Plan Your Next Escape: Winter Park, Florida

  • Written By:Christina Valhouli
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While Winter Park is still attracting its fair share of snow birds, it offers much more than just sunshine.

Winter Park, Florida was founded in the 1880s by a group of well-heeled northerners who were looking for a sunny escape from harsh winters. Their legacy lives on today in the elegant brick cobblestoned residential streets and mansions which border the town’s lakes. While Winter Park is still attracting its fair share of snow birds, it offers much more than just sunshine.

The town is considered a suburb of Orlando, but it feels miles away from mouse ears and amusement parks. Winter Park is known for its blend of art, culture and independent stores, all served up in a relaxed atmosphere where strolling around in resort wear is the best way to blend in.

For a small town, it has a high number of cultural attractions. The Charles Hosmer Morse Museum contains the world’s largest selections of work by Louis Comfort Tiffany. The jewelry exhibits are a standout but the real show stopper is the chapel interior Tiffany created for the 1893 World’s Columbian Exposition in Chicago. It was once moved to the Cathedral of St John the Divine in New York before settling in Florida. The chapel’s Byzantine-inspired interior glitters and glows and is a perfect spot to sit and have a quiet meditation. The Albin Polasek Museum is located right on the banks of Lake Osceola, and showcases the works of Czech sculptor Albin Polasek. Visitors can explore the artist’s Mediterranean-style residence and chapel, as well as an outdoor sculpture garden. His signature work is Man Carving His Own Destiny, depicting a man emerging from a slab of rock.

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Guests of the Alfond Inn don’t have to travel far to see art. The boutique hotel, a member of Preferred Hotels & Resorts, showcases a rotating collection of contemporary art from Barbara and Ted Alfond, who are continuously adding to their collection. Their art has been donated to the Cornell Fine Arts Museum at Rollins College, which is walking distance to the hotel. If you want to learn more about the art, Happy Hour Tours are available on the first Wednesday of every month. The Alfond Inn gives back to the community in other ways beyond the art. The hotel is owned by Rollins College, and 100% of the Inn’s profits go to the Alfond Scholars Fund.

Beyond the art, the Alfond Inn is in a perfect location for guests to explore downtown Winter Park as everything is in walking distance. The guest rooms are spacious and colorful, and when you’re not art hopping and shopping, head to the hotel pool to unwind or do some laps. Start your day with a healthy brunch at Hamilton’s Kitchen which showcases fresh, seasonal fare. Try the quinoa bowl with spiced hearts of palm or a Mediterranean breakfast bowl with Israeli couscous and tandoori spiced kale.

Learn about the town’s history as you sail past mansions, live oaks with Spanish moss and the occasional crew boat from Rollins College.

One of the best ways to take in Winter Park is to sign up for a Scenic Boat Tour of the town’s lakes and canals. The one hour boat cruise sails along Winter Park’s chain of lakes and two man-made canals. You’ll learn about the town’s history as you sail past mansions, live oaks with Spanish moss and the occasional crew boat from Rollins College. If you’d rather be closer to the water, stand up paddleboards are available to rent on Lake Osceola’s Dinky Dock. Another way to squeeze in a work is to book a class at Club Pilates.

If you’re craving greenery rather than water, it’s a short drive to the Harry P. Leu Botanical Gardens in Orlando. The 50-acre gardens showcase vibrant tropical plants and flowers, and this is where you’ll find the largest rose garden in Florida. Keep your eyes peeled for the fairy houses that are tucked among the foliage, as well as sculptures.

You’ll meet your daily quota of steps strolling around Winter Park to browse the shops and boutiques. Stop by the tiny Winter Park Historical Museum, which is next door to the weekly farmer’s market. The one room museum highlights the town’s history. The current exhibit, which runs through June 2020, looks at the history of the motels and hotels in town. Stop by the Impeccable Pig to stock up on resort wear like floaty dresses and tassel earrings. Rifle Paper Co. is headquartered here, and the brand is known for its floral stationery, calendars and accessories like water bottles.

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Just in case you forgot to bring a book to read by the pool, Winter Park is home to two independent bookstores – Writer’s Block as well as Brandywine Books, tucked in a courtyard, for used and out of print tomes. If you have a furry friend in tow (and the Alfond Inn is dog friendly), pick up a treat at Woofgang Bakery & Grooming.

There’s no shortage of healthy places to eat in Winter Park. Get there early to nab a sidewalk table at Bosphorous so you can tuck into Turkish cuisine while people watching. Bring a group of friends to share platters of humus, haydari (a thick yogurt with dill and walnuts) as well as cold cucumber dip. Main dishes like chicken and beef kebabs come with a pickled beet salad. If you eat gluten, ordering a lavas is a must. The hollow, puffy bread is baked to order and is roughly the size of a basketball. Armando’s serves up straightforward Italian cuisine. Sip on a Negroni while browsing the menu. Wood fired pizzas are available as well as salmon roasted with capers, olives and tomatoes. Armando’s also has a location in Portsmouth, New Hampshire.

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Right on the border with Winter Park is Orlando’s Little Vietnam neighborhood, where you can tuck into bowls of pho and spring rolls at Pho 88. It’s a no frills space with an affordably priced menu that’s perfect for a quick lunch. When you need a caffeine boost, the New General coffee shop is a sleek space in downtown Winter Park which sells fair trade coffee and teas. Adaptogens like collagen peptides and reishi (an immune-boosting herb) can be added to drinks.

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