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Cruise Dates

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October 2026

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Odyssey of the Seas

Royal Caribbean

Jan 2, 2028 - Jan 13, 2028 (11 Nights)

Cape Liberty • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Thomas • Cape Liberty

Average Starting Price

Dec 6, 2027 - Dec 20, 2027 (14 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Dominica • St. Lucia • Bridgetown, Barbados • Grenada • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale

Average Starting Price

Nov 21, 2027 - Dec 12, 2027 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$5,094pp

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!

Scarlet Lady

Virgin Voyages

Nov 12, 2027 - Nov 20, 2027 (8 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

$1,112pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Mar 27, 2027 - Apr 3, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Nov 6, 2027 - Nov 21, 2027 (15 Nights)

New York, New York • Tortola • St John's, Antigua • Basseterre, St. Kitts and Nevis • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami

Average Starting Price

Dec 22, 2027 - Jan 5, 2028 (14 Nights)

Port Canaveral (Orlando), Florida • Celebration Key • Tortola • Philipsburg, St. Maarten • Martinique • St. Lucia • St John's, Antigua • St. Kitts • St. Thomas • Grand Turk • Port Canaveral (Orlando), Florida

Average Starting Price

$1,504pp

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!

Celebrity Silhouette

Celebrity Cruises

Dec 19, 2027 - Dec 28, 2027 (9 Nights)

Fort Lauderdale • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

$992pp

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!