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Cruise Dates

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October 2026

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Island Princess

Princess Cruises

Nov 29, 2027 - Dec 13, 2027 (14 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Dominica • Bridgetown, Barbados • St. Lucia • Grenada • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale

Average Starting Price

Dec 11, 2027 - Dec 18, 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

30% OFF

Nov 25, 2026 - Dec 7, 2026 (12 Nights)

Miami • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Tortola • Miami

Average Starting Price

Mar 28, 2027 - Apr 4, 2027 (7 Nights)

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

Average Starting Price

$711pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Marina

Oceania Cruises

Feb 13, 2027 - Feb 23, 2027 (10 Nights)

Miami • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Great Stirrup Cay • Miami

Average Starting Price

Mar 27, 2027 - Apr 6, 2027 (10 Nights)

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

Average Starting Price

34% OFF

Dec 18, 2027 - Dec 26, 2027 (8 Nights)

Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida

Average Starting Price

$1,089pp

Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Norwegian Bliss

Norwegian Cruise Line

Dec 10, 2027 - Dec 22, 2027 (12 Nights)

Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Manhattan

Average Starting Price

Nov 13, 2027 - Dec 1, 2027 (18 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale

Average Starting Price

$4,199pp

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!

Scarlet Lady

Virgin Voyages

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

San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Jan 29, 2028 - Feb 6, 2028 (8 Nights)

Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami

Average Starting Price

Dec 18, 2027 - Dec 26, 2027 (8 Nights)

Fort Lauderdale • Nassau • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fort Lauderdale

Average Starting Price

$1,595pp

Jim's Onboard Credit

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