Caribbean Club

Where the famous movie Key Largo was filmed

Opened in 1938 and run by the Whitehurst family since 1963, the Caribbean Club is the oldest bar in the Upper Keys and one of the last relics of Old Key Largo. Full of character and characters, the Caribbean Club is a watering hole for locals and tourists alike.

With the Florida Bay as our backyard, our sunset views can’t be beat. We’re proud to be repeat winners of “Best Sunset” in the Keys Weekly’s “Best of the Upper Keys Awards” three years in a row.

Join us for live music EVERY DAY including our popular Karaoke Night on Wednesdays. We are honored to host the absolute best of Florida Keys musicians as well as renowned touring artists. Music is on our waterfront stage, but if the weather doesn’t cooperate, we’ll move the party inside.

Stop in and sip our famous Key Lime Pie Rum Punch under the palm trees or try a locally crafted beer while chatting it up with one of our favorite locals. Trust us, they have stories to tell!

Hungry?! We’re excited to have Take Two Kitchen’s Food Truck open Tuesday through Sunday from 11am to 9:30pm-ish .

BAR HOURS: 7AM TO 1AM-ISH Daily

We are a CASH ONLY bar, but we do have an ATM onsite.

Feb
21
6:30 PM18:30

The Lower Case Blues Band - On Tour from Delaware: 6:30pm

On tour from Delaware, we are beyond excited to have this talented trio back at the Caribbean Club for the fourth year in a row! The Lower Case Blues Band is an award winning group that plays a new fusion of old school blues, funk, and rock!

Music starts at 6:30pm. Come early to grab a good seat and enjoy a gorgeous sunset. Then hang around to dance in the sand to a groovy playlist of originals and covers.

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

If you’re hungry, Take Two Food Truck will be open and serving delicious smash burgers, tacos, bowls, and more until 9:30pm.

See you on the dance floor.

View Event →
Feb
22
7:00 PM19:00

The Luke Sommer Glenn Band - Live Music Outside at 7pm

Join us for live music on our waterfront stage starting at 7pm. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Don’t miss this show. Luke is a Key Largo legend for a reason.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Feb
23
5:00 PM17:00

South Groove Party Band - Sunday at 5pm

Get ready to dance in the sand! The South Groove Party Band rocks our stage this Sunday at 5pm. This high energy band plays all your favorite hit dance songs. Their music spans genres covering Classic Rock, Alternative Rock, Blues, Country, and Pop Rock. If it's got a dance beat and heavy guitar, then they love to play it!

Music is rain or shine. If the weather doesn’t cooperate, then we’ll move the party inside.

Hungry? Check out Take Two Kitchen’s delicious offerings including smash burgers, tacos, wings, and more. Their food truck is open in our front yard until around 9pm.

See you on the dance floor!

View Event →
Feb
24
6:00 PM18:00

Monday Music - Liana Gabel with James Bristol 6-9pm

Monday Music at the Caribbean Club is from 6 to 9pm on our waterfront stage! Come enjoy a gorgeous sunset and grab a drink from our backyard tiki bar. This week features a performance by Liana Gabel with James Bristol from 6 to 9pm. Don’t miss this truly unique performance featuring a mix of incredible vocals, bass, guitar, tap dancing, and more!

Music is rain or shine. If the weather doesn’t cooperate, we will move the music inside.

View Event →
Feb
25
6:00 PM18:00

FELIX THE CATT at 6pm

Join us for a night of reggae, rock and blues by Felix the CATT starting at 6pm EVERY Tuesday on our waterfront stage! Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Come hungry! Food is available from Take Two Food Truck until around 9pm.

See you on the dance floor.

View Event →
Feb
28
6:30 PM18:30

Koty James and the Keybillies Band - Live Music Outside 6:30pm - 10:30pm

Koty James and the Keybillies play the best of old school country and classic rock! These local boys will have your toes tapping and your feet dancing. You don’t want to miss this show.

