Things To Do in Siesta Key at Night

Siesta Key is one of the best places to hang out on the gulf. But don’t just assume it’s true. Our guide highlights the best spots to chill, the finest drinking locales, and where you can stay while you enjoy the many options available.

We love to just hang out- no lofty expectations, no other goals. The only thing in mind is relaxation.

Chill Hangout Spots

If this is your speed, we highly recommend the Sarasota Brewing Company. Its chill demeanor will put you right at ease. You can find some awesome craft beers across the bar’s two different Happy Hours. If you stop by in the afternoon, you can jump on a microbrewery tour.

It is not the only craft beer spot on or near the island. We also recommend Calusa Brewing and 14 Pi craft Beer and Spirits. All of them are relaxed and welcoming.

Not up for a drink? We understand. There are some other cozy hangout spots. We really enjoy Lelu’s Coffe Lounge for its comfortable atmosphere and amazing coffee selections. We also suggest heading over to Siesta Key Village. You can visit the numerous boutiques and find a cozy bench to relax for a bit. We have numerous Siesta Key rentals near the village. Easily walk, drive, or bike on over at your convenience.

siesta key things to do in fall

Plan Your Vacation

Vacation should be a little more than just an escape for a bit. We want to make it an experience – grand, beautiful, and rewarding. You can find any old hotel and have a good time, but why settle for less?

Best Drinks

Who has the best drinks in town?

Our money is on Gilligan’s Island Bar and Grill. The restaurant is drenched in tiki décor. It seems that every square foot has some tiki addition or two, with big torches, tiki-inspired art, and tikis surrounding the entire building like a fence.

There are surfboards lining the walls and a dance floor that remains open and inviting throughout the entire evening. The restaurant is famous for its Cold Beach cocktails.

You are certain to find some awesome drinks at The Beach Club. It offers a nightclub type of experience. If you like live bands, DJ music, and a club atmosphere, this is the best place on the island.

We also have to mention the Cottage Restaurant. Atmosphere-wise, it is the total opposite of the Beach Club. It’s cool and casual, with splendid courtyard décor and calm energy. It also boasts some of the best drinks anywhere. The designer cocktails are hand-crafted based on your interests, giving you a nearly limitless number of possibilities.

Live Music

Live music is a staple of island living, and you are never short of it here. The Siesta Key Oyster Bar is a really fun place to listen to some music. You may be more focused on the oyster bar, though.

Daiquiri Deck is probably the most popular place for casual drinking. Its quintessential Florida- big daiquiris, bold views of the town, palm trees as décor, and plenty of seafood. Live music is here a few times a week, featuring contemporary rock and upbeat classics.

Where to Stay

You can compile a long list of things to do in Siesta Key.  But where do you stay?

private beach house siesta key

Stay at one of our luxury vacation rentals, of course. Enjoy furnished kitchens, grand patio or balcony views, close access to the beach, welcoming and Property Manager, on-site property parking, and much more.

We want to give you more than a simple place to hang out. With us, you get the full experience. Take advantage of incredible amenities, from private heated pools to playrooms. Get to the top floor to experience one of the most majestic water views you have ever seen.


Siesta Key Luxury Rental Properties
5111 Ocean Blvd. Suite B, C & D
Siesta Key, Florida USA 34242
#SiestaKeyLuxury #iHeartSiestaKey
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