Best 550 things to do in Siesta Key, FL

Browse local boutiques, enjoy light bites, and uncover Sarasota stories

Sample local flavors while uncovering Sarasota's art, history and circus lore

Taste Sarasota’s food scene with chef-selected pairings and local stories

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

Cruise, swim, and unwind aboard a private Yellowfin charter

Plan a private coastal day with a flybridge, swim platform, and indoor-outdoor space

Design a private Gulf Coast cruise aboard a spacious Prestige 630

Design your own Gulf Coast evening aboard a 63-foot Prestige yacht

Cross Sarasota Bay and paddle secluded mangrove tunnels in a clear-bottom kayak

Taste your way through Venice’s architecture and history on foot

Cruise, swim, and unwind on a private Yellowfin center console

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

Understand Sarasota’s Amish and Mennonite traditions in Pinecraft

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

Sing along, sip cocoa, and see Sarasota's holiday lights from Dolly the Trolley

Ride a singing trolley to Fiorelli Vineyards for six wines, music and garden time

Relax on a Sarasota Bay happy hour cruise and watch for dolphins

Rent a Sea Ray SDX 250 for 6 hours with seating for up to 12

Cruise Sarasota’s intracoastal waterways on a 21' Bennington tritoon for up to 10

Take in Sarasota’s seasonal light displays from the comfort of a festive trolley