Winter Park

Day Trips

Start your day with a leisurely breakfast at a charming cafe in the Historic Center, where you can enjoy locally sourced ingredients. After breakfast, take a stroll through the picturesque streets lined with stunning architecture and boutique shops. Don't forget to stop by the local art galleries to appreciate the vibrant local art scene.

Post-lunch, embark on a guided walking tour to learn about the rich history of Winter Park, including its founding and key historical figures. Visit the iconic Rollins College campus and explore its beautiful gardens, soaking in the serene atmosphere. As the afternoon unfolds, consider renting a bike to explore the scenic bike trails around the area.

In the evening, head to a renowned restaurant for dinner, where you can indulge in a delicious farm-to-table meal. After dinner, take a leisurely walk along the beautifully lit streets, soaking up the festive atmosphere. Wrap up your day with a nightcap at a cozy bar featuring live music.

Begin your morning with a visit to the Charles Hosmer Morse Museum of American Art, home to the largest collection of Tiffany glass. Spend your time admiring the stunning exhibits and learning about the evolution of American art. Enjoy a light snack at the museum café before heading to your next destination.

In the afternoon, venture to the Albin Polasek Museum & Sculpture Gardens, where you can explore the beautiful outdoor gardens and view impressive sculptures. Participate in a guided tour to gain deeper insights into the artwork and the life of the artist. This serene environment is perfect for leisurely walks and photography.

As night falls, treat yourself to a fine dining experience at a local bistro that celebrates seasonal flavors. Post-dinner, enjoy a cultural performance at the Winter Park Playhouse, showcasing local talent in an intimate setting. Conclude your evening with a stroll around the nearby lake for stunning views of the stars reflecting on the water.

Kick off your day with an early breakfast before heading to the Winter Park Ski Resort for an exhilarating day on the slopes. Rent your gear and hit the trails, enjoying the fresh powder and breathtaking scenery. Take a ski lesson if you’re new to the sport, guided by experienced instructors.

After a morning of skiing, take a break for lunch at one of the on-mountain lodges, where you can refuel with hearty comfort food. Spend the afternoon skiing or snowboarding on the various trails that cater to all skill levels, or try snowshoeing for a different perspective of the snowy landscape. The crisp mountain air and stunning views make for an unforgettable experience.

After an adventurous day, unwind at a local alehouse where you can enjoy some craft beers and comfort food. If you're up for it, join a night skiing session for a whole new experience under the stars. End your day relaxing by a fireplace at your accommodation, sharing stories of your ski adventures.

Begin your morning with a hearty breakfast at a local diner before heading to the nearby Mead Botanical Garden. Spend your morning walking through the lush gardens, enjoying the tranquility and diverse plant species. Keep an eye out for local wildlife, including birds and butterflies, as you stroll along the paths.

In the afternoon, take a guided nature walk in the nearby Wekiva Springs State Park, where you can learn about the local ecosystem and its inhabitants. Bring a picnic lunch to enjoy in the serene surroundings, surrounded by towering cypress trees. The park’s crystal-clear springs invite you to take a refreshing dip on a warm day.

As the sun sets, return to Winter Park and treat yourself to a delightful dinner at a restaurant specializing in local cuisine. Afterward, take a scenic boat tour on the Winter Park Chain of Lakes, where you can witness the stunning twilight views. This peaceful evening activity will leave you with lasting memories of the beautiful landscapes.

Start your day with breakfast at a trendy brunch spot known for its unique twists on classic dishes. Afterward, head to the charming Park Avenue for a leisurely shopping experience, where you can discover local boutiques and artisanal shops. Enjoy browsing through unique gifts, clothing, and handmade crafts from local artisans.

Take a break for lunch at a delightful café featuring outdoor seating, perfect for people-watching. In the afternoon, join a culinary tour that highlights Winter Park's culinary scene, sampling various local specialties and learning about the history behind them. This immersive experience is both delicious and educational.

In the evening, attend a cooking class at a local culinary school where you can learn to prepare a signature dish from a professional chef. Afterward, enjoy the fruits of your labor with a communal dinner, sharing stories and laughter with fellow food enthusiasts. End your culinary adventure with a dessert from a local bakery, savoring the sweet flavors of Winter Park.

Begin your day with a delightful breakfast at a lakeside café, enjoying views of the tranquil waters. After breakfast, rent a kayak or paddleboard to explore the serene waters of Lake Virginia or Lake Osceola. Engage with nature as you paddle through the chain of lakes, taking in the beautiful surroundings.

In the afternoon, enjoy a relaxing picnic on the shores of one of the lakes, soaking up the sun and the peaceful atmosphere. Consider joining a guided eco-tour to learn about the local flora and fauna that inhabit the area. The afternoon is best spent immersing yourself in the natural beauty that surrounds Winter Park.

As the sun sets, return to Winter Park for dinner at a fine dining restaurant with a waterfront view. Enjoy a meal made from fresh, local ingredients while watching the beautiful sunset over the lakes. Finish your evening with a leisurely walk along the lakeside path, reflecting on the day’s adventures.

Start your day with breakfast at a popular local café, fueling up before a day filled with creativity. Head over to the Winter Park Art Festival, where you can browse through stunning artworks created by talented local artists. Take your time exploring the different booths and perhaps find a piece to take home.

Continue enjoying the festival atmosphere with live music performances throughout the afternoon, providing a delightful background to your art exploration. Participate in interactive art installations or workshops offered at the festival, allowing you to unleash your own creativity. Take breaks in between to savor delicious food from local vendors.

As the festival winds down, find a cozy spot to enjoy a casual dinner at a nearby restaurant, reflecting on the day’s artistic experiences. After dinner, attend an evening concert featuring local musicians, creating a perfect end to a day filled with art and culture. Embrace the lively atmosphere as you mingle with fellow festival-goers.

Kick off your wellness day with a nourishing breakfast at a health-focused café, enjoying smoothies and acai bowls. After breakfast, treat yourself to a rejuvenating spa treatment at a local spa, where you can indulge in massages or facials designed to relax and refresh. Spend some time in a serene relaxation area, soaking in the peaceful vibes.

In the afternoon, join a yoga class at a local studio, where you can center yourself and find tranquility. Afterward, enjoy a light lunch at a café that specializes in wholesome dishes, perfect for refueling. Take a leisurely walk through the scenic parks in Winter Park, allowing nature to enhance your sense of well-being.

As evening approaches, consider attending a meditation session to wind down after your day of relaxation. Enjoy a wholesome dinner at a farm-to-table restaurant that emphasizes fresh ingredients and healthy options. Conclude your wellness day with a calming herbal tea at a local café, reflecting on your peaceful experiences.

Start your day with an energizing breakfast at a local favorite diner known for its hearty portions. After breakfast, head out for a guided hiking adventure in the nearby trails, where you can experience the stunning natural beauty of the area. Keep an eye out for wildlife as you trek through the diverse ecosystems.

In the afternoon, enjoy a packed lunch amidst nature, soaking in the breathtaking views. Continue your outdoor adventure with activities like zip-lining or rock climbing, perfect for adrenaline seekers. Make sure to capture the stunning landscapes as you explore the great outdoors.

As night falls, prepare for an unforgettable evening of stargazing at a designated dark-sky area. Bring a telescope or simply lay back and enjoy the night sky filled with stars, learning about constellations from a local astronomer. Finish your adventure with a cozy bonfire, sharing stories and enjoying the tranquility of the night.