Top Sarasota Private and Luxury

Sarasota's BEST City Sightseeing Tour, a wonderful way to learn where to eat, shop and visit, and about Sarasota's interesting past, whether you are a longtime resident, a newcomer, or a visitor. Tours with fewer than 10 guests will travel in our air-conditioned 9-passenger van.

This tour is for you if you are looking for a unique food experience, a romantic night out, or to just have fun socializing with friends and family. This 3 hour walking tour of downtown Sarasota will immerse you an exciting and educational culinary experience.

The Greatest Show on Wheels! Our tour guide, circus historian Bob Collins, has loads of great stories about how the Big Top helped to shape Sarasota's quirky arts and culture scene. Tours with fewer than 10 guests will travel in our air-conditioned 9-passenger van.

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.

Hop on board our enclosed, air-conditioned haunted trolley tour for a spellbinding, interactive, narrated adventure! Hear stories about famous murders, visit spirited buildings, and explore unsolved crimes during this 90-minute air-conditioned nighttime tour. Sit back and listen as your Ghost Hostess brings the rich history of Sarasota to life on this spooky and fun tour—keep an eye out for surprise guests along the way! Tour includes complimentary beer or wine at the Trolley Cottage Tiki Bar before boarding. Ages 12+; young people ages 12-20 may attend if accompanied by a parent or legal guardian.

The tour is for up to 6 passengers onboard max, not per adult. Sightseeing, searching for dolphins and manatees along the way, describing the area we pass by and music that you choose will be played if you want. BYOB, I provide a cooler with ice. I also have a bathroom onboard. ABSOLUTELY NO SMOKING OF ANY KIND ALLOWED ONBOARD.

Sunset food tours will cover the hidden gems of Sarasota. Offering food, drink, culture, history, and of course, memories, while savoring every bite.

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.

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.

Come enjoy a culinary experience like you have never done before! On this 3-4 hour walking tour we will enjoy history, architecture and our local beach while stopping at 7 culinary locations on St. Armands Circle. We will learn how to cook with spices, sample fresh juice from an organic juice shop, try local tea's, taste specialty popcorns, and enjoy delicious local seafoods and authentic Italian foods along the way! We will end the tour with a French dessert favorite! We cannot do a tour of St. Armands Circle without a stop at Lido beach! As we stroll along the white sand we will learn about the local habitat and history of the area. In between stops we will be focus on local hot spots and important land marks, showing you the very best of St. Armands Circle!

Join us for a fun filled day that begins with a magical kayak tour through the majestic mangrove tunnels of our beautiful Lido Key and ends with an exciting and educational culinary experience in downtown Sarasota. We will start our day as one of our expert guides takes you on a two-hour kayak adventure in search of dolphins and manatees and through Sarasota’s exotic Mangroves. Once you have finished kayaking you will make your way to downtown Sarasota where we will begin the walking food tour. You will have about an hour and a half to stroll around downtown Sarasota or enjoy Lido Beach before we start the food tour. During the food tour we will be walking to 4 or 5 different family-owned restaurants where we will be enjoying unique foods, stopping at local historical landmarks, and immersing ourselves in the local culture of our beautiful city. Get ready for a full day of food, fun, and adventure! **Guests must provide their own transportation from the Kayak Tour to The Food Tour.

Step onboard our enclosed, air-conditioned Holly Jolly Trolley with guide Jenny Jingle for our special daytime holiday tour with cocoa, carols & Christmas stories of Sarasota. Visit city spots with Christmas story connections, hear about our Sarasota traditions during the holidays & sing along to your favorite Christmas songs. Includes FREE cocoa at the Trolley Cottage before the tour! Tours with fewer than 10 guests will travel in our air-conditioned 9-passenger van.

See the BEST places to visit, shop, and dine through Sarasota’s historic downtown neighborhoods of Gillespie Park, Burns Court, Laurel Park, St. Armands Circle, and the Rosemary Design District as you watch the sun set on beautiful Sarasota Bay! You’ll also see our world-class artistic and cultural organizations: The Ringling Museum, Ringling College, Asolo Theater, Selby Library, Van Wezel Performing Arts Center, Selby Gardens, Sarasota Opera House, Art Center Sarasota, and Sarasota Symphony Orchestra. Learn more about the architects and developers who designed some of our most unique homes and buildings, like the Blue Pagoda, Crocker Memorial Church, and Splendida. Circus history, Amish culture, real estate development booms and busts, and colorful stories about Sarasota’s founders give you a true overview of Sarasota’s rich and amazing cultural history.

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 Mai Tai that are sure to spice up your night. Includes free beer or wine at the Trolley Cottage Tiki Bar before boarding.