Best results for Water Activities in Osprey FL

Paddle a 100% clear kayak to mangroves and a secluded beach near Sarasota

Book a private clear-kayak tour with a guide for groups up to 14

Spend 6 hours on the water with a private Siesta Key boat charter

Plan your own 4-hour charter with sandbars, snorkeling, and stops for food and drinks

Build your own full-day private boat charter from Siesta Key

Ride a Jet Ski through Phillippi Creek and toward Siesta Key

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

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.

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

Spot playful dolphins and relax at a scenic sandbar while enjoying complimentary drinks

Ride new Yamaha jet skis across Florida's largest riding area at your own pace

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

Customize your day exploring sandbars, islands, and marine life on a private catamaran.

Rent a 26-foot tritoon with seating and shade for up to 12

Rent a 26' tritoon for a full day with seating for up to 12

Cruise Sarasota Bay with a 17-foot deck boat rental

Cruise Siesta Key waters on a 25' pontoon for up to 12

Rent a 25-foot pontoon for up to 12 people for a full day on the water

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

Charter a private boat for your group from Anna Maria Island

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