Water Activities in Siesta Key, FL

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

Cruise, swim, and beach-hop around Anna Maria Island aboard a spacious deck boat

Paddle mangrove tunnels and explore Midnight Pass Beach

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

Choose your own way to get on the water with a clean rental fleet

Unwind on the Gulf Coast with your own group and an onboard slide

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

Fish Tampa Bay and Sarasota Bay grass flats with light tackle, live bait, and lures

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

Target bay and nearshore species on a private afternoon charter

Discover island history and coastal nature on a private sunset cruise

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

Explore local waters on a 2026 jet ski with onboard audio

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

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

Cruise Anna Maria Island waterways as the sun sets

Explore more of the waterways with foot-powered kayaking and a tour tailored to you

Look for dolphins and manatees as you paddle Florida's mangrove waterways

Customize a 4.5-hour private sandbar charter with a captain

Customize a Sarasota cruise with an experienced captain

Customize a private cruise with snorkeling and wildlife searching

Cast along grass flats and mangrove shorelines for inshore species

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

Toast the sunset on a guided Gulf Coast kayak paddle