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Mar
1
7:00 PM19:00

The Luke Sommer Glenn Band - Live Music Outside at 7pm

Join us for live music on our waterfront stage starting at 7pm. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Don’t miss this show. Luke is a Key Largo legend for a reason.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Mar
2
5:00 PM17:00

The Bootleg Band - Sunday at 5pm

We’re SO excited to have the BOOTLEG Band back at the Caribbean Club! Join us for live music on our waterfront stage at 5pm. The BOOTLEG Band is a high energy band that plays excellent classic rock.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open in our backyard serving up delicious smash burgers, taco, bowls and more until 9:30pm.

View Event →
Mar
4
6:00 PM18:00

FELIX THE CATT at 6pm

Join us for a night of reggae, rock and blues by Felix the CATT starting at 6pm EVERY Tuesday on our waterfront stage! Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Come hungry! Food is available from Take Two Food Truck until around 9pm.

See you on the dance floor.

View Event →
Mar
7
6:30 PM18:30

The Joker's Gang Rock Band - Friday at 6:30pm

Join us for live music on our outdoor stage by the Jokers Gang Rock Band from 6:30pm to 10:30pm. Come for sunset and stay to enjoy your favorite songs from the 70s, 80s, and 90s!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Make sure to come hungry, Take Two Food Truck is open and serving up delicious smash burgers, tacos, wings and more until about 9:30pm.

View Event →
Mar
8
7:00 PM19:00

The Luke Sommer Glenn Band - Live Music Outside at 7pm

Join us for live music on our waterfront stage starting at 7pm. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Don’t miss this show. Luke is a Key Largo legend for a reason.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Mar
9
5:00 PM17:00

Sunday with The Luke Sommer Glenn Band at 5pm

Join us for live music on our waterfront stage. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Get ready to dance in the sand..

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Mar
10
6:00 PM18:00

Monday Music - Luke Woltanski 6 to 9pm

Monday Music at the Caribbean Club is from 6 to 9pm on our waterfront stage! Come enjoy a gorgeous sunset and grab a drink from our backyard tiki bar. This week features a performance by singer-songwriter Luke Woltanski from 6 to 9pm. Luke has a distinct style that combines Americanan with Gospel and R&B. Come up to enjoy sunset over the bay, a drink from our backyard tiki bar, and some fantastic live music.

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

View Event →
Mar
11
6:00 PM18:00

FELIX THE CATT at 6pm

Join us for a night of reggae, rock and blues by Felix the CATT starting at 6pm EVERY Tuesday on our waterfront stage! Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Come hungry! Food is available from Take Two Food Truck until around 9pm.

See you on the dance floor.

View Event →
Mar
14
6:30 PM18:30

Velvet Moon - Friday at 6:30pm

Kick off your weekend with live music on our outdoor stage from 6:30pm to 10:30pm by the Velvet Moon Band. Join us for a night of excellent classic rock and another gorgeous sunset on the bay.

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Hungry? Food will be available from Take Two Food Truck until around 9:30pm.

View Event →
Mar
15
11:00 AM11:00

Upper Key's Irish Fest Party

Save the date for the BIGGEST Saint Patrick’s Party in the Upper Keys!

It will be a day filled with live music, a parade, green beer by Islamorada Beer Company, Irish whiskey, corned beef and cabbage, Irish dancers, live musi, vendors, and MORE!

This super fun fundraiser will benefit T.I.P.S. and their work with Key Largo School Athletics and Upper Key Kids.

MORE DETAILS TO FOLLOW

Interested in entering the parade (there’s prizes!!!), being a vendor, or have any questions? Shoot an email to UpperKeysIrishFest@gmail.com

Please drink responsibly. Have a designated driver or call a cab 💚💚💚

View Event →
Mar
15
7:00 PM19:00

The Luke Sommer Glenn Band - Live Music Outside at 7pm

Join us for live music on our waterfront stage starting at 7pm. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Don’t miss this show. Luke is a Key Largo legend for a reason.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Mar
16
5:00 PM17:00

Abstract Radio - Sunday at 5pm

Come up for great live music by these super talented Keys musicians. We’ll have our outdoor tiki bar open, so you never have to go inside and miss a song.

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside!

Hungry? Food will be available from Take Two Food Truck until around 9pm-ish!

