Siesta Key has had many names over the years because of its diverse history that all started in the early part of the 20th century. It all started when one ambitious entrepreneur named Harry L. Heigel opened a fertilizer plant and hotel on the beach off of Sarasota in 1848. Since its origins, it has donned many names including Clam Island, Little Sarasota Island, and Siesta Key. Although Heigel is now largely forgotten, he was one of the key factors in making Siesta Key what it is today. His goal was to create a beachside community that he promoted as “a place to rest and have peace and comfort”. He would be thrilled to learn that today Sarasota is home to over 6,500 residents.  Luckily, the Siesta Key charm remains intact and it's why Siesta Key continues to delight thousands of tourists every year.

Fave Five: Restaurants in Siesta Key

Siesta Key Oyster Bar

The Siesta Key Oyster Bar, or SKOB as the locals call it, brings fresh oysters and live music to the beachside. This casual and beachy spot with a covered patio offers seafood and bar bites to all of their beach-goer guests. Their goal is to have their restaurant feel like home, it’s like you’re hanging out with your best friends on the patio in your own backyard. The first-time SKOB customer will see the typical bar bites like chicken wings, jalapeno poppers, and mozzarella sticks but when you look deeper into the menu you see that they take their food VERY seriously. They also sport a full beachside bar so next time you’re in need of a happy hour SKOB is the place to be.

Gulf Gate Food + Beer

Known as the ultimate destination for sporting events and tasty bar bites, Gulf Gate Food + Beer brings a unique flavor to Siesta Key. If you like next-level flavors on your typical sports bar bites, GGF+B will easily become your favorite bar on the key. Some of their staples are their freshly fried pickles, burgers, rice bowls and salads. I love their fried pickles because they’re freshly fried for every order and the PBR batter provides the most delightful crisp. The next time you’re in the mood for a beer and hunger is eating away at you, stop at Gulf Gate Food + Beer to treat your tastebuds to an experience.

The Hub Baja Grill

The Hub Baja Grill serves pan-Latin fare and margaritas that will make your head spin. So if you’re anything like me, this is a huge draw. This tropical eatery also serves up one of the best and most popular happy hours in Siesta Key. With a “Fiesta Hour” Monday through Friday from 11 am-6 pm that features $7.50 House Margaritas, $4 House Wines, $3 Well Drinks and $2 Domestic Drafts. However, they’re also known for their fresh and delicious fare that includes lettuce wraps, street tacos, and unique appetizers like fresh-from-Florida grouper bites.

Seafood Shack Marina, Bar & Grill

This waterfront choice for seafood plates & sandwiches served in a relaxed backdrop with a deck has been a staple in Siesta Key since 1971. Their most popular dish is a “from hook to platter” fresh catch of the day meal for just $16.99 per person. Their fish tacos, shrimp & grits, and gulf shrimp dinner are some other meals that get the locals going. The excitement for fresh seafood is appreciated at the Seafood Shack Marina, Bar and Grill more than most places on the key. Stop by for Happy Hour, fresh seafood and a relaxing atmosphere.

Captain Curt’s Crab & Oyster Bar

If you’re from Boston, you’ll understand the love the SRQ locals have for Captain Curt’s Crab & Oyster Bar. This straightforward seafood house features a tiki bar with live music but it is mostly known for its clam chowder. They’re focused on taking their customers back to an era where fresh seafood was an expectation in every meal from the ocean. What keeps their customers coming back is their reasonable prices, casual family atmosphere, and courteous service. You’ll feel like family at Captain Curt’s!

Fave Five: Nightlife Hotspots in Siesta Key

Daiquiri Deck

The Daiquiri Deck is a bright green building with yellow and purple shutters and details; if you’re driving down Ocean Boulevard, it's hard to miss. With outdoor seating on both the ground floor and upper deck, it’s right in the middle of all the commotion. The daiquiris come from giant vats that are labeled by flavor and built into the walls of the restaurant. They have Happy Hour every day from 3:00 p.m. to 7:00 p.m., and the restaurant gets even more fun after dark! With live music featuring a variety of local artists as well as sporting events, beer pong, and corn hole, they turn dinner into a party every night of the week.

