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Seabourn Ovation
Seabourn
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$5,573pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Apr 8, 2028 - Apr 15, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$838pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Feb 24, 2029 - Mar 6, 2029 (10 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,150pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Jan 12, 2029 - Jan 19, 2029 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$885pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Dec 5, 2026 - Dec 12, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$907pp
Jim's Onboard Credit
FREE Specialty Dining Meal
48% OFF
MSC Meraviglia
MSC Cruises
Dec 19, 2026 - Jan 2, 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
$1,915pp
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
Dec 23, 2028 - Jan 6, 2029 (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
$2,494pp
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 Pride
Windstar Cruises
Mar 6, 2028 - Mar 27, 2028 (21 Nights)
Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • 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 • 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
$6,663pp
Jim's Onboard Credit
48% OFF
MSC Opera
MSC Cruises
Sep 2, 2027 - Sep 16, 2027 (14 Nights)
Bridgetown, Barbados • 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 • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados
Average Starting Price
$1,888pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Mar 25, 2028 - Apr 1, 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
$1,259pp
Jim's Onboard Credit
Viking Sea
Viking
Jan 9, 2029 - Jan 19, 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
Grandeur of the Seas
Royal Caribbean
Nov 13, 2027 - Nov 20, 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
$748pp
Jim's Onboard Credit
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