Top Sarasota Private and Luxury

Discover the best of Sarasota, Florida as you embark on a sightseeing tour of the city. Climb aboard your air-conditioned vehicle and see several points of interest including the Ringling Museum and College, Selby Library, and the Sarasota Opera House. While you ride, learn about the vibrant history and culture of the city from your guide.

Discover the delectable highlights of Sarasota's thriving dining scene on this small-group, dinnertime tasting tour. Meet your guide in central Sarasota, and come with an appetite: you'll visit up to five local restaurants, and will enjoy enough samples to add up to a generous meal (alcoholic drinks additional expense). As you go, soak up the convivial atmosphere, and learn more about Sarasota's unique culture and culinary offerings.

For something different than beaches, discover one of Sarasota's most unique communities on an insider’s tour of Pinecraft, an Amish vacation enclave right on the outskirts of town. Led by a guide with personal connections to the local Amish and Mennonite communities, learn about their roots in Florida, traditional customs, and beliefs. You’ll also have the chance to shop for handmade gifts and sample famous pie at an Amish cafe.

Learn about Sarasota’s history of gruesome murders, unexplained happenings, and supernatural events—and immerse yourself in the city’s spooky ambiance—on this haunted trolley tour. Grab a wine or beer, hop aboard the air-conditioned trolley, and set off as your costumed guide regales you with creepy stories. Discover the city’s most supposedly haunted landmarks as you go—and even witness reenactments of macabre past events.

Enjoy one of Florida's best beaches at sunset on an electric bike tour. With 5-level pedal assist and an on-demand throttle, the electric bike allows you to put in as much or as little effort as you want as you ride along Siesta Key. All experience levels are welcome. Booking in advance ensures you won't miss out on this small-group tour.

Immerse yourself in Sarasota's coastal mangrove forests, look out for dolphins and manatees, and practice your kayaking or stand-up paddleboarding skills on this immersive, small-group tour. After departing from Ted Sperling Nature Park, you'll paddle out on Sarasota Bay and can practice with your equipment. Then, head into the mangrove tunnels for your best chance to see local marine life.

Increase your chances of spotting manatees and dolphins during an eco-friendly kayak tour of the Lido Key in Sarasota. Ideal for lovers of nature and wildlife, this experience lets you escape the crowds on land and is suitable for both beginner and advanced paddlers. Plus, traveling in a non-motorized vessel means you’re less likely to scare away animals.

Enjoy a relaxing boat tour, complete with stops at local tiki bars—and look out for wildlife as you go—on this two-in-one charter trip. Meet your guide at the marina, hop aboard your boat, and settle in: as you head out on the water, you can look out for dolphins, manatees, and more. In between, stop at tiki bars, where you can refresh with drinks and snacks (own expense).

We offer the Ultimate Adventure with our Glass Bottom Kayak LED illuminated Night & Sunset Tours! Our LED Sunset Tours start at 8pm and our LED Night Tours start at 9:30pm every night. We'll start by paddling through mangrove canals and then explore along mangrove shorelines and shallow grass flats. We'll look for various sea-life and seabirds as we paddle through a shallow harbor. We'll explore the underwater views with our custom high powered underwater LED lights as you look for fish, stingrays, crabs, shrimp and other sea-life as we illuminate the waters around us. The views of the John Ringling Causeway Bridge and The City of Sarasota Skyline is awesome! With literally nothing to do at night in Water Sports, our Glass Bottom Kayak LED illuminated Night & Sunset Tours are perfect for families, friends, large groups, or an unforgettable date night under the stars or at Sunset! Our kayaks have no drain holes so you can wear full clothing with shoes and even stay warm in the winter!

Fun, interactive murder mystery theater on the trolley! Someone has murdered the Circus Queen...and suspects abound among the circus folk on board. Everyone seems to have a motive. Wear a circus costume if you wish, find yourself among the suspects, and help our sleuths to solve the mystery!

Sarasota has an outstanding collection of public art pieces. On this 90-minute tour aboard our enclosed, air-conditioned van or trolley, visit more than 50 of the city’s public art sculptures, monuments, and murals in charming neighborhoods and downtown Sarasota. Your guide, painter and public art expert Jerome Chesley, helps you see the city through new eyes! Tours with fewer than 10 guests will travel in our air-conditioned 9-passenger van.

See why Sarasota is often called "Sedona by the Sea," for its ley lines and unusual levels of psychic energy. Includes complimentary orange or pineapple mimosa at the Trolley Cottage Tiki Bar before the tour. Our guide, Michael Newton-Brown, offers personal Tarot readings following the tour, for an additional fee. Tours with fewer than 10 guests will travel in our air-conditioned 9-passenger van.

Combine a kayaking adventure with a food tour of Sarasota with this combo package. You'll start with a 2-hour kayaking tour through Lido Key--if you're lucky, you may even spot dolphins and manatees. You'll then continue to downtown Sarasota (transportation not included) to join a food-focused walking tour, with stops at four or five local restaurants.

Actress and tour guide Kathryn Chesley specializes in donning period costumes and portraying Sarasota's most influential women -- Mable Ringling, Rose Wilson, Marie Selby, and Bertha Palmer -- and telling the story of the Sarasota and how each of these women and their unique contributions helped to make the city what it is today.

Discover downtown Sarasota with a local guide on a comprehensive and fun walking tour! Your expert guide will walk you through the historic bayside streets of downtown Sarasota to historic landmarks while you learn of the rich history and strong art culture of the area. When the tour is over we will finish up with a delicious lunch featuring the town's favorite specialty Tacos at an upscale taco bourbon joint. Book this tour with a group or just a friend!

Hop onboard our fun-filled Sarasota trivia tour, with local performer and guide Steve McAllister. Show off your love of Sarasota trivia, win bar and restaurant gift certificates during trivia games and sing along to your favorite Florida-inspired songs during the 90-minute air-conditioned tour. Enjoy a stop at the Bahi Hut, the oldest tiki bar in Sarasota, for samples of their world-famous Polynesian cocktails that are sure to spice up your night. Includes free beer or wine at the Trolley Cottage Tiki Bar before boarding.

Discover the best that Sarasota has to offer and see the city at its most photogenic on this sunset tour. Explore historic downtown neighborhoods and see top points of interest including the Ringling Museum, Selby Library and Gardens, and the Sarasota Opera House. End your tour by watching a beautiful sunset on Sarasota Bay and a better understanding of the coastal city.