Our most popular tour and it often sells out! Guided by a local expert, you will walk and learn fascinating facts, folklore, culture, famous founders and current residents, the food scene and current events. Sarasota is a unique city, with a vibrant downtown comprised of small, locally-owned restaurants, boutiques and art galleries. Our restaurants are very busy during "season" so are so fortunate that a handful choose to partner with us! This tour includes food but should not be considered a "foodie" tour-it's quick bites of favorite places, among the locals. The emphasis of this tour is on the unique history, culture and lifestyle of Sarasota! Light bites are experienced along the route for quick introductions to some of the popular spots. This is a group activity that requires a minimum of 4 guests to operate! For personal tour groups 10+ and all corporate tours, please inquire-those require advanced planning and more detailed information.

Hop aboard Discover Sarasota Tours’ air-conditioned Dolly the Trolley for our Sunset Cabaret music and craft beer tour with local tour guide, actor, songwriter and raconteur Steve McAllister. This engaging tour kicks off with free wine/beer in the Trolley Cottage Tiki Bar, and then heads on a two-hour adventure. The tour includes stops at Lido Beach timed for the amazing view of the setting sun over the gulf and at Sun King Brewery in the Limelight District for craft beer samples and a mini-tour. Enjoy entertaining tales about Sarasota’s colorful history, seasoned with cabaret-style songs, jokes, city history and trivia along the way. This tour is fun for visitors or locals alike! You’re sure to learn something about Sarasota, even if you’ve lived here all your life. Complimentary beer or wine for guests 21+ at the Trolley Cottage Tiki Bar before boarding! Tour ticket includes FREE Parking!

Guided walking tour of Sarasota's downtown food scene. Learn about the history of downtown Sarasota from a local guide. Sample enough local delights that you won't need that dinner reservation! See a different side of Sarasota as you traverse the streets and make new friends along the way.

This is a dual tour experience. 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. You will meet at 11:30am for check-in for your kayak tour. Kayaking is noon-2pm. You will make your own arrangements for transportation and change clothes prior to the food tour in downtown Sarasota. Check in is 3:20pm for the food tour. You will be contacted by a representative of Sunset Food Tours upon confirmation of booking. **Guests must provide their own transportation from the Kayak Tour to The Food Tour. There are also plenty of public restrooms (parks, grocery stores, etc) between the two locations, if you wish to change into dry & warmer clothes (recommended).

This high energy, highly entertaining tour is the perfect way to celebrate date night, girls night out, birthdays, date night anniversaries or group events. Each tour offers guests the chance to sing their hearts out as a group led by talented singers as we drive by points of interest that relate to the songs' themes. A bar stop mid-way through offers the chance to meet other guests and have fun together. Come in 70'sor 80's costumes for even more of a themed fun tour.

Discover the city in the most exciting way possible with an Escape Crawl—a one‑of‑a‑kind adventure that blends puzzle‑solving, clue hunting, and exploration into an interactive game with a prize waiting at the finish line! This is not your typical scavenger hunt. Expect clever challenges, immersive storytelling, and plenty of surprises as you make your way through town.

Explore Sarasota’s vibrant shopping scene on this unique boutique tour. Enjoy browsing through four locally-owned boutiques, where you can sip on complimentary bubbles while uncovering the rich history of Burns Court and other landmarks. This engaging 3.5-hour experience includes light bites and insights into the local art and culture, making it a delightful outing for shopping enthusiasts and those seeking a taste of Sarasota’s charm. This journey offers a blend of retail therapy and educational exploration without the pressure to make purchases. This is SO fun with friends-get your woman's club, book club or any social group together and enjoy an afternoon downtown!

Discover the charming allure of St. Armands Circle, once owned by circus magnate John Ringling, on this engaging afternoon tour. Delight in a unique blend of shopping and tasting experiences as you browse stylish boutiques while sampling gourmet tea and olive oil. Enjoy a Mediterranean-inspired sampler plate paired with a glass of bubbles, and explore a luxury art and gift boutique with another glass in hand. Conclude your day with a personal shopping experience or visit the enchanting St. Armands Magical Garden, topped off with a sweet treat to savor the day. - Explore locally-owned shops and boutiques on historic St. Armands Circle - Enjoy a Mediterranean-inspired tasting platter and bubbly - Participate in tea and olive oil sampling for a culinary experience - End with a visit to the St. Armands Magical Garden or personal shopping time