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October 2026

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Crown Princess

Princess Cruises

Dec 20, 2028 - Dec 28, 2028 (8 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • St. Thomas • Philipsburg, St. Maarten • Grand Turk • Fort Lauderdale

Average Starting Price

$1,325pp

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 2, 2028 - Dec 16, 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!

42% OFF

MSC Opera

MSC Cruises

Jun 25, 2027 - Jul 2, 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

$1,060pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Mar 11, 2028 - Mar 18, 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

Jun 19, 2027 - Jun 26, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico

Average Starting Price

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

Nov 15, 2026 - Nov 25, 2026 (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

Feb 13, 2028 - Feb 27, 2028 (14 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Feb 14, 2027 - Feb 28, 2027 (14 Nights)

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

Average Starting Price

$1,449pp

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!

Wind Surf

Windstar Cruises

Mar 20, 2027 - Mar 27, 2027 (7 Nights)

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

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

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

Average Starting Price

$1,788pp

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!

51% OFF

MSC World Europa

MSC Cruises

Nov 15, 2026 - Dec 5, 2026 (20 Nights)

Rome (Civitavecchia), Italy • La Spezia, Italy • Marseille (Provence), France • Barcelona, Spain • Arrecife (Lanzarote), Spain • Santa Cruz de Tenerife, Spain • Philipsburg, St. Maarten • St. Kitts • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Grenada • Fort-De-France, Martinique

Average Starting Price

$929pp

Jim's Onboard Credit

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