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New Yorkers 1st Choice
Winter Park's best

Chocolate date spots

Made for those who curate their romantic outings around the shared experience of sophisticated cocoa-based treats.

Based on 653 Opinions
+650
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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
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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.

Scoops include chocolate and mint chocolate chip flavors served in a freshly-made waffle cone.

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.

People are saying

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

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

"The waffle cones were crispy, warm, and tasted so good."

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
480 N Wine Bar image 1

Bar offers live jazz saxophone and a curated art-filled interior with moody lighting that creates a classy, sexy vibe. Outdoor seating overlooks a lively village scene, perfect for people watching. Champagne and sparkling wine selections stand out alongside small, elegant food options.

Champagne pairs well with small chocolates served here. The place offers nice chocolate pairings that complement drinks effectively.

A posh bar with a vibe that suits dressing up for date night or a girls' night out. It works well as a go-to spot for celebrating or just enjoying an evening together.

People are saying

"They have a great selection of champagne and sparkling wines."

"It's a great spot for date night or drinks with friends."

"I enjoyed the champagne and chocolate pairings."

Good to know

1

Reservations are recommended for larger groups to ensure seating.

2

The bar has a strict no-kids policy after 5pm.

3

Parking is accessible and available nearby.

03
Jala Indian Cuisine image 1
Modern Indian restaurant

Modern Indian restaurant offers an elegant and intimate atmosphere with vibrant decor and live music enhancing the experience. Guests enjoy both indoor and outdoor seating in a beautifully designed space that feels luxurious yet welcoming.

Chocolate appears in desserts like the Dubai chocolate gulab jamun and chocolate lava cake, both served alongside traditional dishes. These sweets offer a rich, indulgent finish to meals featuring Indian flavors.

Dinner here offers a fantastic experience from start to finish, making it a solid choice for couples. The atmosphere suits a quiet evening with a partner.

People are saying

"The food here is delicious and outstanding."

"These date spots have amazing food with authentic flavors."

"The chocolate lava cake was beyond delicious."

Good to know

1

They offer Jain and Swaminarayan food menus, which are hard to find in the area.

2

Parking is easy and close to the restaurant.

3

Many gluten-free options are available on the menu.

04
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.

Offers pure Belgian chocolate including a unique liquid hot chocolate served from a tap. Features European chocolate selections and pairs well with wine for tastings.

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

People are saying

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

"The staff here is super friendly and outgoing."

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

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.

05
Gelato-go Orlando image 1
Ice cream shop

Sleek Italian gelato shop offers a wide array of flavors in a clean, modern setting. Cozy atmosphere invites relaxing moments both indoors and at outdoor seating ideal for people watching. Energy stays pleasant and attentive, making it a friendly spot for enjoying quality gelato.

Dubai Chocolate Gelato Cup stands out with rich, creamy texture and intense chocolate flavor. The hot chocolate also offers a deep, satisfying taste that complements the gelato well.

Gelato offers a sweet, casual treat that fits well for a date. The spot works nicely in colder weather and welcomes small families too.

People are saying

"I thought the gelato here was delicious and authentic Italian."

"The Dubai chocolate gelato is out of this world."

"The gelato here is amazing, especially the mango and passion fruit flavors."

Good to know

1

Gelato-go Orlando offers a variety of vegan gelato flavors.

2

The store is conveniently located on Park Ave near the train station.

3

Expect a premium price for gelato, with cones costing around $12.

06
M'ama Napoli Italian Bakery & Deli image 1

Small space with cozy indoor seating and bar-style stools creates an intimate setting. Atmosphere feels like stepping into Italy, with authentic Italian vibe and friendly, welcoming energy. Offers a mini market stocked with imported Italian groceries alongside fresh bakery items.

Chocolate features in treats like the Italian macaron and the coffee and chocolate croissant. Handling these pastries often leaves traces of chocolate on the hands.

Exceptional sandwiches create a memorable experience, with one noted as the best since Italy. The owner shows personal care, even offering his wife to cook for special occasions.

People are saying

"These focaccia sandwiches are incredible and taste so fresh."

"This place feels like an authentic Italian cafe, a perfect date spot."

"I loved the chocolate coconut cookie."

Good to know

1

There is parking available in the back.

