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New Yorkers 1st Choice
Best of Florida

Live music and whiskey

Made for those who believe a glass of whiskey is the only proper accompaniment to a live musical performance.

Based on 690 Opinions
+687
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Updated May 2026
01
Ruby's Elixir image 1
Ruby's Elixir image 2
Live music bar

Small venue combines live music six nights a week with a connected cigar bar offering a wide selection of cigars and cocktails. Dark lighting and vintage instruments create a speakeasy vibe that feels like stepping into another era. Regulars enjoy jazz and expertly crafted drinks in an intimate, lively setting.

Live music plays every night with a variety of performances. The venue pairs good drinks and cigars alongside the music.

Cocktails feature fresh ingredients like turmeric, ginger, lemon, and whiskey in the Grandpa Reviver. The selection includes Habiki 17 Japanese whiskey and pairs well with live music and cigars.

People are saying

"The live music here creates a heavy, lively, and electric atmosphere."

"You can buy cigars and enjoy live R&B music here."

"Mr. Benny's whiskey cocktails are made with fresh ingredients and poured with love."

Good to know

1

Expect live music every night, with jazz performances on Thursdays.

2

Happy hour runs from 4pm to 8pm, but days are not specified.

3

Smoking is allowed inside, which may not suit all guests.

02
Mary Margaret's Olde Irish Tavern image 1

Old world Irish pub with dark wood bar, dim lighting, and walls full of history creates an authentic atmosphere. Live traditional Irish music fills the space, making it lively and enjoyable. Frequented by those seeking genuine Irish vibes and well-poured Guinness, it stands out among local bars.

Frequent live music features Irish folksongs and a live band that plays well. The vibe shifts from relaxing early on to pretty Crunk late at night.

Offers a great selection of Irish whiskeys with whiskey and Guinness specials. The whiskey tastes delicious and well curated.

People are saying

"The drinks here are made really well and mixed perfectly."

"The live music here is amazing and perfect."

"I loved the terrific Irish whiskey selection."

Good to know

1

Wings cost $1 each on Wednesdays.

2

Happy hour menu is available with discounts.

3

Karaoke happens on Mondays.

03
Tarpon Springs Distillery image 1

Small distillery with in-house spirits offers a laid-back atmosphere featuring live music and dog-friendly outdoor seating. The space feels comfortable and casual with a Cheers-like vibe at the bar. Tours include generous tastings and showcase unique flavors like hot and spicy gin and avocado gin.

Free live music plays on weekends and Friday nights with a great setup. The combination of live music and great service creates a relaxing evening atmosphere.

Whiskey offerings include a Single Malt, wheat whisky, and a whiskey flight with detailed descriptions. The spirits are smooth and well-crafted, notable for a small distillery.

People are saying

"They host live music events on weekends."

"I thought the cocktails were some of the best I've ever had."

"I loved the whiskey tasting, it was informative and amazing."

Good to know

1

Reservations are required for the free distillery tour and tasting.

2

Parking is available at a nearby restaurant when the distillery lot fills up.

3

The distillery offers free live music on Friday nights.

04
Grand Cathedral Cigars image 1

Cigar lounge occupies a beautifully restored 118-year-old church with historic stained glass and wood design. Atmosphere blends classy, respectful patrons with live piano music and a well-curated humidor. Outdoor patios offer seating for gatherings including non-smokers.

Live music here is consistently fantastic and delivers an awesome experience.

A great whiskey selection stands out here, with a bar stocked beyond typical high-end whiskey spots. The variety includes whiskey, whisky, rum, and tequila, making it a solid choice for whiskey lovers.

People are saying

"The staff here is so helpful when you buy cigars."

"I loved the fantastic whiskey collection and great cigars."

"The live music here is fantastic, especially the piano."

Good to know

1

Live music events occur Wednesday through Saturday from 6 to 10 pm.

2

Unique events like the 'Tampa Bay Whiskey Voyage' are hosted regularly.

3

Every weekend features live music performances, including Cuban music.

05
The Castle Irish Pub and Restaurant image 1

Space resembles authentic Irish pub with handmade Irish furnishings and imported decor. Atmosphere feels warm and inviting, enhanced by live traditional Irish music that energizes the room. Crowd enjoys late-night pub vibe with plenty of room and sports on TVs.

Live music fills the pub with a late night pub vibe that suits both family dinners and friends hanging out. Performances create a space for conversation and a pint at the bar.

A big selection of whisky, bourbon, and scotch fills the menu. Staff share detailed info and recommend options like the Yellow Spot 12 and Celtic Old Fashion for whiskey drinkers.

People are saying

"The bar has an intimate atmosphere with great Irish music and drinks."

"The live music and Irish dancer really made it feel authentic."

"I loved the fish and chips; they were perfectly light and crispy."

Good to know

1

Happy hour offers discounted food and drinks from 4-7pm on weekdays.

