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Cruise Dates

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October 2026

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Viking Sea

Viking

Jan 5, 2027 - Jan 15, 2027 (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

$6,799pp

Jim's Onboard Credit

Norwegian Luna

Norwegian Cruise Line

Mar 19, 2028 - Mar 26, 2028 (7 Nights)

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

Average Starting Price

Mar 4, 2028 - Mar 11, 2028 (7 Nights)

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

Average Starting Price

44% OFF

Feb 6, 2027 - Feb 14, 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

Mar 25, 2028 - Apr 1, 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

$900pp

Jim's Onboard Credit

Norwegian Aura

Norwegian Cruise Line

Sep 16, 2028 - Sep 23, 2028 (7 Nights)

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

Average Starting Price

Dec 12, 2027 - Dec 19, 2027 (7 Nights)

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

Average Starting Price

$1,589pp

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!

Regal Princess

Princess Cruises

Feb 25, 2029 - Mar 5, 2029 (8 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale

Average Starting Price

Dec 28, 2028 - Jan 5, 2029 (8 Nights)

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

Average Starting Price

$1,325pp

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!