things to do in Longboat Key, FL

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

Take the wheel—no motorcycle endorsement needed

Pair coastal sightseeing with a slide-equipped private boat

Choose your own mix of fishing and island relaxation

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

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

Create your own Tampa Bay day with cruising, sandbars, and your favorite drinks

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

Paddle Lido Key’s mangrove tunnels with a private guide from Ted Sperling Nature Park

Cast a line with fishing gear and licensing included

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

Evening boat cruise with island routes and bridge views

Learn wing foiling basics in a small group over 2 hours

Take the wheel without a motorcycle endorsement

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

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

Discover island history and coastal nature on a private sunset cruise

Paddle Gulf Coast waters at your own pace and explore nearby islands

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

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

Walk Jungle Prada with a historian and explore 1,000 years of St. Petersburg history

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

Customize a captain-led day on Tampa Bay waters

Private coastal cruise with chances to spot dolphins and manatees