Things to do in Osprey

Ride top-quality road bikes and explore Siesta Key at your own pace for three days.

Cruise Siesta Key effortlessly with a high-range e-bike and included gear

Discover Siesta Key at your own pace with a three-day bike rental and included gear.

Enjoy flexible bike rentals for a full week and explore Siesta Key at your own pace.

Ride the 31-mile paved Legacy Trail from Sarasota to Venice with a ready-to-go bike or e-bike rental.

Explore Siesta Key at your own pace with a full-day bike rental including helmets and locks.

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.

Explore Siesta Key at your own pace with a street-legal golf cart rental.

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

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

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

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

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

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

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

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

Customize a 4-hour private cruise with snorkeling, paddleboarding, dolphin watching, and more.

Search for prehistoric shark teeth at Venice’s famed Boneyard while snorkeling, Huka diving, or scuba diving

Refresh your scuba skills with expert instructors and all gear included in a focused four-hour session.

Discover Megalodon fossils on a 3-hour guided shore dive with provided gear

Enjoy a private tiki boat cruise to witness Florida's vibrant sunset and local wildlife.

Ride along Siesta Key at sunset and enjoy a scenic, traffic-free bike adventure.

Soar up to 1,200 feet and enjoy panoramic views on an exhilarating parasail ride.

Paddle through Jim Neville mangroves to a secluded beach accessible only by boat

Explore calm Turtle Beach waterways at your own pace with quality kayaks or paddleboards

Rent a pedal kayak and explore Sarasota Bay with all gear and safety equipment included.

Pedal effortlessly through Sarasota Bay and encounter vibrant marine life on a small-group guided adventure

Enjoy a fun-filled fishing trip with all gear included and expert crew guidance.

Experience custom deep sea fishing with comfort and flexibility on a private charter.

Explore Sarasota's historic neighborhoods and cultural landmarks on a 90-minute air-conditioned trolley ride.

Discover Sarasota’s unique architectural styles on a guided 90-minute air-conditioned tour.

Solve a circus-themed murder mystery on a rolling trolley with interactive fun and complimentary drinks.

Savor Sarasota’s flavors and history in one unforgettable afternoon!

Experience marine life up close on a comfortable pontoon cruise for all ages.

Enjoy a customizable 6–8 hour luxury sail on Sarasota Bay with captain and mate included

Enjoy a customizable luxury sail with captain and mate aboard a spacious 42-ft catamaran.

Explore Lido Key’s mangrove tunnels with included gear and a map for a self-guided adventure.

Explore scenic waters with included gear, map, and lesson for a fun half-day adventure