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Disney Dream
Disney Cruise Line
Jan 22, 2027 - Jan 29, 2027 (7 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • Tortola • Fort Lauderdale
Average Starting Price
$1,591pp
Jim's Onboard Credit
Nieuw Amsterdam
Holland America Line
Jan 29, 2027 - Feb 19, 2027 (21 Nights)
Fort Lauderdale • St John's, Antigua • St. Thomas • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Oranjestad, Aruba • Cartagena, Colombia • Enter Panama Canal at Cristobal • Cruising Panama Canal And Gatun Lake • Gatun Lake, Panama • Cruising Gatun Lake And Panama Canal • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • George Town, Cayman Islands • Fort Lauderdale
Average Starting Price
$4,249pp
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!

Regal Princess
Princess Cruises
Apr 4, 2027 - Apr 11, 2027 (7 Nights)
Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$777pp
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!

Marina
Oceania Cruises
Feb 17, 2028 - Feb 27, 2028 (10 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Croix • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Miami
Average Starting Price
$3,399pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Dec 12, 2027 - Dec 26, 2027 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$1,647pp
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!

Harmony of the Seas
Royal Caribbean
Apr 17, 2027 - Apr 24, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$926pp
Jim's Onboard Credit
CBT Exclusive
$$$ Savings
FREE Specialty Dining Meal
EXPLORA II
Explora Journeys
Jan 9, 2028 - Jan 16, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • Catalina Island, Dominican Republic • St. Thomas • Marigot Bay, St. Lucia • St. John • San Juan, Puerto Rico
Average Starting Price
$3,915pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Dec 18, 2027 - Dec 24, 2027 (6 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Basseterre, St. Kitts and Nevis • St John's, Antigua • San Juan, Puerto Rico
Average Starting Price
$767pp
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!

Scarlet Lady
Virgin Voyages
Dec 11, 2027 - Dec 18, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$903pp
Jim's Onboard Credit
45% OFF
Carnival Celebration
Carnival Cruise Line
Nov 7, 2027 - Nov 14, 2027 (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
$590pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Jan 15, 2028 - Jan 26, 2028 (11 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Tortola • St. Thomas • Manhattan
Average Starting Price
$1,279pp
Jim's Onboard Credit
Resilient Lady
Virgin Voyages
Feb 26, 2028 - Mar 5, 2028 (8 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami
Average Starting Price
$1,112pp
Jim's Onboard Credit
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