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Cruise Dates

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October 2026

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Valiant Lady

Virgin Voyages

Mar 19, 2027 - Mar 27, 2027 (8 Nights)

San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Dec 11, 2027 - Jan 2, 2028 (22 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Fort-De-France, Martinique • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • George Town, Cayman Islands • Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$5,709pp

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!

Azamara Quest

Azamara

Oct 28, 2027 - Nov 21, 2027 (24 Nights)

New York, New York • Hamilton, Bermuda • Hamilton, Bermuda • Hamilton, Bermuda • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico

Average Starting Price

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

San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • St. Croix • Miami

Average Starting Price

$1,024pp

Jim's Onboard Credit

FREE Specialty Dining Meal

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

$4,499pp

Jim's Onboard Credit

29% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Mar 20, 2027 - Mar 30, 2027 (10 Nights)

Miami • St. Thomas • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • St John's, Antigua • Tortola • San Juan, Puerto Rico

Average Starting Price

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

Average Starting Price

Dec 28, 2027 - Jan 4, 2028 (7 Nights)

San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Roseau, Dominica • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

$4,300pp

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!

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

8% OFF

Nov 22, 2027 - Dec 19, 2027 (27 Nights)

Fort Lauderdale • Cozumel • Belize City • Santo Tomas de Castilla, Guatemala • Roatan, Honduras • Limon, Costa Rica • Colon, Panama • Cartagena, Colombia • Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Pointe-à-Pitre, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale • Roseau, Dominica • St John's, Antigua • Gustavia, St. Barts • Tortola • Fort Lauderdale

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

Nov 23, 2027 - Dec 4, 2027 (11 Nights)

Miami • San Juan, Puerto Rico • Saint Barthelemy, Gustavia • Little Bay, Montserrat • Roseau, Dominica • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami

Average Starting Price

$7,153pp

Jim's Onboard Credit

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