35 Things To Do in Winter Park

Winter Park combines cultural, artistic, and recreational attractions, creating a destination that appeals to all travelers. Just north of Orlando, this charming city is known for its elegant shopping districts, inviting cafes, and scenic parks and lakes.

Visitors can stroll through boutique-lined streets or explore the city’s rich cultural heritage in its museums. Winter Park’s unique mix of urban sophistication and natural beauty ensures a variety of experiences for every interest.

Winter Park Scenic Boat Tour

Our Rating: 9.2/10

The Winter Park Scenic Boat Tour offers an intimate view of Florida’s natural beauty right from the water. This one-hour guided tour takes passengers through the interconnected chain of lakes and canals of Winter Park. On the tour, passengers get to enjoy the rich flora and fauna that are characteristic of the area.

The 18-passenger pontoon boats provide a relaxed atmosphere for everyone, making it suitable for families and groups. Operating from 10 a.m. to 4 p.m., the tours are frequent, departing every hour, giving visitors ample opportunity to hop on. No reservations are needed for individuals, though groups may book ahead, allowing for a seamless experience.

Charles Hosmer Morse Museum of American Art

Our Rating: 9.3/10

The Charles Hosmer Morse Museum of American Art in Winter Park provides an enriching experience for art enthusiasts. It houses the world’s most comprehensive collection of works by Louis Comfort Tiffany. Visitors can explore the exquisite jewelry, pottery, and paintings that showcase his talent.

The leaded-glass lamps and windows provide a glimpse into the artistic innovation of the late 19th and early 20th centuries. An extraordinary highlight is the chapel interior from the 1893 World’s Columbian Exposition in Chicago, meticulously reconstructed within the museum. This masterpiece reflects Tiffany’s elaborate design skills and creative depth.

Mead Botanical Garden

Our Rating: 8.5/10

Spanning over 47 acres, visitors can wander along its tranquil hiking trails, where a diverse range of flora and fauna awaits. The garden features a serene creek and a boardwalk that weaves through different natural habitats, offering moments of peace and reflection.

An engaging experience for nature lovers, this garden combines the charm of a butterfly garden and tall pine trees with an open-air amphitheater that hosts occasional events. The presence of yoga classes further enriches the experience, allowing visitors to deepen their connection with their surroundings.

Central Park

Our Rating: 9.0/10

Central Park serves as a scenic retreat where both locals and visitors can unwind. This 11-acre space offers more than just a breath of fresh air. Shady oak trees provide a natural canopy, making it ideal for picnics or leisurely strolls. The park is known for its beautifully landscaped planters and three stunning fountains that add a touch of elegance.

In the southern corner, a rose garden invites you to linger and capture stunning photographs. The open spaces and varied seating areas cater to those who wish to read, daydream, or simply observe life passing by.

Albin Polasek Museum & Sculpture Gardens

Our Rating: 8.5/10

The Albin Polasek Museum & Sculpture Gardens gives art lovers and curious visitors a chance to explore the world of internationally recognized sculptor Albin Polasek. The museum showcases a remarkable collection of over 500 pieces of Polasek’s art, featuring sculptures, sketches, and paintings. The historic home and studio, along with the expansive 3.5-acre sculpture garden, provide an immersive art experience.

The museum also hosts special exhibitions, such as “Wild at Heart: Environmental Sculptures by Paul Baliker.” This exhibition runs from December 2024 to April 2025, offering a fresh perspective on environmental themes.

Kraft Azalea Garden

Our Rating: 8.5/10

Kraft Azalea Garden is a peaceful place enveloped by towering cypress trees, providing shade and a touch of old Florida charm. The garden is a popular spot for photographers, who are drawn to its beauty and the opportunity to capture unique nature shots. Visitors might witness egrets gracefully flying and roosting in trees.

Ideal for a leisurely stroll or a reflective moment on one of the many benches, the garden offers quietude from the city buzz. Without picnic facilities, bring a personal snack to enjoy on a bench. Parking is best early in the day, and the Exedra monument adds a distinctive touch.

