Atly Logo
New Yorkers 1st Choice
Loved by locals

Cool date spots in Winter Park

You are looking for a spot that feels current without trying too hard.

Based on 653 Opinions
+650
User
User
User
Updated May 2026
01
Wafflehead Ice Cream and Coffee image 1
Wafflehead Ice Cream and Coffee image 2
Wafflehead Ice Cream and Coffee image 3
View all

Small, homey shop fills the air with the smell of fresh waffle cones and offers homemade ice cream in a warm, inviting atmosphere. The space feels cute and well-decorated, with limited seating inside and a patio option. It attracts those seeking a cozy spot for sweet treats with a peaceful vibe.

Close to a tattoo shop, it offers a unique combo for a date or day out. Ice cream and coffee create a relaxed vibe after dinner or alongside other activities.

Waffle cones shaped like heads create a unique twist on classic ice cream. Inside, the shop carries a super cool vibe that feels fresh and inviting.

People are saying

"The bubble waffle with ice cream was incredible and fresh."

"The ice cream and bubble waffles make for creative Date Spots."

"I loved the super cool vibe and the cool waffle cone concept."

Good to know

1

The shop offers unique ice cream flavors made from locally sourced ingredients.

2

Expect to pay around $13 for two ice creams with extra charges for toppings.

3

The shop hosts an outdoor movie night biweekly, perfect for a fun outing.

02
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.

Tastings with the owner create a personal and engaging experience. Limited run spirits like their clear rum add a unique touch. The setting suits celebrations and special occasions.

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.

People are saying

"The whiskey tasting experience with Tim was unforgettable."

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

"The staff here are so friendly and informative."

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.

03
mosonori - Winter Park - Japanese handroll sushi bar image 1

Bar seating arranged in a giant U-shape surrounds chefs who craft handrolls with precise movements, creating an intimate dining experience. The space features modern Japanese design, highlighted by a glass-walled dry aging refrigerator showcasing fresh fish. Atmosphere stays quiet and elegant, inviting focus on the fresh, high-quality sushi and thoughtful service.

Seating is accommodating for guests with mobility needs, making it easy to enjoy a meal even with an injury. It suits date nights and special occasions as well as casual weekday dinners.

People are saying

"The Japanese food here is so fresh and flavorful."

"The hand rolls here are amazingly fresh and delicious."

"The hand rolls are cool, with fresh fish and warm rice."

Good to know

1

Reservations are not required, and wait times are typically under 15 minutes on Fridays.

2

The restaurant focuses solely on hand rolls, offering a unique dining experience.

3

Prices for two people usually stay under $150, making it a reasonable option.

04
Cow & Cheese - University image 1

Restaurant space features open kitchen and graffiti-style murals that create a 90s kid hangout vibe. Music plays old school hip hop, setting an energetic atmosphere where some people dance. Seating is ample, supporting both takeout and dine-in with a welcoming, lively crowd.

Welcoming atmosphere suits couples and families alike. The Triple Cow X Triple Cheeseburger stands out as a hearty choice enjoyed during visits.

Walls feature fun graffiti murals and cool art that might be local. Plenty of seating and a kiosk ordering system add to the 90s kid hangout vibe with summer tunes playing.

People are saying

"I thought the burgers here were the best I ever tasted."

"The staff here makes you feel welcome and comfortable on your date."

"The burgers here are juicy, flavorful, and totally fire."

Good to know

1

The initial cost for a burger is $5, with extras costing up to $2.50.

2

The ordering kiosks streamline the process for families and large groups.

3

Expect some confusion with two separate screens for ordering burgers and wings.

05
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 romantic vibe sets the tone for a date night or celebration here. The atmosphere creates a special and memorable evening perfect for couples.

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.

People are saying

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

"The chocolates here are rich, not too sweet, and perfect for Date Spots."

"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.

06
The Axe Trap - The Trap image 1

Venue combines axe throwing lanes with a full bar and espresso martinis known for quality. Lounge area offers comfortable couches and a big screen TV, creating a lively yet relaxed atmosphere. Events include friendly competitions and dance classes, attracting groups for social and team-building activities.

Comfortable setting suits dating with options for playing games like axes, corn hole, and giant Jenga. Space works well for lounging and hanging out during a date.

The spot has a consistently cool vibe with great music setting the tone. Axe throwing adds a unique and fun activity that stands out.

People are saying

"The staff made our fun activities smooth and memorable."

"The staff here makes you feel so welcome and eager to help."

"The staff here is so cool and amazing."

Good to know

1

Tuesdays offer buy one get one free axe throwing sessions.

2

The bar closes at 11 PM, while axe throwing ends earlier than posted hours.

3

Parking is available in a free lot in front of the building.

07
Ta’Chingon Mexican Kitchen image 1

Small Mexican restaurant offers a clean, fresh interior with warm, inviting decor and a lively, authentic atmosphere. The space feels friendly and welcoming, creating a comfortable environment with great energy and cultural touches.

