Best 209 things to do in Siesta Key, FL

Taste your way through Downtown Sarasota with a guided history walk

Eat your way through historic downtown Sarasota with four restaurant stops

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

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

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

Cruise at sunset with a sandbar stop and a closing toast

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

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

Paddle a 100% clear kayak to mangroves and a secluded beach near Sarasota

Book a private clear-kayak tour with a guide for groups up to 14