Best 764 things to do in Holmes Beach, FL

Enjoy a relaxed evening cruise along Siesta Key with music, LED lights and possible dolphin sightings.

Soar above Siesta Key and spot dolphins on a safe, family-friendly 2.5-hour parasailing cruise

Cruise Sarasota’s Gulf waters on a spacious pontoon with flexible 4- or 8-hour options.

Ride the waters around Siesta Key with a guide, a sandbar stop, and island views

Choose a bike style that fits your plans for a full day on Siesta Key

Ride Siesta Key and reach the Legacy Trail with an e-bike rental

Cruise Siesta Key with a Class 1 or Class 2 electric bike

Family bike options with kid sizes and child seats

Cruise the Legacy Trail on a comfortable bike with included essentials

Comfortable Jamis hybrid bike rental for Legacy Trail rides

Choose an easygoing or sporty ride for the Legacy Trail

Smooth pedal-assist rides for exploring more of the Legacy Trail

Ride paved trail miles from Sarasota toward Venice

Private 2-hour sunset sail with downtown St. Petersburg views

Relax on a 3-hour sail with a U.S. Coast Guard–licensed captain from downtown St. Pete

Start the day aboard a classic yacht with optional sailing instruction

Relax across four social spaces on a private Sarasota Bay catamaran

Sail into golden hour aboard a private 48-foot Jeanneau yacht

Cruise Tampa Bay at sunset with flybridge views and space to unwind

Design your own Tampa Bay day aboard a spacious power catamaran

Private catamaran sailing with space to swim, paddle, and unwind

Sail Tampa Bay on a spacious catamaran with room to relax and swim

Sail Tampa Bay at golden hour aboard a 40-foot luxury catamaran

Private, wind-driven sailing aboard a 48-foot Jeanneau yacht