key largo entertainment

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Check out the local scene at Pilot House Glass-Bottom Bar


Local Entertainers
  • The Steve Venini Band
  • Keith McCurdy
  • Jess Atkins
  • Dwayne McGregor
  • Luke Sommer Glenn Band
Favorite Happy Hours
  • Snappers (4PM-7PM, Mon-Sat) 2-for-1 well drinks & beer, $.75 wings, oysters and pell-and-eat shrimp
  • JJ's Big Chill Tiki Bar (4PM-7PM) $1 drafts & 2-for-1 well drinks. Use of pool when spend $25
  • Gilberts (M-F 4PM-7PM) $.50 off wine & beer, $1 off well & blender drinks; live entertainment
  • Breezers Tiki Bar (4PM-7PM) $2.75 beer, $3.75 well,appetizers $4-$6; live entertainment 6PM-10PM


After a full day of enjoying the beautiful turquoise waters and bright sunshine you are ready for a drink and a little downtime. Join the locals for their brand of entertainment – casual, friendly, laidback and relaxed. Most of the entertainment takes place in the restaurants and the best locations are found on the bayside where you get a front row seat to some of the best sunsets in the world.  Come by car, bike or boat, in shorts, jeans or whatever you are comfortable in, and join in the camaraderie. Choose open-air tiki bars, outdoor decks overlooking the ocean, marina or canals, lounge areas around the pool or small dives with plenty of TVs, pool tables and cold beer while waiting for the local musicians to get the party rolling. For muchies, don’t forget to try some of the conch fritters and Key West Pinks (shrimp that is) that are specialties of the area.

Ballyhoo's Island Grille
97860 Overseas Highway, MM 97.8 in the median
Ballyhoos is a great place to find the Keys experience. Housed in an old conch structure from a 1930’s fishing camp, the atmosphere is typical, laidback Florida Keys. Nothing fancy, just good food, good drinks and friendly people. Stop by for Happy hour 4-7 pm featuring 2-for 1 well drinks and $1 domestic draft beers.

Bayside Grill Sunset Bar
99520 Overseas Highway, MM99.5
Wind down the day in their downstairs open-air bar with live music (every day but Sunday) and spectacular views of Florida Bay. Join in their happy featuring a sunset jam session.

Bogie's Café Tiki Bar
99701 Overseas Highway, MM 100 Oceanside at Holiday Inn Key Largo
A real locals’ place, this tiki bar sits in a beautiful tropical setting next to the pool. It’s the perfect place to pull up a seat at the bar and mingle or just relax in a lounger and listen to the nearby waterfall. Wednesday night is for the ladies where ladies drink free and on Friday and Saturday from 2PM-6PM they bring in the live entertainment along with half-price appetizers, $2.25 drafts, $3 well and $3.50 house wines. 

Breezers Tiki Bar
103800 Overseas Highway, MM103.8 at Key Largo Marriott Bay Resort
A great open air bar overlooking the bay and the perfect place to order a frozen drink and watch the sunset. Enjoy a daily happy hour from 4PM-7PM with $3.75 well drinks and $2.75 domestic beer and appetizers priced between $4 and $6. Their 8 wings, mozzarella sticks or sliders for $5 are a great deal.  Live entertainment is offered Wednesday-Saturday from 6PM-10PM. And there is plenty of free parking.

Buzzards Roost
21 Garden Cove Lane, MM106 Oceanside
A friendly locals place located on the water in Garden Cove Marina complete with a relaxing and laidback atmosphere. Come by boat or car to join the crowd for a great happy hour from 4PM-6PM daily. Serving up $1 drafts, $2.50 house wine and $.35 chicken wings, fritters and poppers.

Caribbean Club
MM 104 Bayside
A local watering hole filled with memorabilia from the classic film Key Largo starring Lauren Bacall and Humphrey Bogart. Features live music Thursday through Sunday and a daily Happy Hour from 4PM-6PM. Come by boat, car or bike, have a stiff drink and enjoy the sunset. By the way, it is cash only.

Dillon’s Irish Pub & Grill
91200 Overseas Highway, MM91.2, Tavernier Shopping Center
A casual Irish bar, the only one in town, with plenty of TVs for catching your favorite game or for relaxing and having a drink or two. Have a pint of Guinness, always on tap, and try some of their wings, which have been awarded the best in the Upper Keys.   Happy hour runs Monday-Friday from 4PM-6Pm with $2.25 domestic pints and well drinks, $2.50 domestic bottles and $3.50 margaritas on the rocks.