View Event →
Mar
17
6:00 PM18:00

Monday Music - Lung Duo 6-9pm

Monday Music at the Caribbean Club is from 6 to 9pm on our waterfront stage! Come enjoy a gorgeous sunset and grab a drink from our backyard tiki bar. This week features a performance by the Lung duo, a pair of local singer-songwriters, from 6 to 9pm. Join us for a gorgeous sunset over the bay, grab a drink from our outdoor tiki bar, and dance in the sand to your favorite classic cover songs plus a few island originals.

Music is rain or shine. If the weather is bad, we’ll move the party inside.

View Event →
Mar
18
6:00 PM18:00

FELIX THE CATT at 6pm

Join us for a night of reggae, rock and blues by Felix the CATT starting at 6pm EVERY Tuesday on our waterfront stage! Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Come hungry! Food is available from Take Two Food Truck until around 9pm.

See you on the dance floor.

View Event →
Mar
21
6:30 PM18:30

The Ray Nichols Band - Friday at 6:30pm

This Friday features the Ray Nichols Band on our waterfront stage from 6:30pm to 10:30pm. Join us for night the best country songs from the 80s to today. Grab a cocktail, take a seat by the water, and watch the sun go down over the bay while listening to some great tunes. What could be better?

Hungry? Take Two Food Truck will be open and serving up delicious food until around 9:30pm

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

View Event →
Mar
22
7:00 PM19:00

The Luke Sommer Glenn Band - Live Music Outside at 7pm

Join us for live music on our waterfront stage starting at 7pm. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Don’t miss this show. Luke is a Key Largo legend for a reason.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Mar
23
5:00 PM17:00

Retro Rebel Rock Band - Sunday at 5pm

Join us for live music by the Retro Rebel Rock Band on our outdoor stage Sunday starting at 5pm. Retro Rebel Rock Band is a female fronted rock band that plays hits from the 60s through the 90s.

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Hungry? Check out the delicious food available from Take Two Food Truck - open in our front parking lot until around 9pm.

See you on the dance floor!

View Event →
Mar
24
6:00 PM18:00

Monday Music - Panorama Duo

Monday Music at the Caribbean Club is from 6 to 9pm on our waterfront stage! Come enjoy a gorgeous sunset and grab a drink from our backyard tiki bar. This week features a performance by the Panorama Duo. Come up for the best of classic rock and enjoy a gorgeous sunset over the bay. Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

View Event →
Mar
25
6:00 PM18:00

FELIX THE CATT at 6pm

Join us for a night of reggae, rock and blues by Felix the CATT starting at 6pm EVERY Tuesday on our waterfront stage! Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Come hungry! Food is available from Take Two Food Truck until around 9pm.

See you on the dance floor.

View Event →
Mar
28
6:30 PM18:30

The Bootleg Band - Friday at 6:30pm

We’re SO excited to have the BOOTLEG Band back at the Caribbean Club! Join us for live music on our waterfront stage at 6:30pm. The BOOTLEG Band is a high energy band that plays excellent classic rock.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open in our backyard serving up delicious smash burgers, taco, bowls and more until 9:30pm.

View Event →
Mar
29
7:00 PM19:00

The Luke Sommer Glenn Band - Live Music Outside at 7pm

Join us for live music on our waterfront stage starting at 7pm. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Don’t miss this show. Luke is a Key Largo legend for a reason.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Mar
30
5:00 PM17:00

South Groove Party Band - Sunday at 5pm

Get ready to dance in the sand! The South Groove Party Band rocks our stage this Sunday at 5pm. This high energy band plays all your favorite hit dance songs. Their music spans genres covering Classic Rock, Alternative Rock, Blues, Country, and Pop Rock. If it's got a dance beat and heavy guitar, then they love to play it!

Music is rain or shine. If the weather doesn’t cooperate, then we’ll move the party inside.

Hungry? Check out Take Two Kitchen’s delicious offerings including smash burgers, tacos, wings, and more. Their food truck is open in our front yard until around 9pm.

See you on the dance floor!

View Event →
Mar
31
6:00 PM18:00

Monday Music - "Street Sinatra" Trevor Darden 6 to 9pm

Monday Music at the Caribbean Club is from 6 to 9pm on our waterfront stage! Come enjoy a gorgeous sunset and grab a drink from our backyard tiki bar. This week features a performance by Trevor Darden aka “Street Sinatra”. Trevor is a classic crooner. Come enjoy the best of R&B, modern soul, big band classics, and originals. You won’t want to miss this performance.