Winter Park Farmers’ Market

Our Rating: 8.7/10

Winter Park Farmers’ Market is a weekly gathering that offers an engaging and lively atmosphere for locals and visitors. Taking place every Saturday morning from 8:00 AM to 1:00 PM at the Central Park West Meadow, it provides a diverse selection of fresh produce, plants, and artisanal goods.

Visitors can explore a variety of stalls featuring everything from freshly baked goods to handcrafted items. The vibrant setting, filled with the scents of fresh produce and baked goods, enhances the overall experience.

Cornell Fine Arts Museum

Our Rating: 9.0/10

With a collection of over 5,000 pieces, the Cornell Fine Arts Museum showcases an impressive range of artwork, from contemporary pieces to historical treasures. Visitors can explore diverse exhibitions that include paintings, sculptures, and photographs, providing a comprehensive journey through different artistic eras and styles.

This museum is particularly noted for its curated events and educational programs that foster an appreciation for art amongst all ages. Art enthusiasts can partake in guided tours or attend informative lectures that delve deeper into the stories behind the works.

Casa Feliz Historic Home Museum

Our Rating: 8.5/10

Casa Feliz Historic Home Museum, known for its stunning architecture, is a testament to the work of James Gamble Rogers II. This Andalusian-style farmhouse captures the attention with its unique masonry and cultural significance. Visitors can explore beautifully restored rooms that host cultural events and exhibitions throughout the year.

The museum also provides an opportunity for guided tours, recounting the rich history and architectural details of the structure. Guests can enjoy the serene ambiance of the surrounding gardens, making it an ideal spot for photography or a peaceful stroll.

The Wine Room on Park Avenue

Our Rating: 8.5/10

The Wine Room on Park Avenue invites enthusiasts of fine wines to an experience that blends tasting and learning. This spot features an innovative Enomatic dispensing system. Guests can sample a wide variety of wines, choosing from 1, 2.5, or 5-ounce pours, allowing them to savor international selections by the sip or the glass.

Visitors have the option to load a card with a chosen dollar amount and explore the 156 different wines available, making it an adventure in tasting without the commitment of purchasing a full bottle. It’s a delightful opportunity to discover new favorites or indulge in familiar classics.

Rollins College

Our Rating: 8.3/10

Rollins College is a picturesque campus that is a perfect blend of natural beauty and architectural elegance. Visitors can enjoy a stroll around Lake Virginia, which provides serene views and a peaceful atmosphere. The campus itself features stunning Spanish-Mediterranean style buildings designed by prominent architects, making it a beautiful spot for an afternoon wander.

Art enthusiasts will appreciate the on-campus Cornell Fine Arts Museum, which showcases an impressive collection of American and European art. For those interested in performances, the Annie Russell Theatre provides engaging theater productions by talented students and faculty, offering everything from classic plays to contemporary works.

Panera Bread Winter Park Square

Our Rating: 7.8/10

Panera Bread Winter Park Square is cherished for its comforting soups, fresh salads, and handcrafted sandwiches. Visitors can enjoy a warm, inviting atmosphere with the option for in-cafe dining or grabbing something to go. Perfect for a relaxed breakfast or lunch break, the menu includes delightful options that cater to various tastes.

Regulars appreciate the consistent quality Panera delivers, making it a go-to place for those on the move or simply looking to enjoy a peaceful meal time. It’s a tasteful spot that effortlessly combines convenience with flavor, ideal for fueling up during your Winter Park exploration.

Prato

Our rating: 9.0/10

Prato is a stylish Italian eatery offering modern takes on classic dishes in rustic-chic surroundings. The restaurant’s menu features a variety of Italian-inspired dishes, including wood-fired pizzas, handcrafted pastas, and seasonal specialties, all prepared with fresh, locally sourced ingredients.

The warm space welcomes guests with its contemporary design balanced by rustic elements, including a long bar, which encourages a vibrant and communal atmosphere.

Park Plaza Hotel

Our Rating: 8.5/10

Park Plaza Hotel is a charming historic boutique offering a unique blend of comfort and old-world charm. Its rich history, dating back to the early 20th century, is evident in its architectural elements, such as the beautiful wrought-iron balcony. Visitors can enjoy modern amenities while soaking in the atmosphere of this cultural icon.

