Living in Florida means we get to enjoy the outdoors for almost the entire year. Lunch and dinner dates are a beautiful experience no matter where you dine, but when you get the chance to experience the outdoors with your love, especially amongst the beauty of Winter Park, it enhances the afternoon or evening. Winter Park has several options for courtyard dates that we couldn’t resist highlighting!
348 N Park Ave #5
Nestled inside Winter Park’s Hidden Garden, Garp & Fuss serves up American fare including a selection of sandwiches, salads, wings, flatbreads, and more. Happy hour is offered Tuesday-Friday from 4-7pm, featuring $5 apps, a $5 Drink O’ the Day, $4 house wines and $6 house martinis. The restaurant features five rooms each giving a different dining experience, but dining in the enclosed solarium is a must as it provides the best view of the Hidden Garden area. Bonus: you’ll be able to enjoy courtyard dining no matter the weather!
118 S Park Ave
Barnie’s is located in Greeneda Court, one of the more well-known courtyards in Winter Park. The courtyard’s gorgeous marble tables, fountain, and lush greenery compliment the vintage look of the surrounding buildings. You’ll feel like you’re tucked away from the rest of Park Avenue. Barnie’s serves breakfast, brunch and lunch items, but just a heads up, the kitchen closes at 3pm most days.
331 S Park Ave
Mon Petit Cheri is known to Winter Park locals as a great place to grab a morning latte or breakfast with a friend, and most recently the cafe’s Honey Nougat Glacé won Orlando’s Signature Dish competition. Pastries and desserts are served alongside coffee and lunch items, including sandwiches, pizza and crepes. The cafe boasts a beautiful outdoor courtyard. For date night, pair the Friday night dinner special with a glass of wine or a cigar from neighbor Cigarz on the Avenue.
400 Orlando Ave.
One of my personal favorite date nights involves Italian food. Pair that with courtyard dining and I’m in heaven. Rocco’s Italian Grille provides you with an authentic Italian experience while dining in the dreamy courtyard, plus live music from Thursday-Saturday evening. For a budget-friendly date, visit during happy hour Monday-Friday from 5-7:30pm.
358 North Park Ave.
While Boca is located on the corner of Park Avenue and E Canton Avenue, their rear dining room overlooks the gorgeous Hidden Garden, a picturesque semi-hidden courtyard. The food at Boca is fresh, local, seasonal, and sustainable, with a farm-to-table approach. You’ll be able to catch happy hour from 3-6p Monday-Friday, and brunch is served on the weekends from open until 4pm. Whether you’re in the mood for a nice wine or a cocktail, Boca will provide an excellent experience with a beautiful view to cap it all off.
- ABO Winter Park
- Hillstone (not technically a courtyard, but the outdoor seating overlooking Lake Killarney is unbeatable!)
Looking for more outdoor dining ideas? Check out our guide to Orlando’s Best Patios.
Arlene Laboy is a professional brand photographer based out of Orlando, Florida. A wife and a mother, Arlene shares her love for adventuring around Florida and her professional work through her Instagram account, @arlenemlaboy. Find out more about Arlene here.