Best 133 things to do in Osprey, FL

Book a 3- or 4-hour private sunset cruise on a 38-foot Sea Ray

Private sunset cruise on Kai Fin with premium seating and water toys

Fish offshore with a USCG-licensed captain, mate, bait, and standard fuel included

Charter the 50' Memory Maker for 3 hours with four lounge areas

A custom chef‑curated feast celebrating bold local flavors and dietary wellness—served right in your home or rental

Rent a kayak or paddleboard for 4 hours with gear, route map, and lesson

Paddle between Anna Maria Island and Longboat Key with a guided wildlife-focused route

Paddle Longboat Pass for 4 hours with a map and basic lesson

Paddle Lido Key’s mangrove tunnels with a local naturalist guide

Explore Lido Key’s mangrove tunnels with included gear, map, and a brief lesson

Paddle the waters between Anna Maria Island and Longboat Key with your own private guide

Paddle into a Florida Gulf Coast sunset with a guided kayak tour

Paddle a private sunset route with a dedicated guide in Sarasota Bay

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

Private 2-hour sunset cruise to spot dolphins in Sarasota Bay

Rent a tritoon for up to 12 and cruise Sarasota Bay for 4 or 8 hours

Private sandbar cruise to Jewfish Key for swimming, snorkeling, and shelling

Experience dolphins, sandbars, and a relaxing sunset cruise in the bays of Anna Maria Island.

See non-migratory dolphins and unique wildlife while exploring the bays of Manatee and Sarasota.

Cruise to Egmont Key for shelling, snorkeling, and a Florida state park stop

Cruise local sandbars and look for dolphins from Bradenton Beach Marina

Cruise to Egmont Key for shelling, snorkeling, and beach time on a private boat

Cruise Sarasota Bay on a private dolphin eco tour aboard the Anna Maria Explorer