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Best Things to Do in Winter Park

A Story By

Winter Park, FL. The picturesque storybook town any Orlando native knows and loves. Whether you live close by or you take the SunRail and get off at the train station in the middle of the charming Central Park, there’s so much for you to explore in this town.

Some of the best restaurants and prettiest views are located in Winter Park, and we’ve got all the details to share with you so you don’t miss out on anything.

Winter Park offers everything from the stunning Rollins College, scenic Park Avenue, and art museums to the historic Hannibal Square, street festivals, and food that you’ll be thinking about for days. Continue reading to see all of our top picks!

Grab A Bite

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📷 The Ravenous Pig / @foodie.girly

565 W Fairbanks Ave, Winter Park, FL 32789

Without a doubt, The Ravenous Pig is one of the most noteworthy restaurants in Winter Park. Husband-and-wife duo, James and Julie Petrakis, bring so much passion and craft for food to Orlando with their various dining experiences including Swine & Sons, Cask & Larder, and The Polite Pig. 

Ravenous is an award-winning American Gastropub where they share their appreciation for sustainable and local ingredients through their unique dishes and handcrafted cocktails.

We highly recommend you try the Ravenous Pub Burger, truffle fries, and their G & T on tap. You can have a full and magnificent dining experience or just stop by for happy hour with friends from 3PM–6PM daily!

108 S Park Ave, Winter Park, FL 32789

Turkish cuisine might not be something you’re super familiar with, but if you haven’t tried Bosphorous on Park Avenue in Winter Park, you must check it out. Known for their fragrant aromas, fresh ingredients, and family-like hospitality,  you’ll feel like you just landed in Turkey!

Be sure to order the famous lava bread with hummus and ezme. It’s hollow bread that’s torn apart by hand and we can’t stress this enough, it’s delicious.

Everything they serve is authentic and fresh. You can sit inside in the warm setting or choose to sit outside with a lovely view of Central Park.

 215 S Orlando Ave, Winter Park, FL 32789

How could you ever pass up great food, wine, and a stunning sunset over the banks of Lake Killarney? You can’t, and the only way to experience that is by having dinner at Hillstone Restaurant, formerly known as Houston’s if you’ve been in Orlando for a while.

Enjoy a fine meal for celebrations with the whole family or just a simple date night. From classic salads to roasted prime rib, you’ll find something perfect on their diverse American fare menu. Enjoy genuine hospitality, exceptionally prepared dishes, and an exquisite view all in one night at this scenic upscale restaurant!

1971 Aloma Ave, Winter Park, FL 32792

If you’re looking for something a little more family-friendly with quicker service, Bolay is the perfect stop on your way to explore the rest of Winter Park. It’s a fast-casual establishment that pays close attention to allergens and fresh ingredients.

You can build your own bowl or choose one of the already created bowls off the menu. You can’t go wrong with the lemon chicken or spicy Thai shrimp over the delicious orange basil quinoa or classic baby spinach. Bolay proves that healthy food can also be insanely tasty! 

Drinks & Happy Hour

📷 Prato Winter Park

110 Orlando Ave #7, Winter Park, FL 32789

Bulla is inspired by the various tapas restaurants all around Spain. You’ll turn meeting up with your friends at Bulla for happy hour into a weekly occurrence.

With an abundance of cheese and meat boards, tapas, delicious beers, perfect cocktails, and delectable wine, there’s something here for everyone’s ideal happy hour. Not to mention the atmosphere is fun, bright, and lively with a super friendly staff.

Be sure to try the patatas bravas and sautéed garlic shrimp!

290 S Park Ave, Winter Park, FL 32789

Luma is a great place to enjoy happy hour because it’s right on the avenue, so you’ll be surrounded by the bustling locals and visitors when you spend your happy hour here.

It’s a sophisticated atmosphere that offers delicate bites to pair with whatever you fancy off of their extensive wine list. They also have a lounge where you have a beautiful view of the park and can enjoy crafted cocktails and small plates. Their wine list changes every week and offers tastes from around the world by the bottle, glass, and even half-glass.

124 N Park Ave, Winter Park, FL 32789

Not only does Prato have the best Italian food in Winter Park, but their wine and cocktail menu also offers some of the best drinks in town. Their Italian dishes are classic plates but with a modern twist to fit the “rustic-chic” aesthetic. Stop by for happy hour during the week or enjoy the full dinner experience with salad, pasta, and pizza of your choice. It’s the perfect spot for date night whether you’re local to Park Avenue or not.  

Coffee, Art, and Culture

📷 New General

155 E New England Ave, Winter Park, FL 32789

A full coffee bar right on a side street off of Park Avenue. What makes New General even more unique is that it’s also a retail store hybrid. They offer local goods and products in their store, so you can shop for cool, new finds but also sit and relax and enjoy a delicious latte, as they serve Lineage Coffee (our local roasters).

The cafe provides a minimalist environment and also serves breakfast and lunch including various salads, toasts, and more. They also serve Buttermilk Bakery pastries and treats from Peterbrooke Chocolatier.

445 N Park Ave, Winter Park, FL 32789

The absolutely stunning Morse Museum is the home of the world’s most comprehensive collection of works by Louis Comfort Tiffany. These works include jewelry, pottery, art glass, paintings, glass lamps, and windows.

Walking through this museum will truly blow your mind and give you a new appreciation for art. The museum also offers many programs for visitors (including families) to tour the galleries at no charge and learn more about the collection and be a part of lectures and films.

You can explore the avenue, grab lunch, and finish off your day at the museum. 

312 E Morse Blvd, Winter Park, FL 32789

If you only have time to do one thing when visiting Winter Park, the Scenic Boat Tour has to be what you choose to do! It’s the perfect way to spend your time if you love beautiful nature and intriguing history.

You’ll learn so much about Winter Park in a setting that is tranquil and in a way you can’t get on foot or by car. You’ll observe fish, cranes, flora, fauna, breathtaking homes, and pristine waters. It’s a delightful way to experience this charming and picturesque suburb of Orlando. 

Winter Park Events

Winter Park is always hosting all sorts of events that you and your family will absolutely adore! Whether it’s the farmers market, Rollins musical or cultural events, art festivals, or Wine & Dine, there’s inevitably something fun going on in this endearing crevice of Orlando. The best way to stay up to date with events happening in Winter Park is to download the UNATION App. We’ll provide all the details you need for upcoming fun stuff to do in Winter Park!

If you decide to stop by and try any of these awesome places in Winter Park, be sure to tag us in your photos on Instagram and let us know how you liked it! Don’t forget to use our hashtag #StuffToDoInOrlando as well so we can repost you.

We hope you enjoy these locations as much as we do, and have fun discovering new parts of Orlando!

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Katie Schwartz

Katie Schwartz

Katie is the City Manager for UNATION and author of the  Stuff to Do in Orlando blog. For more insight on the best events and things to do in the Orlando area, download the UNATION app and follow @StufftoDoinOrlando on Instagram and Facebook.

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