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New Yorkers 1st Choice
Top picks in Winter Park

Cool spots with outdoor space

An outdoor space that feels genuinely cool instead of just being a patch of concrete with a few chairs.

Based on 739 Opinions
+736
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Updated May 2026
01
Tommy Bahama Marlin Bar image 1
Tommy Bahama Marlin Bar image 2
Tommy Bahama Marlin Bar image 3
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Bright island decor and an outdoor patio with live music create a laid-back atmosphere. Self-seating and cooling fans on the patio support a relaxed vibe where conversation can be lively. The bar draws a crowd looking to unwind with quality cocktails and casual bites.

Shaded patio features a misting system that sprays a cool, gentle mist. This keeps the outdoor area comfortable even in hot weather.

Spacious outdoor seating offers shade and misting fans that keep the area cool and comfortable. The pet friendly patio features live music that adds to the cozy and romantic atmosphere.

People are saying

"The food here is top-notch, especially the coconut shrimp."

"The outdoor space has a misting system that keeps it cool."

"The misting system keeps the patio cool and comfortable."

Good to know

1

Happy hour occurs every day from 3-6pm with discounted drinks.

2

All seating is outdoor with no air conditioning available.

3

The happy hour menu offers drinks only a few dollars off normal price.

02
Morse Code Lounge image 1

Wine bar offers an elegant interior with stylish decor and an upscale atmosphere. Live jazz and DJs provide a dynamic music scene that encourages dancing and relaxation. The space includes an inviting outdoor area, making it suitable for both quiet evenings and lively nights.

Stylish decor and a cool DJ set the tone for a relaxed vibe. The bar staff and crowd, especially during the SUNDAY FUNDAY JAM SESSION, add to the cool atmosphere.

A cozy outdoor patio offers a homey vibe where people chat and mingle. A nice outdoor area for cigars adds to the relaxed, social atmosphere.

People are saying

"This bar has a super chill, cozy, and stylish vibe."

"The vibe here is so cool, especially with the outstanding decor."

"The outdoor space is social and relaxed, perfect for mingling."

Good to know

1

The lounge hosts 'SUNDAY FUNDAY JAM SESSIONS' every 3rd Sunday.

2

Check their website or Facebook for live music and upcoming events.

3

Happy hour is a great time to visit for drinks and bites.

03
Forward Slash Distillery & Blending House image 1

Warehouse-style distillery and blending house offers a quiet, small batch vibe with unique whiskey flights and a wall of experiments. Indoor and outdoor seating includes a large smoking area with a great cigar selection. The atmosphere feels like relaxing with old friends, enhanced by R&B and Hip Hop music.

Flights of whiskey and a wall of experiments create a cool vibe in the tasting room and blending lab. Unique cups for drinks and insights into the still and barrels add to the chill spot atmosphere for catching up with friends.

A large outside smoking area offers plenty of space to enjoy cigars and drinks. The outdoor patio adds a chill ambiance with both outdoor and indoor seating available.

People are saying

"The whiskey tasting experience with Tim was unforgettable."

"This is a great spot for a fun date or drinks after dinner."

"I loved the amazing craft cocktails here."

Good to know

1

The distillery offers tours until 9 pm on weekdays.

2

Parking is easy at the location.

3

The whiskey tasting experience is highly recommended.

04
Bricks & Bowls image 1
Restaurant

Courtyard restaurant offers outdoor-only seating with fans and misting machines that keep the space cool and comfortable. The atmosphere feels cozy and peaceful, tucked away in a private, clean patio that invites relaxation and quiet dining.

Outdoor seating features misting fans and water mists that help cool the area. Small fans exist but could be stronger for better cooling.

Outdoor seating offers a clean, quiet, and comfortable spot to relax. The patio is pet friendly and features misting machines that keep it cool even on hot days.

People are saying

"The outdoor seating is beautifully furnished and kept cool with misting fans."

"The outdoor seating area is beautiful and unique."

"The misting fans really keep you cool on a sunny day."

Good to know

1

The restaurant has no indoor seating, only outdoor options available.

2

Expect to dine outside in potentially uncomfortable weather conditions.

3

Happy hour is available in the courtyard, providing a relaxed atmosphere.

05
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.

The pub has a super cool vibe that stands out. It offers a cool break from daily activities and shopping.

Cozy patio seating faces the parking lot and welcomes pets. The outdoor area feels inviting and well-kept.

People are saying

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

"The pub's vibe is super cool and dark inside."

"The outdoor space here is really nice and cozy."

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.

06
Winter Park Biscuit Company image 1

Outdoor seating with garden picnic tables and dog-friendly shade creates a relaxed vibe. The space feels hipster-ish and trendy, nestled among small shops in a lively market setting. Energy stays upbeat with a pristine, compact layout that maximizes limited space.

Multiple floors house different spots, creating a dynamic vibe. The atmosphere feels trendy and inviting.

People are saying

"The vegetarian chicken sandwich is the best I've ever tasted."

"You can sit outside at picnic tables, enjoying the flowers and herbs."

"It's a cool place with lots of other shops and food options."

Good to know

1

The restaurant only accepts card payments; no cash is accepted.

2

Parking can be difficult, especially during busy hours.

3

The restaurant closes at 7 PM, so plan your visit accordingly.

07
AJ Chocolate House image 1
Chocolate cafe

Chocolate cafe combines European-inspired design with live jazz music and a romantic, cozy atmosphere. Guests enjoy gourmet chocolates alongside espresso martinis and wine, creating a setting suited for celebrations or intimate evenings.

A cool euro cafe style vibe sets the tone with a romantic ambiance that feels like being in Europe. The place has a unique and charming atmosphere that stands out.

Outdoor seating includes a few tables outside and many inside. The decor adds a unique touch to the space.

People are saying

"The chocolates here are exceptional, rich, and full of flavor."

"I loved the great espresso and excellent chocolate-focused items."

"I found the euro cafe style vibe to be pretty cool."

Good to know

1

Bottomless mimosas are available on weekends for $25.

2

Musical entertainment occurs every Friday night.

3

Ladies night with live music happens every Tuesday.

08
Gideon's Bakehouse image 1

Small, dimly lit bakery with gothic, Tim Burtonesque decor and Harry Potter-style theming creates an enchanting, spooky vibe. Space feels cramped and busy, located inside a food hall with plenty of outdoor seating. Known for exceptional cookies that draw long lines and consistent praise.

The atmosphere has a gothic, Edgar Allen Poe vibe with a hint of Harry Potter style. Staff stay friendly and polite, and the checkout desk adds to the cool feel.

Staff provide umbrellas while waiting outside. The outdoor dining area offers a spot to enjoy cookies and coffee.

People are saying

"These cookies are shockingly good and worth every penny."

"These cookies are unique, massive, and dense culinary art."

"There's plenty of outdoor seating to enjoy your treats."

Good to know

1

Parking can be difficult in the area because of the high foot traffic.

2

Hot cookie hour offers a unique experience; plan your visit around it.

3

Placing an order ahead is recommended to avoid long wait times.

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Winter Park, Florida

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