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Cruise Dates

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October 2026

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Celebrity Eclipse

Celebrity Cruises

Mar 22, 2027 - Apr 2, 2027 (11 Nights)

Fort Lauderdale • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Grenada • Roseau, Dominica • St John's, Antigua • Fort Lauderdale

Average Starting Price

Mar 14, 2027 - Mar 28, 2027 (14 Nights)

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

Average Starting Price

Oct 28, 2027 - Nov 14, 2027 (17 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

Average Starting Price

Dec 6, 2027 - Jan 4, 2028 (29 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • George Town, Cayman Islands • Cartagena, Colombia • Panama Canal, Panama • Puntarenas, Costa Rica • Puerto Quetzal, Guatemala • Zihuatanejo (Ixtapa), Mexico • Manzanillo, Mexico • Ensenada • Los Angeles

Average Starting Price

Nov 1, 2027 - Nov 15, 2027 (14 Nights)

San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico

Average Starting Price

Nov 28, 2027 - Dec 10, 2027 (12 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • Miami

Average Starting Price

Dec 11, 2027 - Dec 21, 2027 (10 Nights)

San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • St. Kitts • Gustavia, St. Barts • Fort-De-France, Martinique • Grenada • Bequia Island, Saint Vincent • Castries, St. Lucia • St John's, Antigua • St. John • San Juan, Puerto Rico

Average Starting Price

$4,800pp

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

Mar 19, 2027 - Mar 29, 2027 (10 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale

Average Starting Price

$1,530pp

Jim's Onboard Credit

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!

Star Legend

Windstar Cruises

Dec 27, 2027 - Jan 3, 2028 (7 Nights)

San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico

Average Starting Price

$2,691pp

Jim's Onboard Credit

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