SIESTA KEY, FLORIDA

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Are you trying to find the best restaurants in Siesta Key? With so many options, it can be hard to decide which restaurant is worth it!

Siesta Key is a small barrier island known for its beautiful white quartz sand found on Siesta Key Beach, which is located near Sarasota, Florida. This small town seems up-and-coming, but it still holds a small beach town feeling. While being mostly known for its beaches, Siesta Key contains many eateries, ranging from casual joints to take a break from the beach, to fine dining establishments to have a fancy date.

See below for the 5 best places to dine at Siesta Key!!

1. Siesta Key Oyster Bar (SKOB)

Calling all fellow oyster lovers! SKOB is the best place to grab a bite while embodying the “island spirit”. The deck embodies a laid-back vibe and is beach-hut themed, which proves to be very relaxing. There is inside seating and a bar as well, if you prefer. Live music plays every day, and BIG G’s happy hour happens EVERY DAY from 3 PM- 6 PM. During happy hour, enjoy a dozen oysters for only $12. They offer fantastic food and outstanding cocktails, all while feeling like you’re chatting with some friends on an outdoor deck.  

All of the ingredients at SKOB are fresh and locally sourced, and you can truly taste the difference. The oysters tasted salty, plump, and paired perfectly with a dollop of cocktail sauce and homemade horseradish. SKOB makes the best lavender mojito as well. It tastes fresh, tart, refreshing, and has a slight floral vibe.

Their menu offers a wide variety of seafood options, from fried calamari to crab-stuffed lobster. I ordered a special, which contained red snapper with a savory, creamy sauce on top. Pro tip: get the coconut rice as a side. This rice tastes fluffy and soft, with a hint of both salty and sweet.

Three unique aspects of the bar: Chicago Bears gear lines the bar, the lights have been crafted from old license plates, and a bunch of dollar bills line the inside of the bar. They take this money and donate it to a good cause occasionally. Most recently, SKOB donated the cash to help with damage caused by Hurricane Ian.

Restaurant Menu: https://www.skob.com/menu/food-menu

2. The Cottage

The Cottage uniquely combines the “Old Florida” vibe with a tropical, modern twist. They offer an extensive variety of farm-to-fusion food on their menu, incorporating flavors and cuisine from all over the world. All of the seafood, meat, and other ingredients are locally and sustainably sourced. The restaurant has two different patios, one out front and one out back. The outback patio offers live music, which contributes to the beachy, relaxing atmosphere. 

The lobster bisque was creamy, rich, and succulent, and contains a bunch of fresh lobster. The Siesta Seafood Scampi is the best meal on the island without a doubt. Mussels, clams, and shrimp are served over bucatini pasta and doused with tomato sauce and garlic butter. Therefore, the pasta tastes buttery, rich, and filling. The meal comes with a side of crispy garlic bread as well, which pairs perfectly with the pasta. If you are not a big seafood fan, the menu also offers land meat options, such Short Rib Bites and Roasted Peruvian Chicken.

Although the food is outstanding and diverse, the atmosphere makes this restaurant special. It’s an extremely laid back, tropical feeling, all while indulging in delicious food. To drink, i’d recommend the Signature Sangria, made with fresh fruits, liquor, and your choice of red or white wine.

Restaurant Menu: https://cottagesiestakey.com/menu/

3. Captain Curts Crab and Oyster Bar

Calling all clam chowder lovers! The New England Clam Chowder makes this restaurant a fan favorite. In fact, the soup won Great Chowder Cook Off in Newport, RI. It tastes creamy and rich, with over 2.5x more clams than the average clam chowder. Along with this award-winning soup, Captain Cuts is the great place to enjoy good seafood, fantastic drinks, and experience unique entertainment. Although it is a seafood restaurant, the portions are rather big, and the prices are very fair. It has a “old Florida” beachy atmosphere, which is perfect for families. You can sit inside, or outside on the largest outdoor patio on the Key!

