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31% OFF
Carnival Horizon
Carnival Cruise Line
Oct 14, 2028 - Oct 28, 2028 (14 Nights)
Galveston • Fun Day at Sea • Fun Day at Sea • Ocho Rios, Jamaica • Fun Day at Sea • Fun Day at Sea • Bridgetown, Barbados • St. Lucia • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$1,360pp
Jim's Onboard Credit
Zuiderdam
Holland America Line
Dec 5, 2026 - Dec 19, 2026 (14 Nights)
Miami • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Miami • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Miami
Average Starting Price
$2,034pp
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!

Sonata
Oceania Cruises
Mar 15, 2029 - Mar 29, 2029 (14 Nights)
Miami • George Town, Cayman Islands • Ocho Rios, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Fort-De-France, Martinique • Philipsburg, St. Maarten • Miami
Average Starting Price
$6,999pp
Jim's Onboard Credit
Norwegian Joy
Norwegian Cruise Line
Feb 9, 2028 - Feb 18, 2028 (9 Nights)
Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Ocho Rios, Jamaica • Miami
Average Starting Price
$1,199pp
Jim's Onboard Credit
48% OFF
MSC Poesia
MSC Cruises
Oct 31, 2027 - Nov 11, 2027 (11 Nights)
Miami • Ocho Rios, Jamaica • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Roatan, Honduras • Belize City • Miami
Average Starting Price
$1,153pp
Jim's Onboard Credit
Norwegian Aqua
Norwegian Cruise Line
Feb 20, 2028 - Feb 27, 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
$1,039pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Dec 20, 2026 - Jan 5, 2027 (16 Nights)
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 • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Samana, Dominican Republic • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$16,985pp
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!

57% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Jul 24, 2027 - Jul 31, 2027 (7 Nights)
Miami • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Nassau • Miami
Average Starting Price
$799pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Jan 24, 2027 - Jan 31, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Great Stirrup Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Port Canaveral (Orlando), Florida
Average Starting Price
$439pp
Jim's Onboard Credit
Resilient Lady
Virgin Voyages
Jan 9, 2028 - Jan 16, 2028 (7 Nights)
Miami • Key West, Florida • Ocho Rios, Jamaica • George Town, Cayman Islands • Bimini • Miami
Average Starting Price
$903pp
Jim's Onboard Credit
Eurodam
Holland America Line
Feb 23, 2028 - Mar 15, 2028 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Cabo Rojo, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • 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
$5,089pp
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!

62% OFF
MSC Seashore
MSC Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Nassau • Ocho Rios, Jamaica • George Town, Cayman Islands • Ocean Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$706pp
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!

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