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Norwegian Pearl
Norwegian Cruise Line
Jan 3, 2028 - Jan 15, 2028 (12 Nights)
Philadelphia • Philipsburg, St. Maarten • Bridgetown, Barbados • St. Lucia • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia
Average Starting Price
$898pp
Jim's Onboard Credit
Norwegian Breakaway
Norwegian Cruise Line
Jan 5, 2028 - Jan 10, 2028 (5 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$609pp
Jim's Onboard Credit
49% OFF
MSC Grandiosa
MSC Cruises
Jun 26, 2027 - Jul 10, 2027 (14 Nights)
Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • Cozumel • Costa Maya • Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • Puerto Plata, Dominican Republic • Port Canaveral (Orlando), Florida
Average Starting Price
$1,560pp
Jim's Onboard Credit
48% OFF
MSC World America
MSC Cruises
Oct 23, 2027 - Nov 6, 2027 (14 Nights)
Miami • Roatan, Honduras • Costa Maya • Cozumel • Ocean Cay • Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$1,621pp
Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

Norwegian Dawn
Norwegian Cruise Line
Jan 28, 2028 - Feb 7, 2028 (10 Nights)
Jacksonville • Grand Bahama Island • Great Stirrup Cay • Samana, Dominican Republic • Puerto Plata, Dominican Republic • Tortola • San Juan, Puerto Rico • Jacksonville
Average Starting Price
$979pp
Jim's Onboard Credit
Sonata
Oceania Cruises
Jan 30, 2029 - Feb 11, 2029 (12 Nights)
Miami • Puerto Plata, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia • Limon, Costa Rica • Panama Canal, Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama
Average Starting Price
$6,599pp
Jim's Onboard Credit
Norwegian Aqua
Norwegian Cruise Line
May 16, 2027 - May 23, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,129pp
Jim's Onboard Credit
Norwegian Escape
Norwegian Cruise Line
Sep 1, 2027 - Sep 6, 2027 (5 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$689pp
Jim's Onboard Credit
43% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Sep 11, 2027 - Sep 18, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$679pp
Jim's Onboard Credit
Freedom of the Seas
Royal Caribbean
Feb 6, 2027 - Feb 11, 2027 (5 Nights)
Miami • Nassau • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$379pp
Jim's Onboard Credit
47% OFF
MSC Seashore
MSC Cruises
Nov 20, 2027 - Nov 28, 2027 (8 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • Miami
Average Starting Price
$878pp
Jim's Onboard Credit
Resilient Lady
Virgin Voyages
Dec 19, 2027 - Dec 26, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Bimini • Miami
Average Starting Price
$1,253pp
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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