View Event →
Apr
7
6:00 PM18:00

Monday Music - Luke Woltanski 6 to 9pm

Monday Music at the Caribbean Club is from 6 to 9pm on our waterfront stage! Come enjoy a gorgeous sunset and grab a drink from our backyard tiki bar. This week features a performance by singer-songwriter Luke Woltanski from 6 to 9pm. Luke has a distinct style that combines Americanan with Gospel and R&B. Come up to enjoy sunset over the bay, a drink from our backyard tiki bar, and some fantastic live music.

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

View Event →
Apr
21
6:00 PM18:00

Monday Music - "Street Sinatra" Trevor Darden 6 to 9pm

Monday Music at the Caribbean Club is from 6 to 9pm on our waterfront stage! Come enjoy a gorgeous sunset and grab a drink from our backyard tiki bar. This week features a performance by Trevor Darden aka “Street Sinatra”. Trevor is a classic crooner. Come enjoy the best of R&B, modern soul, big band classics, and originals. You won’t want to miss this performance.

View Event →
Apr
28
6:00 PM18:00

Monday Music - Lung Duo 6-9pm

Monday Music at the Caribbean Club is from 6 to 9pm on our waterfront stage! Come enjoy a gorgeous sunset and grab a drink from our backyard tiki bar. This week features a performance by the Lung duo, a pair of local singer-songwriters, from 6 to 9pm. Join us for a gorgeous sunset over the bay, grab a drink from our outdoor tiki bar, and dance in the sand to your favorite classic cover songs plus a few island originals.

Music is rain or shine. If the weather is bad, we’ll move the party inside.

View Event →
May
2
6:30 PM18:30

The Joker's Gang Rock Band - Friday at 6:30pm

Join us for live music on our outdoor stage by the Jokers Gang Rock Band from 6:30pm to 10:30pm. Come for sunset and stay to enjoy your favorite songs from the 70s, 80s, and 90s!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Make sure to come hungry, Take Two Food Truck is open and serving up delicious smash burgers, tacos, wings and more until about 9:30pm.

View Event →

Feb
18
6:00 PM18:00

FELIX THE CATT at 6pm

Join us for a night of reggae, rock and blues by Felix the CATT starting at 6pm EVERY Tuesday on our waterfront stage! Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Come hungry! Food is available from Take Two Food Truck until around 9pm.

See you on the dance floor.

View Event →
Feb
17
6:00 PM18:00

Monday Music - Liana Gabel with James Bristol 6-9pm

Monday Music at the Caribbean Club is from 6 to 9pm on our waterfront stage! Come enjoy a gorgeous sunset and grab a drink from our backyard tiki bar. This week features a performance by Liana Gabel with James Bristol from 6 to 9pm. Don’t miss this truly unique performance featuring a mix of incredible vocals, bass, guitar, tap dancing, and more!

Music is rain or shine. If the weather doesn’t cooperate, we will move the music inside.

View Event →
Feb
16
5:00 PM17:00

Abstract Radio - Sunday at 5pm

Come up for great live music by these super talented Keys musicians. We’ll have our outdoor tiki bar open, so you never have to go inside and miss a song.

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside!

Hungry? Food will be available from Take Two Food Truck until around 9pm-ish!

View Event →
Feb
15
7:00 PM19:00

The Luke Sommer Glenn Band - Live Music Outside at 7pm

Join us for live music on our waterfront stage starting at 7pm. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Don’t miss this show. Luke is a Key Largo legend for a reason.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Feb
14
6:30 PM18:30

Retro Rebel Rock Band - Friday at 6:30pm

Join us for live music by the Retro Rebel Rock Band on our outdoor stage Friday night starting at 6:30pm. Retro Rebel Rock Band is a female fronted rock band that plays hits from the 60s through the 90s.

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Hungry? Check out the delicious food available from Take Two Food Truck - open in our front parking lot until around 9pm.

See you on the dance floor!

View Event →
Feb
13
6:00 PM18:00

Girls Night Out Market and Fundraiser 6 to 9pm

Grab your girlfriends and join us for a Girls Night Out Market on Thursday, February 13th from 6pm to 9pm.

