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Norwegian Pearl
Norwegian Cruise Line
Dec 13, 2027 - Dec 23, 2027 (10 Nights)
Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Philadelphia
Average Starting Price
$1,081pp
Jim's Onboard Credit
Eurodam
Holland America Line
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!

31% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Jan 5, 2028 - Jan 15, 2028 (10 Nights)
Miami • Tortola • Gustavia, St. Barts • Philipsburg, St. Maarten • Pointe-à-Pitre, Guadeloupe • Roseau, Dominica • Fort-De-France, Martinique • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$6,749pp
Jim's Onboard Credit
Coral Princess
Princess Cruises
Dec 20, 2027 - Jan 3, 2028 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Dominica • St. Lucia • Bridgetown, Barbados • Grenada • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$1,364pp
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!

Odyssey of the Seas
Royal Caribbean
Jan 13, 2028 - Jan 24, 2028 (11 Nights)
Cape Liberty • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • Basseterre, St. Kitts and Nevis • Cape Liberty
Average Starting Price
$1,485pp
Jim's Onboard Credit
Norwegian Escape
Norwegian Cruise Line
Jan 6, 2027 - Jan 15, 2027 (9 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,149pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Mar 28, 2027 - Apr 4, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$644pp
Jim's Onboard Credit
Star Princess
Princess Cruises
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!

Scarlet Lady
Virgin Voyages
Nov 27, 2027 - Dec 4, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
Dec 26, 2027 - Jan 2, 2028 (7 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$3,931pp
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!

Celebrity Silhouette
Celebrity Cruises
Dec 28, 2027 - Jan 8, 2028 (11 Nights)
Fort Lauderdale • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,529pp
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!

Celebrity Summit
Celebrity Cruises
Jan 2, 2028 - Jan 6, 2028 (4 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$481pp
Jim's Onboard Credit
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