things to do in Longboat Key, FL

Cruise Madeira Beach waterways with a captain as the sun sets

Cast for inshore fish with a private captain and fishing gear provided

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

Electric island transport with delivery and pickup on Siesta Key

Look for bottlenose dolphins at play in their natural habitat

Paddle Lido Key’s mangrove tunnels with a guide in 2 hours

Shape a private tiki cruise around sandbars, music, and your own drinks

Explore Shell Key’s mangrove preserve by kayak

Toast the sunset on a guided Gulf Coast kayak paddle

Cruise, swim, and island hop on a fully loaded pontoon

Private island boating with swim, snorkel, and paddleboard time

Target sharks on an evening catch-and-release charter under the stars

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

Follow the seasonal bite with fishing gear and licenses included

Cruise Anna Maria Island waterways as the sun sets

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

Discover island history and white-sand shores at the mouth of Tampa Bay

Paddle mangrove tunnels and explore Midnight Pass Beach

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

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

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

Guided island cruising with photo stops and group-paced riding

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

Cruise Gulf waters and explore barrier islands on a private boat tour