islamorada entertainment

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Check out the Sunset Celebration at Loreleis


Local Entertainers
  • The Steve Venini Band
  • Daft Like Jack
  • Jess Atkins
  • The Dana Collins Band
  • Big Dick & the Extenders
Favorite Happy Hours
  • Hog Heaven (3PM-7PM, M-F) $.50 10-oz drafts, $1.50 well drinks & $.35 wings
  • Rum Runners (Happy Hour) $1 drafts, $3 well drinks and wine/ Friday - All Day Happy Hour with ½ priced beer, wine and well drinks
  • Lorelei (4PM-6PM) sunset, live entertainment & magician


Next to Key West, Islamorada is the place to party. And the partying has the same flavor as the rest of the Keys - casual, laidback and fun. Enjoy sipping on your favorite cocktail while taking part in a sunset celebration complete with live music and magicians or at a full moon party on a beach lit with tiki torches and beach bonfires. Maybe you prefer a locals bar where “Best Thong” contests are held, an outdoor deck overlooking the marina or you could try the unusual and head out to a sandbar in the bay. Whatever you choose it will be the perfect ending of a beautiful day.

Green Turtle Inn
88507 Overseas Highway (MM88.5)
A local favorite, this cozy and quaint restaurant features a daily happy hour from 3PM-6PM with drink discounts and a $4 appetizer menu. Late at night they feature a second happy hour from 10PM-1AM with half-priced well drinks, beer and live jazz. And if you are hungry they are one of the few places you can still grab a bite to eat after 10PM.

Hog Heaven Sports Bar & Grill
85361 Overseas Highway (MM85.3)
Grab a seat by the ocean and enjoy the happy hour Monday through Friday from 3PM-7PM.  Among their happy hour specials they serve 10-oz domestic drafts for $.50 or 14-oz drafts for $.75, well drinks for $1.50 and $.35 wings. Late Night Sundays there is a "Best Thong" contest with a prize of a $100 bar tab and on Wednesday nights they celebrate the ladies from 10PM-12AM when ladies’ drinks are on the house.

Islamorada Grille
82758 Overseas Highway (MM82.7)
Happy Hour at this spacious restaurant features $1.50 domestic beer and $.35 wings,  peel & eat shrimp or conch fritters.

Jaws Raw Bar
84001 Overseas Highway at Holiday Isle (MM84)
A great casual outdoor bar, steps from the ocean, featuring live bands 7 nights a week as well as a nice raw bar.

Lorelei Restaurant & Cabana Bar
81924 Overseas Highway (MM82)
Fun for all at this waterside restaurant - find a seat at the bar or on the sand and enjoy their sunset celebration. Listen to live entertainment 7 nights a week from 6PM-10PM along with a roving magician that will amaze the kids. Happy hour runs from 4PM-6PM daily at the Cabana Bar. See their website for a calendar of events.

Morada Bay Beach Café
81600 Overseas Highway (MM81.6)
This outdoor bistro café, right on the beach, is a fun place to watch the sun go down. Relax in an Adirondack chair on the beach or grab a seat at the bar and let the music, live Thursday-Saturday, ocean breezes and glorious sunset take you away.  As dark settles in, the tiki torches are lit and it becomes a romantic spot for dinner. Plan your visit around the next full moon and take part in their Full Moon Party starting around 9PM. On that evening they pull out all the stops and put on a beach bash you won’t soon forget with specialty drinks, a beach bonfire and live performers including flamenco guitarists, jazz musicians, reggae bands, balloon artists and stilt walkers. Bring your blanket and relax on the sand or dance under the full moon and all for just a $15 cover. On Friday nights, if you are out late, stop in after 10:30PM and listen to the live jam sessions until close.  

Oceanview Inn & Pub
84500 Overseas Highway (MM84.5)
Whether you are a sports fan or just looking for a friendly place to share a few drinks, this newly renovated pub is a great choice. Sit at the bar with plenty of TV’s tuned into the latest sports or outdoors on the deck overlooking the pool and Florida Bay and enjoy a cold one. Happy Hour specials run Monday-Friday from 4PM-7PM and, if you are there for the weekend, enjoy their live entertainment.  Like football? Stop in for Monday Night Football’s "Jocks on the Rocks" with a live pre-game radio show, drawings and drink special. There is even a free halftime buffet with roasted turkey and all the trimmings.

Rum Runners Island Bar & Deli
84001 Overseas Highway (MM84)
Everyone has to visit this world famous tiki bar at least once and enjoy their open air bar and views of the Florida Bay. Climb the stairs to the 2nd floor and take a seat and watch the action on the beach while enjoying one of the all day every day $5 drink specials. Later in the day, stop by for the sunset show and enjoy their happy hour which features $1 drafts, $3 well drinks and wine. On Friday the happy hour lasts all day with ½ priced beer, wine and well drinks - can’t beat that! Live entertainment is featured on Thursday, Friday and Saturday nights from 8PM-1AM, so put on your dancing shoes and dance the night away on the beach or in the bar.  And join some famous celebrities who have done the same - Gary Busey, Don Johnson, Susan Sarandon and Jeff Daniels among others. Tip: If you order their famous rum runner the recipe is written on the plastic cup for you to take home with you.

Safari Lounge
73814 Overseas Highway (MM73.5 Oceanside)
A true locals’ bar with friendly people and a great ocean view. Inside the place is a little dark and full of smoke but you can always take it outside to the gazebo. They have live entertainment, pool tables, darts and even a sand volleyball court.  No eats here but you can get Yeungling for only $2.25 and, as many people have found out, there is no better bar to become a local in!

Smugglers Cove Restaurant & Marina
85500 Overseas Hwy
Another locals’ place with that casual, laid-back keysy atmosphere. Located on the water overlooking the marina, you can hear live entertainment every night and grab some good happy hour specials from 3PM-6PM.

Wahoos Bar & Grill
83413 Overseas Highway (83.5 Oceanside)
Located in the Whale Harbor Marina, overlooking the Atlantic, this casual bar with 2 waterfront decks is the perfect place to enjoy your evenings’ happy hour. From 4PM-7PM weekdays, sit back and enjoy drink specials and nightly entertainment while watching the fishing fleet come in.

Zane Grey Long Key Lounge
81576 Overseas Highway at World Wide Sportsman (MM81.5)
After perusing all the fantastic outdoor gear downstairs, take a trip to the 2nd floor and you will find a quiet wood-paneled bar that looks like it is straight out of the 1930s. Take a seat in the indoor lounge and enjoy looking at all the historical memorabilia on hand or wander outside to the deck and get a ring-side seat to the sunset.  It is a great place for a quiet drink, a cigar and some great happy hour specials.