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Marina
Oceania Cruises
Dec 20, 2027 - Dec 27, 2027 (7 Nights)
Miami • Costa Maya • Belize City • Roatan, Honduras • Cozumel • Miami
Average Starting Price
$2,249pp
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!

Silver Ray
Silversea
Feb 7, 2027 - Feb 19, 2027 (12 Nights)
Miami • San Juan, Puerto Rico • St. John • St. Kitts • Gustavia, St. Barts • St John's, Antigua • Deshaies, Guadeloupe • Roseau, Dominica • Fort-De-France, Martinique • Bequia Island, Saint Vincent • Bridgetown, Barbados
Average Starting Price
$7,200pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Apr 4, 2027 - Apr 21, 2027 (17 Nights)
San Juan, Puerto Rico • Ponta Delgada (Azores), Portugal • Funchal, Portugal • Melilla, Morocco • Motril, Spain • Ibiza, Spain • Palma (Majorca), Spain • Marseille (Provence), France • Nice, France • Livorno, Italy • Rome (Civitavecchia), Italy
Average Starting Price
$2,619pp
Jim's Onboard Credit
Brilliant Lady
Virgin Voyages
Jan 10, 2028 - Jan 20, 2028 (10 Nights)
Miami • Philipsburg, St. Maarten • Tortola • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami
Average Starting Price
$1,390pp
Jim's Onboard Credit
43% OFF
Carnival Freedom
Carnival Cruise Line
May 29, 2027 - Jun 6, 2027 (8 Nights)
Norfolk, Virginia • Fun Day at Sea • Fun Day at Sea • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Fun Day at Sea • Fun Day at Sea • Norfolk, Virginia
Average Starting Price
$799pp
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!

17% OFF
Seven Seas Splendor
Regent Seven Seas Cruises
Jan 12, 2027 - Jan 26, 2027 (14 Nights)
Miami • Cruising the Caribbean Sea • Cozumel • Costa Maya • Harvest Caye, Belize • Roatan, Honduras • Cruising the Caribbean Sea • George Town, Cayman Islands • Ocho Rios, Jamaica • Cruising the Caribbean Sea • Limon, Costa Rica • Cruising the Caribbean Sea • Cartagena, Colombia • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama
Average Starting Price
$15,699pp
Jim's Onboard Credit
44% OFF
Carnival Mardi Gras
Carnival Cruise Line
Apr 17, 2027 - Apr 24, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Nassau • Relaxaway Half Moon Cay • Fun Day at Sea • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$658pp
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!

Viking Sea
Viking
Dec 27, 2027 - Jan 6, 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
$3,599pp
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!

29% OFF
Seven Seas Mariner
Regent Seven Seas Cruises
Nov 29, 2028 - Dec 11, 2028 (12 Nights)
Miami • Tortola • Basseterre, St. Kitts and Nevis • Oranjestad, Aruba • Falmouth, Jamaica • George Town, Cayman Islands • Galveston
Average Starting Price
$7,199pp
Jim's Onboard Credit
Icon of the Seas
Royal Caribbean
Jun 19, 2027 - Jun 26, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,761pp
Jim's Onboard Credit
Utopia of the Seas
Royal Caribbean
Aug 6, 2027 - Aug 9, 2027 (3 Nights)
Port Canaveral (Orlando), Florida • Nassau • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$899pp
Jim's Onboard Credit
51% OFF
Margaritaville at Sea Islander
Margaritaville at Sea
Oct 17, 2027 - Oct 23, 2027 (6 Nights)
Tampa • Roatan, Honduras • Belize City • Cozumel • Tampa
Average Starting Price
$429pp
Jim's Onboard Credit
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