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Harmony of the Seas
Royal Caribbean
Apr 15, 2028 - Apr 22, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,170pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Jan 23, 2029 - Feb 3, 2029 (11 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,400pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Feb 9, 2029 - Feb 20, 2029 (11 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$1,093pp
Jim's Onboard Credit
46% OFF
MSC Meraviglia
MSC Cruises
Jan 2, 2027 - Jan 16, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Grand Turk • Ocean Cay • Nassau • Miami
Average Starting Price
$1,175pp
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!

Star Princess
Princess Cruises
Nov 11, 2028 - Nov 25, 2028 (14 Nights)
Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$2,044pp
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!

49% OFF
MSC Opera
MSC Cruises
Sep 3, 2027 - Sep 10, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique
Average Starting Price
$629pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Jan 17, 2027 - Jan 24, 2027 (7 Nights)
San Juan, Puerto Rico • Kralendijk, Bonaire • Philipsburg, St. Maarten • St. Thomas • Tortola • San Juan, Puerto Rico
Average Starting Price
$839pp
Jim's Onboard Credit
Viking Sea
Viking
Nov 20, 2028 - Nov 30, 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
$3,799pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Jan 3, 2028 - Jan 16, 2028 (13 Nights)
Philipsburg, St. Maarten • Road Bay, Anguilla • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Soper's Hole, Tortola • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$4,020pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Mar 5, 2028 - Mar 19, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,908pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Mar 19, 2028 - Mar 26, 2028 (7 Nights)
Miami • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Miami
Average Starting Price
$749pp
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 of the Seas
Royal Caribbean
Apr 2, 2028 - Apr 9, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,576pp
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!

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