things to do in Osprey, FL

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

Paddle Midnight Pass on your own schedule

Cruise Siesta Key’s western coast on a private 2-hour daytime or sunset boat ride

Charter a 38-foot Sea Ray for 6 hours of Sarasota Bay cruising

Explore Midnight Pass at Your Own Pace

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

Plan a private coastal cruise with your own food and drinks

Bring music and evening lighting to your group ride

Paddle Anna Maria canals or venture into Tampa Bay

Cruise Florida's Gulf Coast on a private outing with flexible routes and onboard coolers

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

Cruise Sarasota Bay with space to swim, socialize and relax

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

Roll across sandy beaches with balloon tires

Customize a Gulf Coast cruise with sandbar swims and waterfront stops

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

Customize a private cruise along Florida's western coast

Charter the 54’ Pardo Exit Strategy for 4 hours on Sarasota Bay

Private coastal cruising with flexible routes and sunset options

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

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

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

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

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