Best Date Night Restaurants in Maitland

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFrenchIndian

Regions

Orlando

Neighborhoods

Altamonte SpringsDowntown OrlandoHeathrowLake MaryLake TerraceLongwood

Top Rated

CharmingFancyGood for business mealsGood for groupsGood for special occasionsGreat for brunch

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarStandardHigh TopOutdoor

Award-winning

MICHELIN

Accessibility

Gender-neutral restroomWheelchair access

49 restaurants available nearby

A photo of Parea Greek Taverna restaurant

1. Parea Greek Taverna

4.6

Exceptional(90)

$$$$Price: Moderate

• Greek • Maitland

Booked 11 times today

Introducing a fresh and innovative concept, Parea Greek Taverna coming soon to Maitland,

2. Jazz Tastings

4.8

Exceptional(651)

$$$$Price: Expensive

• American • Maitland

Booked 24 times today

• $10 Entertainment Fee Per Person on Friday, Saturday & Monday Night Jazz Jam (first Monday of the month)• • $25 Minimum Food & Beverage Purchase Per Person Monday-Thursday•• $50 Minimum Food & Beverage Purchase Per Person for on Friday & Saturday•• Friday & Saturday: Reservations available until 7:30pm, after that time we accept walk ins only!••Parties of 7 or more must purchase a group package, contact us at 407-795-1582•**If minimums are not met you will be charged the remaining balance**Weekly Deals:Happy Hour Tuesday-Thursday from 5:30pm-7pm: Half off appetizersTuesday- Burger & Brew $15, 1/2 off Wine Bottles all night!Wednesday- 1/2 off select Whiskey & Wine all night!Located in Maitland, Florida, Jazz Tastings combines the intimate atmosphere of a jazz bar with a classy menu. There is also an impressive alcohol list to enjoy along with the soothing music and great food.

A photo of AJ CHOCOLATE HOUSE restaurant

3. AJ CHOCOLATE HOUSE

4.6

Exceptional(100)

$$$$Price: Moderate

• Dessert • Winter Park

Booked 8 times today

Now serving brunch! Every day till 3pmWith over 150 different amazing chocolate delicacies, AJ Chocolate House is truly a place to come unwind and enjoy the sweetest things life has to offer. Whether you want to get together with an old friend to enjoy great chocolates or a slice of delicate cake with a cup of coffee or hot chocolate, bring your other half for a sweet brunch with Brussels waffles or a date with chocolate fondue and a glass of wine, planning a party or an event, or simply need to find the perfect gift for a chocolate lover, as well as if you are shopping for a special occasion or corporate gifts - we are happy to welcome you to our house.

A photo of Bar Italia Winter Park restaurant

4. Bar Italia Winter Park

4.7

Exceptional(756)

$$$$Price: Expensive

• Italian • Winter Park

Booked 67 times today

Hello Winter Park - We are beyond excited to welcome you to Bar Italia! We will be open for dinner service only starting Monday, March 27th at 4:00pm. We will be brining lunch to you soon! Mangia! Fresh pasta, and homemade sauces in a stunning restaurant.

A photo of Luca Turci - Winter Park restaurant

5. Luca Turci - Winter Park

4.5

Awesome(95)

$$$$Price: Moderate

• Italian • Winter Park

Booked 28 times today

**Welcome to LUCA TURCI - An Italian Culinary Experience**At LUCA TURCI, we take you on a culinary journey through Italy without leaving Winter Park, Florida. Our restaurant combines the rustic and cozy charm of an Italy with modern and elegant touches, creating the perfect atmosphere for any occasion, from a romantic dinner to a special celebration with friends and family.**Our Menu**We take pride in offering a diverse menu that celebrates the rich culinary of Italy. From handmade pastas and creamy risottos to fresh seafood and irresistible desserts, each dish is prepared with high-quality ingredients and a passion for authenticity. Try our house specialties, and Chef Creations.**Ambiance and Service**At LUCA TURCI, the ambiance is as important as the food. Our space is carefully designed to provide a pleasant and memorable experience. Our dedicated staff is always ready to offer exceptional service, ensuring that every visit is special.

