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Norwegian Bliss
Norwegian Cruise Line
Dec 10, 2027 - Dec 22, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Manhattan
Average Starting Price
$1,219pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Mar 20, 2027 - Mar 27, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,148pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Rhapsody of the Seas
Royal Caribbean
Dec 24, 2027 - Dec 31, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$1,079pp
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!

46% OFF
MSC Meraviglia
MSC Cruises
Mar 21, 2027 - Apr 4, 2027 (14 Nights)
Miami • Grand Turk • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$1,415pp
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 Gem
Norwegian Cruise Line
Nov 28, 2026 - Dec 10, 2026 (12 Nights)
Tampa • San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Falmouth, Jamaica • George Town, Cayman Islands • Tampa
Average Starting Price
$909pp
Jim's Onboard Credit
Eurodam
Holland America Line
Dec 12, 2027 - Jan 2, 2028 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Fort Lauderdale
Average Starting Price
$5,169pp
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!

23% OFF
Carnival Dream
Carnival Cruise Line
Jan 2, 2027 - Jan 16, 2027 (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
$2,105pp
Jim's Onboard Credit
Celebrity Apex
Celebrity Cruises
Mar 13, 2027 - Mar 20, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida
Average Starting Price
$1,238pp
Jim's Onboard Credit
Carnival Firenze
Carnival Cruise Line
Feb 26, 2027 - Mar 8, 2027 (10 Nights)
Miami • Fun Day at Sea • Fun Day at Sea • San Juan, Puerto Rico • St. Croix • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$1,472pp
Jim's Onboard Credit
31% OFF
Carnival Horizon
Carnival Cruise Line
Jan 6, 2029 - Jan 20, 2029 (14 Nights)
Galveston • Fun Day at Sea • Fun Day at Sea • Ocho Rios, Jamaica • Fun Day at Sea • St. Croix • Philipsburg, St. Maarten • St. Kitts • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$1,335pp
Jim's Onboard Credit
66% OFF
MSC Poesia
MSC Cruises
Nov 12, 2026 - Dec 3, 2026 (21 Nights)
Miami • St. Thomas • St. Kitts • Philipsburg, St. Maarten • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami • Ocho Rios, Jamaica • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Roatan, Honduras • Belize City • Miami
Average Starting Price
$9,300pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 9, 2028 - Jan 23, 2028 (14 Nights)
Miami • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami
Average Starting Price
$1,023pp
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!

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