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Cruise Dates

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October 2026

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Crown Princess

Princess Cruises

Jan 3, 2027 - Jan 17, 2027 (14 Nights)

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

Average Starting Price

Dec 30, 2028 - Jan 13, 2029 (14 Nights)

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

Average Starting Price

$2,344pp

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 Prima

Norwegian Cruise Line

Feb 26, 2028 - Mar 4, 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

Jan 2, 2029 - Jan 13, 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

Jan 26, 2029 - Feb 2, 2029 (7 Nights)

Port Canaveral (Orlando), Florida • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Port Canaveral (Orlando), Florida

Average Starting Price

$925pp

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!

Scarlet Lady

Virgin Voyages

Apr 15, 2028 - Apr 22, 2028 (7 Nights)

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

Average Starting Price

Feb 6, 2028 - Feb 13, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

47% OFF

Sep 18, 2027 - Sep 25, 2027 (7 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami

Average Starting Price

$784pp

Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

Vision of the Seas

Royal Caribbean

Feb 21, 2027 - Feb 28, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

$609pp

Jim's Onboard Credit

FREE Specialty Dining Meal

EXPLORA III

Explora Journeys

Dec 28, 2026 - Jan 5, 2027 (8 Nights)

San Juan, Puerto Rico • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Samana, Dominican Republic • Puerto Plata, Dominican Republic • Miami

Average Starting Price

$12,750pp

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!