Located just 20 minutes north of the happiest place on earth, Winter Park is a charming town filled with world-class art museums, an upscale shopping district, fine-dining, sidewalk cafes, and luxury accomodations. Winter Park has all the feel of a charming European village without the crowds of the bustling city nearby. With over 70 different parks that feature festivals and events throughout the year, Winter Park is the perfect destination for nature lovers. Also located in the heart of Winter Park is Florida’s first four-year university, Rollins College, which is known for some of its famous alumni like Mister Rogers himself and Meg Crofton who served as president of the Walt Disney Parks and Resorts Operations in the U.S. and France. This is the ultimate guide to Winter Park, Florida including the best places to dine, stay, and play.
Guide to Winter Park, Florida: Where to Eat
The Ravenous Pig is a seasonal gastropub created by James Beard-nominated chefs, James and Julie Petrakis. You can also enjoy their cuisine in the happiest place on Earth, at The Polite Pig in Disney Springs.
Easily one of Winter Park’s most popular and iconic restaurants, the Briarpatch has a central location right along Park Avenue and serves American cuisine for breakfast, lunch, and dinner. Most locals will tell you that breakfast/brunch here is something that cannot be missed! Make sure to get their early as the Briarpatch can get very crowded, especially on the weekends.
Prato and Luma on Park
Prato and Luma on Park are both owned by the same chef, Brandon McGlamery. These restaurants are both located on Park Avenue. Luma specializes in progressive American, while Prato features innovative Italian cuisine.
Blu on the Avenue
With fresh seafood and sushi, prime steaks, and classic cocktails, blu on the avenue is the perfect spot for a evening date night or a relaxing lunch with family.
Umi Sushi provides a bold twist to traditional Japanese cuisine, giving you a unique experience with an authentic robata grill and sushi bar.
Serving French cuisine, Chez Vincent transports you to a French bistro in Paris with a beautiful lounge, large dining room, and a private wine cellar!
Reel Fish Coastal Kitchen
Reel Fish Coastal Kitchen provides a contemporary take on a “fish camp” with fresh local seafood cooked southern style in a family-friendly atmosphere.
The COOP is a neighborhood joint celebrating the classic home-cooked foods of the South, such as fried chicken, mac and cheese, and shrimp and grits. Created by the team behind the 4 Rivers Smokehouse, the COOP brings you the perfect homestyle Southern meal with all the pickings for a great inexpensive price!
Bulla Gastrobar was originally created in Miami and has since expanded to the Orlando area. Come to this unique restaurant for an innovative take on Spanish cuisine, with the use of a Josper oven/grill and charcoal.
Hamilton’s Kitchen, located in the Alfond Inn, focuses on serving local, fresh ingredients in a rustic setting for a farm-to-table experience.
The Glass Knife
Looking for some delicious dessert options? The Glass Knife is the go-to spot for Southern cakes, European style pastries, doughnuts, champagne, fine wines, and craft beers. They are also open for breakfast, lunch, and dinner to satisfy all your savory needs as well.
Guide to Winter Park, Florida: Where to Caffeinate
New General has a modern approach on a general store, with unique apparel items and home goods that support small businesses, a full coffee bar featuring Lineage Coffee, and a cafe serving freshly prepared foods. New General is located just a little bit off the beaten path from Park Avenue and is worth finding for some of the best coffee in all of Orlando!
After being founded only two years ago, Foxtail Coffee has become a staple around the Orlando area, with 10 shops open currently and many more planned for the future. The founders term the experience of visiting one of their shops as the “Foxtail experience,” with perfectly crafted design, beautifully brewed coffee, and a customer service experience that cannot be beat. The Winter Park location in actually Foxtail’s flagship store, with a package room, cafe, and roastery. Attached to this shop is Foxtail Farmhouse, a mixed-use artisan setting. The Farmhouse features a gravity bar with all the coffee your heart can desire, a wine and bubbles bar, juice, cocktails on tap, and small appetizers and pastries. Also located at this location is the world’s largest coffee siphon bar.
