Things to Do

Siesta Key’s natural boardwalk – the firm wet sand next to the Gulf of Mexico – is the perfect place for a great conversation and a long walk. Roslyn and Callum have hatched many plans, including naming this very weekend, on walks down to Crescent Beach and back. It’s one of the simplest, most delightful things you can do on Siesta Key.

Beach WALK

Every day, about half an hour to sunset, a familiar scene materializes on Siesta Key. Young families in their best linen outfits, gaggles of college friends, or smiling locals; all head across the sand for the most unifying and peaceful experience on the Key; sunset.

Sunset at this time of year is ~6:30 PM so go down before 6 PM and enjoy the most beautiful sunset over the Gulf.

SunsetS

Tennis: There are two public courts at the Siesta Key public beach. They are really nice and usually not terribly busy. There is plenty of parking or you can take a shuttle.

Pickleball: There are multiple pickleball courts alongside the tennis courts at the Siesta Key public beach. There’s usually a longer wait. Beware of intense pickleballers, they’re no joke.

Activities

restaurants

We love food, it’s basically the reason we moved to New York. Siesta Key and Sarasota’s food scene is centered around fresh air, fish, and live music.  

Walt’s Fish Market Restaurant - Casual fish market joint with same-day catches and fun atmosphere. There’s usually a wait, but you can have a drink at the outdoor bar.
Callum’s fav: Hush Puppies, Stone Crab, and Red Snapper!
Roslyn’s fav: Grouper Bites, Tripletail and garlic sautéed green beans

Owen’s Fish Camp - A downtown fish house with Southern cooking. Get there early or be prepared to wait. More boozy and vibey than Walt’s. 
Callum’s fav: Crab Cake, Shrimp and Grits 
Roslyn’s fav: Naked Fish with Lemon Caper Butter

Perq Coffee Bar - A legit third-wave shop for coffee nerds with ample indoor and outdoor seating. Be prepared for a line. Pick up a bag of Three Ships (Virginia Beach, VA) to take home.
Callum’s fav: Flat White
Roslyn’s fav: Piccolo

Sarasota

Siesta Key Village

Siesta Key Oyster Bar (SKOB) - The OG of the Village, there’s always a band and a lively scene. Get there early or expect a wait if you go at dinner time. 
Callum’s fav: Blackened Grouper Reuben
Roslyn’s fav: Seafood Tacos

Gilligan’s Island Bar & Grill - A large outdoor / indoor venue with live music. Try the Piña colada. It’s what Callum was drinking when he let it slip that he was researching rings before proposing to Roslyn. 

Sun Garden Cafe - A relaxed brunch spot with lots of indoor and outdoor seating. It’s usually busy but worth the wait. 
Callum’s fav: Cajun seafood benedict (the only place I’ll go against Anthony Bourdain’s warning and order hollandaise)
Roslyn’s fav: Baba O’Riley Omelette