Weekend in Sarasota, Florida Gulf Coast

Weekend Itinerary

Weekend in Sarasota

Your curated weekend plan for October 16-18.

01 — The Plan

October 16-18, 2026

Day 1

Friday Night

Bayfront Sunset Paddle + Downtown Dinner
5:30 PM

Join the REI Guided Sunset Paddle at The Bay (The Bay Kayak Launch, 1055 Boulevard of the Arts): a guided sunset paddle along the Mangrove Preserve, gear provided, registration through REI. Friday, October 16.

7:30 PM

Dinner at Duval's Fresh. Local. Seafood. (1435 Main Street), downtown Sarasota’s 4.6-star seafood favorite with a happy-hour and late-night menu. Order the local catch and watch Main Street come alive.

9:30 PM

A late stroll down Main Street, where the downtown lights and the Gulf breeze make the short walk home feel like part of the night out.

Day 2

Saturday Morning

Sarasota Farmers Market + Craft Festival
7:00 AM

The Sarasota Farmers Market runs every Saturday, 7 AM-1 PM at Lemon Avenue and Main Street: 70-plus vendors, local produce, prepared foods, and live music, rain or shine.

10:00 AM

Walk over to Five Points Park for the 30th anniversary Downtown Sarasota Craft Festival: juried artists and craftspeople from across the country, live music, and the best people-watching of the fall. Free to wander.

12:30 PM

Grab lunch from the festival vendors or a downtown cafe, then head toward the bayfront for the afternoon.

Day 3

Saturday Afternoon

The Bay + Fleetwood Mac at the Van Wezel
2:00 PM

Afternoon at The Bay Park (1055 Boulevard of the Arts): the waterfront park’s 4th anniversary celebration (One Park FOUR All) runs through November 1 with 70-plus free events, lawns, and bay views.

5:30 PM

Early dinner or happy hour on the bayfront before the show.

7:00 PM

Rumours of Fleetwood Mac at the Van Wezel Performing Arts Hall (777 North Tamiami Trail): the international tribute act plays the band’s greatest hits, Saturday, October 17.

Day 4

Sunday

Brunch + Art Museum Opening
10:00 AM

Brunch at Station 400 (400 North Lemon Avenue): the downtown staple inside a restored 1800s railroad depot, known for lemon-ricotta French toast and hearty breakfast plates.

12:00 PM

The Sarasota Art Museum (1001 South Tamiami Trail) opens its new season with Presence: The Photography Collection of Judy Glickman Lauder, a major survey of modern photography through the collector’s eye.

2:30 PM

A slow walk along the bayfront promenade to close out the weekend, with the Gulf breeze and the skyline as the last stop before heading home.

03 — Stay Inspired

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