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New Yorkers 1st Choice
Guide to Windy Hill

Date spots with outdoor seating

Sitting outside under the evening sky makes any conversation feel a little more intentional.

Based on 776 Opinions
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Updated May 2026
01
Cigars International Superstore image 1
Cigars International Superstore image 2
Cigars International Superstore image 3
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Humidor offers an exceptional, vast selection of cigars with a spacious walk-in design. Lounge combines comfortable indoor and outdoor seating with a full bar and fire pit, creating a laid-back atmosphere suited for enjoying cigars and drinks. Ventilation is strong, making the indoor air feel like a breeze outside.

Evenings here feature favorite drinks and a chance to enjoy puffing in a relaxed setting. Staff like Zora provide wonderful and attentive service, creating a welcoming atmosphere to meet nice people.

Outdoor seating includes a fire pit and a patio with a great atmosphere. The lounge offers a full bar with TVs and a space that blends indoor and outdoor areas for relaxing.

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."

"The service at these date spots is wonderfully attentive."

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
Tequilas D´ Oro Mexican Restaurant | Jacksonville image 1

Mexican restaurant with impeccable decor and a self-serve salsa bar that stands out. Atmosphere feels like being in Mexico, lively with phenomenal Mariachi music and perfect margaritas. Guests enjoy personalized guacamole service and authentic dishes like handmade tortillas and fajitas.

Lunch offers a relaxed vibe with large margaritas and spicy Camarones a la Diabla that bring bold flavors. Portions suit sharing and add to a casual date experience.

A dog friendly patio offers plenty of outdoor seating. Live Mexican music adds to the atmosphere outside.

People are saying

"Our server Paul was amazing and super attentive."

"The food here is amazing and delicious for Date Spots."

"The salsa bar here is amazing with so many fresh varieties."

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.

03
Dolce Vita Modern Italian image 1
Italian restaurant

Small space with intimate seating and carefully curated decor creates a cozy, upscale vibe. Live performances by saxophone and violin players add phenomenal music that lifts the atmosphere. Guests enjoy balanced cocktails and authentic Italian dishes in a setting that feels like a refined home.

Authentic Italian food sets the mood for date nights here. The staff creates a warm atmosphere that makes evenings feel special.

Patio seating offers a picturesque ambience filled with flowers and decorations that evoke an Italian summer. Options include indoor, outdoor, buffet, table service, and bar seating, with the outdoor patio standing out as beautiful and inviting.

People are saying

"I thought the food here was great."

"The food here is great for a memorable date night."

"The outdoor seating here is amazing, especially with perfect weather."

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
Culhane's Irish Pub & Restaurant image 1

Pub offers authentic Irish vibes with big screens showing sports and live music events. Atmosphere shifts from lively bingo nights to relaxed dining with ample seating and a spacious layout. Crowd enjoys classic drinks like Guinness and hearty food such as fish and chips and Reuben sandwiches.

Fish and chips come with coleslaw and taste great. The Guinness beef stew is a solid choice. The manager checks in often, adding a nice touch to the experience.

Large groups enjoy the spacious patio for celebrations and dining. Staff provide attentive service with a full section dedicated to outdoor guests.

People are saying

"I found the food here to be great and incredible."

"The food here is always top notch, especially the Guinness stew."

"The waitstaff at the outdoor seating were super helpful and personable."

Good to know

1

Trivia night happens every Wednesday at 7pm with a $5 entry fee.

2

Karaoke takes place every Friday and Saturday night starting at 10pm.

3

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

05
Whiskey Cake Kitchen & Bar image 1
New American restaurant

New American restaurant offers classy and cozy decor with inside and outside seating, including a cool patio perfect for evenings. Atmosphere feels unique and lively, blending fine dining with a welcoming vibe that suits various occasions. Bourbon enthusiasts find a wall of bourbons and a whiskey cart enhancing the experience.

Friendly staff create a welcoming vibe for couples. The menu features Rooster Royale with home fries and excellent salads, offering solid choices for a date meal.

The patio offers a cool outdoor vibe with an inviting exterior and a unique Airstream on the patio. Seating outside suits casual meals and is dog-friendly, making it pleasant for various occasions.

People are saying

"The food here is delicious and fresh."

"The whiskey cake was the highlight of our date."

"The outdoor seating offers a fantastic vibe with delicious food."

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.

