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New Yorkers 1st Choice
Local picks

Chill spots in Windy Hill

The noise of the day fades away when there is finally a quiet place to sit and do nothing.

Based on 493 Opinions
+490
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Updated May 2026
01
Cigars International Superstore image 1
Cigars International Superstore image 2
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Humidor boasts a vast cigar selection and a spacious walk-in humidor. Lounge offers comfortable seating indoors and outdoors with a full bar and fire pit. Strong ventilation keeps air fresh, while a laid-back crowd creates a chill vibe perfect for watching games and relaxing.

A laid back crowd creates a very chill environment. The lounge offers a spot to watch games and relax casually.

People are saying

"It's a great place to buy cigars and relax with a good bourbon."

"The nightlife here is amazing, especially Adriana's service and the exceptional cocktails."

"It's a chill spot with a laid-back, mature crowd."

Good to know

1

Trivia night happens every Wednesday at 8pm with a $5 entry fee.

2

The establishment hosts theme nights for football, basketball, and baseball games.

3

Parking can be an issue during busy nights, so arrive early.

02
Bottlenose Brewing image 1

Brewpub offers a laidback atmosphere perfect for chilling with friends. Enjoy live music and multiple TVs for sports fans. Pet-friendly space with board games and a pinball machine keeps energy fun and social.

A relaxed, casual atmosphere sets the tone here. It offers a nice spot to chill with friends and unwind.

People are saying

"I loved the great beer selection, including craft and N/A options."

"I thought the food was so good and fresh."

"It's a nice place to go and chill with friends."

Good to know

1

Trivia night happens every Tuesday at 8pm with a $5 entry fee.

2

Half-price Zeppole is available on trivia nights, making it a must-try.

3

Live music occurs every Saturday starting at 8pm, featuring various bands.

03
Dolce Vita Modern Italian image 1
Italian restaurant

Small space offers intimate seating and authentic Italian dishes. Live saxophone and violin create a phenomenal music vibe. Atmosphere is super chill and cozy, perfect for dates or casual drinks.

Atmosphere feels super chill and cozy, blending casual vibes with a touch of romance. Suitable for date nights or casual drinks with friends.

People are saying

"I thought the food here was great."

"The servers here are so friendly and attentive during dinner."

"The food here is delicious, fresh, and flavorful."

Good to know

1

Happy hour runs from 4-6pm, Monday to Friday.

2

Karaoke night occurs weekly; check the schedule for specific dates.

3

Entertainment events are scheduled on select dates; visit the website for details.

04
Q Ball Billiards image 1

Pool hall features many pool tables and dartboards in a clean, well-lit space with a smoke-free area thanks to an enclosed smoke room. Vibes stay laid back and chill, attracting active league players and groups hanging out.

Vibes stay laid back and chill with cool people hanging out and playing pool.

People are saying

"The bar food and snacks here are pretty good."

"This place is a chill spot with cool, laid-back people."

"It's a fun place to play pool or darts."

Good to know

1

Parking might be difficult because the lot isn't too big.

2

Expect a wait on weekends due to league play.

3

A mandatory 18% service charge applies to bills over $100.

05
Tequilas Dยด Oro Mexican Restaurant | Jacksonville image 1

Mexican restaurant offers impeccable decor and a lively vibe with phenomenal Mariachi music. Guests enjoy personalized guacamole and a self-serve salsa bar. Atmosphere is chill and casual, perfect for a relaxed dinner or fun night out.

A very chill and relaxing atmosphere sets the tone here. The environment feels beautiful and casual, making it great for a laid-back dinner or a fun night out.

People are saying

"Our server Paul was amazing and super attentive."

"You have to try the table-side guacamole; it's made right in front of you!"

"The vibe here is so chill and amazing."

Good to know

1

Happy hour offers great deals on drinks and appetizers from 4-7pm on weekdays.

2

Taco Tuesday features special pricing on tacos all day.

3

Live music occurs every Friday and Saturday night, enhancing the dining experience.

06
Whiskey Cake Kitchen & Bar image 1
New American restaurant

New American spot blends classy decor with a chill vibe perfect for casual hangouts. Cozy patio and intimate lighting create a relaxed feel. Bourbon lovers enjoy a whiskey cart and wall of bourbons adding to the lively atmosphere.

Inviting and relaxed vibe with an intimate interior and low lighting creates a cozy atmosphere. The spot feels chill and happy, fitting for unwinding or casual hangouts.

People are saying

"The food here is delicious and fresh."

"The servers here are so friendly and knowledgeable about the dinner spots."

"It's a chill place with an inviting and relaxed vibe."

Good to know

1

Happy hour runs from 4-7pm on weekdays with special whiskey deals.

2

Reservations are recommended for private parties and events.

3

Whiskey tasting flights are available, featuring five different bourbons.

07
Shake Shack St. John's Town Center image 1

Bright, clean space with modern roadside-stand charm and roomy indoor and outdoor seating creates a lively, welcoming vibe. Busy atmosphere features quick kiosk ordering and a mix of casual and suburban energy. Known for juicy burgers and best-in-town fries, it draws crowds who appreciate fast food with a twist.

People are saying

"I thought the burgers were delicious, juicy, and flavorful."

"The milkshakes here are pretty tasty and not overly sweet."

"The burgers here are juicy, flavorful, and satisfying."

Good to know

1

Expect long wait times during the tree lighting festival due to increased crowds.

2

The restaurant is clean, including tables and bathrooms.

3

Prices are high for the portion sizes offered.

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Windy Hill, Jacksonville

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