This event is a fundraiser for the Florida Keys Healthy Start Coalition and the amazing work they do with pregnant women and new families. In Monroe County, 3 out of 4 pregnant women and their families receive assistance through Healthy Start programs each year. They are a vital resource in our community.

Our Girls Night Out Market will feature over 20 female owned businesses set up in our backyard showcasing and selling their goods.

Make sure to check out our raffle!
*50/50 Raffle
*Lotto Basket with $500 of scratch off tickets!
*Each booth will have donated an item to be raffled off!

The Caribbean Club’s outside bar will have fun girly drink specials and a mimosa bar set up!

Adam Musick will be playing our outdoor stage from 6pm to 9pm.

It is going to be a great night for a wonderful cause. Hope to see you all there!

Here are just some of the exciting vendors to expect:

Linking in the Keys - Permanent Jewelry

Ho-Made Doggie Delectables - Homemade dog treats & more

Lion Fish Jewelry - Jewelry & more

Costa Vida Design - Handmade, artisan jewelry

Anchors Away Art & Antiques - Candles, salt scrubs, decor & more

Owl Talyn Press - Fantasy novels written by a FL Key local

Tatts N Tits - Fun apparel, accessories, & more

Florida Keys Wild Bird Center - Themed merchandise

Kadan Swimwear - Unique bikinis and more

Carrlee’s Designs - Handmade and up-cycled yoga accessories

Anchors Away Art & Antiques - Candles, buoy art, salt scrubs and more

Reps & Relax - Personal training and mobile stretching and massage

Key Largo Group Exercise Program - Zumba, yoga, strength, & more group classes

Moana & Kai - Organic baby and kid clothing

Angagi Jewels - Handmade artisan jewelry

Cary Castro Designs - Resort wear

Jannac-Resin Art. -handmade resin art

Lighthouse Learning = handmade crochet animal toys and collectables

Key Z Crafts - handmade art and more

Interested in being a vendor? We are currently at capacity, but if you’d like to be put on our waitlist, please fill out our application here: https://form.jotform.com/243175858579172

See less

View Event →
Feb
11
6:00 PM18:00

FELIX THE CATT at 6pm

Join us for a night of reggae, rock and blues by Felix the CATT starting at 6pm EVERY Tuesday on our waterfront stage! Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Come hungry! Food is available from Take Two Food Truck until around 9pm.

See you on the dance floor.

View Event →
Feb
10
6:00 PM18:00

Monday Music - Panorama Duo

Monday Music at the Caribbean Club is from 6 to 9pm on our waterfront stage! Come enjoy a gorgeous sunset and grab a drink from our backyard tiki bar. This week features a performance by the Panorama Duo. Come up for the best of classic rock and enjoy a gorgeous sunset over the bay. Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

View Event →
Feb
9
5:00 PM17:00

Sunday with The Luke Sommer Glenn Band at 5pm

Join us for live music on our waterfront stage. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Get ready to dance in the sand..

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Feb
8
7:00 PM19:00

The Luke Sommer Glenn Band - Live Music Outside at 7pm

Join us for live music on our waterfront stage starting at 7pm. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Don’t miss this show. Luke is a Key Largo legend for a reason.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Feb
7
6:30 PM18:30

The Joker's Gang Rock Band - Friday at 6:30pm

Join us for live music on our outdoor stage by the Jokers Gang Rock Band from 6:30pm to 10:30pm. Come for sunset and stay to enjoy your favorite songs from the 70s, 80s, and 90s!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Make sure to come hungry, Take Two Food Truck is open and serving up delicious smash burgers, tacos, wings and more until about 9:30pm.

View Event →
Feb
4
6:00 PM18:00

FELIX THE CATT at 6pm

Join us for a night of reggae, rock and blues by Felix the CATT starting at 6pm EVERY Tuesday on our waterfront stage! Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Come hungry! Food is available from Take Two Food Truck until around 9pm.

See you on the dance floor.

View Event →
Feb
2
11:00 AM11:00

The 16th Annual Ralphie Walk - A Poker/Pub/Bra Crawl for Charity

Join us for one of our favorite events of the year!

The 16th annual Ralphie Walk is Sunday, February 2nd starting at 11am at Sharkey’s.

