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Cruise Dates

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October 2026

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Sonata

Oceania Cruises

Feb 22, 2029 - Mar 8, 2029 (14 Nights)

Miami • Cruising the Atlantic Ocean • Cruising the Atlantic Ocean • St. Thomas • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • Miami

Average Starting Price

Jan 22, 2028 - Jan 29, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

$768pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Feb 27, 2027 - Mar 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

Jun 12, 2027 - Jun 19, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 23, 2027 - Jan 3, 2028 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Fort-De-France, Martinique • St John's, Antigua • St. Thomas • Fort Lauderdale

Average Starting Price

$2,166pp

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!

Viking Sea

Viking

Jan 6, 2028 - Jan 27, 2028 (21 Nights)

San Juan, Puerto Rico • Sail the Caribbean Sea • Bridgetown, Barbados • Sail the Atlantic Ocean • Iles du Salut (Ile Royale), French Guiana • Sail the Atlantic Ocean • Sail the Mouth of the Amazon River • Santarem, Brazil • Parintins, Brazil • Manaus, Brazil • Manaus, Brazil • Sail the Amazon River • Sail the Amazon River • Belem, Brazil • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Jan 8, 2028 - Jan 18, 2028 (10 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico

Average Starting Price

$4,299pp

Jim's Onboard Credit

21% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Feb 16, 2028 - Mar 2, 2028 (15 Nights)

Miami • Tortola • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • George Town, Cayman Islands • Miami

Average Starting Price

Feb 12, 2028 - Feb 19, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Jan 5, 2028 - Mar 22, 2028 (77 Nights)

Miami • Cozumel • Belize City • Roatan, Honduras • Limon, Costa Rica • Bocas Del Toro, Panama • Panama Canal (Cruising) • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Manta, Ecuador • Lima, Peru • Lima, Peru • General San Martin, Peru • La Serena (Coquimbo), Chile • Valparaíso, Chile • Puerto Montt, Chile • Castro, Chile • Chacabuco, Chile • Sailing In The Chilean Fjords • Sailing In The Chilean Fjords • Punta Arenas, Chile • Punta Arenas, Chile • Ushuaia, Argentina • Sailing Snow Island • Sailing Bransfield Strait • Sailing Gerlache Strait • Sailing Paradise Bay • Sailing Wilhelmina Bay • Sailing Penguin Island • Sailing King George Island • Port Stanley, Falkland Islands • Punta del Este, Uruguay • Montevideo, Uruguay • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina • Buenos Aires, Argentina • Montevideo, Uruguay • Rio Grande Do Sul, Brazil • Porto Belo, Brazil • Sao Francisco do Sul, Brazil • Paranagua, brazil • Santos (Sao Paulo), Brazil • Ilhabela, Brazil • Paraty, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Salvador da Bahia, Brazil • Salvador da Bahia, Brazil • Natal, Brazil • Belem, Brazil • Iles du Salut (Ile Royale), French Guiana • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Saint George's, Grenada • Castries, St. Lucia • St. Pierre • Roseau, Dominica • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

Mar 26, 2028 - Apr 2, 2028 (7 Nights)

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

Average Starting Price

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

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

Average Starting Price

$639pp

Jim's Onboard Credit

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