Beach Club

Beach Club is the premier nightlife destination on Siesta Key.  Head out any time during the year and enjoy live music all throughout the week, drink specials like 2-4-1 beer and kamikaze shots, and more. The Beach Club is perfect for a night filled with dancing and drinking until your heart's content. It's a fun and exciting tiki bar atmosphere with live music and great happy hour specials!

Gilligan’s Island Bar & Grill

Right across the street from the Daiquiri Deck, Gilligan’s Island Bar and Grille is another spot that's popular for Siesta Key nightlife. Located in the center of Siesta Key village, Gilligan's Island offers great eats and delicious drinks from their island bar.  Sip on their specialty drinks including the Rum Runner, Tropical Pina Colada, Gilligan's Island Margarita, and the Hurricane. Not only is it a bar, but it also has a club portion called the Rhino Room that has DJs, bottle service, and a dance floor.

3.14 Pi Craft Beer + Spirits

3.14 Pi Craft Beer + Spirits is a great place to go for hot and cheesy pizza, craft beer, and high-end cocktails with bourbon and whiskey. The bar has a casual beachy feel to it so wear your flip flops, cut-off denim shorts and comfiest t-shirts for a casual happy hour with friends or family.

White Buffalo Saloon

This Southern-themed eatery and bar offer comfort food including sweet and tangy BBQ, plus live concerts & line-dancing lessons. Their goal is to keep the spirit of the Urban Cowboy alive at their rootin’ tootin’ saloon. They showcase local, national and worldwide talent on their small stage for their guest's entertainment. Since 2013, they’ve created a very homey atmosphere where everyone can feel like a member of the White Buffalo family.

Fave Five: Destinations in Siesta Key

Siesta Key Beach

Back in 2011, Siesta Key Beach was named the finest and whitest sand beach in the country because of its 99% pure quartz sand that is both soft and cool on your bare feet. Head there for a relaxing day with family and friends, grab a tan under the harsh rays of sunshine in the summer or bring some burgers and dogs to grill in the sunset at South Florida’s most beautiful beaches on Siesta Key.  

Munchies 420 Cafe

For those of you that celebrate 4/20, this is the ultimate destination for munchies in Sarasota. It all started when creator and owner, JD Chester, discovered a need for late-night bites in Sarasota. Fifteen years later, Munchies 420 Cafe has become a tourist attraction and local phenomenon for foodies all over Florida. Let me tell you, they take munchies to the next level! Their most popular items come from the fat sandwiches menu where they combine all of the munchies under the sun (including mozzarella sticks, chicken fingers, mac and cheese and more) and slap them between a fat hoagie roll. Check out their “fire in your hole” wing challenge that few have conquered for a red hot meal at Munchies 420 Cafe.

Ringling Museum

The Ringling Museum is home to the largest collection of art and culture that ranges back to the early 20th century. John Ringling, the beloved circus impresario and his wife, Mable, shared a love for the beauty of Sarasota and Italy. The Building of Ca’D’Zan was Mable’s pride and joy as she supervised every aspect of its design. The Museum of Art represents the couples' travels throughout Europe in search of circus acts. The exhibits include many of his treasures from paintings to sculptures and more. The museum was opened, two years after Mable's passing to help promote education and art appreciation among the newer generations.

Siesta Key Jet Ski

If your family has a hard time sitting still, go fast and glide through the water on a jet ski, parasail or boat through Siesta Key Jet Ski. Their new location is at 1536 Stickney Point Road. Rent a watersport transportation device to adventure through the waterways around Siesta Key and Sarasota. You’ll be able to see the sun-soaked charm from a whole new perspective.

Turtle Beach Campground

Need an escape from everyday life, including your cell phones, computers and any other technological device you find yourself getting lost in? Check out the sunny shores of Turtle Beach in Siesta Key at the Turtle Beach Campground. Whether Camping or Glamping is your thing, this campground will make it work for you. They offer 36 sites for either tents or RV’s, whichever you’re ideal mode for camping is! Take the free open-air trolley into Siesta Village to take advantage of the restaurants, recreational rentals and more in the village. From sunrise to sunset, there is nothing like camping along the Gulf of Mexico.

For more information on Siesta Key return to 941area, your free and local guide to Sarasota, Bradenton and more neighborhoods in the SRQ.