How to Experience Siesta Key Like a Local

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).


Before you keep reading: is making use of affiliate links, which in some cases will end up in a commission for purchases originated from this website. However, all referred companies/products/accommodations have been tried out or researched by us first.
Where to stay?

Sunset at Crescent Beach in Siesta Key with SeniorsSunset 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 are looking for more space, take a look at the Airbnb’s and VRBO’s in the area. Click here for $40.00 USD travel credit on your first Airbnb booking.

You can stay a little further from the beach, but keep in mind 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 what is an excellent rental property, recently, I 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 on 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 that you overpack. Book the Dolphin Cottage at Siesta Key Here!

What to eat & drink?


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If you want to stay close to the beach, Clayton’s Siesta Grille should be your first choice. 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 for private parties too. For something more filling, order the Pan Roasted Diver Scallops with Bacon braised chard or the Mahi Mahi Fish Tacos. 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, here you can find artisan shops, local stores, and a variety of restaurants ready to please different tastes and budgets. For a full 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
Some additional recommendations regarding food and drinks 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 3.14 Pi Craft Beer & Spirits.

If 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 make it to a tour at Drum Circle Distilling. The tour is free, includes rum samples, and it 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 that 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

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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?

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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.