Known for its personalized service, the hotel provides cozy and exclusive lodging, making it a perfect retreat for travelers. Extended stay options are available, catering to those relocating or renovating. Guests can enjoy a relaxed stay while exploring the delightful surroundings.

Hannibal Square Heritage Center

Our Rating: 8.5/10

Hannibal Square Heritage Center is an engaging destination that delves into the rich history of Winter Park’s African-American community. The center features an award-winning collection of over 200 archival photographs and oral histories, which provide a vivid portrayal of life in the area throughout the 20th century. Visitors can explore The Hannibal Square Timeline, a fascinating exhibit highlighting pivotal local and national events.

Additionally, the center is a result of a collaboration between Crealdé School of Art, community residents, and the City of Winter Park, emphasizing the ongoing contributions of this historic community.

Scenic Tree-lined Streets of Park Avenue

Our Rating: 9.3/10

Park Avenue provides a delightful walking experience along its charming tree-lined streets. This picturesque street is lined with sprawling oaks, creating a unique ambiance that invites leisurely strolls year-round. Visitors are treated to a vibrant mix of upscale boutiques and cozy cafes.Whether shopping at unique boutiques or enjoying a coffee at a sidewalk café, there is something for everyone.

Park Avenue is also home to a range of dining options. From casual eateries to fine dining restaurants, the avenue caters to every palate. Many choose to dine al fresco, taking advantage of the scenic surroundings. Art lovers will appreciate the nearby museums and galleries, which add a cultural touch to the area.

Paddleboarding on Lake Killarney

Our Rating: 8.7/10

Lake Killarney promises an exciting paddleboarding experience that caters to both beginners and experienced paddlers. Visitors can explore the calm waters while enjoying the scenic views around the lake. Paddleboard rentals are available, allowing adventurers to glide across the lake at their own pace.

The area provides opportunities for nature photography, with lush greenery and diverse birdlife in the surroundings. Paddleboarding at Lake Killarney ensures a refreshing and enjoyable outdoor activity.

Choulala Winter Park

Our Rating: 8.5/10

Choulala Fine Pastries brings a taste of France to the local community. Specializing in French pastries, their signature choux cream puffs are a standout, alongside eclairs, macarons, and tarts. The bakery offers a cozy and inviting atmosphere, making it an ideal spot for a leisurely coffee and dessert.

Choulala also provides vegan options, including sorbets and plant-based milk for beverages, catering to diverse dietary preferences. Whether indulging in a sweet treat or seeking a unique gift, Choulala Fine Pastries offers a delightful experience for all visitors.

Boca Winter Park

Our Rating: 8.5/10

Boca Winter Park provides a farm-to-table dining experience with a focus on fresh, seasonal ingredients. The menu features a variety of dishes, including seafood, steaks, and vegetarian options, all crafted with locally sourced produce. The restaurant’s interior combines rustic charm with modern elegance, creating a warm and inviting atmosphere for diners.

An open kitchen design allows guests to observe the culinary team at work, adding an interactive element to the dining experience. Boca also offers an extensive wine list and craft cocktails, complementing the diverse menu selections.

Briarpatch Restaurant

Our Rating: 8.5/10

The Briarpatch Restaurant draws guests in with its promise of contemporary American cuisine. Known for breakfast, brunch, and lunch, its menu showcases a commitment to using fresh, local ingredients. Visitors and locals alike flock to enjoy dishes that feature the rich, seasonal flavors of Florida.

The atmosphere is warm and inviting, making it the perfect spot for a relaxed brunch or a bustling, sociable lunch. Unique offerings like the California Benedict or Pork Belly Waffle highlight the restaurant’s playful take on classic meals.

The Glass Knife

Our Rating: 9.0/10

The Glass Knife gives an elegant setting where patrons enjoy breakfast, lunch, and scrumptious desserts. The café’s charming retro vibe invites guests to relax on the covered outdoor patio, making it perfect for a leisurely brunch or coffee date. Their menu features a delightful array of pastries and donuts, each crafted with precision.

Customers rave about the inventive flavors, which often incorporate fresh, local ingredients. Known for its impeccable service, The Glass Knife ensures every visit feels welcoming and special.

