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Cruise Dates

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October 2026

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Marina

Oceania Cruises

Dec 10, 2026 - Dec 22, 2026 (12 Nights)

Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

$2,640pp

Jim's Onboard Credit

Independence of the Seas

Royal Caribbean

Feb 7, 2027 - Feb 14, 2027 (7 Nights)

Miami • Perfect Day Cococay • San Juan, Puerto Rico • St. Thomas • Miami

Average Starting Price

$660pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Sun Princess

Princess Cruises

Feb 5, 2028 - Feb 19, 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

$1,639pp

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 Luna

Norwegian Cruise Line

Nov 28, 2027 - Dec 5, 2027 (7 Nights)

Miami • Great Stirrup Cay • St. Thomas • Tortola • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Jan 18, 2028 - Jan 28, 2028 (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

$4,499pp

Jim's Onboard Credit

Norwegian Pearl

Norwegian Cruise Line

Feb 2, 2027 - Feb 12, 2027 (10 Nights)

Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • Philadelphia

Average Starting Price

Feb 14, 2027 - Feb 21, 2027 (7 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,489pp

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!

48% OFF

MSC Seashore

MSC Cruises

Dec 12, 2027 - Dec 26, 2027 (14 Nights)

Miami • Ocean Cay • Puerto Plata, Dominican Republic • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Jan 27, 2028 - Feb 6, 2028 (10 Nights)

Average Starting Price

Nov 24, 2026 - Dec 3, 2026 (9 Nights)

Fort Lauderdale • St. Thomas • Tortola • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Fort Lauderdale

Average Starting Price

$4,200pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Jan 23, 2027 - Jan 30, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 5, 2027 - Dec 12, 2027 (7 Nights)

San Juan, Puerto Rico • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

$764pp

Jim's Onboard Credit

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