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Local picks in Florida

Jazz on rooftops

You want the atmosphere of a live jazz performance paired with the open air of a rooftop.

Based on 530 Opinions
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Updated May 2026
01
Sterling Cigar Lounge & Bar image 1
Sterling Cigar Lounge & Bar image 2
Sterling Cigar Lounge & Bar image 3
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Rooftop cigar lounge offers city views and a laid-back atmosphere with live jazz music enhancing the experience. The space features premium cigars and classy indoor-outdoor seating, attracting those who appreciate a mellow, intimate vibe.

Live jazz plays on the rooftop terrace, creating a relaxed atmosphere. Music often fills the balcony area, especially on Fridays, adding a vibrant touch to the evenings.

Rooftop offers great views of Ybor from the 4th floor with a vibe that stands out at night. It combines cigar lounge comfort with a spot for drinks, making it a notable rooftop bar experience.

People are saying

"This Day Lounge has a beautiful, relaxed atmosphere with great rooftop views."

"The cigar lounge here is unreal, with a great selection of premium cigars."

"This rooftop cigar lounge is the best I've experienced in Tampa."

Good to know

1

Live music is featured from Thursday to Sunday between 8 and 11 pm.

2

Jazz night occurs on Thursdays from 9 to 11 pm, perfect for date night.

3

Latin night is hosted every Tuesday, offering a vibrant atmosphere.

02
The Roof at Esme Hotel image 1

Rooftop bar with breathtaking city views and a vibrant yet relaxed atmosphere. Music ranges from live jazz bands to vinyl DJ sets, creating a smooth, chill vibe. Crowd energy feels genuine and unpretentious, fitting both casual and business occasions.

Live jazz bands bring a laid-back atmosphere with super talented musicians. Weekly jazz nights offer a fun vibe, best enjoyed from a table on the rooftop.

A cozy rooftop with a nice pool and a serene atmosphere offers a great spot for drinks like espresso martinis. Sunday Soul & Jazz Night adds a lively vibe, best enjoyed from a table rather than the bar.

People are saying

"Federico, the bartender, made the rooftop experience so welcoming and fun."

"The atmosphere here is super laid back and chill."

"The live jazz band was amazing and created a perfect laid-back atmosphere."

Good to know

1

Happy hour runs from 4-7pm with discounted drinks and appetizers.

2

Jazz Night occurs every Sunday, featuring live music and a vibrant atmosphere.

3

Expect a premium for off-menu drinks; ask for prices before ordering.

03
Tom's Watch Bar- Sky Bar image 1

Sports bar with numerous screens and immaculate rooftop views creates an energetic atmosphere, especially during NFL Sundays. Outdoor seating and live music, including jazz and DJs, add to the lively vibe. The crowd includes many passionate fans, making it a prime spot for game watching.

Jazz music creates an amazing atmosphere that really enhances the vibe. The jazz band performs phenomenally and keeps the energy high while the bar service stays attentive.

Rooftop patio offers a great vibe with a beautiful view of the International Drive area and all around Orlando. Attentive service and knowledgeable staff enhance the rooftop dining experience.

People are saying

"I found the food here to be great."

"Hector, our server, was attentive and knowledgeable."

"The jazz music here is amazing and really enhanced the atmosphere."

Good to know

1

Bring your parking ticket for validation of the first hour of parking.

2

A service fee is added to bills without clear disclosure.

3

VIP tickets are available for special events like the Super Bowl.

04
The Betsy Hotel image 1

Historic building blends old colonial charm with stylish sophistication in spacious, comfortable rooms. Quiet atmosphere features live jazz and a rooftop pool and bar that draw a relaxed, art-loving crowd. Multiple entrances and cozy atrium create a welcoming, home-like vibe.

Live jazz plays in the background creating a welcoming atmosphere. The hotel hosts jazz evenings featuring performers like Tal Cohen alongside poetry readings and exhibitions.

People are saying

"The hotel staff here are genuinely engaging and treat you like owners."

