Weekend in Sarasota, Florida Gulf Coast: October 16-18, 2026

Archived 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.

02 · Make It Yours

Save These Stops to My Plan

Every stop in this Sarasota weekend can be saved to My Plan, the site's private browser-based planner. Add the ones you like, then open My Plan to build your own Gulf Coast weekend around them.

Paddling

REI Guided Sunset Paddle at The Bay

The Bay Kayak Launch, 1055 Boulevard of the Arts, Sarasota FL

Restaurant

Duval's Fresh. Local. Seafood.

1435 Main Street, Sarasota FL

Market

Sarasota Farmers Market

Lemon Avenue & Main Street, Sarasota FL

Park

The Bay Park

1055 Boulevard of the Arts, Sarasota FL

Performing Arts

Van Wezel Performing Arts Hall

777 North Tamiami Trail, Sarasota FL

Restaurant

Station 400

400 North Lemon Avenue, Sarasota FL

Arts & Culture

Sarasota Art Museum

1001 South Tamiami Trail, Sarasota FL

03 · Go Deeper

Guides for This Weekend

Pair this Sarasota itinerary with the guides behind it: beaches, fishing, dining, events, live music, and performing arts across the Gulf Coast.

04 · Stay Inspired

Get Weekend Plans Every Week

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