Florida’s Suncoast · Sailing since 2007
Trade the shoreline for a story—true sailing, wild dolphins, sandbar afternoons and Gulf sunsets from Sarasota, Longboat Key and Anna Maria Island.
Trade the shoreline for a front-row seat to Sarasota’s most beautiful moments. Sail, swim, kayak, spot dolphins, or simply watch the sun disappear across the Gulf. From Sarasota and Longboat Key to Anna Maria Island, Kathleen D Sailing Catamarans turns an ordinary day into a memory worth keeping.
Choose your passage
Compare the signature sails at a glance, then open the details that matter.
2 HoursThe signature sail
A stable, spacious catamaran gives families an easy vantage point for watching the Gulf’s wild dolphins and learning about the marine life around them.
3 HoursMore wind. More water.
For guests who want more than a quick cruise: an extended true-sailing experience with time to settle into the rhythm of the Gulf and look for dolphins.
4 HoursHalf-day adventure
Sail, swim and kayak around Big Sarasota Pass, Longboat Pass or New Pass, with the day shaped by conditions on the water.
2 HoursGolden-hour favorite
Depart before sunset and watch the Gulf Coast shift from daylight to color from the open deck of a sailing catamaran.
Four hours changes the pace
The Big Pass Adventure makes room for all of it—plus lunch, sandbars and the freedom to follow the best conditions of the day.
Meet the Big Pass AdventureThree ways onto the water
Public sails from Sarasota, private charters from Sarasota and Longboat Key, and custom days around Anna Maria Island.
The Kathleen D difference
American-built catamarans, experienced captains and a team that knows these waters. Come for the view; leave with a new favorite Florida story.
Meet the crew
Guest log
“Captain Charlie exceeded our expectations. The boat was clean and comfortable for all, from age 17 to 80.”
— N. Holt · Google review
“We couldn’t believe the dolphins came and swam with our boat. Thank you so much for the lovely day!”
— Tyler Geyen · Google review
“The boat ride was wonderfully peaceful. It was exactly as we had imagined.”
— Martin Camargo · Google review
Tripadvisor recognition
Local tourism partners
