How to Experience Siesta Key Like a Local

Last Updated On: February 8, 2025 by: Sheila Berrios 4327 0 0

It doesn’t matter if you’re planning a winter or a summer getaway to Siesta Key in Florida of the US of A. The best way to enjoy one of the top beaches in the United States is experiencing Siesta Key like a local. On this post, we’ll tell you where to stay, what to eat, and what to do to vacation in Siesta like Garrett and Kelsey (a reference we’re hoping you don’t catch).

UPDATED ON AUGUST 2019.

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Where to stay?

Sunset at Crescent Beach

To avoid spending your vacations trying to find parking, and to get the chance of living the dream of having a private beach, check out Tropical Beach Resorts and The Capri at Siesta. Tropical Beach Resorts has a direct footpath to the Public Beach and a Volleyball playing area. It also has amenities such as grills, beach towels, and beach chairs.

The Capri at Siesta is more private and preferred by couples. This ten-room-only boutique hotel also has a private pathway to Crescent Beach and a courtyard where it would be a shame not to share a bottle of wine.

If you’re on a tighter budget or looking for more space, look at the Airbnbs and VRBOs in the area.

You can stay a little further from the beach, but keep in mind that traffic and parking can be a problem during weekends and holidays. You will need to use a rideshare service or drive to get to Siesta.

Bedroom & Living Room of the Dolphin Cottage at Siesta Key

For an example of an excellent rental property, I recently stayed at a Cottage just steps (2 mins.) from the beach and about 8 minutes from Siesta Key Village. It was perfect for my husband, my dog, and me. Not having to look for parking in Siesta Key was a game-changer!

But if a bigger group is going, there’s also a property in the same building that has three rooms instead of one. Cottages like this one sometimes include beach chairs, towels, a full kitchen, and other amenities that’ll prevent you from having to overpack. Book the Dolphin Cottage at Siesta Key Here!

What to eat & drink?

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A post shared by Clayton’s Siesta Grille 🍷🍸 (@claytons_siesta_grille_) on Aug 14, 2018 at 10:03am PDT

Clayton’s Siesta Grille should be your first choice if you want to stay close to the beach. Its Goat Cheese and Tomato Jam Jar have built such an excellent reputation that locals are known to order it not only when they go to the restaurant but also for private parties. Order the Pan Roasted Diver Scallops with Bacon braised chard or the Mahi Mahi Fish Tacos for something more filling. Also, don’t forget to ask what’s on draft.

Fresh Strawberry Mojito from Baker and Wife

Fresh Strawberry Mojito from Baker & Wife

However, if you’re willing to move ten to fifteen minutes away from the beach, you’ll encounter Baker & Wife. It’s described as globally-inspired cuisine, but I can describe it with only one word, delicious. Food from here is consistently good, and if you see short ribs, mac & cheese, a burger, or Korean BBQ ribs on the menu, you can’t go wrong.

As the name suggests, the dessert course should not be skipped. The crème brûlée I had from here has probably been the best I’ve ever had in my life.

If you’re venturing to Downtown Sarasota, you can find artisan shops, local stores, and a variety of restaurants ready to cater to different tastes and budgets. For a complete guide about Sarasota, including recommendations on where to eat, check out Planning a Vacation to Sarasota, FL: All You Need to Know.

Additional Food & Drinks Recommendations

Additional food and drinks recommendations include Sun Garden Cafe for breakfast and Bean Coffeehouse for coffee, tea, smoothies, and sandwiches. For wine, check out Siesta Key Wine Bar, and for beer Blase Martini Bar.

If you are looking for something sweeter, then Meaney’s Mini Donuts & Coffee House should be your go-to place. For more decadent desserts in the Sarasota area, click here.

If you like rum, try to go on a tour at Drum Circle Distilling. The tour is free, includes rum samples, and runs for about an hour. Don’t forget to register for the tours in advance because this might be the place where you can find the best souvenirs for those who were not as lucky as you to visit Siesta Key.

Please Note the Website’s Warning: The Distillery is located on the north side of Sarasota in a rather ordinary-looking industrial park. But don’t let that fool you; you are going the right way!

What to do?

Thanks #caribbeanjournal “without a doubt the world’s best spiced rum”! #siestakeyrum #spicedrum
A post shared by Siesta Key Rum (@siesta_key_rum) on Dec 23, 2016 at 1:52pm PST

As you can see, aside from going to the beach and the endless offering of water sports, there are numerous things to do and places to check out in Siesta Key and surrounding areas. You can enjoy tasty and local food & drinks, wander in art galleries, and have fun at special events.

If time is not a constraint, don’t forget to check other keys and their events, such as the St. Armands Circle Craft Festival in June and Taste of St. Armands in October.

What to Pack?

Read: What to Pack for Siesta Key (With a Downloadable Checklist)

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The beach, great food & rum are some of the things locals love about Siesta Key. If you're thinking about paying us a visit, keep reading.

Category: Destinations Florida

About Sheila Berrios

Sheila is a freelance writer and content creator based in Lakewood Ranch, Florida. A biology and quality management major, night owl, and pseudo-photographer. She is originally from Puerto Rico and lives for finding magnificent sunsets and delicious food.