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69% OFF
MSC Meraviglia
MSC Cruises
Dec 5, 2026 - Dec 13, 2026 (8 Nights)
Miami • San Juan, Puerto Rico • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$368pp
Jim's Onboard Credit
Allure of the Seas
Royal Caribbean
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Miami
Average Starting Price
$1,524pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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!

Norwegian Pearl
Norwegian Cruise Line
Mar 2, 2027 - Mar 12, 2027 (10 Nights)
Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • Philadelphia
Average Starting Price
$889pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Jan 15, 2028 - Jan 25, 2028 (10 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,144pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Nov 1, 2027 - Nov 8, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$2,443pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Jan 8, 2028 - Jan 15, 2028 (7 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$1,679pp
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!

Star Princess
Princess Cruises
Jan 9, 2028 - Jan 16, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Port Canaveral (Orlando), Florida
Average Starting Price
$619pp
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!

Symphony of the Seas
Royal Caribbean
Jan 15, 2028 - Jan 23, 2028 (8 Nights)
Fort Lauderdale • Samana, Dominican Republic • San Juan, Puerto Rico • Perfect Day Cococay • Nassau • Fort Lauderdale
Average Starting Price
$1,161pp
Jim's Onboard Credit
Silver Shadow
Silversea
Jan 30, 2027 - Feb 6, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Little Bay, Montserrat • St John's, Antigua • Gustavia, St. Barts • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$5,100pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Mar 7, 2027 - Mar 21, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,688pp
Jim's Onboard Credit
47% OFF
MSC World America
MSC Cruises
Jun 12, 2027 - Jun 26, 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
$2,441pp
Jim's Onboard Credit

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

Grandeur of the Seas
Royal Caribbean
Sep 25, 2027 - Oct 2, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$606pp
Jim's Onboard Credit
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