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Norwegian Prima
Norwegian Cruise Line
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Philipsburg, St. Maarten • St. Thomas • Tortola • San Juan, Puerto Rico
Average Starting Price
$939pp
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!

Crown Princess
Princess Cruises
Jan 15, 2027 - Jan 22, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,489pp
Jim's Onboard Credit
47% OFF
MSC World America
MSC Cruises
Apr 22, 2028 - May 6, 2028 (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
$1,641pp
Jim's Onboard Credit

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

Regal Princess
Princess Cruises
Feb 19, 2029 - Mar 5, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,974pp
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!

Sky Princess
Princess Cruises
Feb 25, 2029 - Mar 4, 2029 (7 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale
Average Starting Price
$725pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Dec 6, 2026 - Dec 13, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$767pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 6, 2028 - Mar 13, 2028 (7 Nights)
Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$3,034pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Nov 13, 2027 - Nov 27, 2027 (14 Nights)
Barcelona, Spain • Valencia, Spain • Cartagena, Spain • Malaga, Spain • Cadiz, Spain • Tangier, Morocco • Casablanca, Morocco • San Juan, Puerto Rico
Average Starting Price
$815pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Nov 26, 2027 - Dec 3, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,654pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Dec 6, 2026 - Dec 13, 2026 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Lucia • Bridgetown, Barbados • St. Kitts • St. Thomas • Tortola • San Juan, Puerto Rico
Average Starting Price
$859pp
Jim's Onboard Credit
50% OFF
MSC World America
MSC Cruises
Jan 9, 2027 - Jan 23, 2027 (14 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami • Roatan, Honduras • Costa Maya • Cozumel • Ocean Cay • Miami
Average Starting Price
$1,485pp
Jim's Onboard Credit

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

Crown Princess
Princess Cruises
Jan 8, 2027 - Jan 15, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,299pp
Jim's Onboard Credit
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