Park Avenue Brunch and Wine Crawl Itinerary

It wasn’t until I left my hometown, Winter Park, and traveled abroad that I realized how special it is to have a street like Park Avenue in a community. Park Avenue embodies one of Europe’s most celebrated civic designs–the strolling promenade. Its cobblestoned streets, Central Park, and tasty Park Avenue Restaurants are beloved by all who amble along its sidewalks.

With restaurants and cuisines to match its worldly vibe, Park Avenue is brimming with fresh food and local ingredients. The old oaks dripping in Spanish Moss shade the streets where you can dine al fresco most of the year. So for your next day date or date night, grab a croissant and explore Park Ave’s hidden courtyards, sip an espresso while sitting in its rose garden, or pick up a baguette and lounge on its open lawn.

Updated December 2023 by Meghan Roth

Park Avenue Restaurants



Boca Winter Park

358 N Park Ave Suite A, Winter Park

At the heart of Boca’s mission is freshly prepared farm-to-table-fare. They believe everyone benefits by using local ingredients from farmer, to chef, to diner. Check it out for happy hour, lunch, dinner, or brunch. Everything is prepared fresh with a vibrant taste.

Brunch is served on Saturday and Sunday from 9:30 a.m. to 3 p.m., and Happy Hour, which features ½ off wines by the glass, $5 signature cocktails, and $5 appetizers is Monday through Friday from 3 p.m. to 6 p.m.

Orchid Thai

305 N. Park Avenue, Winter Park

You’ll find all of your Thai favorites on the menu at Orchid Thai, like green curry and pad thai. Their use of fresh vegetables and proteins like shrimp is sure to impress. On Wednesday through Saturday, Orchid Thai also serves sushi. Sit inside or outside at this elegant spot.

Image credit: Orchid Thai


252 N Park Ave, Winter Park

This breakfast and lunch spot is ideal for a boozy brunch. No reservations are allowed at this local favorite, so arrive early if you want a full stack of their raspberry lemon creme pancakes (which you do). Consider adding some eggs or other protein to your meal so you can enjoy some brunch cocktails. Favorites like Bourbon Blackberry Lemonade and Blood Orange Mimosas are worth the out-the-door wait.

Or consider ordering online for takeout.


124 N Park Ave, Winter Park

This casual Italian restaurant has just the right vibe. Plants waterfall down its brick walls while breeze billows through the restaurant's folding glass doors that open up to face Central Park. Prato’s menu celebrates the best in Italian cooking: fresh, simple ingredients. You can’t go wrong on the menu whether you’re in the mood for pasta or wood-fired pizza. You may want to arrive hungry so you can share one of the delicious appetizers.

Don’t leave without trying something from their full bar. I suggest their spin on the Aperol Spritz–the Italian Citrus: Finlandia Grapefruit Vodka, Aperol, House Made Lemonade, and Pomegranate Juice.

Happy Hour is Monday through Thursday from 4 p.m. to 6 p.m.

Prato happy hour
Image credit: Stephanie Patterson

Bosphorous Turkish Cuisine

108 S Park Ave, Winter Park

If you’re looking for a Far East experience, head to Bosphorous for the best Anatolian cuisine in Central Florida. This Turkish restaurant has been on Park Avenue since 2004. It’s known for its enormous domed Lavash bread that entices hungry diners walking past its outdoor tables. Don't miss their fresh olives for that perfect pucker.

A warm atmosphere and exquisite Turkish food make this a Park Avenue staple for an exotic date night.

AVA MediterrAegean

290 S. Park Ave, Winter Park

Meaning life, water, island, bird in Greek, AVA is a celebration of splendor, freedom, escapism and joy. Delectable food and a very vibrant atmosphere combine to entertain the senses and transport guests to celebrate the night away.

One of the newer Park Avenue Restaurants, AVA has quickly become the place to be seen. Its sleek atmosphere may remind you of Miami or New York.

Croissant Gourmet

120 E Morse Blvd, Winter Park

This little French bakery is a personal favorite. Their croissants are as flakey as those you’d find in Paris, fresh out of the oven. After you’ve salivated over the bakery counter and picked up a few many items to go, grab a hot espresso or refreshing lemonade and wander over to Central Park to sit by the fountain and people watch while you eat.