Creamy Suiza enchiladas with jalapeño sauce and seasoned chicken offer a rich, comforting meal. The dishes bring a taste that reminds some of Texas home cooking, making it a cozy spot for couples.

Spacious and clean with authentic atmosphere and cultural, fun decor. The design feels really cool throughout.

People are saying

"The food here is authentic, fresh, and full of flavor."

"The Mexican food here is simply delicious and the portions are perfect."

"This Mexican food is the best I've had in years."

Good to know

1

The restaurant recently obtained its liquor license and now serves a full bar.

2

You can order food for delivery if you prefer to stay in.

3

The restaurant can accommodate large takeout orders for families or offices.

08
The Neighbors Orlando image 1

Eclectic space blends local craft retail with a cozy bar and intimate seating. Live music and a well-curated cocktail menu create a chill, inviting atmosphere. The vibe stays relaxed, making it a spot to slow down and enjoy quality drinks and food.

Live music and food and drinks create a lively setting. The upstairs area offers a quaint atmosphere ideal for date nights.

A calm and collected vibe sets the tone here, making it a cool hangout spot. The bar space adds to the atmosphere, and the servers bring a friendly, conversational energy.

People are saying

"I thought the cocktails here were the best I ever had."

"The cocktails here are breathtakingly good and consistently great."

"The drinks here are really well thought out and tasty."

Good to know

1

Happy hour runs from 4-7pm on weekdays with discounted drinks.

2

Live music performances occur on Thursdays featuring local artists.

3

Reservations are recommended for private events in the Audubon Room.

09
Tommy Bahama Marlin Bar image 1

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.

A hidden gem for date night or a casual afternoon, offering delicious cocktails that complement the relaxed vibe. Suitable for both intimate meals and friendly outings.

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

People are saying

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

"The service here makes it a great spot for date nights."

"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.

10
Sushi Island image 1
Japanese restaurant

Modern Japanese restaurant offers a calm, clean atmosphere with pristine, elegant design and family-friendly vibes. Music features Japanese pop and anime songs, complementing the fresh, beautifully made sushi and a self-serve dessert bar with unique Japanese sodas.

Perfect for date night with a focus on customized rolls that accommodate allergies. The Salmon tartar stands out as a favorite dish to share.

A welcoming atmosphere sets a cool tone right away. The interior design adds to the vibe, creating a relaxed, family-friendly feel.

People are saying

"I loved the all-you-can-eat sushi buffet with fresh, delicious options."

"The service here is so cool, with friendly and attentive staff."

"The food here is amazing and fresh, perfect for Date Spots."

Good to know

1

The all-you-can-eat option is available for lunch and dinner.

2

Expect a 30-35 minute dining experience as rolls come out quickly.

3

The restaurant can customize rolls for dietary restrictions, including allergies.

11
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.

Low lighting creates an intimate vibe ideal for a romantic glass of wine. Booth-type seats offer cozy spots for couples or small groups, making it a solid choice for date nights or special occasions.

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.

People are saying

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

"The lounge's vibe is super cute and intimate, perfect for date spots."

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

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.

12
Ômo by Jônt image 1
Restaurant

Dining unfolds across distinct rooms resembling a private home, including a living area, kitchen, and dessert room. Atmosphere blends elegant design with 90’s and 2000’s hip hop music, creating a relaxed yet sophisticated vibe. Guests experience wood-fired grill flavors and curated sake or wine pairings that complement the intimate, modern setting.

Personalized service shines with staff preparing a happy birthday card. Chef Ryan Ratino crafts an exceptional dining experience that suits special occasions well.

The atmosphere feels cool and chill throughout the visit. It stays a bit cool inside, so bringing layers helps.

People are saying

"The food here is amazing, super flavorful and well-balanced."

"The tasting menu here is a work of art, truly a fantastic experience."

"The food here is awesome, creative, and fresh."

Good to know

1

Reservations are recommended for the chef's tasting menu experience.

2

The tasting menu is priced around $550 for two, including a cocktail.

3

The restaurant offers a unique 'Magic Box' dessert experience.

13
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.

Vegan chicken here tastes very close to real chicken, making it a standout choice for couples. The chicken sandwich and burrito offer satisfying options that keep people talking after their visit.

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 have to try their chicken sandwich; it's out of this world."

"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.

14
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.

People are saying

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

"The fish and chips were classic, crispy, and delicious."

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

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.

15
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.

Staff are pleasant and patient, helping with bowl assembly. Options include a garlic free menu for allergies. Food like turkey focaccia sandwiches and pizza work well for sharing on dates.

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

People are saying

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

"It's a great spot for a date with delicious, fresh food."

"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.

Discover more

Winter Park, Florida

Area guide
Loading Map...