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Cruise Dates

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October 2026

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Silver Shadow

Silversea

Feb 6, 2027 - Feb 16, 2027 (10 Nights)

San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • St. Kitts • Little Bay, Montserrat • Les Saintes, F.W.I. • Roseau, Dominica • Trois Ilets, Martinique • Castries, St. Lucia • Grenada • Bridgetown, Barbados

Average Starting Price

Dec 7, 2027 - Dec 17, 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

Feb 6, 2028 - Feb 17, 2028 (11 Nights)

San Juan, Puerto Rico • Little Bay, Montserrat • Bridgetown, Barbados • Devil's Island, France • Macapa, , Brazil • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil

Average Starting Price

$7,745pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Nov 13, 2027 - Nov 20, 2027 (7 Nights)

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

Average Starting Price

Oct 16, 2027 - Oct 23, 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 9, 2027 - Dec 19, 2027 (10 Nights)

Average Starting Price

Nov 29, 2026 - Dec 20, 2026 (21 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St. Kitts • Key West, Florida • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,164pp

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!

25% OFF

Seven Seas Voyager

Regent Seven Seas Cruises

Dec 19, 2027 - Jan 13, 2028 (25 Nights)

Miami • Tortola • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • Grenada • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • Falmouth, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

$13,149pp

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!

9% OFF

Crystal Grace

Crystal Cruises

Dec 22, 2028 - Jan 3, 2029 (12 Nights)

Fort Lauderdale • Grand Turk • St John's, Antigua • Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • St. Kitts • Fort Lauderdale

Average Starting Price

$8,350pp

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!