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Cruise Dates

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October 2026

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Star Legend

Windstar Cruises

Jan 10, 2028 - Jan 24, 2028 (14 Nights)

San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Dec 5, 2027 - Dec 19, 2027 (14 Nights)

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

Average Starting Price

Mar 27, 2027 - Apr 3, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida

Average Starting Price

$1,046pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Vision of the Seas

Royal Caribbean

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

$681pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Nieuw Statendam

Holland America Line

Jan 24, 2027 - Jan 31, 2027 (7 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,289pp

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

Dec 22, 2026 - Jan 5, 2027 (14 Nights)

Miami • Grand Turk • St. Kitts • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • St. John • San Juan, Puerto Rico • Miami

Average Starting Price

$10,100pp

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!

Celebrity Summit

Celebrity Cruises

Dec 19, 2027 - Dec 26, 2027 (7 Nights)

San Juan, Puerto Rico • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

$763pp

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!