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Date spots for cocktails in Windy Hill

Sharing a round of drinks is the easiest way to settle into a conversation that lasts all night.

Based on 665 Opinions
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Updated May 2026
01
Cigars International Superstore image 1
Cigars International Superstore image 2
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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.

Exceptional cocktails stand out here, especially the Campfire Bourbon served in a smoke filled humidor. The drinks pair well with a relaxed, enjoyable atmosphere and attentive service.

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.

People are saying

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

"The cocktails here are exceptional and elevate the whole experience."

"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 Dยด 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.

Cocktails here stand out for their delicious flavors and amazing mixes like Piรฑa colada and Coco Loco. Staff remain awesome even late in the evening.

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.

People are saying

"Our server Paul was amazing and super attentive."

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

"The cocktails here were amazing and delicious."

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.

Spectacular cocktails feature balanced flavors, not too strong or sweet. Bartenders like Sergio and Teresa craft incredible drinks including a delightfully sweet lychee martini.

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

People are saying

"I thought the food here was great."

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

"The cocktails were a true treat, truly impressive."

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
Norikase - Modern Japanese Omakase & Sushi image 1

Sushi restaurant offers an elevated elegant atmosphere with stunning decor and a peaceful, private setting ideal for intimate occasions. Guests enjoy watching chefs prepare fresh, top-quality sushi alongside a selection of unique cocktails and sake pairings. Occasional live performances add an unexpected, lively touch to the refined experience.

Cocktails feature Japanese spirits like Mars Iwai Whiskey and Haku Vodka. Drinks include the Nori Old Fashioned with umami bitters and the fruity Donโ€™t Break My Heart with yuzu, lychee, and berries.

Offers a romantic atmosphere with thoughtful touches like complimentary sake and mango cheesecake for special occasions. Ideal for celebrating anniversaries and birthdays with a partner.

People are saying

"I experienced the best sushi and Japanese food in Jacksonville."

"This is an amazing spot for a date night, the food is phenomenal."

"I found the sushi here to be a gourmet experience."

Good to know

1

Happy hour runs from 5 to 7pm with discounted appetizers and sushi.

2

Reservations are recommended for the 17-course meal experience.

3

Dress code requires no shorts or t-shirts; business casual is preferred.

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.

An amazing cocktail list offers a variety of interesting and good cocktails. The Down by the Bay stands out, and social hour features quality drinks for $7.

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.

People are saying

"The food here is delicious and fresh."

"Mila made the best sidecar cocktail I've ever had."

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

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
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.

Bartenders craft refreshing cocktails and frozen beverages with a wide selection of tropical flavors. Drinks come well-balanced and highlight the menu alongside food options.

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.

People are saying

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

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

"You've got to try their expertly mixed and refreshing cocktails."

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.

07
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.

Mixed drinks come with good flavor and cocktail specials that appeal to many. People who order alcohol enjoy their drinks here.

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.

People are saying

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

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

"I really enjoyed the great cocktails here."

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.

08
Bazille at Nordstrom image 1
American restaurant

Restaurant combines cozy and elegant vibes with a posh feel, suitable for casual meals and special occasions. Atmosphere stays warm and inviting, attracting families and shoppers alike. Menu features diverse, flavorful dishes with seasonal ingredients and a decent wine and cocktail selection.

Cocktails here are refreshing and well balanced, especially the cucumber and basil mix. Drinks taste delicious and pair well with a shopping break.

Small portion appetizers like chicken tacos suit light eaters well. The menu includes hearty options such as the French dip sandwich, making it a solid choice for date night.

People are saying

"The French dip and salmon couscous at this Lunch Spot are addictive."

"I could have ordered another bowl of the French onion soup and left happy."

"You have to try the French onion soup for your date spot."

Good to know

1

The menu features a diverse selection highlighting seasonal ingredients.

2

Happy hour offers half-price appetizers from 4-6pm on weekdays.

3

Parking is available in the mall garage, with validation options.

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Windy Hill, Jacksonville

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