Best 568 things to do in Longboat Key, FL

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

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

Fish Gulf waters with a licensed captain, mate, and fully equipped boat

Private sailing with spacious lounges, swim access, and Sarasota Bay views

Sail into golden hour with four spacious places to gather aboard

Cruise Sarasota Bay and relax at anchor aboard a crewed 112-foot Westport

Cruise, swim, and relax aboard a crewed 112-foot Westport yacht

Rent a pedal kayak and explore Sarasota Bay with all gear and safety equipment included.

Design a private day of fishing, snorkeling, and sandbar stops

Sample Sarasota bites and paired drinks on a guided culinary walk

Learn to surf in Sarasota with a coach-led lesson

Rent a kayak or paddleboard and explore Turtle Beach waterways with a provided map

Sip signature cocktails and learn the stories behind Sarasota’s spirits

Explore Sarasota's paranormal tales and historic murders after dark

Explore Sarasota's historic neighborhoods and cultural landmarks on a 90-minute air-conditioned trolley ride.

See Sarasota’s Art Deco, Mediterranean Revival, and Mid-Century Modern architecture by van

Join an interactive circus-themed whodunnit on a rolling Sarasota trolley

Tour Sarasota’s Pinecraft community to learn Amish and Mennonite culture

Ride an air-conditioned trolley at night for musical ghost stories and Sarasota history in October.

Ride a Sarasota metaphysical trolley tour with sound healing and mini tarot readings

Sing 70s & 80s hits on a trolley with a bar stop at 99 Bottles

Watch Key West's sunset from a private sport yacht

Create a spa-like bathroom setting tailored to your bath or shower

Enjoy a styled picnic with personalized décor and sparkling water