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Rhapsody of the Seas
Royal Caribbean
Jan 2, 2027 - Jan 9, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$697pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Jan 21, 2029 - Feb 4, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale
Average Starting Price
$1,625pp
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!

EXPLORA I
Explora Journeys
Nov 12, 2026 - Nov 17, 2026 (5 Nights)
St John's, Antigua • Road Bay, Anguilla • San Juan, Puerto Rico • Miami
Average Starting Price
$2,600pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Nov 4, 2028 - Nov 11, 2028 (7 Nights)
Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$975pp
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!

47% OFF
MSC World America
MSC Cruises
Oct 21, 2028 - Nov 4, 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
$1,601pp
Jim's Onboard Credit

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

Sun Princess
Princess Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Fort Lauderdale • San Juan, Puerto Rico • Grand Turk • Celebration Key • Fort Lauderdale
Average Starting Price
$819pp
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 Legend
Windstar Cruises
Dec 6, 2027 - Dec 27, 2027 (21 Nights)
Lisbon, Portugal • Funchal, Portugal • Great Harbor Jost Van Dyke, British Virgin Islands • 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
$6,298pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Mar 18, 2028 - Mar 25, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • Bridgetown, Barbados • St. Lucia • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,229pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Feb 27, 2028 - Mar 12, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,713pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Nov 22, 2026 - Nov 29, 2026 (7 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$4,480pp
Jim's Onboard Credit
Viking Sea
Viking
Jan 19, 2029 - Jan 29, 2029 (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
$4,999pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Dec 13, 2026 - Dec 20, 2026 (7 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$3,843pp
Jim's Onboard Credit
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