Winter Park Florida: An Appealing Escape from Orlando’s Convention Center Chaos

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Turn your Orlando business trip into a memorable getaway.

Let’s be honest. Most of my travel isn’t for vacation—it’s for work. While I don’t work in the travel industry, I spend enough time on the road to know one thing: every business trip has the potential to become a memorable experience.

That’s why every time I go to Orlando for a conference, I face the same problem. The convention center area is convenient, but after a long day there, it’s the last place I want to be at the end of the day to unwind.

I’m not interested in chain restaurants, crowded tourist spots, or hotels surrounded by parking lots and no character. I want to step outside, find a nice patio or rooftop bar, meet friends or colleagues for dinner, have a cocktail, and feel like I’ve discovered something special.

For me, that place is Winter Park, Florida.

My Winter Park Tale and a Bit of History

The first time I visited, I quickly saw why so many locals love this neighborhood.

My friend Marie, who lives nearby, first showed me Winter Park. She took me on the Winter Park Scenic Boat Tour. The town started in the late 1800s as a winter resort for people from the North looking to escape the cold. It was originally called Lakeview, but the name was changed to “Winter Park” to reflect its origins better.

Rollins College, a liberal arts school, was founded in Winter Park in 1885. Many historic buildings from that era remain, giving Winter Park a timeless feel that’s rare in modern Orlando.

I like Winter Park, Florida, for its historic character. It’s quiet, walkable, and upscale, with plenty of restaurants and shops (if I feel like shopping). There are plenty of people, but it never feels crowded. It feels like a real community, not a tourist spot.

Where I Stay

Park Plaza Hotel Winter Park: The Balcony That Won Me Over

I have a soft spot for The Park Plaza Hotel. It’s historic and comfortable. My favorite part isn’t just the room, it’s the balcony. There’s something special about sitting outside with coffee in the morning or a glass of wine in the evening and watching Winter Park below.

From my balcony, I can watch people walking along Park Avenue while the train crossing bells ring behind the hotel. Moments like this make me forget I spent the day inside a convention hall. With a glass of wine in hand and the sound of train bells, I’m reminded of being at home on my porch, listening to distant train horns and waving to neighbors walking their dogs. That’s the sense of community I feel while on the balcony at The Park Plaza Hotel.

The hotel has its distinct story too. It was built in 1922 as the Hamilton Hotel to serve visitors to nearby Rollins College, the oldest college in Florida.

The Park Plaza Hotel has creaky wood floors, thin plaster walls, and plenty of character. Another reason it feels like home.

The Alfond Inn: A Courtyard I love

The Alfond Inn is elegant, beautiful, and relaxed. As an art hotel, you’ll see art everywhere. It’s connected to Rollins College. I stayed here once and loved it. Did it feel like home? No, but I loved it all the same, BECAUSE it was different, and who doesn’t love art? I met a friend for wine in the courtyard, and then we walked just two blocks to Park Avenue for dinner.

Even if you’re not staying here, it’s worth stopping in for a drink or to relax in the courtyard before dinner and stroll to take in the art.

The Real Reason I Love Winter Park: The Restaurants

I know Winter Park is famous for Park Avenue shopping, but honestly, that’s not what keeps me coming back. I come for the food, the drinks, and the chance to relax somewhere beautiful and catch up with people.

Park Avenue in Winter Park is lined with boutiques, cafés, wine bars, trees, and brick sidewalks that make you want to slow down and wander.

Breakfast in Winter Park

Briarpatch Restaurant

252 N Park Ave #3814, Winter Park, FL 32789

If I have extra time in the morning before heading to the convention center, you’ll usually find me at Briarpatch. Their omelets never disappoint, and the outdoor tables are perfect for lingering over breakfast with another cup of coffee.

Keke’s Breakfast Cafe

345 W Fairbanks Ave, Winter Park, FL 32789

When I need something quick before heading to the convention or for having a breakfast meeting, Keke’s is my go-to spot. I’ve also met friends here before heading to work. Keke’s is just around the corner and always worth a visit. Parking is easy, and it’s never hard to get a table. The food is great, and be sure to ask for the Petal Sauce with the Southwest Omelet.

Dinner and Drinks Along Park Avenue

BoVine Steak House

319 S Park Ave, Winter Park, FL 32789

BoVine Steakhouse is right next to The Park Plaza Hotel, which makes it convenient—and it’s fantastic. On both my first and second visits, I started with an Old Fashioned. Now, ordering an Old Fashioned at BoVine is part of my Winter Park tradition.

I met a good friend and a colleague here, and we had a great dinner. The Chicken Chasseur with creamy risotto is outstanding.

The Wine Room on Park Avenue

270 S Park Ave, Winter Park, FL 32789

If you want a bottle of wine to enjoy on the Park Plaza Hotel balcony, a glass with some small plates onsite, or a wine tasting, The Wine Room has it all. It looks small from the outside, but it’s actually spacious. You can buy a card and sample over 148 wines from their ready-pour machines. Or pick a bottle, grab a table, order some food, and relax. You can even take your wine to go. I’ve picked up a bottle here to enjoy back on my Park Plaza Hotel balcony. Whatever you’re in the mood for, they’ll take care of you.

Prato

124 N Park Ave, Winter Park, FL 32789

Prato is an Italian restaurant, and my first visit was a bit overwhelming because it was crowded. I was here for a business meeting, and it was his suggestion, as it was a good central meeting spot. We waited for a table, but it wasn’t too bad. We eventually were seated at a table outside, and the food was fantastic. I went back a couple of years later and it reminded me of evenings spent lingering over dinner in Italy. Great food and great wine.

The Perfect Orlando Alternative for Business Travelers

Orlando is known for its theme parks and huge hotels, but sometimes the real gems are just a short drive away. Winter Park, Florida, gives me everything I crave after a long day at a conference: charm, easy walkability, tasty food, and the feeling of a real destination rather than just a spot to crash for the night.

The next time your travels bring you to Orlando, consider staying somewhere that lets you see a different side of Florida.

For more ideas on places to visit in Florida.

An Afternoon in Historic Mount Dora: Florida’s Charming Lakeside Town