Destinations Downtown Sarasota

Sarasota New Years Eve Pineapple Drop Block Party

Saturday, Dec. 31, 2022 from 1PM to 1AM

Downtown Block Party Celebration

The BIG New Year’s Eve party in Sarasota is the annual Pineapple Drop Block Party! The dropping of the big glowing pineapple comes at midnight and takes place at the intersection of Lemon Avenue and Main Street in downtown.  There will be live music, with DJs and bands performing, carnival rides, games for the kids and of course plentiful food and drink, with special offers at local bars and restaurants. Live music begins at 9 p.m. on the corner of Main and Lemon Street with performances by 22N, Chas Collins and SRQ Beats.  Just after the Pineapple Drop there is also a big fireworks display over Sarasota Bay.  This annual event is hosted by the Sarasota Downtown Merchants.  Become A Sponsor! Call Ron Soto at (941) 321-0562.

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Sarasota Winter Fine Art Festival

January 7 & 8, 2023 in JD Hamel Park

Outdoor Fine Art Festival

The Sarasota Winter Fine Art Festival returns January 7-8, 2023 for its tenth season. Whether you are an art collector of wish to find original, creative handmade arts and fine crafts for home or office, come see the palette of art the event will lay for you. 

This fine art festival is held in downtown Sarasota in JD Hamel Park at Gulfstream and Main Street. The event is produced by Paragon Festivals and hosted by the Sarasota Downtown Merchants.

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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.  As a reference, performers in 2022 included the Kara Nally Band (blues, funk, soul), Billy Rice Band (country rock), Kettle of Fish (rock, blues, reggae), the Whole Band featuring Callie Chappell (Americana, rock, variety), Twinkle & Rock Soul Radio (rock, soul), Thunder Beach (classic dance rock), Selwyn Birchwood (electric swamp funkin’ blues), Damon Fowler (blues), Bryan Spainhower & Friends (Musica Eclectica), JP Soars & The Red Hots (Americana, rock) and Ronnie Dee & The Superstars (funk, soul).


Band Performance schedule subject to change.  Address: 199 Bayfront Drive Sarasota Florida 34236.  Festival Hours: Friday 4-10 PM | Saturday 11-10 PM & Sunday 11-6 PM.

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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.  Tourist and locals, even the occasional celebrity, enjoy caricatures by as the perfect souvenir, something hand-drawn and one of a kind.


Sarasota Festival of the Arts

February 25-26, 2023

Looking ahead for fun things to do? Please put us on your “To Do” list on February 25-26, 2023 in JD Hamel Park: the premiere of the Sarasota Festival of the Arts. The event will showcase the original works of artisans and crafters from throughout Florida and across the United States. The event is graciously hosted by the Downtown Sarasota Enrichment Association.

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Le Marché Bohémien Outdoor Market & Art Show

March & November 2023 – Dates Pending

10AM – 5PM at Five Points Park Downtown Sarasota.

Join us for Downtown Sarasota’s French style Marketplace and see the many talented artists. Enjoy a fun day with refreshments, 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


15th Annual Dog-A-Ween Event

The Annual Dog-A-Ween costume contest returns Saturday, October 28th to the Sarasota Farmers Market Halloween Festival. All proceeds benefit the Donte’s Den Foundation. Guest moderator: Tyler Butler with Out & About.  The judges for the 15th annual event will be Mayor TBD, ABC 7’s Chief Meteorologist Bob Harrigon and Marsha Panuce, founder of Donte’s Den Foundation. Become A Sponsor!  Match funds or donate a gift basket!  Call Pro It Out Marketing at (941) 323-7754.

Sarasota Christmas Tree Lighting

Thursday, December 7, 2023 in Five Points Park

Join the celebration

Downtown Sarasota’s Christmas Tree is the perfect backdrop for your holiday snapshot. The annual tree lighting event will take place the first Thursday in December 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.  Facebook live coverage sponsored by Out & About Sarasota with Tyler Butler.


Come early and stroll downtown’s many gift stores!  Toys for Tots boxes will be available throughout the downtown district thru December 15th.

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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.

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