Paddle a glass-bottom LED kayak and feed fish at night
A custom chef‑curated feast celebrating bold local flavors and dietary wellness—served right in your home or rental
Learn wing foiling basics in a small group over 2 hours
Learn windsurfing basics in a 3-hour small-group lesson
Cruise into the Florida sunset with a US Coast Guard licensed captain
Customize your route with snorkeling, sightseeing, and island stops on a private boat
Customize a private Anna Maria & Long Boat Key boat tour for up to 6 people
Cruise to a local sandbar and swim or snorkel
Cruise the Gulf and back bay to look for dolphins and seasonal manatees
Cruise into the evening and watch the sunset from the water
Customize a 3-hour beach picnic with setup and cleanup included
Reserve a beach suite setup for six, ready from 10am–4pm
Cruise Anna Maria Island by captained tritoon with room for up to 6
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
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
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