Fish House Encore
102401 Overseas Highway
Get laidback like the locals do and enjoy happy hour in one of Fish House Encore’s three bars, an indoor piano lounge and a full service bar or their outdoor bar. All are equipped with plenty of TVs for all the sports fans out there. Happy hour runs Monday-Friday 5PM-7PM (only at the bars) with half price well drinks, house wines and domestic beers. Live entertainment, featuring  Caribbean guitar music or light jazz, is featured Wednesday through Saturday at 7PM, 6:30PM on Sunday.  Monday is Ladies Night where ladies drink free and men get 2 for 1 with a free appetizer. Monday nights entertainment is provided from 6PM-7PM by WKEZ Radio Show.

107900 Overseas Highway, MM107.9 at Gilbert’s Resort
A simple waterfront tiki bar that is a locals’ secret. Get there by boat, bike or car and enjoy the camaraderie and mellow out with a drink in your hand while watching the sun go down and listening to the live entertainment. Stop by between 4PM-7PM, Monday – Friday, and find special deals like $.50 off wine & beer and $1 off alcohol and blender drinks. On Saturdays, join them at sundown and get treated to a fun-filled magic show.

JJ’s Big Chill
MM104 Bayside
A great dining and entertainment complex that features a restaurant, martini bar and sports bar in the main building and an outdoor tiki bar located bayside. Happy hours are held at the tiki bar daily from 4PM-7PM with drink specials that include draft beers for $1 and 2 for 1 well drinks. There are no food specials during happy hour but, if you spend at least $25, you can use their swimming pool.  And it is the perfect place to enjoy one of Key Largo’s beautiful sunsets.

Mandalay Tiki Bar & Restaurant
MM 97.5 Oceanside
A casual, laidback restaurant, right on the ocean, with a great bar that offers live entertainment every night from 5PM-9PM with an additional set on weekends from 12PM-4PM.  Join with the locals in celebrating happy hour from 4PM-6PM daily with 20% off drinks and 10% off any menu item.

Paradise Pub
102041 Overseas Highway, MM103
A no-frills, locals’ bar with pool tables, ice cold beer and live entertainment most nights. Happy hour runs daily from 4PM-7PM with $1.50 draft beers and $.50 chicken wings and peel-and-eat shrimp.

Pilot House
MM99.5 Oceanside
A favorite of the locals, and a little hard to find, but it is well worth the effort. Take a seat at the glass bottom bar for a fun experience and watch the fish under your feet. There is evening entertainment, usually starting between 5PM-7PM depending on the day, and a great happy hour from 4PM-7PM. This is the type of fun, casual place you come to the Keys to find!

Sharkey's Pub & Grill
522 Caribbean Drive, MM100 next to Marina Del Mar
A local’s favorite, this sports bar and restaurant serves up good food, good drinks and nightly entertainment right beside the canal. A great place to relax, play a game of pool or darts, watch your favorite team on TV or just sit back on the outdoor deck and listen to some great live music (Tuesday-Saturday). Feel the breeze, chat with the friendly clientele and enjoy the night. 

Shipwreck Bar & Grill
45 Garden Cove Drive, MM106
Shipwrecks is definitely a locals place with a rustic atmosphere, but if you are simply looking for a cold beer and friendly people – this is the place. They have $1 draft beer all day long until 6PM as well a decent happy hour and live music. Located right on the ocean, you can relax, have a drink and watch the dive boats come in. There are no food specials, but their regular menu is definitely less expensive than most of the other touristy places in Key Largo.

139 Seaside Avenue, MM 94.5   
A great little local’s “saloon” with both an indoor and outdoor bar and located right on the ocean.  A little hard to find the first time, down a little side street, but well worth the effort. Take a seat at their outdoor tiki bar for happy hour, Monday-Saturday from 4PM-7PM featuring 2 for 1 well drinks and domestic beer. From 4PM-6PM, you can also get $.75 wings, oysters and peel-and-eat shrimp. Later in the evening, if you stick around for dinner, there is live entertainment, Thursday-Saturday starting at 7PM or 7:30PM. Every Monday is $5 Ketel One Martini night and on Friday they offer a free gourmet snack for happy hour starting at 5PM.  Sunday they host a fabulous brunch with live jazz music by Frank Carmelitano drifting in from the floating dock.

MM104, Bayside
Sundowner’s beach deck provides a fantastic location for watching the sunset over Florida Bay. Relax and let the live entertainment get you in a “Margaritaville” mood and enjoy the pleasant breeze and some delicious cocktails.