Best Date Night Restaurants in Maitland

52 restaurants available nearby

1. Jazz Tastings

4.8

Exceptional(574)

Price: Expensive

• American • Maitland

Booked 14 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!Thursday- 1/2 off Don Julio Anejo, Blanco and Reposado 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 AVA MediterrAegean restaurant

2. AVA MediterrAegean

4.7

Exceptional(2211)

Price: Expensive

• Mediterranean • Winter Park

Booked 49 times today

AVA MediterrAegean is a modern Greek Agora, a multi-sensory transporting venue bringing dining experience and pleasure together in a refined and spirited atmosphere.Meaning life, water, island, bird in Greek, AVA is a celebration of splendor, freedom, escapism and joy, where genuine hospitality, delectable food and vibrant atmosphere combine to entertain the senses and transport guests to celebrate the night away.Deeply rooted in the Mediterranean, AVA lives by its mantra “PAREA”, from Greek, meaning a group of friends, who gather to share life experiences, philosophies, values and ideas.Lunch | Brunch | Dinner.

A photo of Permanent Vacation restaurant

3. Permanent Vacation

4.9

Exceptional(272)

Price: Moderate

• American • Maitland

Booked 36 times today

Permanent Vacation is a tropical destination with an extensive rum list, rum mixed with exotic flavors, exquisite bites, immersive special effects and vibes that never stray too far from the equator!You must be at least 21 to dine or drink with us.

A photo of AJ CHOCOLATE HOUSE restaurant

4. AJ CHOCOLATE HOUSE

4.6

Exceptional(68)

Price: Moderate

• Dessert • Winter Park

Booked 4 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

5. Bar Italia Winter Park

4.7

Exceptional(677)

Price: Expensive

• Italian • Winter Park

Booked 40 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 Antonio's - Maitland - Upstairs restaurant

6. Antonio's - Maitland - Upstairs

4.6

Exceptional(1798)

Price: Expensive

• Italian • Maitland

Booked 4 times today

Antonio's has built a reputation for high quality, great value and friendly service. Our menu features authentic Northern and Coastal Italian cuisine. We prepare a wide variety of original seafood, veal, steaks and pastas with the freshest ingredients, at competitive prices. To complete your experience we offer an extensive bottle wine list, a full liquor bar and warm, gracious service in a comfortable and elegant atmosphere overlooking Lake Lily.

A photo of Fleming's Steakhouse - Winter Park restaurant

7. Fleming's Steakhouse - Winter Park

4.7

Exceptional(2216)

Price: Expensive

• Steak • Winter Park

Booked 16 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. With premium Prime steak options on our Dinner Menu as well as best-in-class seafood and innovative plant-based options, we have something to offer everyone you are dining with.

A photo of Christner's Prime Steak and Lobster restaurant

8. Christner's Prime Steak and Lobster

4.8

Exceptional(4747)

Price: Very Expensive

• Steak • Winter Park

Booked 28 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 Bulla Gastrobar - Winter Park restaurant

9. Bulla Gastrobar - Winter Park

4.7

Exceptional(2630)

Price: Moderate

• Spanish • Winter Park

Booked 17 times today

Bulla (boo-ya), which is slang for chatter and what people are talking about, is devoted to delight you by serving your favorite Spanish dishes such as “Patatas Bravas," "Huevos Bulla," "Buñuelos de Bacalao," and other tapas, as well as tantalizing daily specials from our kitchen to bed shared amongst friends.We select only the finest and freshest ingredients, accented in our authentic, savory cuisine. Our ambiance is created to stir the senses and stimulate your appetite. We invite you to join us to indulge in a celebration of good taste!

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

10. Ruth's Chris Steak House - Winter Park

4.6

Exceptional(2640)

Price: Very Expensive

• Steakhouse • Winter Park

Booked 49 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.

See what locals rave about

From verified diners like you

T
Talayah
Orlando / Central Florida East •1 review
5.0
Dined today
Unique and incredible experience! Not a venue for children or teens. Definitely an adult experience. The food is outstanding and the live jazz was incredible! My husband and I had a date night out and Jazz Tastings did not disappoint!
More info
Jazz TastingsPrice: Expensive• American• Maitland
•
4.8
D
Donna
Greater Boston •8 reviews
5.0
Dined 2 days ago
We love Ava. The food is so delicious; taste and presentation. Our servers were so accommodating. Every time we visit Winter Park we make a reservation at Ava! It’s perfect!
More info
AVA MediterrAegeanPrice: Expensive• Mediterranean• Winter Park
•
4.7
L
Larryvip
Washington, D.C. Area •83 reviews
5.0
Dined 4 days ago
Great food and great ambience. The brunch crowd at the restaurant makes it pretty energetic. This means that servers are doing the best they can and in spite of a short wait to get served they were excellent. We’ve been here a couple times and both times had excellent food and great drinks. Put this one on your list.
More info
Bar Italia Winter ParkPrice: Expensive• Italian• Winter Park
•
4.7
J
Jim
Coastal Georgia •13 reviews
5.0
Dined 6 days ago
Food was fantastic. Tapas (small plates) were larger than others I’ve had at other restaurants. Stuffed dates wrapped in bacon were outstanding. Server stopped by often and offered suggestions based on our likes. Would go again.
More info
Bulla Gastrobar - Winter ParkPrice: Moderate• Spanish• Winter Park
•
4.7
E
Edward
Orlando / Central Florida East •8 reviews
5.0
Dined on Nov 3, 2024
What a fun experience! The theming was 100% on point and the cocktails were delicious (and strong)! We’ll be back for sure.
More info
Permanent VacationPrice: Moderate• American• Maitland
•
4.9

Explore OpenTable

Maitland

Best Date Night Restaurants in Maitland

Price

Cuisine

Regions

Neighbourhoods

Top Rated

Dining Options

Seating Options

Award-winning

Accessibility

52 restaurants available nearby

1. Jazz Tastings

2. AVA MediterrAegean

3. Permanent Vacation

4. AJ CHOCOLATE HOUSE

5. Bar Italia Winter Park

6. Antonio's - Maitland - Upstairs

7. Fleming's Steakhouse - Winter Park

8. Christner's Prime Steak and Lobster

9. Bulla Gastrobar - Winter Park

10. Ruth's Chris Steak House - Winter Park

See what locals rave about

Explore OpenTable