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Cruise Dates

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November 2026

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Star Pride

Windstar Cruises

Oct 11, 2027 - Nov 1, 2027 (21 Nights)

Montreal, Quebec • Cruising St. Lawrence River • Quebec City, Quebec • Gaspe, Quebec • Sydney, Nova Scotia • Sydney, Nova Scotia • Halifax, Nova Scotia • Halifax, Nova Scotia • Bar Harbor, Maine • Portland, Australia • Boston • Hamilton, Bermuda • Hamilton, Bermuda • Royal Naval Dockyard, Bermuda • Royal Naval Dockyard, Bermuda • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Jan 17, 2027 - Jan 24, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St John's, Antigua • Fort-De-France, Martinique • Kingstown, Saint Vincent Island, Saint Vincent • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

$648pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Regal Princess

Princess Cruises

Feb 25, 2029 - Mar 11, 2029 (14 Nights)

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

Average Starting Price

$1,974pp

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!

Sky Princess

Princess Cruises

Feb 4, 2029 - Feb 11, 2029 (7 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale

Average Starting Price

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

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

Average Starting Price

Nov 21, 2026 - Nov 28, 2026 (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

Mar 10, 2029 - Mar 17, 2029 (7 Nights)

Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale

Average Starting Price

$1,025pp

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!

Crown Princess

Princess Cruises

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

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

Average Starting Price

47% OFF

Feb 26, 2028 - Mar 11, 2028 (14 Nights)

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

Average Starting Price

$1,731pp

Jim's Onboard Credit

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

Norwegian Prima

Norwegian Cruise Line

Jan 3, 2027 - Jan 10, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Tortola • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico

Average Starting Price

Mar 26, 2028 - Apr 2, 2028 (7 Nights)

San Juan, Puerto Rico • Willemstad, Curacao • Oranjestad, Aruba • Kralendijk, Bonaire • Fort Lauderdale

Average Starting Price

Apr 9, 2028 - Apr 16, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico

Average Starting Price

$902pp

Jim's Onboard Credit

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