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October 2026

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Viking Sea

Viking

Nov 27, 2027 - Dec 7, 2027 (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

Nov 29, 2027 - Dec 9, 2027 (10 Nights)

Average Starting Price

$4,499pp

Jim's Onboard Credit

21% OFF

Seven Seas Mariner

Regent Seven Seas Cruises

Mar 26, 2027 - Apr 10, 2027 (15 Nights)

Miami • Tortola • Gustavia, St. Barts • Fort-De-France, Martinique • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Grenada • Willemstad, Curacao • Kralendijk, Bonaire • Puerto Plata, Dominican Republic • Miami

Average Starting Price

$14,209pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Nov 20, 2027 - Nov 27, 2027 (7 Nights)

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

Average Starting Price

Sep 18, 2027 - Sep 25, 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 19, 2027 (12 Nights)

Miami • San Juan, Puerto Rico • St. John • St. Kitts • Gustavia, St. Barts • St John's, Antigua • Deshaies, Guadeloupe • Roseau, Dominica • Fort-De-France, Martinique • Bequia Island, Saint Vincent • Bridgetown, Barbados

Average Starting Price

$7,200pp

Jim's Onboard Credit

20% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Mar 5, 2027 - Mar 17, 2027 (12 Nights)

Miami • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • Pointe-à-Pitre, Guadeloupe • Tortola • Miami

Average Starting Price

$12,149pp

Jim's Onboard Credit

27% OFF

Seven Seas Voyager

Regent Seven Seas Cruises

Dec 19, 2027 - Jan 14, 2028 (26 Nights)

Miami • St. Thomas • Tortola • Philipsburg, St. Maarten • Gustavia, St. Barts • St. Kitts • St. John's • Dominica • St. Lucia • Bridgetown, Barbados • St. George's • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Cartagena • Colon, Panama • Panama Canal, Panama • Puerto Limon • Falmouth • George Town, Cayman Islands • Miami

Average Starting Price

$12,449pp

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!

Adventure of the Seas

Royal Caribbean

Feb 9, 2028 - Feb 18, 2028 (9 Nights)

Port Canaveral (Orlando), Florida • Basseterre, St. Kitts and Nevis • Bridgetown, Barbados • St John's, Antigua • Perfect Day Cococay • Port Canaveral (Orlando), Florida

Average Starting Price

Jan 6, 2028 - Feb 3, 2028 (28 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Fort-De-France, Martinique • Scarborough (Tobago), Trinidad and Tobago • Barra Norte Sea, Brazil • Crossing the Amazon River Bar, Brazil • Barra Norte River, Brazil • Cruising the Amazon River • Macapa, , Brazil • Cruising the Amazon River • Crossing the Equator • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Crossing the Equator • Cruising the Amazon River • Barra Norte River, Brazil • Crossing the Amazon River Bar, Brazil • Barra Norte Sea, Brazil • Crossing the Equator • Devil's Island, France • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Fort Lauderdale

Average Starting Price

$8,384pp

Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

9% OFF

Crystal Grace

Crystal Cruises

Nov 20, 2028 - Dec 1, 2028 (11 Nights)

Fort Lauderdale • Gustavia, St. Barts • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • St. Kitts • San Juan, Puerto Rico • Fort Lauderdale

Average Starting Price

Mar 14, 2027 - Mar 29, 2027 (15 Nights)

Miami • Providenciales, Turks and Caicos Islands • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Bequia Island, Saint Vincent • Bridgetown, Barbados • Grenada • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • Miami

Average Starting Price

$9,205pp

Jim's Onboard Credit

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