Water Activities in Osprey, FL

Cruise by boat to Rumbay Restaurant on Private Palm Island

Search nearby beaches for shark teeth and seashells from a shaded tritoon boat

Spot dolphins and explore a sandbar on an educational North Sarasota Bay eco-tour

Cruise North Sarasota Bay at sunset with narrated island and wildlife views

Build your ideal day on the water

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

Explore Midnight Pass at Your Own Pace

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

Private coastal cruising with flexible routes and sunset options

Target snapper, grouper and more on an offshore fishing trip

Explore Midnight Pass on a self-guided, all-ages paddle

Cruise Venice’s coast with time for dolphin searching, swimming, and waterfront stops

Charter the 63' Prestige Peace for 4 hours with captain, mate, and fuel included

Cruise to a sandbar with a jet ski, paddleboard, and snorkel gear

Cruise coastal waters with time for a sandbar swim, waterfront stops, or an eco-focused outing

Design a private Gulf Coast day with open-air lounging, swimming, and sandbar stops

Design your own Sarasota Bay day aboard a 50-foot power catamaran

Fish Gulf waters with a licensed captain, mate, and fully equipped boat

Shape a private coastal cruise, sandbar stop, or harbor outing aboard a 42-foot yacht

Shape your own coastal cruise, sandbar stop, or waterfront outing aboard a private yacht

Private sunset cruising with a water-level lounge on Sarasota Bay

Shape your own coastal cruise, sandbar stop, or harbor outing aboard Giddy Up

Cruise Sarasota Bay aboard a private 38-foot Sea Ray with room to relax and swim

Private sailing with spacious lounges, swim access, and Sarasota Bay views