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Cruise Dates

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October 2026

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Sun Princess

Princess Cruises

Jan 8, 2028 - Jan 22, 2028 (14 Nights)

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

Average Starting Price

$1,308pp

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!

Silver Dawn

Silversea

Jan 4, 2028 - Jan 15, 2028 (11 Nights)

San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • St. Kitts • Fort-De-France, Martinique • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico

Average Starting Price

$4,700pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Nov 27, 2027 - Dec 4, 2027 (7 Nights)

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

Average Starting Price

51% OFF

May 9, 2027 - May 16, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Celebration Key • Fun Day at Sea • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida

Average Starting Price

$531pp

Jim's Onboard Credit

27% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Jan 17, 2028 - Jan 27, 2028 (10 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Gustavia, St. Barts • St John's, Antigua • Tortola • Miami

Average Starting Price

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

Fort Lauderdale • Philipsburg, St. Maarten • San Juan, Puerto Rico • Disney Castaway Cay, Bahamas • Fort Lauderdale

Average Starting Price

Jan 12, 2028 - Jan 22, 2028 (10 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$2,459pp

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!

Viking Sea

Viking

Dec 27, 2027 - Jan 6, 2028 (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

$3,599pp

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

Jan 3, 2029 - Jan 19, 2029 (16 Nights)

Fort Lauderdale • Grand Turk • Samana, Dominican Republic • Great Harbor Jost Van Dyke, British Virgin Islands • St John's, Antigua • St. Kitts • Gustavia, St. Barts • San Juan, Puerto Rico • Gustavia, St. Barts • St. Kitts • St John's, Antigua • Great Harbor Jost Van Dyke, British Virgin Islands • Samana, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$9,080pp

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!