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Cruise Dates

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October 2026

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Insignia

Oceania Cruises

Nov 9, 2026 - Dec 19, 2026 (40 Nights)

Lisbon, Portugal • Arrecife (Lanzarote), Spain • Las Palmas (Gran Canaria), Spain • Santa Cruz de la Palma, Spain • San Juan, Puerto Rico • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami • Tortola • St John's, Antigua • Castries, St. Lucia • Scarborough (Tobago), Trinidad and Tobago • Cruising the Amazon River • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Cruising the Amazon River • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico • Nassau • Miami

Average Starting Price

Dec 17, 2027 - Dec 28, 2027 (11 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Bequia Island, Saint Vincent • Grenada • Willemstad, Curacao • Kralendijk, Bonaire • Oranjestad, Aruba • St. Kitts • Fort-De-France, Martinique • Bridgetown, Barbados

Average Starting Price

Oct 30, 2027 - Nov 6, 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

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

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Nov 27, 2026 - Dec 12, 2026 (15 Nights)

Bridgetown, Barbados • Anse Mitan, Martinique • Rodney Bay, Saint Lucia • Rodney Bay, Saint Lucia • Castries, St. Lucia • Scenic Cruising the Pitons • Mayreau Island, Saint Vincent and the Grenadines • Grenada • Bequia Island, Saint Vincent • Bridgetown, Barbados • Rodney Bay, Saint Lucia • Scenic Cruising the Pitons • Scarborough (Tobago), Trinidad and Tobago • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Grenada • Willemstad, Curacao • Oranjestad, Aruba

Average Starting Price

49% OFF

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

Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe

Average Starting Price

9% OFF

Apr 10, 2029 - May 27, 2029 (47 Nights)

Rio de Janeiro, Brazil • Buzios, Brazil • Salvador da Bahia, Brazil • Maceio, Brazil • Recife, Brazil • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Devil's Island, France • Bridgetown, Barbados • Roseau, Dominica • St. Kitts • San Juan, Puerto Rico • Samana, Dominican Republic • Grand Turk • Fort Lauderdale • Royal Naval Dockyard, Bermuda • Royal Naval Dockyard, Bermuda • New York, New York • Newport, Rhode Island • Boston • Halifax, Nova Scotia • Sydney, Nova Scotia • Havre-Saint-Pierre, Quebec • Saint John, New Brunswick • Cork (Cobh), Ireland • Plymouth, England • Portsmouth, England

Average Starting Price

$18,370pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

23% OFF

MSC World Europa

MSC Cruises

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

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

$773pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

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

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

Average Starting Price

Dec 26, 2027 - Jan 2, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

$904pp

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!

33% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Feb 4, 2028 - Feb 14, 2028 (10 Nights)

Bridgetown, Barbados • Willemstad, Curacao • Oranjestad, Aruba • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados

Average Starting Price

$6,099pp

Jim's Onboard Credit

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