Guide to Winter Park: Where to Stay
The Alfond Inn at Rollins College
The Alfond Inn, owned and operated by Rollins College, contains 112 rooms, plenty of amenities, and a large art collection. And, even better, all the hotel’s profits go towards scholarships at Rollins College!
Since Winter Park is officially a suburb of Orlando, the best way to truly immerse yourself in this area is to stay in one of the neighborhoods at an Airbnb. With plenty of homes to meet your needs, Airbnb is a great option for visitors wanting to get a true experience of Winter Park. For a list of all the available Airbnb homes, make sure to check out their website here.
Park Plaza Hotel Winter Park
Built in 1922, the Park Plaza Hotel is a vintage boutique hotel located in the heart of Winter Park, on Park Avenue. It has a total of 28 rooms and is perfect for those wanting a cozy, intimate stay in this beautiful town. The rooms feature all kinds of antiques and a balcony garden filled with greenery and flowers.
Guide to Winter Park, Florida: Where to Shop
Park Avenue Shopping District
Park Avenue has been the central point to this winter retreat since 1887. Often termed “Little Europe”, Park Avenue has all the feel of a European street with boutiques, fine dining, and one-of-a-kind museums, as well as Southern charm with expansive parks, farmers markets, and art festivals.
As you walk down the cobblestone street you will find some of the most unique shops such as Rifle Paper Company, the flagship store of this stationary company that has quickly expanded past their roots to home decor and shoes. From adult boutiques such as Tuni and John Craig to kids shops like Bebe’s and Liz’s and Tugboat & the Bird, there are shops here for everyone in the family. There also big brand name stores located on Park Avenue like Lilly Pulitzer and Williams Sonoma.
The Heavy WP
Located off the beaten path, the Heavy WP is a plant shop/flower bar/cafe/home goods store. Whether you are picking out a new succulent, drinking a latte with Mercantile Coffee, creating a flower arrangement for your living room, or buying a gift for your best friend, you are sure to have an amazing [and instagrammable] time at the Heavy WP!
Winter Park Village
Winter Park Village is an outdoor shopping center with restaurants, shops, and one of the nicest movie theaters in the area. Here you will find mostly brand-name stores and chain restaurants.
Guide to Winter Park, Florida: What to Do
Winter Park Farmers Market
Easily one of the most popular farmer’s market in the Orlando area, the Winter Park Farmers Market happens every Saturday morning from 7 AM to 1 PM at the Old Train Depot. Here you will find everything from fresh produce and baked goods to plants and fresh flowers!
Cornell Fine Arts Museum
Cornell Fine Arts Museum is a part of Rollins College and features more than 5,500 fine art pieces. It has been recognized as one of the biggest and most distinguished art collections in the state. What makes this museum even better? Free admission!
This park is located at the heart of Winter Park and boasts 11 acres of shaded oak trees, fountains, and sitting areas. Central Park is the perfect spot for an afternoon picnic and people-watching before heading to find dessert on Park Ave.
Popcorn Flicks in the Park
Popcorn Flicks in the Park is held on the second Thursday of every month at 8 PM. The films are classic films made for the entire family to enjoy! The films are shown in Central Park and all of the films are free to the public.
Mead Botanical Garden
Mead Botanical Garden is a 48-acre urban garden oasis. The garden is open from sunrise to sunset every day and is completely free to the public.
Winter Park Scenic Boat Tour
Winter Park Scenic Boat Tour is the best way to explore the 12 lakes and over 2,781 acres of beautiful waterways located in Winter Park. On this tour, you will be able to enjoy views of multi-million dollar homes, all sorts of wildlife, and views of big landmarks, such as Rollins College and Kraft Azalea Gardens. The boat tour lasts an hour long and costs $10 per person.
Rollins College, located along Virginia Lake, has been voted one of the most beautiful college campuses in the US (for good reason)! With Spanish-Mediterranean architecture and lush gardens and greenery, Rollins College is the perfect place for an afternoon stroll through their 80 acres of campus.
