 2027 (10 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Apr 5, 2027 - Apr 22, 2027 (17 Nights)

San Juan, Puerto Rico • Gustavia, St. Barts • Gustavia, St. Barts • Little Bay, Montserrat • Basseterre, St. Kitts and Nevis • Key West, Florida • Miami • Ocho Rios, Jamaica • Willemstad, Curacao • Oranjestad, Aruba • Santa Marta, Colombia • Cartagena, Colombia • Cartagena, Colombia • Crossing the Panama Canal • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama

Average Starting Price

Dec 18, 2027 - Dec 28, 2027 (10 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Martinique • Philipsburg, St. Maarten • Celebration Key • Fort Lauderdale

Average Starting Price

$1,174pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Nov 3, 2027 - Nov 13, 2027 (10 Nights)

Manhattan • Royal Naval Dockyard, Bermuda • Tortola • St. Kitts • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico

Average Starting Price

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

San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico

Average Starting Price

$899pp

Jim's Onboard Credit

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