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October 2026

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Celebrity Ascent

Celebrity Cruises

Feb 26, 2027 - Mar 8, 2027 (10 Nights)

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

Average Starting Price

Apr 1, 2028 - Apr 10, 2028 (9 Nights)

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

Average Starting Price

Jan 17, 2028 - Jan 31, 2028 (14 Nights)

San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • 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

Jan 25, 2027 - Feb 4, 2027 (10 Nights)

Miami • Philipsburg, St. Maarten • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Bimini • Miami

Average Starting Price

Dec 19, 2027 - Dec 26, 2027 (7 Nights)

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

Average Starting Price

$739pp

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!

Disney Fantasy

Disney Cruise Line

Apr 15, 2028 - Apr 23, 2028 (8 Nights)

Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

Dec 12, 2027 - Dec 27, 2027 (15 Nights)

Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

Jan 4, 2027 - Jan 20, 2027 (16 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Little Bay, Montserrat • Tortola • Miami • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • Miami

Average Starting Price

Jan 2, 2027 - Jan 9, 2027 (7 Nights)

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

Average Starting Price

48% OFF

Jan 15, 2028 - Jan 29, 2028 (14 Nights)

Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami • Puerto Plata, Dominican Republic • Ocean Cay • Nassau • Miami

Average Starting Price

Dec 9, 2028 - Dec 16, 2028 (7 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

$938pp

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!

46% OFF

MSC Meraviglia

MSC Cruises

Mar 21, 2027 - Apr 4, 2027 (14 Nights)

Miami • Grand Turk • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami

Average Starting Price

$1,415pp

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!

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