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Norwegian Prima
Norwegian Cruise Line
Feb 21, 2027 - Feb 28, 2027 (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
$1,099pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Feb 7, 2028 - Feb 21, 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 • Philipsburg, St. Maarten • Gustavia, St. Barts • 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
Nov 10, 2026 - Nov 21, 2026 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$1,969pp
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
Dec 30, 2028 - Jan 13, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$2,344pp
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!

Norwegian Bliss
Norwegian Cruise Line
Nov 29, 2026 - Dec 11, 2026 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Tortola • Manhattan
Average Starting Price
$1,529pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Miami
Average Starting Price
$1,646pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 16, 2028 - Jan 30, 2028 (14 Nights)
Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami
Average Starting Price
$1,138pp
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!

Emerald Princess
Princess Cruises
Jan 16, 2028 - Jan 30, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • St. Lucia • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,308pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Jan 28, 2029 - Feb 11, 2029 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,804pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Mar 17, 2028 - Mar 27, 2028 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,805pp
Jim's Onboard Credit
44% OFF
MSC Opera
MSC Cruises
Jul 9, 2027 - Jul 16, 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
$2,037pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Jun 12, 2027 - Jun 19, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$795pp
Jim's Onboard Credit
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