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Upcoming Trips

Join Us on Our Upcoming Trips

We'll curate cruises and itineraries specifically for you. We'd also welcome you to join us on any of the cruises we'll be on below. Some have special amenities you can only get by working with us!

San Juan and the Virgin Islands

January 23-30, 2026 from San Juan, Puerto Rico

We'll be sailing on Windstar's newest yacht, the Star Seeker in her inaugural season.  Sailing on this small ship adventure is unlike larger cruise ship experiences.  You'll sail into smaller ports that larger ships cannot reach like Montserrat, Tortola and Jost Van Dyke.  The beauty of sailing Windstar is no two days are alike. Whether you are relaxing onboard this beautiful yacht or enjoy each of these unique ports, this will be a cruise you will always remember.

A Journey into Historic Charm & Tropical Bliss

February 20 - March 2, 2026 from San Juan, PR

Join us on Explora 1 as we head back to one of our favorite ship!  Set sail from San Juan, where Spanish heritage dances with tropical warmth. Venture into the vivid charm of Oranjestad, then drift among Willemstad’s coral wonders. Kralendijk blushes with pink-hued serene shores, a tranquil prelude to Bridgetown’s storied past. Scale the peaks of Terre-de-Haut and bask in the elegance of Philipsburg’s regal allure. Then surrender to the peaceful embrace of Jost Van Dyke before circling back to San Juan’s island paradise.  

Special Amenities!

Antigua, St. Kitts, San Juan & Puerto Plata

March 28 - April 5, 2026 from Ft. Lauderdale, Florida

Join us as we sail on the newly updated Celebrity Eclipse from Ft. Lauderdale.  This is a beautiful time of year to sail to the Southern Caribbean.  We'll visit St. John, Antigua; St. Kitts and Nevis; San Juan and Puerto Plata and enjoy several sea days along the way.  

Special Amenities!

California Seller of Travel Registration # 2089491-50. Registration as a seller of travel in California does not constitute the state's approval. Agent is not a participant in the Travel Consumer Restitution Fund. Florida Seller of Travel Registration # ST37113. Hawaii Seller of Travel License # TAR 7231. Washington Seller of Travel UBI # 602 775122.

© 2024 Cruisin’ with the Drennans  |  All Rights Reserved

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