06
RH Rooftop Restaurant at RH Jacksonville image 1

Rooftop setting offers spectacular views and an elegant casual atmosphere with stylish design and beautiful outdoor decor. Energy stays relaxed and inviting, enhanced by nice music and an open roof option. Guests often enjoy signature cocktails and well-prepared dishes in a space suited for celebrations and quiet chats.

Cozy and creative space sets a perfect mood for date nights. Staff provide extra care and attention during special celebrations.

Large windows open to beautiful outdoor seating with fire pits and plenty of greenery. The rooftop patio offers a stylish design perfect for drinks and chats.

People are saying

"The atmosphere here is so elegant and dreamy, perfect for date spots."

"The service for dinner spots is attentive and professional."

"The outdoor seating is gorgeous with stunning designer decor."

Good to know

1

Water costs $10; it's not complimentary.

2

Expect lengthy wait times for a table during peak hours.

3

Parking is free and plentiful near the restaurant.

07
Light On The Sugar Bakery Café image 1

Small, modern bakery café with cozy atmosphere and live plants on tables creates an intimate, chill vibe. Outdoor seating adds space beyond the few indoor tables, which fill quickly. Desserts are not overly sweet, pairing well with coffee served in spill-proof cups.

Offers a cozy spot for a first date or winding down with someone close. Desserts like the ube crepe cheesecake and s'mores puff stand out and add a sweet touch to the experience.

Outdoor seating includes tables outside that let you enjoy fresh air while dining. The café provides a casual spot to sit outdoors.

People are saying

"I thought the latte was smooth and so good."

"You have to try the ube crepe cake; it's divine."

"You can sip your latte in the sunshine on sunny winter days."

Good to know

1

The café is cashless; only credit cards and mobile payments are accepted.

2

Parking is ample and easily accessible near the café.

3

Prices are reasonable for the quality, with a small mocha costing $6.

08
Bahama Breeze image 1
Caribbean restaurant

Huge space combines hybrid indoor and outdoor seating with a tropical island vibe and a sports bar atmosphere at the outdoor bar. Live music blends island soul and reggae, creating a laid-back yet lively mood. Quiet indoor areas suit sophisticated diners, while the patio attracts beachcombers and groups.

Jamaican jerk chicken and chowder stand out as tasty choices for a date. The spot works well for both first meetings and special occasions like birthdays.

Outdoor seating includes a patio with aluminum chairs and tables made from 55-gallon steel barrels. Fans keep the area comfortable, and live island tunes play on Fridays, creating a lively atmosphere.

People are saying

"The food portions here are huge and incredibly filling."

"The outdoor seating service was great and attentive."

"The food and drinks here are amazing for Date Spots."

Good to know

1

Happy hour runs from 4 to 6 PM Monday through Friday with half-price appetizers.

2

The venue can accommodate large groups, making it suitable for celebrations.

3

Reservations are recommended for large parties to ensure seating together.

09
Dave's Hot Chicken image 1
Chicken restaurant

Bright interior with graffiti-style artwork creates a colorful, playful vibe that feels both friendly and electric. Seating options include both indoor and dog-friendly outdoor areas, supporting a lively, packed atmosphere. The place draws a crowd looking for spicy chicken in a chill, fun setting.

Spicy chicken challenges add a fun twist to date nights. Sharing the slider set with mild flavor works well for couples wanting to split dishes.

People are saying

"I found the food here to be amazing."

"It's nice that they have plenty of outdoor seating available."

"I thought the food here was some of the best I ever ate."

Good to know

1

The restaurant offers Halal options for all menu items.

2

Expect smaller portion sizes compared to other locations.

3

The restaurant can get crowded, especially during peak hours.

10
Chuy's image 1
Tex-Mex restaurant

Indoor space blends 50s diner style with Spanish-style art and playful, colorful decor featuring hubcap ceilings. Atmosphere feels fun and welcoming with lively music and multiple seating areas including outdoor patio. Guests enjoy generous Tex-Mex dishes and a variety of well-regarded margaritas.

Service stays attentive even when busy, making sure couples feel cared for. Menu includes Panchos, a solid choice for sharing during date night or brunch.

Outdoor seating includes a patio that suits nice weather well. Music plays loud on the patio, adding to the atmosphere.

People are saying

"The staff showed such kindness and grace with my tab."

"I loved sitting outside because the weather was beautiful."

"Our bartender Kiara made our experience really awesome."

Good to know

1

Happy hour runs from 3 to 6pm on weekdays with special pricing.

2

Chuy's has a full bar available for drinks during lunch and dinner.

3

Outdoor seating is available for guests who prefer dining outside.

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Windy Hill, Jacksonville

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