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30% OFF
Allura
Oceania Cruises
Dec 12, 2026 - Dec 21, 2026 (9 Nights)
Miami • St. Thomas • Gustavia, St. Barts • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$3,290pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,565pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Feb 1, 2027 - Feb 13, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • St. Kitts • Philipsburg, St. Maarten • Manhattan
Average Starting Price
$1,119pp
Jim's Onboard Credit
55% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Apr 24, 2027 - May 1, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$529pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Nov 14, 2027 - Nov 21, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,476pp
Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Norwegian Prima
Norwegian Cruise Line
Jan 8, 2028 - Jan 15, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,219pp
Jim's Onboard Credit
48% OFF
MSC Seashore
MSC Cruises
Dec 26, 2027 - Jan 9, 2028 (14 Nights)
Miami • Grand Turk • Puerto Plata, Dominican Republic • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,824pp
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!

Viking Sea
Viking
Feb 6, 2028 - Feb 16, 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
$4,299pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Feb 15, 2027 - Feb 26, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,989pp
Jim's Onboard Credit
Icon of the Seas
Royal Caribbean
Apr 10, 2027 - Apr 17, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,353pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Star Legend
Windstar Cruises
Jan 24, 2028 - Feb 7, 2028 (14 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,014pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Jan 12, 2027 - Feb 2, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$3,939pp
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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