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Cruise Dates

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October 2026

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Sun Princess

Princess Cruises

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

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale

Average Starting Price

$1,642pp

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!

Scarlet Lady

Virgin Voyages

Feb 12, 2028 - Feb 19, 2028 (7 Nights)

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

Average Starting Price

Jan 31, 2027 - Feb 14, 2027 (14 Nights)

San Juan, Puerto Rico • St. Thomas • Pointe-à-Pitre, Guadeloupe • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 12, 2026 - Dec 28, 2026 (16 Nights)

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

Average Starting Price

44% OFF

Mar 11, 2028 - Mar 19, 2028 (8 Nights)

Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

$713pp

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!

Carnival Celebration

Carnival Cruise Line

Nov 8, 2026 - Nov 15, 2026 (7 Nights)

Miami • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Miami

Average Starting Price

Dec 20, 2026 - Jan 10, 2027 (21 Nights)

Fort Lauderdale • St. Thomas • Virgin Gorda, British Virgin Islands • St John's, Antigua • San Juan, Puerto Rico • Samana, Dominican Republic • Nassau • Fort Lauderdale • Cozumel • Belize City • Santo Tomas de Castilla, Guatemala • Roatan, Honduras • George Town, Cayman Islands • Ocho Rios, Jamaica • Fort Lauderdale • Nassau • Fort Lauderdale

Average Starting Price

$11,500pp

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!