Water Activities in Longboat Key, FL

Pair coastal sightseeing with a slide-equipped private boat

Follow the seasonal bite with fishing gear and licenses included

Trade the shoreline for shallow-water exploring on Anna Maria Island’s shifting sandbars

Sip happy hour drinks on a 1.5-hour cruise from Gulfport Marina

Toast the sunset on a guided Gulf Coast kayak paddle

Cruise Madeira Beach waters near John's Pass on a spacious pontoon

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

Set your own bay itinerary with drinks, music, and sandbar time

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

Paddle mangrove tunnels and explore Midnight Pass Beach

Choose your own mix of fishing and island relaxation

Cast a line with fishing gear and licensing included

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

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

Discover island history and coastal nature on a private sunset cruise

Enjoy an island party with a lively crew and room to unwind

Paddle with a dedicated guide as the Florida Gulf Coast sun sets

Captain-led pontoon time for your own day on the water

Learn wing foiling basics in a small group over 2 hours

Cruise Tampa Bay on a tiki boat as sunset gives way to city lights

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

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

Cast your line at multiple fishing spots along St. Petersburg's coast

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