Weekend Itinerary
Weekend in Sarasota
Your curated weekend plan for October 16-18.
01 — The Plan
October 16-18, 2026
Day 1
Friday Night
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.
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.
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
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.
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.
Grab lunch from the festival vendors or a downtown cafe, then head toward the bayfront for the afternoon.
Day 3
Saturday Afternoon
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.
Early dinner or happy hour on the bayfront before the show.
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 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.
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.
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.
02 — Keep Exploring
More Weekly Features
The itinerary is one part of the picture. Pair it with this week's events, the What's Hot list, and the Beach of the Week to round out your weekend on the Gulf Coast.
Past Itineraries: Browse the ArchiveThis Week's Events
Festivals, shows, farmers markets and concerts happening on the Gulf Coast this weekend.
ExploreWhat’s Hot
The buzziest openings, listings and local news across Sarasota, Venice and Bradenton this week.
ExploreBeach of the Week
This week’s featured beach with parking, amenities and the honest scoop before you go.
Explore03 — Stay Inspired
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