Cocoplum Boutique

Our Rating: 8.5/10

Cocoplum Boutique thrives as a beacon of style and affordability, offering a curated selection of women’s fashion. Established in 2013, it continues to capture the essence of Florida’s vibrant lifestyle with its colorful and stylish pieces.

Shoppers can easily find the latest trends in clothing and accessories, each item thoughtfully chosen to reflect a sunny, cheerful vibe. The boutique’s delightful and unique fashion collections make it a happy place for anyone seeking fresh and exciting wardrobe additions.

Rocket Fizz Winter Park

Our Rating: 8.5/10

This locally owned shop invites visitors into a colorful world where shelves brim with over 1,000 candies and around 500 different sodas. The eclectic inventory showcases an impressive range of flavors and brands, some long forgotten and others waiting to be discovered.

As you wander through the aisles, the atmosphere buzzes with nostalgia, transporting everyone back to simpler, carefree days. Whether it’s taffy, root beer, or an obscure soda flavor that you’re after, Rocket Fizz offers a whimsical experience for young and old alike.

Bosphorous Turkish Cuisine

Our Rating: 8.5/10

Bosphorous Turkish Cuisine serves an authentic culinary experience with a menu rich in traditional Turkish dishes. Visitors can indulge in a variety of flavorful items, from succulent kebabs to delicate baklava, all showcasing the flavors of Turkey.

This family-owned establishment, operating since 2004, provides a warm and inviting atmosphere, ideal for both intimate dinners and lively group gatherings. The outdoor seating area, perfect for enjoying Florida’s temperate climate, further enhances the dining experience.

The Ravenous Pig

Our rating: 9.2/10

The Ravenous Pig is an acclaimed gastropub known for its inventive New American cuisine and on-site brewery. The menu features seasonal dishes crafted from locally sourced ingredients, offering a modern twist on Southern classics.

The stylish yet welcoming atmosphere is complemented by a selection of house-brewed beers and handcrafted cocktails. Recognized with a Bib Gourmand in the 2024 MICHELIN Guide, The Ravenous Pig continues to be a standout in the Orlando dining scene.

Luma on Park

Our Rating: 8.5/10

Luma on Park stands as a prominent dining destination showcasing contemporary American cuisine with a dynamic flair. The restaurant features a diverse menu that includes Italian influences alongside unexpected delights like soft shell crab and steak tartare. Visitors can explore a unique dining experience with its popular three-course prix fixe menu.

Wine enthusiasts will be impressed by the extensive selection stored in the basement wine cellar, complementing the sophisticated cocktail bar offerings. As patrons enjoy these fine wines and cocktails, they are enveloped in a stylish, modern ambiance that enhances the overall dining adventure.

Hillstone Restaurant

Our Rating: 8.5/10

Hillstone Restaurant in Winter Park attracts diners with its upscale ambiance and picturesque views of Lake Killarney. Guests can enjoy a delicious meal while taking in the sights from the patio. Known for its classic steak, seafood, and pasta dishes, Hillstone offers a menu that caters to diverse tastes.

The smoked salmon and BBQ pork ribs are popular choices, complemented by an array of signature cocktails. The warm, modern atmosphere, managed by culinary experts, ensures a memorable dining experience for lunch or dinner outings.

Menchie’s Winter Park

Our Rating: 8.5/10

Menchie’s Winter Park is an exciting destination for frozen yogurt enthusiasts looking to create their perfect treat. It offers a delightful self-serve experience with an extensive selection of flavors and a vast assortment of toppings. Guests can mix and match various flavors, ranging from classic vanilla to vibrant seasonal specials.

The toppings bar features a variety of choices, including fresh fruits, candies, and sauces, allowing for truly personalized creations. The inviting atmosphere makes it a fun and relaxing spot to enjoy a sweet treat in all seasons.

Shady Park

Our Rating: 8.5/10

Shady Park is a lovely spot in Winter Park where visitors can enjoy the peacefulness of nature. It features winding pathways ideal for a leisurely walk or reflection. This park provides park benches where people can relax and take in the surroundings. Families often come here to enjoy quality time together, making use of the open spaces for picnics and games.

