First Friday Sip & Shop

The Sarasota Downtown Merchants First Friday event runs along the 1400, 1500, 1600 blocks of Main Street, Palm Ave., 1st & 2nd Street.  The event is open to the public. Stroll trendy fashion boutiques, art galleries, experience wine tastings, and live music throughout Main Street.  Tourists and locals, even the occasional celebrity, enjoy caricatures by as the perfect souvenir, something hand-drawn and one of a kind.



March 11, 2023 10 AM-5 PM

Join us for Downtown Sarasota’s French-style Marketplace and see the many talented artists. Enjoy a fun day with amazing creations and beautiful music by Michelet Innocent!  Admission is free and the event is open to the public.  Michelet is an International Romantic singer. He sings in French, English, Spanish and Italian in concerts, from the New York Metropolitan Opera, for the UN to a performance for French President Jacques Mitterand’s wife. His sound is a blend of Charles Aznavour, Nat King Cole and Johnny Matthis.  GPS Address: 100 Central Ave. Sarasota FL 34236


Great Eats & Beats! Free Admission.

January 27-29, 2023 in JD Hamel Park

Relax to live musical performances by some of Florida’s top musical talents in such genres as R&B, blues, jazz, rock, soul and more.  Address: 199 Bayfront Drive Sarasota Florida 34236.  Festival Hours: Friday 4-10 PM | Saturday 11-10 PM & Sunday 11-6 PM.

Learn More

Sarasota Festival of the Arts

February 25-26, 2023

Learn More

15th Annual Dog-A-Ween Costume Contest

The Annual Dog-A-Ween costume contest returns Saturday, October 28, 2023 to the Sarasota Farmers Market Halloween Festival. All proceeds benefit the Donte’s Den Foundation. Become A Sponsor!  Match funds or donate a gift basket!  Call Pro It Out Marketing at (941) 323-7754.


Join the celebration

Downtown Sarasota’s Christmas Tree is the perfect backdrop for your holiday snapshot. The annual tree lighting event will take place Thursday, December 7th from 6 – 8 PM in Selby Five Points Park, located across the street from the Selby Public Library.


Enjoy refreshments are donated by Pastry Art, holiday carols will be performed by the Sarasota Military School, and photos with Santa Claus! The Christmas Tree will be lit at 7 PM where photos can be taken. Come early and stroll downtown’s many gift stores!  Toys for Tots boxes will be available throughout the downtown district thru December 15th.

Share & Invite
In 2021, Sarasota County Toys For Tots Distributed 16,973 Toys! 🧸 As we kick off the 2022 Toys for Tots Campaign, our thoughts and hearts go out to all those affected by Hurricane Ian and are suffering at this tragic time. Please support our campaign to ensure no child goes without a present this Holiday Season.
All toy donations are greatly appreciated! If you are looking for a suggestion, here are items in high need this year: Toys for ages 0-24 months, gifts for teens, and bicycles 24″, 26″, 28″.  Sponsored by the DestinationDowntownSarasota.com, The Downtown Sarasota Enrichment Association.  Members can sign up to receive a box at the Sarasota Downtown Merchants annual fall members meeting.

Sarasota NYE Pineapple Drop Block Party

Sunday, Dec. 31, 2023 from 1PM to 1AM

Celebrate the last day of 2023 in Downtown Sarasota with thrilling midway rides and games for all ages and your favorite fair food, live music and DJs, special offers at local bars and restaurants, and the annual Pineapple Drop followed by a fireworks display over Sarasota Bay.  Event admission is free.

Unlimited ride wristbands (for riders 36 inches and taller), valid from 1 pm – 6 pm, are $30 online until 3 pm Dec. 31 or on site till 5 pm while supplies last.

Ride tickets, valid anytime, are available at the carnival or online till 3 pm for $50/50 tickets plus 1 free ride. (Rides take 2 or more tickets each.)

Carnival hours are 1 pm – 1 am. Parent/guardian supervision is required for ages 17 and younger. Please check the website for updates before attending.

The annual Pineapple Drop Block Party runs from 1 pm – 1 am. Live music starts at 8:30 pm.
The giant glowing pineapple will drop at midnight at the intersection of Lemon Avenue and Main Street. The Pineapple Drop Block Party is hosted by the Sarasota Downtown Merchants.  For more information on the carnival, call 866-666-3247 or visit DreamLandAmusements.com.
Click here to view Midway Video 

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