2

Live Irish music sessions occur on select Sundays, featuring various musicians.

3

St. Patrick's Day features traditional dishes like fish and chips and shepherd's pie.

06
Central Cigars image 1
Cigar shop

Classic cigar lounge with indoor and outdoor seating offers a top-notch cigar and whiskey selection. Atmosphere blends live jazz and dancing, creating a lively yet relaxed vibe. Regulars enjoy camaraderie and sports viewing with drinks in a space that feels both luxurious and welcoming.

Live music plays every night in the back lounge after 7 PM, featuring great bands and a variety of styles. The crowd is mixed and dancing is common, with excellent service throughout.

Selection includes premium cigars paired with top-shelf whiskey and Scotch. Bourbon and whiskey options cover a good range.

People are saying

"Paul, the bartender, was awesome company."

"I loved their great and top-notch whiskey selection."

"You can catch live music every night with great bands."

Good to know

1

Parking is available via pay-by-app street parking, which is usually full.

2

There is a nearby paid parking garage for additional parking options.

3

The restroom and table seating are wheelchair accessible, both indoors and outdoors.

07
Red Phone Booth image 1

Entrance through an iconic red phone booth leads to a speakeasy vibe with an upscale lounge feel. The atmosphere stays relaxed and sophisticated, featuring expertly crafted cocktails and a classy cigar lounge with impressive ventilation and humidor selection.

Live jazz music creates a velvety sound that enhances the atmosphere. Impressively crafted cocktails complement the music seamlessly, making live music nights a notable feature.

An extensive rare whiskey selection stands out here, paired with expertly crafted cocktails. The lounge offers a craft cocktail menu that complements the whiskey choices well.

People are saying

"These craft cocktails are some of the best I've ever tasted."

"The whiskey selection here is rare, just like the speakeasy vibe."

"The craft cocktails here are expertly crafted and complement the live music."

Good to know

1

Red Phone Booth is an ideal spot for both corporate and private events.

2

Reservations are recommended for private events to ensure availability.

3

The venue offers a unique speakeasy vibe that enhances the event experience.

08
Smoke & Barrel Cigar Lounge image 1

Leather chairs and soft lighting create a cozy, inviting atmosphere ideal for relaxing with cigars. Live music, including jazz and piano, adds a lively, engaging mood to the space. A state-of-the-art smoke extraction system keeps the air fresh despite the extensive premium cigar selection and full bar.

Live music sets an incredible tone with a live singer creating a strong vibe. The owners focus on ambience and have improved the music experience significantly.

Whiskey selection includes whisky and tequila options that pair well with cigars. Bartenders may lack familiarity with basic drinks like the whiskey sour.

People are saying

"The bar staff, especially Gene, makes you feel so welcome."

"It's a truly welcoming community with friendly, attentive staff."

"I loved their whisky and tequila selections."

Good to know

1

Live music happens every Friday and Saturday night, creating a lively atmosphere.

2

Weekly alcohol tastings are offered, providing a chance to try new drinks.

3

Reservations are recommended for busy weekend nights to secure a spot.

09
Flute & Dram image 1

Bar offers indoor and outdoor seating with a welcoming patio and live music seven days a week. Atmosphere suits whiskey and cigar enjoyment alongside people-watching and socializing. Space includes multiple areas for relaxation and features a classy vibe with a dance floor and scenic views.

Live music features a wonderful acoustic singer and live singers that create a great atmosphere. The music pairs well with good drinks and attentive service.

Wide variety of whiskey options and great cocktails fill the menu. The excellent bourbon and whiskey selection pairs well with a relaxed atmosphere for sipping and people-watching.

People are saying

"The drinks here stack up quickly and are excellent."

"I found the live music here really enjoyable."

"I loved their great and excellent whiskey selection."

Good to know

1

Happy hour runs from 4-7pm on weekdays with half-price appetizers.

2

Live music performances occur at 4pm on select days, including 12/8.

3

The bar accepts credit cards and mobile payments, but cash is preferred for tips.

10
James Joyce Irish Pub & Eatery image 1

Small space with dive bar style and fun decor creates a comfortable, authentic Irish pub vibe. Live music adds energy while inside and outside seating offer options. Known for excellent Guinness and classic Irish dishes.

Lively atmosphere with live music every day. Karaoke nights add to the fun vibe and keep the energy up.

A strong Irish whiskey selection stands out here, with unique options like the Dick Pic shot that pairs whiskey with a pickle back chaser. Whiskey challenges and trivia nights add a fun, engaging twist to the experience.

People are saying

"The pub food here is excellent, fresh, and tasty."

"They have an excellent and large selection of beers on tap."

"The staff here are outstanding and fantastic."

Good to know

1

Karaoke happens every Saturday night at 9 pm with no cover charge.

2

Trivia night is on Thursdays, starting at 7 pm with a $5 entry fee.

3

Lady's night offers half off drinks every Wednesday.