"The rooftop pool offers beautiful views and great service."

"I loved the live jazz piano evenings here."

Good to know

1

Live music is available until 11pm every night, enhancing the relaxed vibe.

2

Free live jazz sessions feature Grammy-awarded artists on select evenings.

3

Yoga sessions on the roof start at 7:30 AM, offering a unique experience.

05
Red Rooster Overtown image 1
American restaurant

Vibrant interior with lush greenery and colorful murals creates an upscale yet welcoming atmosphere. Live music featuring saxophone and DJ sets adds a lively southern vibe. Outdoor spaces include a covered patio under a large tree and a rooftop with Caribbean influences.

Live jazz music sets a great vibe with a gospel jazz trio and a jazz singer adding to the lovely ambiance.

Upstairs offers a cozy and relaxing atmosphere with strong Caribbean vibes. Monthly house music parties add energy to the rooftop nights.

People are saying

"The oxtail here is so tender and explodes with flavor."

"The food here is amazing, especially the fried chicken."

"The rooftop vibes at night create a great atmosphere."

Good to know

1

Happy hour runs until 7 p.m. daily with discounted drinks and appetizers.

2

Reservations are recommended as the restaurant can get very packed.

3

Parking is available but can be challenging; arrive early to secure a spot.

06
Hotel Greystone image 1

Small art deco building offers a quiet, charming atmosphere with a spacious rooftop pool and stylish interior design. Guests enjoy creative cocktails and a serene pool area with great music. The hotel sits just one block from the ocean, blending boutique comfort with easy beach access.

Live jazz performances happen Thursday through Saturday with artists like pianist Tal Cohen. The jazz lounge serves creative cocktails such as the Oaxaca old fashioned, and the staff in the jazz bar are friendly and attentive.

People are saying

"Julie at the Hotel provided personalized, professional, and helpful service."

"The rooftop pool area was clean and inviting."

"The jazz bar has live music and friendly staff."

Good to know

1

The hotel charges a daily resort fee for towels, pool, and beach access.

2

There is no parking available, and valet service is nonexistent.

3

The hotel offers a rooftop happy hour with 2 for 1 cocktails.

07
The Catalina Hotel & Beach Club image 1

Boutique hotel with modern design and bright, spacious rooms offers an upbeat atmosphere fueled by loud music from an on-site bar and restaurant. Rooftop pool area attracts a crowded, lively crowd often smoking hookah. Common areas remain clean and well maintained despite some noisy surroundings.

Lively jazz performances create a vibrant atmosphere. Staff like Jazz and Ale offer friendly and accommodating service during events.

A rooftop pool offers a refreshing spot with great views. The rooftop bar adds a nice perk for drinks and relaxation.

People are saying

"The rooms were comfortable and very clean."

"The rooftop pool is pretty sweet and great for kids."

"Jazz and Ale were amazing and very accommodating."

Good to know

1

Parking costs $43 and is only available as valet parking.

2

The hotel charges a hidden resort fee of $70 for two nights.

3

Guests receive a complimentary drink at the bar next door during happy hour.

08
Grand Bohemian Orlando, Autograph Collection image 1

Hotel offers spacious rooms with a bohemian vibe and modern decor. Atmosphere blends elegance and comfort with artistic touches and a luxury feel. Rooftop pool and bar provide great views and a lively social spot.

Sundays feature a jazz brunch with a live pianist creating a wonderful atmosphere. The combination of live jazz, great food, and unique architectural elements makes the experience stand out.

The rooftop features a pool with stunning views and a lounge with perfect temperature. Food and service at the rooftop bar are excellent, with friendly and attentive staff.

People are saying

"The hotel staff's kindness and helpfulness made my stay so special."

"The Rooftop bar's food was excellent and the servers were great."

"The live jazz here creates a wonderful atmosphere."

Good to know

1

Reservations are required for the jazz brunch on Sundays due to high demand.

2

Sam performs live on Saturday nights from 5 PM to 8 PM.

3

Valet parking is the only option available upon arrival.

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