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48% OFF
MSC Grandiosa
MSC Cruises
Dec 30, 2027 - Jan 6, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Ocean Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$1,250pp
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!

Nieuw Statendam
Holland America Line
Jan 3, 2027 - Jan 17, 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
$2,284pp
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!

Zuiderdam
Holland America Line
Nov 21, 2026 - Dec 5, 2026 (14 Nights)
Miami • Key West, Florida • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Miami • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Nassau • Miami
Average Starting Price
$2,024pp
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!

47% OFF
MSC Poesia
MSC Cruises
Oct 31, 2027 - Nov 21, 2027 (21 Nights)
Miami • Ocho Rios, Jamaica • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Roatan, Honduras • Belize City • Miami • Kralendijk, Bonaire • Oranjestad, Aruba • Cabo Rojo, Dominican Republic • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$2,060pp
Jim's Onboard Credit
56% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
May 29, 2027 - Jun 5, 2027 (7 Nights)
Miami • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Nassau • Miami
Average Starting Price
$699pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Dec 13, 2026 - Dec 28, 2026 (15 Nights)
San Juan, Puerto Rico • Road Bay, Anguilla • St John's, Antigua • Basseterre, St. Kitts and Nevis • Grand Turk • Miami • Ocho Rios, Jamaica • Catalina Island, Dominican Republic • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$13,050pp
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!

Norwegian Aqua
Norwegian Cruise Line
Mar 5, 2028 - Mar 12, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$1,119pp
Jim's Onboard Credit
Norwegian Joy
Norwegian Cruise Line
Mar 8, 2028 - Mar 17, 2028 (9 Nights)
Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Ocho Rios, Jamaica • Miami
Average Starting Price
$1,289pp
Jim's Onboard Credit
Eurodam
Holland America Line
Mar 4, 2028 - Mar 15, 2028 (11 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Nassau • Fort Lauderdale
Average Starting Price
$2,859pp
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!

Resilient Lady
Virgin Voyages
Feb 28, 2027 - Mar 7, 2027 (7 Nights)
Miami • George Town, Cayman Islands • Ocho Rios, Jamaica • Nassau • Bimini • Miami
Average Starting Price
$903pp
Jim's Onboard Credit
68% OFF
MSC Seashore
MSC Cruises
Nov 22, 2026 - Dec 3, 2026 (11 Nights)
Port Canaveral (Orlando), Florida • Nassau • Ocho Rios, Jamaica • George Town, Cayman Islands • Ocean Cay • Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$663pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Nov 15, 2026 - Nov 22, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • Ocho Rios, Jamaica • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$399pp
Jim's Onboard Credit
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