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Disney Fantasy
Disney Cruise Line
Jan 30, 2028 - Feb 6, 2028 (7 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • St. Thomas • Disney Castaway Cay, Bahamas • Fort Lauderdale
Average Starting Price
$1,995pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,309pp
Jim's Onboard Credit
Independence of the Seas
Royal Caribbean
Feb 26, 2028 - Mar 4, 2028 (7 Nights)
Miami • St. Thomas • Samana, Dominican Republic • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$874pp
Jim's Onboard Credit
28% OFF
Seven Seas Mariner
Regent Seven Seas Cruises
Dec 22, 2028 - Jan 6, 2029 (15 Nights)
Galveston • Progreso, Mexico • George Town, Cayman Islands • Ocho Rios, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • St John's, Antigua • St. Thomas • Miami
Average Starting Price
$9,099pp
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!

Viking Sea
Viking
Jan 6, 2028 - Jan 27, 2028 (21 Nights)
San Juan, Puerto Rico • Sail the Caribbean Sea • Bridgetown, Barbados • Sail the Atlantic Ocean • Iles du Salut (Ile Royale), French Guiana • Sail the Atlantic Ocean • Sail the Mouth of the Amazon River • Santarem, Brazil • Parintins, Brazil • Manaus, Brazil • Manaus, Brazil • Sail the Amazon River • Sail the Amazon River • Belem, Brazil • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$11,999pp
Jim's Onboard Credit
Viking Sky
Viking
Jan 8, 2028 - Jan 18, 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
$4,299pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
May 22, 2027 - May 29, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$2,673pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Feb 12, 2028 - Feb 19, 2028 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$770pp
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!

Norwegian Luna
Norwegian Cruise Line
Dec 5, 2027 - Dec 12, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$949pp
Jim's Onboard Credit
Norwegian Pearl
Norwegian Cruise Line
Mar 7, 2028 - Mar 17, 2028 (10 Nights)
Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • Philadelphia
Average Starting Price
$1,199pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Feb 6, 2027 - Feb 13, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Grenada • San Juan, Puerto Rico
Average Starting Price
$868pp
Jim's Onboard Credit
Nieuw Statendam
Holland America Line
Feb 14, 2027 - Feb 28, 2027 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$2,694pp
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!

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