11
Angry Moon Cigars image 1

Lounge offers indoor and outdoor seating next to a marina view, creating a relaxing atmosphere with an upscale vibe. Live music features piano and woodwind instruments, adding to the lively energy on weekend nights. A large walk-in humidor and full bar provide an extensive cigar and drink selection.

Great live bands play here with classic woodwind instruments and piano music. Occasional DJ sets add variety to the live music experience.

Offers a very good selection of scotch, whisky, bourbon, and cognac. The whiskey Scotch collection stands out but tends to be on the expensive side.

People are saying

"It's a great place to relax and smoke cigars with a nice marina view."

"The nightlife here offers comfortable seating with a beautiful marina view."

"The live music here felt like being front row at a concert."

Good to know

1

Drinks and cigars can cost around $30 each, so be prepared to spend.

2

Live music is available from Tuesday through Saturday, starting around 8pm.

3

Expect to spend about $80 per person for a decent experience.

12
Fiddlers Green Irish Pub & Eatery image 1

Irish pub offers authentic Irish atmosphere with dark interior and cozy pet-friendly patio. Live music plays on weekends, enhancing the lively vibe. Multiple dart boards and a huge projector screen add to the entertainment options.

Live music creates a fun atmosphere with lively patrons and pairs well with good drinks and authentic Irish fare.

An outstanding assortment of Irish whiskey stands out here, with a killer whiskey list that pairs well with hearty pub fare. Bartenders offer personalized whiskey recommendations to guide your choice.

People are saying

"This pub has such an authentic, cozy vibe."

"They have lots of beer options on tap."

"They have a nice selection of whiskey."

Good to know

1

Trivia night happens every Thursday, which can get loud and rowdy.

2

On weekends, enjoy $4 mimosas and $5 Bloody Marys.

3

Parking can be difficult depending on the timing of your visit.

13
King Corona Cigars Bar And Cafe image 1

Cigar lounge offers spacious indoor and outdoor seating with a giant humidor featuring a wide cigar selection. Atmosphere stays relaxed and classy with live music and multiple TVs for sports. Renovated interior includes upgraded fittings and a sheltered terrace, creating a comfortable place to unwind.

Live music plays on weekends, creating a relaxed vibe that fits well with conversation and catching up. The bar and cafe both host performances, adding a musical backdrop to the atmosphere.

An incredible whiskey selection includes Elijah Craig Kentucky Straight Bourbon and Red Breast Canadian whiskey. The bar stocks every whiskey and whisky needed to pair with cigars perfectly.

People are saying

"You can buy cigars here with a great selection and knowledgeable staff."

"The live music here is a perfect backdrop for conversation."

"I found the whiskey selection to be incredible."

Good to know

1

Live music happens on Saturday nights, creating a lively atmosphere.

2

A tasting event is planned soon, offering a chance to sample various cigars.

3

Saturday night is popular for watching cars cruise by the lounge.

14
St. Petersburg Distillery image 1

Industrial-chic space with covered seating and a large outdoor garden hosts live DJs and food trucks, creating a vibrant, welcoming atmosphere. Art installations like a glass vat sculpture add creative flair, while the crowd enjoys finely crafted spirits and cocktails in a laid-back setting.

Live music plays on Fridays and Saturdays with performances at the Garden and the distillery. The shows create a lively atmosphere with regular weekend sets and varied musical acts.

The whiskey here includes a solid 8-year option that stands out during tastings. Visitors can select from a variety of spirits, but the whiskey offers a real treat for those interested in liquor production and flavor.

People are saying

"The matcha martini with strawberry cold foam is something I'll be dreaming about."

"The Whiskey guides are so knowledgeable and passionate."

"I liked the live music they had."

Good to know

1

Tastings are available, but no actual bar service is offered.

2

The distillery frequently hosts new events and classes.

3

Live music occurs on Fridays and Saturdays.

15
Callahanโ€™s Irish Bistro image 1

Irish bistro with cozy, authentic pub decor and warm lighting creates a friendly, inviting atmosphere. Live music and multiple TVs offer a lively, laid-back vibe, especially during sports events. Known for properly poured Guinness and standout Irish dishes like Bangers and Mash and Irish egg rolls.

Live music features talented musicians and local bands playing energetic tunes. The atmosphere stays fun, laid-back, and lively during music nights.

Selection features authentic Irish whiskey and whiskey flights alongside a well-curated ale menu. Creative signature cocktails complement the beer and whiskey bar offerings.

People are saying

"The staff here make you feel right at home on your date."

"The live music here creates a fun, lively atmosphere."

"The Irish dishes here are incredible, with a fresh twist."

Good to know

1

Karaoke night happens every Tuesday at 8pm with a two-drink minimum.

2

Trivia night is held every Wednesday at 7pm; no reservations needed.

3

Happy hour runs from 4-6pm on weekdays with discounted drinks.

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