Eat, drink and enjoy live music outdoors within walking distance of world-famous Siesta Beach.
A view down Ocean Boulevard in Siesta Key Village. (Photo: [HERALD-TRIBUNE STAFF PHOTO / DAN WAGNER / 2019])
Again ranked among the best beaches in the United States by Tripadvisor, Siesta Beach on the north end of Siesta Key remains the most popular place to visit in Sarasota County. Especially during spring break, which, yes, is right around the corner.
Featuring sugary sand made almost exclusively of pure quartz that remains cool on the feet even when baked in the Florida sun, Siesta Beach provides the perfect setting for swimming, sunbathing and perhaps a few games of beach volleyball.
Eventually, though, even the most devout sun lovers will want to seek food, drink and probably some shade – while following social distancing guidelines and other pandemic precautions.
Luckily, Siesta Beach visitors will find Siesta Key Village located less than a mile away. Centered around Ocean Boulevard, it’s a vibrant mix of restaurants, bars and shops that should appeal to beachgoers of all ages.
So regardless if you’re a local looking for a fun evening or escaping some ridiculously cold place up North, here are 15 of our favorite places to eat and drink adult beverages outdoors in Siesta Key Village, presented in alphabetical order.
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3.14 Pi Craft Beer & Spirits is at 5263 Ocean Blvd. in Siesta Key Village. (Photo: HERALD-TRIBUNE STAFF PHOTO / WADE TATANGELO)
3.14 Pi Craft Beer & Spirits
5263 Ocean Blvd.; 941-346-1188; siestapi.com
At the south end of Ocean Boulevard away from the more crowded sections of the village, 3.14 Pi Craft Beer & Spirits offers an impressive craft beer selection and cocktails to pair with some of the best comfort foods – including, yes, pizza pies, and baked chicken wings – on Siesta Key. Plus, there’s plenty of outdoor seating spilling out into the parking lot shared with sister restaurant Blasé Café.
The Beach Club is at 5151 Ocean Blvd. (Photo: [HERALD-TRIBUNE PHOTO / DAN WAGNER])
5151 Ocean Blvd.; 941-349-6311; beachclubsiestakey.com
Established in 1947 and still one of the most popular bars in Sarasota County, Beach Club serves as a great spot to day drink, with select outdoor seats offering front row views of the Village’s most bustling intersection. But it’s best known as a nightspot with DJs and other live music acts, a huge dance floor and various theme nights. Looking to meet a cast member from the MTV reality show “Siesta Key”? Here’s your best bet, along with Gilligan’s (keep reading.)
Big Olaf Creamery in Siesta Key Village is a popular spot for tourists and locals, especially in July. (Photo: HERALD-TRIBUNE STAFF PHOTO / MIKE LANG)
Big Olaf Creamery
5208 Ocean Blvd., Sarasota; 941-349-9392; bigolafsiestakey.com
This is where children of all ages have been going for ice cream, made by local Amish experts since 1982. Mask up to order inside and then enjoy your treats at one of the many surrounding benches. In addition to the famous ice cream and frozen yogurts served in waffle cones, Big Olaf serves such favorites as smoothies, blended coffee drinks and their hand-spun milkshakes. It’s one of several spots for sweet treats in Siesta Village, along with fellow landmark Meaney’s Mini Donuts.
5263 Ocean Blvd.; 941-349-9822; theblasecafe.com
Here’s where locals have been going to enjoy martinis in a wonderfully eclectic, European setting for nearly a quarter-century. The cafe serves many of the same comfort foods as its next door sister business 3.14 Pi, along with items such as the Famous Crab Bisque and 1997 Salad. Like Pi, there’s indoor and outdoor seating, with a large tent where guests can often enjoy live music.
The Cottage is at 153 Avenida Messina. (Photo: HERALD-TRIBUNE ARCHIVE / 2020)
153 Avenida Messina; 941-312-9300; cottagesiestakey.com
At once trendy and cozy, Cottage is one of the best restaurants on Siesta Key, specializing in skillfully crafted seafood dishes with gorgeous, tropical garden seating in the back. Popular items include the lobster bisque, bronzed black grouper and Siesta seafood scampi. It also has an impressive cocktail list, featuring a must-try jalapeno watermelon margarita.
Daiquiri Deck’s original location is at 5250 Ocean Blvd. (Photo: HERALD-TRIBUNE ARCHIVE / 2019)
5250 Ocean Blvd; 941-349-8697; daiquirideck.com
This local chain remains most famous for its frozen daiquiris, which are essentially alcoholic slushies, including the dangerously potent Deck Diesel concoction of orange, vodka and grain alcohol. The original Daiquiri Deck is right on Siesta Village’s main drag, with additional sidewalk seating in use during our recent visit, and it has other locations including a multi-floor spot on south Siesta Key as well as the newest one, which can be found to the north on Anna Maria Island.
Gilligan’s Island Bar & Grill is located at 5253 Ocean Boulevard. (Photo: HERALD-TRIBUNE ARCHIVE / 2020)
Gilligan’s Island Bar & Grill
5253 Ocean Blvd.; 941-346-8122; gilligansislandbar.com
Featuring tropical-style indoor and outdoor bars, a dance floor and area for bands to perform, Gilligan’s offers plenty of options for day drinking and nightlife action, plus a full menu of fun beach food. Come spring break season, it also hosts bikini contests, with one such showdown even making its way onto an episode of “Siesta Key.”