The file fish tasted flaky, mild, and seasoned to perfection. This was my first-time trying file fish, so I ordered it grilled with light seasoning to get the real taste. It was served with homemade tartar sauce, and I ordered a side of cheesy grits and coleslaw. The cheesy grits tasted identical to a creamy mac and cheese, and I absolutely would recommend them! To drink, I got the Strawberry Lemonade, which was super refreshing after a long day on the beach!

One interesting note about this restaurant: Captain Curts is actually not in Siesta Key Village, so you will have to venture out of the downtown area for this. The restaurant is part of Captain Curts Village, and there are many options for entertainment here, which makes the trip worth it! After enjoying a nice dinner, go to the Sneaki Tiki Outdoor Bar next door, and sing karaoke every Tuesday and Thursday night! The village also includes The Coffee Garden, The Tiki Trading Co, Orange Octopus, and Siesta Key Bike and Kayak. 

Restaurant Menu: https://www.captaincurts.com/captain-curts-menu/

4. Spearfish Grill

If you find yourself anywhere near the Siesta Key Marina, Spearfish Grill is the place for you! Located directly next to the Siesta Key Marina, Spearfish Grill embodies the fishing atmosphere. The Marina owners actually helped design the interior, and there are fishing rods, fish, and other fishing equipment lining the walls. I liked sitting on their tiki-hut like patio, as you get a great view of the marina while enjoying a delicious meal. This restaurant is small and quaint, tucked into the corner of Siesta Key Marina.  

I started off with Sushi Nachos, which includes Ahi tuna, crispy wonton strips, avocado, salsa, and topped off with wasabi aioli drizzle. The flavors were fantastic. The tuna was extremely fresh and tender, and the crisp of the wonton strips made this meal delicious. Because they are known for their local and fresh fish, I decided to order the Gulf Caught Grouper tacos. It was served inside flour tortillas, topped with cojita cheese, chives, pickled onions, sour cream, black beans, corn, and crispy slaw. They were fresh, very flavorful, and filling as well. One note about this restaurant: it is not a full bar, so if you wish to enjoy an alcoholic beverage, you will need to choose from wine and beer. I got the sangria, and it was great. They have live music Mon-Sun as well. The full schedule of live entertainment is found at https://www.spearfishgrille.com/music-calendar.

Restaurant Menu: https://www.spearfishgrille.com/menu

5. Gilligan’s Island Bar and Grill

Calling all beach bums! The atmosphere here feels tropical and laid back. It consists of indoor and outdoor seating at the biggest Tiki bar in Siesta Key. Locals and visitors fill this joint, which is located in the heart of Siesta Key Village. The VW bus parked out front serves all the food guest’s order. In fact, the VW bus presents a great photo opportunity if interested! The main bar area certainly embodies the Old Florida feeling, and surfboards, and other beachy inspired decor line the walls of the bar. a few games are on the outdoor deck too, which, needless to say, are super fun to play in between drinks/meals. Tiki torches flicker throughout the night as well, and palm trees are dispersed throughout the patio, which really makes it feel like your in paradise!

To start, I ordered the island quesadilla with grilled chicken. Monterey jack cheese, sour cream, sauteed onions and peppers, and fresh pico de Gallo fill the quesadilla. The tortilla was very crispy on the outside, and the fillings I just mentioned paired so well together. Additionally, I ordered the classic painkiller, which consists of rum, pineapple juice, cream of coconut, and orange juice. The painkiller tasted very refreshing, and basically is perfect for a sweet treat! One note about this: they serve the painkille in a giant tiki head glass, and they actually give you the option to buy your own tiki mug!

After enjoying drinks and dinner, feel free to head to the back patio to enjoy games, such as pool, giant jenga, and hook and ring. Instead of playing games, enjoy the store found on the back patio as well. Here, they have Gilligan’s merchandise, as well as local goodies such as handcrafted jewelry, and cool mugs.

Restaurant Menu: https://www.gilligansislandbar.com/menu/?doing_wp_cron=1687966317.0767199993133544921875

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