Best 203 things to do in Osprey, FL

Ride a 13-mile historic railroad excursion in open-air or air-conditioned cars.

Rent a street-legal 6-passenger golf cart with delivery included

Paddle a tandem kayak from the canals to Tampa Bay

Rent cornhole for easy, all-ages beach-day fun

Play Slammo at the beach with a 1–7 day rental

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

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

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

Choose a 3–8 hour private boat charter with a captain in Sarasota

Customize a 4–8 hour private Sarasota cruise with a captain

Rent a kayak or paddleboard and explore Turtle Beach waterways with a provided map

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

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

Tour Sarasota’s Pinecraft community to learn Amish and Mennonite culture

Ride an air-conditioned trolley at night for musical ghost stories and Sarasota history in October.

Ride a Sarasota metaphysical trolley tour with sound healing and mini tarot readings

Cruise Sarasota Bay on a 112' Westport with a private crew

Shop boutiques and enjoy bubbles and light bites in Sarasota’s historic districts

Paddle Lido Key’s mangrove tunnels with a private guide from Ted Sperling Nature Park

Cruise into the Florida sunset with a US Coast Guard licensed captain

Enjoy a self-guided paddle adventure with a versatile inflatable board.

Ride the latest 3-seater jet skis and enjoy hassle-free fun on the water.

Cruise with up to 13 friends on a spacious pontoon equipped for sandbar hopping

Cruise Anna Maria Island by captained tritoon with room for up to 6