What to Do in Winter Park, Florida: The Perfect Weekend Itinerary

    By Ana Connery

    Winter Park a city of 25,000 just five miles north of downtown Orlando, has been a tony retreat pretty much since it was first developed in the late 1800s by wealthy northerners who wanted to take advantage of the lakeside setting. That describes the wealth of Winter Park, FL activities.

    The entrepreneurs drew plans for a city that would embrace the park-like setting and provide opportunities for local businesses to thrive.

    Today, Winter Park still feels more town than city, with its walkable grid of brick-paved streets flanked by a European style of architecture that celebrates Gothic arches, clay-barrel roofs and intricate ironwork. Wandering around is a must on your what to do in Winter Park, FL list.

    Park Avenue is Winter Park’s main artery, running for eight blocks from Rollins College to the Charles Hosmer Morse Museum of American Art before fading into a residential neighborhood shaded by moss-draped oaks.

    what to do in Winter Park, FL

    Winter Park feels more town than city, with its walkable grid of brick-paved streets flanked by a European style of architecture that celebrates Gothic arches, clay-barrel roofs and intricate ironwork.

    - Julie Fletcher for VISIT FLORIDA

    Winter Park, FL activities

    Park Avenue is Winter Park’s main artery, running for eight blocks from Rollins College to the Charles Hosmer Morse Museum of American Art before fading into a neighborhood shaded by moss-draped oaks.

    - Julie Fletcher for VISIT FLORIDA


    What to do in Winter Park, FL: Art and Academia

    As you stroll the garden paths and side streets, a sense of collegiate history echoes, but perhaps no more so than at the new Alfond Inn. Long a popular getaway for the nation’s elite, including President and Mrs. Reagan, who celebrated their 25th wedding anniversary here, what was then the legendary Langford Inn sat empty for years.

    Eventually a pair of Rollins alumni, Ted and Barbara Alfond, invested millions to rebuild it in part to showcase their extraordinary art collection, the centerpiece of the Cornell Fine Arts Museum on the nearby campus. The renowned art lovers wanted the 112-room hotel to serve as much as a “visual syllabus” as a place for students’ parents and visitors to lay their head.

    Check in on a Friday afternoon and the myriad courtyards and conservatory will likely be abuzz with well-heeled locals kicking off the weekend with one of the bar’s happy hour specials. Having a drink in hand is not a bad way to embark on a self-guided tour of the contemporary art collection found primarily on the first and second floors. It's a must-see for an art lover's what to do in Winter Park, FL list.

    From high-energy video to neon signs that promote the Alfond’s mission with words like, “Language must speak for itself,” the collection’s highlights include “Afghan Girl,” the famous photo by Steve McCurry that graced the cover of National Geographic and is commonly referred to as the Afghan Mona Lisa.

    A group of 19 paintings of the covers of famous books comprises a collection that connotes the intellectual curiosity of the Rollins faculty members who chose the works as their fave pieces of literature.

    To experience Winter Park, FL activities rich in culture, walk north on Park Avenue past the many family-owned jewelry shops, cafes and boutiques tucked in between preppy chain stores to the Morse Museum, where admission is free every Friday between 4 and 8 p.m. except during summer.



    If you get tired of walking, take a two-wheeled adventure down the city streets.

    - Julie Fletcher for VISIT FLORIDA


    Winter Park's wide variety of restaurants means there is something for everyone.

    - Julie Fletcher for VISIT FLORIDA

    The draw here is the exquisite glass art of Louis Comfort Tiffany, the most comprehensive collection of his work in the world. His chapel interior, the original from the 1893 World’s Columbian Exposition in Chicago, is as full of detail and spiritual prowess as any you’d find in Europe.

    The galleries featuring the ornate art and furnishings from his famed Laurelton Hall residence on Long Island provides a peek at what an artist can do with enormous wealth (Tiffany’s father was the founder of the famed Fifth Avenue jewelry store in New York).

    Stop for dinner at Prato on Park Avenue, where a floor-to-ceiling glass storefront opens to reveal a seamless transition from the inside out.

    Ask for a table near the sidewalk so you catch the scent of the Central Park rose garden across the street and watch Amtrak trains shuffle passengers in and out of the town depot. With a setting like this, you’ll be tricked into thinking you’ve gone back in time—with more appropriate clothes.

    There are few light dishes at Prato, but the modern Italian cuisine does subscribe to the trendy farm-to-table approach to food with many local farmers highlighted on the menu. Start with the savory meatballs in a roasted tomato pulp before indulging in the Widow Maker pizza from the wood-burning oven in the open kitchen. Topped with fennel, sausage, prosciutto and a sunny-side up egg, it’s a hearty take on a popular dish. You’ll be glad for the walk back to the Alfond Inn.

    Natural Winter Park, FL Activities and Wonders

    Wake up early to beat the crowds at the Winter Park Farmer’s Market just two blocks west of Park Avenue. Next to produce and plant stands from nearby farms a lineup of food stalls and trucks serve everything from French croissants to fresh smoothies.

    Inside the adjacent brick building that once housed the original Winter Park train depot, you’ll find fresh bagel sandwiches as well as homemade pastas and cheeses. Sit on the breezy patio to enjoy your breakfast before peeking into the Winter Park History Museum at the northern end of the building. Run by volunteers, it features rotating exhibits that showcase the history of the city, including a recent retrospective of the local high school.

    Spend the afternoon partaking in Winter Park, FL activities at the Alfond Inn’s rooftop pool with its tree-line view of the apartment building across the street. Sir Paul McCartney reportedly bought the top floors for his stepson, who attends Rollins College.

    Catch the sunset during the last Winter Park Scenic Boat Tour of the day. From the dock on the east end of Morse Street, this family-owned business has been taking passengers across three of the seven lakes on the tranquil Winter Park chain since 1938. Besides great views of the sprawling backyards of the city’s wealthiest residents, you’ll sneak a peek at the beautiful Rollins campus and might even catch a gator or crane sunbathing along the mangroves as you slide across two narrow canals.

    What to do in Winter Park, FL: Sunday stroll

    Come Sunday, if it hasn’t already, Winter Park makes it clear this is a playground for the upper crust. Stroll west past the cardigans and linen pants toward Hannibal Square, a section of the city originally designed as a separate community for African Americans.

    The two blocks here are like a mini Park Avenue of fine restaurants and specialty shops except for the casual local hangout known simply as Dexter’s. One of the few restaurants around with live music performed by bands and musicians that longtime patrons follow, Dexter’s is a fun spot for an al fresco brunch. Let the mimosas flow as you create your own omelets and do your best people-watching.

    On the rare weekend that a festival of some sort is not in full swing, wrap the weekend with a little window shopping at Tuni, a trendy boutique owned by a local mother and daughter. Linger over the baubles at another family-owned biz, Simmons Jewelry, and the handcrafted home accents at Ten Thousand Villages before sliding into a sidewalk cafe for one last taste of the Florida good life.

    For more about Winter Park, visit www.cityofwinterpark.org.