Bach Festival Society of Winter Park
The Bach Festival Society of Winter Park is central Florida’s oldest operating performing arts group as well as the third-oldest operating Bach Festival in the country. The Bach Festival Choir is the heart of the society, with over 160 singers that auditioned for the spot and chose to volunteer for the choir.
Kraft Azalea Garden
Kraft Azalea Garden is a beautiful 11-acre park with views of Lake Maitland and plenty of areas for sitting on a bench or picnicking. The best time to visit this garden is when the azaleas are in bloom, which is from January through March.
Cultural Walking Tour
Don’t want to pay money for the boat tour, but would still like to learn more about the area? The cultural walking tour is the perfect option for you. This self-guided walk starts at the Winter Park golf club and heads south down Park Avenue. You can download the guide for the tour here.
Winter Park Playhouse
The Winter Park Playhouse, one of the only professional musical theaters in Florida, is a non-profit charitable organization dedicated to bettering the lives of guests and locals alike through programs and musicals. With 123 seats in this venue, it is the perfect theater for an intimate, up-close play experience. Tickets range from $20-$45.
Charles Hosmer Morse Museum of Natural Art
This museum is home to the world’s most comprehensive collection of art by Louis Comfort Tiffany, an American designer. As you walk through the museum you will be able to see magnificent stained glass, American art pottery, iconic Tiffany lamps, and more. It costs $6 for adults for admission, $5 for seniors age 60+, free for kids 12 and under, and $1 for students with valid ID. If you go on Friday from November- April from 4:00-8:00 PM, you will be able to get in free. For more information on the museum and their hours, check out their website here.
Winter Park hosts two outdoor art festivals, the Winter Park Sidewalk Arts Festival and the October’s Winter Park Autumn Art Festival. The Winter Park Sidewalk Arts Festival features more than 200 artists and over 350,000 guests, and admission for the event is free. The October’s Winter Park Autumn Art Festival features exclusively Florida artists, and admission for this festival is also free.
Olde Fashioned 4th of July Celebration
The 2019 Olde Fashioned 4th of July Celebration marked the 24th year of this tried-and-true Winter Park tradition. This event usually lasts the entire day of 4th of July, and it occurs right in Central Park off Park Avenue. With family-friendly events like the children’s bicycle parade, games, and inflatables, and adult events like performances by local musicians and the Bach Festival Choir and Brass Band, there is activities for everyone in your party to enjoy. Some free food is usually offered with additional purchases available. The Charles Hosmer Museum will also offer free admission for select hours on this day. The Winter Park History Museum also offers free admission on this day.
Pumpkins & Munchkins
This fall time event is free and includes a trick-or-treat trail, costume contest, bounce houses, and games. This is the perfect place to bring your kids for trick-or-treating since it occurs every year on Halloween!
Winter Park goes all out for their holiday season with several yearly events happening that are tradition to this charming town. The 67th Annual Ye Olde Hometown Christmas Parade has been around since the 1950s and includes marching bands, dance groups, Santa Claus, and fire and police departments. The Annual Christmas in the Park features an exhibition of 100 year old Tiffany windows and a free Christmas concert by the Bach Festival Society choir and brass band, and admission to the event is free. During Winter on the Avenue, Park Avenue becomes a wintertime wonderland for a fun-filled street party with carolers, a tree-lighting ceremony, and Santa Claus. The Orlando Philharmonic Orchestra Holiday Pops concert occurs in Central Park and is a free concert featuring holiday favorites for everyone in the family.
Guide to Winter Park, Florida: Overall Experience
While experiencing all the fun and thrill of the themes parks in Orlando should definitely be a must on your list, a visit to Winter Park is perfect for a relaxing, romantic, nature-filled day in this charming European-inspired town. Whether you are a family looking for fun events and on a search for wildlife or a couple looking for a break from the crowds and in need of a romantic dinner and shopping date, Winter Park can fill all your needs. With all the amenities of a large city and all the uniqueness of a small town, Winter Park is a place every person should experience at some point in their life. It will be sure to capture your heart, and leave you wanting to go back as soon as possible!