The park’s ambience is enriched by historical Hannibal Square nearby, offering a slice of local history. Shady Park is a great choice for those looking to unwind and soak in the simple pleasures of being outdoors.

AVA MediterrAegean

Our rating: 9.0/10

AVA MediterrAegean is a modern Greek dining experience that blends traditional flavors with contemporary culinary techniques. The restaurant’s menu features a variety of Mediterranean dishes, including fresh seafood, artisanal cheeses, and seasonal vegetables, all prepared with a focus on authenticity and quality.

The elegant interior design, characterized by clean lines and natural materials, creates a sophisticated yet inviting atmosphere for diners. AVA MediterrAegean also boasts an extensive wine list and handcrafted cocktails, enhancing the overall dining experience

Barnie’s Coffee & Tea Co.

Our Rating: 8.6/10

Barnie’s Coffee & Tea Co. is a must-visit for coffee lovers. The café serves an array of beverages, including iced coffee, honey lavender lattes, and their signature cold brews. Their menu also features farm-to-table breakfast and lunch options that are perfect for a leisurely morning or afternoon bite.

The café is housed in a charming, historic building designed by James Gamble Rogers II, adding a unique architectural charm to your visit. Guests can enjoy their drinks and meals in a beautiful Mediterranean-style courtyard, providing a serene retreat from the bustling avenue.

4 Rivers Smokehouse

Our Rating: 8.7/10

4 Rivers Smokehouse is a destination for BBQ enthusiasts seeking authentic Southern flavors. Located at 1600 West Fairbanks Avenue, this renowned venue provides a delightful culinary experience. Diners can expect savory brisket, tender ribs, and a variety of other smoked meats, all expertly prepared.

The menu also features sides like creamy mac ‘n’ cheese and sweet potato casserole, enhancing the main dishes. Families and large groups find the casual, welcoming atmosphere perfect for gatherings. The smokehouse offers both indoor and outdoor seating, making it a fitting spot for enjoying Florida’s pleasant weather.

Tuni Winter Park

Our Rating: 8.5/10

Tuni Winter Park is a chic boutique located on Park Avenue, offering a unique shopping experience. Managed by a dynamic mother-daughter duo, Tuni and Paige Blackwelder, the store boasts a carefully curated selection of fashion-forward clothing, shoes, and accessories from both renowned and emerging designers.

Visitors are charmed by the store’s elegant setup and the personalized attention provided by enthusiastic personal stylists. These knowledgeable stylists help customers find the perfect outfit for any occasion, ensuring every shopping trip is memorable and enjoyable.

Peterbrooke Chocolatier

Our Rating: 8.5/10

Peterbrooke Chocolatier tempts visitors with an array of handcrafted chocolates. Upon entering, the rich aroma of cocoa welcomes you, drawing you to explore the varied selection. Favorites include chocolate-covered popcorn, hand-dipped strawberries, and pretzel rods, each carefully prepared to satisfy diverse tastes.

In addition to the staple treats, Peterbrooke frequently rotates seasonal items, ensuring that return visits are met with something new and exciting to try. The shop also caters to different dietary needs with sugar-free options, so everyone can enjoy a bit of indulgence.

Wildtree Winter Park

Our Rating: 8.5/10

Wildtree Winter Park offers a refreshing escape into nature’s beauty, right in the heart of Florida. Visitors can explore its scenic trails that weave through lush landscapes, offering opportunities for hiking and peaceful walks. The park’s well-maintained pathways invite wanderers to breathe in the fresh air and capture stunning views of the surrounding greenery.

This destination is perfect for picnicking, with ample space for setting up a cozy lunch spot under the shade of towering trees. Adventurous spirits can try their hand at birdwatching, with various species making their home in this natural setting. Parents will appreciate the family-friendly areas where kids can play freely, making it a perfect spot for a day out.

Winter Park provides a variety of experiences to enjoy. Whether exploring its rich history, attending lively community events, or relaxing in its scenic outdoor spaces, Winter Park ensures a memorable visit. The city’s inviting atmosphere and diverse offerings leave a lasting impression on all who come.