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Cruise Dates

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October 2026

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Celebrity Summit

Celebrity Cruises

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

San Juan, Puerto Rico • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Fort-De-France, Martinique • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Dec 11, 2026 - Dec 22, 2026 (11 Nights)

Miami • San Juan, Puerto Rico • St. John • St. Kitts • Gustavia, St. Barts • Deshaies, Guadeloupe • Tortola • Miami

Average Starting Price

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

Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$649pp

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!

Regal Princess

Princess Cruises

Dec 12, 2027 - Dec 27, 2027 (15 Nights)

Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

$1,448pp

Jim's Onboard Credit

Independence of the Seas

Royal Caribbean

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

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

Average Starting Price

$939pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Disney Dream

Disney Cruise Line

Dec 27, 2026 - Jan 3, 2027 (7 Nights)

Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • Tortola • Fort Lauderdale

Average Starting Price

$3,668pp

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!

EXPLORA II

Explora Journeys

Jan 30, 2028 - Feb 6, 2028 (7 Nights)

Miami • Puerto Plata, Dominican Republic • Catalina Island, Dominican Republic • St. Thomas • Road Bay, Anguilla • St. John • San Juan, Puerto Rico

Average Starting Price

Jan 8, 2028 - Jan 15, 2028 (7 Nights)

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

Average Starting Price

48% OFF

Oct 16, 2027 - Oct 30, 2027 (14 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami • Roatan, Honduras • Costa Maya • Cozumel • Ocean Cay • Miami

Average Starting Price

$1,621pp

Jim's Onboard Credit

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

Norwegian Pearl

Norwegian Cruise Line

Jan 27, 2028 - Feb 7, 2028 (11 Nights)

Philadelphia • St John's, Antigua • St. Lucia • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia

Average Starting Price

Jan 2, 2028 - Jan 8, 2028 (6 Nights)

San Juan, Puerto Rico • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Sep 11, 2027 - Sep 18, 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

$609pp

Jim's Onboard Credit

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