Orlando may be synonymous with Disney World for most, but just north of this Florida city there’s a different vacation for those who wish to explore it.
The historic resort town of Winter Park is a stately haven for those who like their downtime a little more on the grown-up side – or just want to unwind from a trip to the Magic Kingdom.
Lazy boat rides, craft cocktails and a diverse range of galleries are abundant in this manicured town of eight square miles, which manages to make even the Amtrak train seem quaint, stopping as it does in the middle of the town’s mini-Central Park.
Brunch with a side of modern art
Bring on the day with brunch at the Alfond Inn, a boutique hotel with walls adorned with lively and engaging modern art, including Alfredo Jaar’s sunrise-hued neon “Be Afraid of the Enormity of the Possible.”
The Rollins College-owned inn’s works are a satellite gallery of the Alfond Collection of Contemporary Art at the nearby school’s Cornell Fine Arts Museum. (The inn’s profits fund scholarships.)
At the inn’s restaurant, Hamilton’s Kitchen – named for a former Rollins president, not the trending Founding Father – the shrimp and grits is a must. Its North Florida-sourced grits are freshly milled, which makes this kitchen’s take on the Southern staple extra tasty.
A day in Winter Park is entirely walkable, although bikes can be rented at Breakaway Bicycles just off the main drag of Park Avenue ($10 per hour or $35 daily).
A pontoon tour of the lakes
Grab your sunscreen before heading to the Scenic Boat Tour, where guests board a small pontoon for an hourlong (and shade-free) wander around Lake Osceola and two other canal-linked lakes.
Floating past countless Gatsby-esque lakeside mansions, the captain will keep up a rolling commentary of fascinating facts and gossip about residents both old and new.
One manor apparently began as a private men’s club, while another was featured in scenes from 1954’s classic horror flick “The Creature From the Black Lagoon.”
Casa Feliz, a replica of a white Andalusian farmhouse by architect James Gamble Rogers, was constructed with an intentional sag in the roof to make it look authentically rustic. It functions as a historic home museum and weekly host to live music in the main parlor.
Banana trees and bamboo provide occasional cool spots of shade as boats drift through the narrow canals. Graceful large black anhingas – or “Florida ducks,” as your captain may call them – perch atop pier poles, while purple martins, seasonal visitors from the Amazon basin, flit in and out of one mansion’s cushy bird hotels.
Cool off with a stroll through the Charles Hosmer Morse Museum of American Art, home to a gorgeous collection of glass works by Louis Comfort Tiffany. Pottery, leaded-glass lamps, jewelry and stained glass creations line its galleries. We recommend lingering in the Tiffany Chapel, a breathtaking stained-glass masterpiece created in 1893 for the World’s Columbian Exposition in Chicago.
Heritage of a segregated community
A 10-minute walk with a stroll over the railroad tracks brings you to Hannibal Square, the heart of the historically African-American neighborhood of Winter Park and home to the Hannibal Square Heritage Center.
Hannibal’s permanent collection, “Photographs and Oral Histories of West Winter Park,” is a painstakingly documented monument to the history of this once segregated community, whose voting activism is detailed in a glittering public mosaic across the street.
Photos submitted from longtime Hannibal Square residents are displayed alongside text describing their memories of the area and a small accompanying current photo, taken by the center’s resident photographer.
Chief historian Fairolyn Livingston, who grew up here, contributed a portrait of herself from sixth grade at a school that, her text explains, “according to Brown v. Board of Education was separate and unequal. However, that never stopped us from academic and social success. I look happy because I loved school.”
Shopping on swanky Park Avenue
Back across the railroad tracks on swanky Park Avenue, there’s no shortage of dress, accessory, kitchen and flower shops, but you may want to fortify yourself for shopping with a cocktail at one of the many eateries lining the main drag, most with al fresco sections abutting the tree-lined sidewalk.
Sip a Cetriolo, a refreshing vodka-agave-basil cocktail, at the rustic-chic Italian restaurant Prato and watch the foot traffic wandering by at a heat-appropriate, languid pace.
If wine is more your style, head for Luma on Park or the Wine Room. For dinner, check out the locally sourced options at Boca, where the salads feature veggies from nearby farms and the seafood special is “whatever the fishermen bring in.”
If you have a second day, check out the Mead Botanical Garden, the Albin Polasek Museum and Sculpture Gardens and the Rollins College campus, voted the nation’s most beautiful by Princeton Review in 2015.
Or put them on your itinerary for your next, non-Magical Kingdom visit to Orlando.
The Amtrak train goes directly to Winter Park. Check the city’s arts & culture calendar for upcoming events.
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