The Hub Baja Grill is located at 5148 Ocean Boulevard on Siesta Key. (Photo: HERALD-TRIBUNE ARCHIVE / 2019)
The Hub Baja Grill
5148 Ocean Blvd.; 941-349-6800; thehubsiestakey.com
A great spot to enjoy libations, live music and beachy grub, The Hub specializes in Mexican-inspired food and drinks, including a variety of margaritas available by the glass or, watch out, pitchers. There’s indoor as well as covered patio seating along Ocean Boulevard across the way from Beach Club, making it prime for people watching.
Il Panificio is at 215 Avenida Madera in Siesta Key Village. (Photo: HERALD-TRIBUNE STAFF PHOTO / WADE TATANGELO / 2021)
215 Avenida Madera; 941-800-5570; panificiousa.com
A local tradition dating back to 1991, when the family-owned business opened its original pizzeria in downtown Sarasota, this new location can be found within a stone’s throw of Ocean Boulevard. Il Panificio specializes in Italian thin-crust pizzas prepared with various high-quality toppings to be enjoyed by the pie or slice. The pizzeria also serves appetizers, deli sandwiches, beer, wine, and assorted desserts.
Island House Tap & Grill is at 5110 Ocean Blvd. on Siesta Key. (Photo: HERALD-TRIBUNE ARCHIVE / 2020)
Island House Tap & Grill
5110 Ocean Blvd.; 941-487-8116; islandhousetapandgrill.com
If you’re looking for a top-shelf burger and pint pairing, here ya go. The rotating list of local and national craft drafts, cans and bottles nicely complement the tasty selection of burgers and tacos, as well as fresh fish and chicken sandwiches. Island House Tap & Grill also offers outdoor seating.
MVP – My Village Pub is at 5200 Ocean Blvd. in Siesta Key Village. (Photo: HERALD-TRIBUNE STAFF PHOTO / WADE TATANGELO)
MVP – My Village Pub
5200 Ocean Blvd., Siesta Key; 941-777-6787; mvpsiestakey.com
Siesta Key Village’s only sports bar, MVP is a fun place to enjoy the big game or just people watch from under the big clock at the outdoor bar, stretching about halfway around the building, or from the al fresco tables along Ocean Boulevard. Enjoy American comfort foods, including their outstanding selection of burgers, chicken wings and The Big Daddy Pretzel accompanied with a side of some highly addictive beer cheese.
Mojo Risin’ Coffee Co. is at 5251 Ocean Blvd. in Siesta Key Village (Photo: HERALD-TRIBUNE STAFF PHOTO / WADE TATANGELO /2021)
Mojo Risin’ Coffee Co.
5251 Ocean Blvd.; 941-349-6656; mojorisincoffee.com
Located next door to Gilligan’s in the space formerly known as LeLu Coffee, Mojo Risin’ brings a tropical twist to the coffeehouse, with an interior sporting decor such as surfboards, an outdoor courtyard, a drink list that includes a Siesta coconut mocha, and a food menu featuring acai bowls. It also serves cocktails, including classic tropical drinks and coffee-themed concoctions like an espresso martini or Kentucky cold brew.
Old Salty Dog is at 5023 Ocean Blvd. in Siesta Key Village. (Photo: HERALD-TRIBUNE STAFF PHOTO / WADE TATANGELO / 2021)
Old Salty Dog
5023 Ocean Blvd.; 941-349-0158; theoldsaltydog.com
Opened in 1985 in this Siesta Key spot that offers covered outdoor seating and now with additional locations on City Island and Venice Island, no trip to the Old Salty Dog is complete without munching on the signature hot dog, dipped in batter and fried to golden-brown perfection. Feeling adventurous? Order the “fully loaded” option featured on “Man v. Food.”
Siesta Key Oyster Bar is at 5328 Ocean Blvd. (Photo: HERALD-TRIBUNE ARCHIVE / 2020)
Siesta Key Oyster Bar
5238 Ocean Blvd.; 941-346-5443; skob.com
Siesta Key Oyster Bar – or S.K.O.B., as locals affectionately call it – gets its name from the oysters, among other seafood, it serves. But it’s also one of Siesta Village’s busiest watering holes, decorated with dollar bills from past customers, and regularly features live music. S.K.O.B. offers open-air deck seating, as well as patio seating overlooking Ocean Boulevard.
Summer House is one of several Siesta Key restaurants owned and operated by Above the Bar Hospitality Group. (Photo: HERALD-TRIBUNE ARCHIVE)
Summer House Steak & Seafood
149 Avenida Messina; 941-260-2675; summerhousesiestakey.com
Named one of the Top 10 most romantic restaurants in the U.S. in 2019 by TripAdvisor, Summer House places diners in a luxurious yet still beachy setting, with a menu featuring premium steaks and chops as well as various seafood dishes. While most of the seating is inside, Summer House does offer very limited outdoor seating on its front porch, with about three to four tables. Fun fact: Beach Club, The Cottage, The Hub, MVP and Summer House are all owned by the same Above the Bar Hospitality Group.
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Wade Tatangelo, the Herald-Tribune’s entertainment editor, may be reached via email at email@example.com. Email entertainment reporter Jimmy Geurts at firstname.lastname@example.org.
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