If you follow me here, you already know that Winter Park holds a permanent piece of my culinary heart. With many of Orlando’s best restaurants in Winter Park, it’s a foodies dream!
And It’s easily one of Orlando’s most sophisticated, walkable, and beautiful neighborhoods. From the European charm of Park Avenue to the hidden gems tucked away in Hannibal Square, I am constantly exploring these streets looking for the next incredible dish or perfectly balanced craft cocktail.
Because I get asked all the time how to spend a perfect food-centric weekend out here, I’ve put together my foodie dream itinerary.(Plus some fun activities!) These are all places I have personally been to, fallen in love with, and return to time and time again.
Grab your most comfortable (and stylish) walking shoes—here is exactly how to execute the ultimate, indulgent, 48-hour weekend fun & foodie crawl through my favorite Winter Park spots!
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Saturday: Farmers Market Finds & Trendy Bites (Market hours 8:00am-1:00pm)
9:30 AM | Market Grazing & Local Flavors
Where: Winter Park Farmers Market (New York Ave & Morse Blvd)
- Why I love it: There is nothing quite like the smell of fresh baked goods and local produce in the morning. This farmers market is bustling with people and full of delicious things, and the best way to support local vendors while getting a true taste of the community!
- My Order: Skip a heavy sit-down breakfast (we have a lot of other eating to do!) and graze your way through the market. I love grabbing a fresh pastry, a cup of local cold brew to walk around with, and I never leave without a bag of spicy microgreens and local honey to take home.
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PRO TIP: Always have a cooler in your car. You never know what the day will bring or what tasty treats you may find.
12:30 PM | A Midday Italian Feast
Where: Grappolo (526 S Park Ave)
This is one of my favorite places when I’m craving Italian food.
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- Why I love it: When I want an upscale, elegant, and intimately authentic Italian lunch, this is exactly where you’ll find me. Sitting right on the Avenue, it feels like a mini-escape to Europe.
- My Order: Snag a table and pace yourself, because their house-made pastas are phenomenal. I highly recommend a rich, perfectly sauced rigatoni or a flawless cacio e pepe. Pair it with a crisp Pinot Grigio or a classic Aperol Spritz, and you have my recipe for the ultimate long, leisurely weekend lunch.
2:00 PM | The Afternoon Stroll on Park Ave.
- Why I love it: We just had an amazing lunch but we need to burn off some calories. Park Avenue is full of charming local shops and high-end shopping. You never know what you may see or find tucked away in a delightful shop!
- Check out: There’s so many shops but I’m calling out “Scott Laurent Collection”. It’s a beautiful shop tucked away in what’s called the “hidden garden”. He’s been here for over 30 years and features local and international artists. From glass and sculptures to jewelry and housewares….lots of beautiful delights!
4:00 PM | The Afternoon Intermission: Wine & Charcuterie
Where: The Wine Room on Park Avenue
- Why I love it: This place is a total playground for wine lovers. I love the interactive experience of loading up a smart card and sampling different pours from their automated dispensers. It’s a Winter Park staple for a reason.
- My Order: I like to use this time to sample a few robust reds or crisp whites I’ve never tried before. Definitely build a custom charcuterie board with their artisanal cheeses and cured meats to graze on—it’s the perfect, relaxed mid-afternoon pause.
9:00 PM | The Hip Saturday Night Afterparty: Pizza, Cocktails & Vinyl
Where: Perla’s Pizza (959 West Fairbanks Ave)
- Why I love it: When Park Ave starts to wind down, this is where I head to completely shift the vibe. Curated by Michelin-starred chef Michael Collantes, this effortlessly cool, late-night vinyl record listening bar is one of my absolute favorite spots in the city right now.
- My Order: Pull up a seat at the bar have a craft cocktail and listen to a local DJs spin incredible LPs. I always order a banana-infused Old Fashioned and split one of their unconventional, chef-driven pies. The “Mikey’s Hot Double Down” with double pepperoni and hot honey is a total crowd-pleaser, but if you’re feeling adventurous, you have to try their famous banana-topped pizza. The warm vinyl hum and incredible energy make this the perfect Saturday finale!
Slow Sunday in Winter Park
11:00 aM | The Trendsetting Brunch
Where: Sixty Vines (110 Orlando Avenue)
We need a slow start after our big day yesterday! Let’s brunch!!
- Why I love it: Sunday Brunch should always be bright, airy, and full of great flavor. I love having options that feel fresh and forward-thinking.
- My Order: If you want a gorgeous wine-country inspired experience, head to Sixty Vines. They have 60 wines on tap and they pair perfectly with their curated menus. And brunch here is amazing, you gotta try the Winemaker’s breakfast, avocado bene croast, or carrot cake pancakes and get a greenhouse spritz! It’s all delish! You can’t go wrong here…reserve a table!
1:00 PM | Winter Park Scenic Boat Tour
Where: 312 E. Morse Blvd. Winter Park
- Why I love it: This is a beautiful tour of canals and lakes of Winter Park. It’s also one of the oldest tours in the State of Florida dating back to 1938! We saw lots of birds, turtles, and beautiful homes. Read my experience here. If you are planning to do this tour in the summer or hotter months, plan to go earlier or later in the day!!
4:00 PM | Sweet Sophistication
Where: AJ Chocolate House (522 S Park Ave)
- Why I love it: To me, a proper foodie weekend requires a luxurious sweet treat. Walking into this place feels like stepping straight into a high-end European chocolate boutique.
- My Order: This has been quite the weekend crawl and we need a little pick-me-up! Let’s get a sugar rush with a rich, molten hot chocolate or latte macchiato! And I always select a small, custom box of their handmade, jewel-like truffles to enjoy there (or save for a late-night treat later….see, you need a cooler!).
7:30 PM | Dinner in the Square
Where: The Corner Chophouse (558 W New England Ave-Hannibal Square)
- Why I love it: I adore the historic charm of Hannibal Square, and this sleek, modern steakhouse completely elevates the neighborhood’s dining scene. The atmosphere is upscale but welcoming, making it feel like a true hidden gem just a short stroll from the main drag.
- My Order: I go all out here. This is quite a splurge, but the quality is there! They serve up some of the most perfectly seared, premium cuts of beef in town, complemented by indulgent, elevated sides. Don’t skip their signature cocktail menu—their mixology game is incredibly strong and sets the perfect tone for a night out. I got the after dinner Grasshopper cocktail…..this cocktail was invented around 1918 but really blew up in the 50’s and 60’s. It’s having a bit of a revival now…and I really enjoyed it!
My Pro-Tips for the Perfect Winter Park Crawl:
- Reservations are an Absolute Must: These are some of my personal favorites, which means they are also favorites for a lot of other locals! So grab a reservation for Corner Chophouse or Grappolo they fill up weeks in advance for weekend peak times, so book early!
I’ve shared my absolute favorites, so now I want to hear from you! What’s your go-to, can’t-miss dish when you’re eating your way through Winter Park? Let me know in the comments below!
Want to bring this itinerary with you on your next date night or girls’ weekend? I’m thinking about turning this exact guide into a downloadable, aesthetic pocket map or a Pinterest-ready visual checklist for the blog—which one would you guys use more? Let me know!
Thanks for reading!
