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Cruise Dates

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October 2026

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Enchanted Princess

Princess Cruises

Feb 13, 2029 - Feb 24, 2029 (11 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

48% OFF

Aug 19, 2027 - Sep 2, 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

$1,938pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Nov 22, 2026 - Nov 29, 2026 (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

42% OFF

Nov 18, 2026 - Dec 2, 2026 (14 Nights)

Barcelona, Spain • Arrecife (Lanzarote), Spain • Santa Cruz de Tenerife, Spain • Philipsburg, St. Maarten • St. Kitts • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados

Average Starting Price

Jan 16, 2028 - Jan 30, 2028 (14 Nights)

Philipsburg, St. Maarten • St John's, Antigua • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • 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

Feb 5, 2028 - Feb 12, 2028 (7 Nights)

Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados

Average Starting Price

Mar 26, 2027 - Apr 4, 2027 (9 Nights)

Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale

Average Starting Price

Nov 28, 2026 - Dec 12, 2026 (14 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$1,009pp

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 of the Seas

Royal Caribbean

Nov 15, 2026 - Nov 22, 2026 (7 Nights)

Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida

Average Starting Price

$968pp

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!