Best 188 things to do in Longboat Key, FL

Rent a street-legal 8-passenger golf cart with delivery included

Rent a beach cruiser with delivery, helmet, and lock included

Cruise Siesta Key by e-bike with a rental timed for sunset

Stretch, unwind, and rejuvenate—right in the comfort of your vacation rental.

Explore pristine sandbars, collect shells, and relax on a fun 3-hour boat excursion

Cruise Sarasota Bay at sunset and look for dolphins

Cruise Anna Maria Island waterways and look for dolphins with drinks included

Cruise Sarasota Bay at sunset and look for dolphins

Cruise the bay with gourmet donuts and wildlife spotting

Cruise Sarasota Bay for dolphin sightings with donuts and coffee

Cruise the Intracoastal Waterway with dolphin and manatee spotting

Charter a private boat for your group from Anna Maria Island

Charter a private FunBoat on Anna Maria Island with paddleboards and beach games

Charter the FunBoat with crew, paddleboards, and beach games

Private boat charter for up to 20 with paddleboards, beach games, and crew

Charter a FunBoat with paddleboards and beach games for your group

Experience Siesta Key like never before—from 400 feet above the ocean!

Rent a street-legal 6-passenger golf cart and explore Siesta Key

Cruise Siesta Key’s waterways on a 2024 tiki boat with music, drinks and coastal wildlife views.

Soar above Florida's top-rated beach and spot dolphins during a 12–15 minute parasail flight.

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

Watch playful dolphins and a vibrant Gulf sunset while enjoying complimentary beer and wine.

Enjoy a morning cruise with complimentary drinks while spotting dolphins in Siesta Key.

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