Best 281 things to do in Longboat Key, FL

Rent a 23.5 ft Mako center console for cruising or fishing in Sarasota

Relax on a 2-hour private cruise through Sarasota and Roberts Bays

Private 6–8 hour Bali 4.2 catamaran charter on Sarasota Bay

Enjoy a customizable luxury sail with captain and mate aboard a spacious 42-ft catamaran.

Charter a 38-foot Sea Ray for 6 hours of Sarasota Bay cruising

Charter a 38-foot Sea Ray for a 4-hour Sarasota Bay cruise

Book a 3- or 4-hour private sunset cruise on a 38-foot Sea Ray

Private sunset cruise on Kai Fin with premium seating and water toys

Fish offshore with a USCG-licensed captain, mate, bait, and standard fuel included

Charter the 50' Memory Maker for 3 hours with four lounge areas

Charter the 54’ Pardo Exit Strategy for 4 hours on Sarasota Bay

Cruise Sarasota Bay on a 112' Westport with a private crew

Private 46' power catamaran charter in Tampa Bay (6–8 hours)

Charter the 63' Prestige Peace for 4 hours with captain, mate, and fuel included

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

Pedal kayak Sarasota Bay to seagrass beds and mangrove tunnels

Pedal kayak 2 miles through mangrove tunnels at Emerson Point

Pedal through seagrass beds and mangrove tunnels on a 2-mile Neal Preserve tour

Private inshore fishing charter with short runs and all gear included

Cruise at sunset with a sandbar stop and a closing toast

Reserve a private 4-hour boat party for your bachelor or bachelorette group

Drive a Corvette-inspired Jetcar on Palma Sola Bay with safety briefing included

Paddle Lido Key, then taste your way through downtown Sarasota

Shop boutiques and enjoy bubbles and light bites in Sarasota’s historic districts