things to do in Osprey, FL

Spot Gulf Coast wildlife with an experienced local captain

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

Customize your 2-hour private TriToon cruise with a captain included

Create a spa-like bathroom setting tailored to your bath or shower

Private coastal cruise with chances to spot dolphins and manatees

Electric island rides with delivery, pickup, and easy standard-outlet charging

Rent a single or tandem kayak and paddle the Lido Key mangrove tunnels

Explore Anna Maria Island waters and look for dolphins with a private captain

Private Gulf sunset charter with room for your favorite refreshments

Paddle mangrove tunnels and explore Midnight Pass Beach

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

Cruise, swim, and explore with triple-pontoon stability and Mercury 150HP power

Target bay and nearshore species on a private afternoon charter

Toast the sunset on a guided Gulf Coast kayak paddle

Customize a 4.5-hour private sandbar charter with a captain

Enjoy a styled picnic with personalized décor and sparkling water

Explore historic ruins and snorkel submerged batteries on a private Egmont Key charter

Enjoy a morning cruise with complimentary drinks while spotting dolphins in Siesta Key.

Launch from Turtle Beach and paddle to Midnight Pass

A private sunset cruise with Gulf views, wildlife searching, and a possible sandbar stop

Customize a double-decker day on the water with a slide, sound system, and captain

Paddle mangrove tunnels and visit Midnight Pass Beach with a local guide

Rent a 22' Bentley pontoon and cruise Sarasota’s Intracoastal waterways

Cruise Anna Maria Island waters on a stable 23-foot catamaran