Everyone is encouraged to decorate your most creative bra and/or tutu and join in on the fun.

Registration is at Sharkey’s on the day of the event and is a $25 donation and includes 6 poker sheets. Additional poker sheets are available for purchase.

Participants with the best poker hand at the end of the walk will win exciting prizes!

All money raised is donated directly to the Cancer Foundation of the Florida Keys and the Upper Keys Humane Society.

We’ll finish with a HUGE party at the Caribbean Club featuring live music by the BEST of Upper Keys musicians.

Other exciting things to look for:

Jell-O shots

50/50 raffle

Basket of cheer raffle

Restaurant raffle

Silent auction

and much, much more!

Hope to see you there!

View Event →
Feb
1
7:00 PM19:00

The Luke Sommer Glenn Band - Live Music Outside at 7pm

Join us for live music on our waterfront stage starting at 7pm. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Don’t miss this show. Luke is a Key Largo legend for a reason.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Jan
31
6:30 PM18:30

Koty James and the Keybillies Band - Live Music Outside 6:30pm - 10:30pm

Koty James and the Keybillies play the best of old school country and classic rock! These local boys will have your toes tapping and your feet dancing. You don’t want to miss this show.

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

View Event →
Jan
28
6:00 PM18:00

FELIX THE CATT at 6pm

Join us for a night of reggae, rock and blues by Felix the CATT starting at 6pm EVERY Tuesday on our waterfront stage! Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Come hungry! Food is available from Take Two Food Truck until around 9pm.

See you on the dance floor.

View Event →
Jan
27
6:00 PM18:00

Monday Music - Thor Platter 6 to 9pm

Monday Music at the Caribbean Club is from 6 to 9pm on our waterfront stage! Come enjoy a gorgeous sunset and grab a drink from our backyard tiki bar. This week features a performance by singer-songwriter Thor Platter from 6 to 9pm. Know for his soulful, Americana-infused sound and poetic lyrics, Platter is sure to create a night of music you won’t gorget. Come enjoy sunset, grab a drink from our backyard tiki bar, and groove to the best of classic country, rock and roll, and original tunes.

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

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Jan
26
5:00 PM17:00

South Groove Party Band - Sunday at 5pm

Get ready to dance in the sand! The South Groove Party Band rocks our stage this Sunday at 5pm. This high energy band plays all your favorite hit dance songs. Their music spans genres covering Classic Rock, Alternative Rock, Blues, Country, and Pop Rock. If it's got a dance beat and heavy guitar, then they love to play it!

Music is rain or shine. If the weather doesn’t cooperate, then we’ll move the party inside.

Hungry? Check out Take Two Kitchen’s delicious offerings including smash burgers, tacos, wings, and more. Their food truck is open in our front yard until around 9pm.

See you on the dance floor!

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Jan
25
7:00 PM19:00

The Luke Sommer Glenn Band - Live Music Outside at 7pm

Join us for live music on our waterfront stage starting at 7pm. The Luke Sommer Glenn Band plays the best of Classic Rock and Outlaw Country! Don’t miss this show. Luke is a Key Largo legend for a reason.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open and serving up delicious smash burgers, tacos, and more until about 9:30pm.

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Jan
24
6:30 PM18:30

The Bootleg Band - Friday at 6:30pm

We’re SO excited to have the BOOTLEG Band back at the Caribbean Club! Join us for live music on our waterfront stage at 6:30pm. The BOOTLEG Band is a high energy band that plays excellent classic rock.

Come enjoy the bayside breeze, a beautiful sunset over the bay, and great live music!

Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party to the indoor stage.

Hungry? Take Two Food Truck will be open in our backyard serving up delicious smash burgers, taco, bowls and more until 9:30pm.

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Jan
21
6:00 PM18:00

FELIX THE CATT at 6pm

Join us for a night of reggae, rock and blues by Felix the CATT starting at 6pm EVERY Tuesday on our waterfront stage! Music is rain or shine. If the weather doesn’t cooperate, we’ll move the party inside.

Come hungry! Food is available from Take Two Food Truck until around 9pm.

See you on the dance floor.

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104080 Overseas Hwy,
Key Largo, FL 33037
(305) 451-4466