2

The bakery offers authentic Italian specialties and coffees.

3

Credit cards and mobile payments are accepted.

07
Croissant Gourmet image 1

Small cafe with cozy indoor space and shaded outdoor seating along the sidewalk. Atmosphere blends French-inspired decor with Sinatra-era music, creating a relaxed, upscale vibe. Popular for fresh, buttery croissants and a variety of top-tier pastries.

Chocolate croissants stand out with flaky layers and rich filling. The chocolate eclair and chocolate chip bread pudding offer creamy, sweet chocolate flavors in different textures.

Large portions of Quiche Lorraine come with a small salad, making for a filling meal. Early Sunday breakfasts offer a quiet time that feels like sitting in the shadows of the Eiffel Tower.

People are saying

"These croissants are buttery, flaky, and rival those from France."

"I ordered the chocolate croissant and it was so delicious."

"The pastries here are flaky, homemade, and super delicious."

Good to know

1

The bakery opens at 7:00 am daily.

2

Expect a wait for seating when the restaurant is full.

3

Prices for pastries are generally high compared to other bakeries.

08
The Glass Knife image 1
Restaurant

Bright, chic interior with plush velvet booths and a beautiful pastry display creates an elegant yet welcoming setting. Atmosphere stays pleasant and quiet even when busy, supporting a relaxed dining pace. Guests enjoy indoor and outdoor seating options with tasteful decor matching an upscale vibe.

S'mores chocolate cake balances texture and sweetness well. The chocolate croissant melts in your mouth. Desserts like the Red Velvet Cake and Warm Chocolate Chip Cookie look almost too good to eat.

Plush velvet booths near the front create a cozy, intimate setting. The BLT sandwich stands out as a solid choice, and the staff adds a light, fun vibe with their humor.

People are saying

"I found the brunch here to be fresh, flavorful, and beautifully presented."

"Jeremiah's recommendations made our Date Spots delicious."

"The chocolate desserts are almost too beautiful to eat."

Good to know

1

The new Park Ave location offers a similar experience to the original.

2

Reservations are recommended for larger parties to avoid long wait times.

3

A virtual waitlist is available to minimize wait times for guests.

09
Luca Turci Italian Restaurant image 1

Outdoor seating under an oak tree and fresh pasta made in the dining room create a beautiful, authentic Italian atmosphere. Soft music and thoughtful touches like real roses at each table add to the romantic, intimate vibe. Guests often enjoy sharing dishes with a lazy Susan centerpiece and pairing meals with well-chosen wines.

Desserts showcase high-quality Belgian chocolate with standout items like a light mousse tiramisu topped with chocolate crumble designed to look like a potted plant, and a rich chocolate lava cake.

Cozy yet elegant setting suits special occasions like birthdays and anniversaries. Delicious pasta matches quality found in Brooklyn, making it a solid choice for a date night.

People are saying

"The food here is delicious and flavorful."

"The pasta here is as good as Brooklyn, truly exceptional."

"The gnocchi was fresh, stuffed, and topped with Alfredo sauce."

Good to know

1

Reservations are recommended for dinner, especially on weekends.

2

Expect a wait time of 30-60 minutes during peak dinner hours.

3

The average cost per person is around $100, including drinks.

10
Paris Baguette image 1

Bakery with modern design and black and white decor offers a quiet, relaxed atmosphere and outdoor terrace that feels like Paris. Plenty of seating invites lingering over fresh, high-quality pastries and desserts. Clean, organized space enhances the calm, cozy vibe.

Chocolate options include Dubai chocolate matcha and coffee, a rich and unique flavor, and a chocolate strawberry cake that is soft with fresh fruit and not too sweet. The chocolate supreme croissant offers a flaky, rich pastry experience.

Warm hospitality from the manager creates a friendly vibe for couples. The spot suits morning dates and offers donuts to share, encouraging repeat visits.

People are saying

"The pastries here are fresh, beautifully made, and delicious."

"The chocolate cake is rich without being too sweet."

"The pastries here are amazing, especially the French ones."

Good to know

1

The bakery opens at 7:00 am and closes at 10:00 pm.

2

Expect cleanliness issues, as tables and seating areas are often dirty.

3

The air conditioning frequently malfunctions, affecting the dining experience.

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