The Resort at Longboat Key, renovated in 2020, sits on 410 acres of land on a barrier island off Sarasota. Besides a private beach, the hotel has its own golf course, tennis gardens and a spa. Rooms start at $999 a night.

Gilligan’s Island Bar is synonymous with the vibrant, lively atmosphere that characterizes the best beach bars in Siesta Key, Florida. As one of the top-rated destinations for nightlife and live music on the island, this well-established tiki bar offers visitors a unique chance to experience authentic island vibes in a welcoming environment. Located right at the heart of Siesta Key Village under an iconic tiki roof, Gilligan’s Island Bar provides ample outdoor seating options for those keen on enjoying happy hour while soaking up some sun or cooling down after a long day at the beach.

Gilligan’s Island Bar & Grill: 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. It’s also the place you’re most likely to find yourself in a bikini contest with a cast member of “Siesta Key.” (5253 Ocean Blvd.; 941-346-8122; gilligansislandbar.com) HERALD-TRIBUNE STAFF PHOTO / DAN WAGNER(/gcdn/authoring/2019/11/12/NSHT/ghows_image-LK-b48ef655-c0ff-45aa-8258-eb6c16888865.jpeg?width=660&height=451&fit=crop&format=pjpg&auto=webp)

I go out a lot both downtown and siesta key, (mostly gulf gate actually) and the crowd is very noticeably younger and much less stuffy and more interaction……..all the bars by daiquiri deck and gilligans and the clubs right next door……you can also bar hop very easily……….much more likely meeting prople and getting laid by tourists…..IF you must go downtown then gator club for sure…..was just there, younger crowd..,..also downtown the rooftop bars there’s a few…even if it’s in hotel they all welcome general public.

Aside from oysters and shrimp, there are plenty of other restaurants serving up international cuisine of a very high standard. A Taste of Germany is a quaint restaurant with a menu packed with strudel, liquor cakes, bratwurst and sauerkraut, while Bonjour French Café serves up crepes, croissants and a delightful variety of other French delicacies. Visit The Cottage Restaurant for authentic tapas-style Spanish food, or hit Solorzano’s Pizzeria for pasta, pizza, calzones and all your other Italian favorites.

If you're looking for a place to let loose, have some fun and see where the night takes you, it's probably across the street at Gilligan's Island Bar. Here you'll find sand, surfboards, a thatched roof, cold drinks and even an old VW bus parked inside the restaurant. It's hard to walk past this place without wondering what is going on past the tiki bar or inside on the dance floor, and there's live music every night of the week.

Gilligan's Island - 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.

You won’t find The Professor or Mary Ann here, and the only three-hour tour that may embark from here is a tour of the tasty food, cocktails, and entertainment you’ll find. A hotspot on Siesta Key for twenty years, you can spot their tiki bar with its thatched tiki roof from the street. Whether you start or end up here, you’ll find amazing food and drink with a Florida beach vibe like no other.

Just a short 8-minute walk from The Inn on Siesta Key, Gilligan’s provides the best of both worlds – plenty of TVs to watch the game along with an unparalleled island setting. Gilligan’s has the largest tiki bar in Sarasota. Their large menu has a decidedly island theme, from seafood to appetizers, there’s something for everyone, including a wide variety of libations.

Gilligan’s is far from trades subtlety for spirit, quiet lunches with family for exciting and energetic afternoons out. The restaurant is surrounded by big tiki torches and a covered by a thatched roof, allowing you to enjoy an afternoon of tropical cocktails, music, and laughter at a real beach bar. Live music is offered every day from 6 to 10 p.m.

Between the tiki torches, the captivating straw and wood-heavy décor, and the tiki torch natural lighting, Gilligans Island Grill is an ideal stop for couples and romantics. The restaurant is bustling with energy late into the night. For about 14 years, Gilligan’s has been welcoming visitors with its famously-tasty homemade salsas and sauces.

Gilligan’s Island Bar is more than just a bar; it’s a tropical oasis nestled in the vibrant nightlife of Siesta Key Village. This venue offers the best of both worlds, with cozy indoor seating and a spacious outdoor patio. Whether you’re looking for an intimate evening or a lively gathering with friends, Gilligan’s sets the perfect scene.

Conveniently located near Siesta Key Beach, Gilligan’s is a fun Floridian-style restaurant and bar with live music and great food!. It’s honestly the restaurant ambiance you probably think of when picturing a place to dine near the beaches of Florida. Don’t miss the World-Famous Fries, which are everything you dreamed of.

