Siesta Key Drum Circle

Enjoying Bayfront Park during downtime

Itinerary: Make the Most of Your Sarasota Meeting

It’s late afternoon, and you’ve had a day full of work meetings in Sarasota. You want to explore the area during your free time, but you’re not sure where to start. 

Don’t worry—we’ve got you covered! Here are some ways to discover Sarasota after hours.

Day 1

Hop Aboard The Bay Runner, Providing a Free Ride Around Sarasota

Get to know the beauty of Sarasota without worrying about parking when you use the Bay Runner, an open-air trolley that operates daily. The Bay Runner runs from 8 a.m. to midnight and goes through downtown Sarasota, St. Armands Circle and Lido Beach. And it’s free! Use the Bay Runner to take you to and from your after-hours choices and to check out the area. Find the Bay Runner trolley route stops on their handy map

Enjoy a Happy Hour 

Kick back with a drink of choice and some eats at one of Sarasota’s many great happy-hour destinations. Cask & Ale in downtown Sarasota offers happy-hour specials on Monday to Friday from 4 p.m. to 7 p.m. Come by for cocktail concoctions like Spring Fling and The Bay Runner. Flavio’s on Main offers hand-crafted cocktails as well as food specials from 4 p.m. to 6 p.m. at its bar. In its lounge, Michael’s on East, famous for memorable meals, also has impressive happy hours all evening on Tuesdays and Wednesday to Saturdays from 5 p.m. to 7 p.m.

McCurdy’s Comedy Theatre and Humor Institute

Let go of stress by having a good laugh at McCurdy’s Comedy Theatre and Humor Institute. McCurdy’s welcomes nationally known comedians like Pauly Shore, Patrick Gerrity, Andrew Dice Clay and Lynne Koplitz but also has Open Mic Nights. Check out its schedule for current performances. 

Day 2
Mall at UTC-summer-2020_rgb_hd.jpg

Mall at UTC

The Mall at UTC has more than 100 stores and dozens of restaurants both in and near the mall, so you have plenty of choices to grab a bite to eat or do some shopping. Plus, there are many other stores and dining destinations right across the street from the mall and in the surrounding area. Whether you want to shop till you drop at stores like Dillard's, enjoy an upscale meal at The Capital Grille or stop by for one of the mall’s special events, you’ll find something fun for all of your traveling partners.

Enjoy Local Live Music

You’ve got your choice of local live music during your visit to Sarasota, ranging from rock to blues to Latin and more. Consider The Beach Club Siesta Key, which has a festive feel to it and features a dance floor if you want to keep the party going. Bahi Hut Tiki Bar, a Sarasota legend that’s been around since 1954, is famous for its Mai Tais (limit two per person!) and live music on Fridays and Saturdays. If you’re in Sarasota on a Sunday, enjoy some live music off the beaten path at the Siesta Key Drum Circle, which brings together free-spirited drummers an hour before sunset every Sunday, right on Siesta Beach. 

Smugglers Cove Adventure Golf

A pirate ship! Waterfalls! Alligators! Are you trapped on a deserted island? No, you’re just playing mini golf at Smugglers Cove Adventure Golf. Smugglers Cove features an 18-hole course with a cool layout and an educational American Alligator exhibit that is home to 20 to 30 alligators you can feed. Smugglers has several locations throughout Southwest Florida, including in Sarasota.

Day 3

LeBarge Tropical Cruises

O’Leary’s Tiki Bar and Bayfront Park

Have a refreshing drink while taking in local nature views when you visit O’Leary’s Tiki Bar and Bayfront Park. Bayfront Park is a popular park for both tourists and locals to see what’s new on the water and watch the goings-on at scenic Bayfront Marina. O’Leary’s Tiki Bar is located right inside the park. Plus, O’Leary’s and Bayfront are great places to visit right before your sunset cruise (keep reading...).

Check Out a Stunning Sunset on the Water

If you’re in Sarasota, you must take in at least one sunset on the Gulf of Mexico. LeBarge Tropical Cruises has its Tropical Sunset Cruise where you can enjoy a tropical cocktail (maybe a Siesta Key Sunset or a Captain’s Rum Runner) and a light snack while watching the sky change colors. You’ll hear the sounds of Jimmy Buffett-style entertainers, and you may even see dolphins frolicking in the water. You’ll board the Tropical Sunset Cruise right at Bayfront Park and Marina.