A photo of Christner's Prime Steak and Lobster restaurant

6. Christner's Prime Steak and Lobster

4.8

Exceptional(4871)

$$$$Price: Very Expensive

• Steak • Winter Park

Booked 63 times today

The Christner family invites you to join them at Orlando's favorite steakhouse. Opened in 1993, Christner's is truly a family business "we have very little turnover because our employees are part of the family"! Our customers are locals...business people... travelers...vacationers and sports stars...including many celebrities. Everyone agrees...outstanding menu...professional staff and America's Most Award Winning Steakhouse! The Christners maintain an informal flavor of warm, hands-on, personal hospitality. As Russ said, "Hey, we're just a humble little steakhouse" Enter a guest, leave a friend. Reservations for Private Rooms must be made in advance by calling the restaurant directly at 407.645.4443.Bread: Baked fresh daily and served piping hot to your table. Rip it. Break it. Just don't cut it with a knife.Beef: USDA Prime, aged corn-fed straight from the Midwest and cut to order.Lobster: Cold Water Australian

A photo of Fleming's Steakhouse - Winter Park restaurant

7. Fleming's Steakhouse - Winter Park

4.7

Exceptional(2315)

$$$$Price: Very Expensive

• Steakhouse • Winter Park

Booked 25 times today

Your Winter Park Fleming's is located in Winter Park on the corner of Lee Road and Orlando Avenue. Fleming's in Winter Park is an outstanding choice to enjoy an exceptional Prime steak, glass of wine or handcrafted cocktail in Orlando. Whether you're celebrating a special occasion, hosting a business dinner or simply wanting to enjoy a night out - we will create a safe and memorable evening in our Dining Room. If you prefer to enjoy your fine dining experience at home, you can order and pay for lunch or dinner online and then pick up curbside or select from one of our delivery partners.

8. Turci Pasta

4.6

Exceptional(1154)

$$$$Price: Moderate

• Italian • Downtown Orlando

Booked 20 times today

TURCI PASTA - The Best Italian Restaurant in Orlando - by YelpFresh pasta, homemade sauces, unique and authentic Italian dishes.Delicious Italian desserts like Tiramisu, Limoncello cake, fresh filled Cannoli and Gelato.Watch us cutting your pasta in front of you

A photo of Ruth's Chris Steak House - Winter Park restaurant

9. Ruth's Chris Steak House - Winter Park

4.7

Exceptional(2704)

$$$$Price: Very Expensive

• Steakhouse • Winter Park

Booked 33 times today

Now Open: We look forward to serving you soon.Ruth's Chris Steak House in Winter Park, FL serves the finest USDA Prime beef available, broiled at 1,800° and served on 500° plates, so your steak stays hot, juicy and delicious from first bite to last. Enjoy our New Orleans-inspired appetizers, USDA Prime steaks, fresh seafood, signature side dishes and homemade desserts. All this while you enjoy our warm, inviting atmosphere and Ruth’s Chris’ genuine hospitality. So whether you’re a regular or have just been wondering what all the buzz is about, Ruth's Chris is the perfect excuse to enjoy the perfect night out. Dinner is served nightly, reservations are suggested and private dining and offsite catering may be arranged.

A photo of Boca - Winter Park restaurant

10. Boca - Winter Park

4.4

Awesome(1315)

$$$$Price: Moderate

• American • Winter Park

Booked 42 times today

Boca - Winter Park is a perfect spot for a date night. With a cozy and comfortable neighborhood ambiance, it's described as a 'great date night spot' by a reviewer. The food and service are consistently rated highly, making it a great choice for a romantic evening out. The creative and well-executed menu, beautiful space, and laid-back atmosphere only add to the appeal.

‘About the restaurant’ descriptions have been generated using an artificial intelligence model comprised of OpenTable proprietary data that has not been independently verified by OpenTable. The content is presented as-is, for informational purposes only.

See what locals rave about

From verified diners like you

A
Anna MarieVIP
Orlando / Central Florida East •157 reviews
4.0
Dined 2 days ago
Service is always impeccable. The food is very good. Parea is a great place for appetizers. The spanakopita is delicious. Parea has some of the best taramasalata, very creamy and not too salty for a fish roe dip. They still have the flaming cheese Saganaki but took the Tiropita off the menu. A great place to dine with friends to share bites.
More info
Parea Greek TavernaPrice: Moderate• Greek• Maitland
•
4.6
D
David
Orlando / Central Florida East •8 reviews
5.0
Dined 5 days ago
Great experience as usual.
More info
Fleming's Steakhouse - Winter ParkPrice: Very Expensive• Steakhouse• Winter Park
•
4.7
OT
OpenTable Diner
Central Kentucky •2 reviews
5.0
Dined on Mar 4, 2025
It was a great night celebrating my son’s 19th birthday. Thank you for the excellent service and hospitality. Cheers, Jonah
More info
Bar Italia Winter ParkPrice: Expensive• Italian• Winter Park
•
4.7
DJ
DonJay
Georgia •7 reviews
5.0
Dined on Mar 3, 2025
Great celebration for 34th Anniversary & Janelle was fabulous!!! #thelovecouple91
More info
Jazz TastingsPrice: Expensive• American• Maitland
•
4.8
M
Mary sueVIP
Orlando / Central Florida East •39 reviews
5.0
Dined on Mar 3, 2025
Had a nice late lunch with family. The swordfish was cooked perfectly over couscous
More info
Boca - Winter ParkPrice: Moderate• American• Winter Park
•
4.4

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