(She thought it was the Easter bunny) We enjoyed SKOB, Orange Octopus, took a sunset cruise with Parasail Siesta, listened to live music at Gilligans, had a blast at Pop Stroke, and more than anything just time together with our family in a beautiful place. Thank you so much for sharing a piece of your heaven with us!

One of Sarasota’s hottest upscale bars…always classy, never snobby. The RHINO features an extensive Martini and Cocktail list along with the finest Champagnes and full-bottle service. It is open 7 nights a week after sundown with special themed parties every Wednesday, Friday and Saturday night.

Gilligan’s Island Bar & Grill is a solid option to enjoy a burger and an ice-cold beer while sitting in a spacious tiki hut. This open-air restaurant is close enough to the beach to “The Village” for a quick bite. While I like burgers, the coconut shrimp is also an excellent choice.

Gilligan’s Island Bar & Grill is a beach bar on Siesta Key that features a lively patio, stage for live music, lunch and dinner, plus a tiki bar where they serve their famous drinks. Don’t leave without trying the Key Lime Colada or the Shipwreck, a house cocktail specialty.

Like a lot of the Siesta Key bars, it has a neighborhood bar feel during the day and it’s more of a club at night. Men and women both love Ladies Night on Thursdays (women drink free) and there’s live music from early afternoon straight through to early morning Sunday.

Gilligans Island Grill prides itself for providing the best quality of foods, cocktails, service, atmosphere and local entertainment on the Key. Walking in, you’ll see there are options on where to spend your time at Gilligan’s. Take it all in and look around a bit.

Known for its quirky tiki decor and laid-back vibe, Gilligan’s Island Bar & Grill is a fantastic spot for a casual night out. The outdoor seating area is perfect for enjoying tropical cocktails, while the live music and fun events keep the energy going.

Gilligan’s Island and Bar has everything you could come to hope for out a beach-themed restaurant. Tiki poles light up the summer décor and a big bar sits by an open patio space. There’s even a large bright green 1950’s van sitting in the restaurant.

With its vast dance floor and rotating selection of local DJs and live bands, you can stay moving to the beat all though the night. Or sit back with a cold one at the Tiki bar and drink it all in. Gilligan’s signature drink: The Classic Painkiller.

Named after the classic TV Show, this tiki bar is a wonderful addition to your experience at Siesta Key. Live bands play daily from 6-10pm. They serve a variety of beach food and cocktails, ranging from burgers, tacos, and seafood sandwiches.

For a fun, tropical dining experience, Gilligan’s is the place to be. This lively spot serves up island-inspired dishes like Coconut Shrimp and Key Lime Pie. The tiki bar and outdoor seating create a relaxed, vacation-ready ambiance.

The Hub looks like a tourist spot thanks to acres of faux island décor. Still, it’s difficult to argue with a big, open-air covered deck that sits right on the sidewalk in the center of Siesta activity and some great margaritas.

Gilligan’s Island Bar & Grill: Featuring one of the largest tiki bars in Sarasota, Gilligan’s is a great spot to grab a tropical drink and a casual meal. They serve a variety of seafood, burgers, and beach fare.

My favorite places to listen to live music on Siesta Key include: Big Tiki Lounge, The Sniki Tiki Bar at Captain Curt’s Village, The Beach Club, and Gilligan’s Island Bar, and Siesta Key Oyster Bar.

Whether you’re a local or just passing through, our tiki bar offers an unforgettable escape filled with refreshing cocktails, mouthwatering dishes, and the best live entertainment on Siesta Key.

Or, grab a drink and people-watch at Gilligan’s (5253 Ocean Blvd., 941-346- 8122, gilligansislandbar.com) and Daiquiri Deck (5250 Ocean Blvd., 941-349-8697, daiquirideck.com)

The Parrot Patio Bar & Grill has the best nachos in Sarasota. They have an awesome outdoor patio with live music. The service was fast and the staff was friendly.

You find yourself wandering into Siesta Key Village after an epic day on the #1 Beach in the USA. Sandy feet and salty skin, searching for shade and refreshment.

Gilligan’s Island Bar & Grill is decorated with a tropical theme. You will sit under a thatched roof. The restaurant is just a 4-minute walk from the beach.

I wish they had a few more options for food and gluten free bread (not a major issue just a suggestion). Our waitress was great as well!

Founded in 2001, Gilligan’s Island prides itself for being the largest Tiki Bar in Sarasota and a staple for many locals.