Image credit: Arlene Laboy @arlenelaboyphoto

The Imperial Winter Park

170 E. Morse Blvd, Winter Park

This wine bar is The Imperial's third location in Central Florida; the others are located in Sanford and Ivanhoe Village. A furniture store by day and wine bar by night, the menu includes wines, beers, cocktails, and a food menu of bar snacks and lighter fare.

Umi Japanese Fusion Restaurant

525 S Park Ave., Winter Park, FL

Umi, located on Park Avenue near Rollins, offers a unique twist to the Japanese cuisine found here in Central Florida. The chefs select only the finest and freshest produce, seafood and meats sourced locally and from around the world, ensuring that each handmade dish is prepared just for you.


558 W New England Ave #135, Winter Park

PIANO is a corner gem with big windows and even bigger heart – your home away from home. The bar serves an extensive list of carefully curated wines from all around the world. With delicious gourmet foods, imported Italian pasta, cheeses, and meats, combined with a warm, sociable experience. PIANO is a cozy spot for a quick breakfast, elegant lunches, relaxed dinners or lazy brunches. 

PIANO offers Happy Hour specials from 4-7pm, Monday through Friday. They have live music Friday & Saturday nights from 6:30-9:30pm

Barnie's Coffee Kitchen

118 S Park Ave, Winter Park

This chain coffee spot exceeds the service and product of competitor Starbucks. You’ll find fine fair trade coffee here alongside farm-to-table breakfast and lunch. In fact, this Park Avenue staple now has a refreshed look and a new menu.

Enjoy a casual breakfast or lunch while people watching the Park Ave crowds or for an intimate conversation in its secluded Mediterranean courtyard.

AJ Chocolate House

552 S. Park Ave., Winter Park, FL

With over 150 different amazing chocolate delicacies, AJ Chocolate House is truly a place to 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, or simply need to find the perfect gift for a chocolate lover, they are happy to welcome you to their house.

*BONUS Date Night Idea: Every month, AJ Chocolate House hosts signature events where you can mingle, network, and delight with their staff—learning about the magical world of chocolate and how it pairs with everything from wine to coffee.

The Parkview

136 S Park Ave, Winter Park

This American fare restaurant boasts…wait for it…a park view of Central Park. Dine here for lunch, dinner, or brunch. What could be better than bacon and a mimosa flight? The Parkview also serves up epic charcuterie platters, delicious flatbreads, and seasonal offerings that are always changing.

The Parkview Winter Park brunch French toast
Seasonal French Toast at The Parkview | Image credit: Stephanie Patterson

Cocina 214

151 E Welbourne Ave, Winter Park

For modern Tex Mex in an elegant setting, look no further than Cocina 214. You’ll find all of your favorite Mexican flavors and dishes here. Hello, fresh avocado! You can’t miss indulging in their award-winning cocktail menu. Don’t miss their Elderflower Margarita, made with Elderflower liqueur, fresh raspberries, and lime.

Happy Hour runs Monday through Friday from 4 p.m. to 6:30 p.m.
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The Wine Room

270 S Park Ave, Winter Park

The Wine Room offers a unique way to sample many wines without a steep bill. Upon entering, you first purchase a refillable card that acts as your bartender for the night. Wander around and sample wines by using your card to swipe your way to a full glass.

If you like a wine, simply swipe and order a full pour. Then, sink into the rich leather seating and get lost in conversation and the comfortable atmosphere. An assortment of cheese and charcuterie, small plates, flatbreads and desserts offer perfect pairings. The Wine Room is a classic and one of our favorite Park Avenue restaurants.

The Wine Room on Park Avenue
Image credit: The Wine Room on Park Avenue

Peterbrooke Chocolatier of Winter Park

300 S Park Ave, Winter Park

No need to tell you where Peterbrooke is, just follow your nose. This European-style chocolate shop makes all of its chocolate in-house, along with eighteen flavors of gelato. All chocolate here is made from ethically sourced cocoa beans.

Peterbrooke Chocolatier of Winter Park | Image credit: Stephanie Patterson