The peaceful neighbourhood of Winter Park offers an arty escape that feels a world away from Florida’s theme park capital
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Through a canopy of palm fronds and Spanish moss, I feel the warmth of dappled sunlight on my face as I float through a canal, admiring the huge houses and even bigger backyards of the rich and famous.
This affluent Orlando suburb was founded in the 1880s as a place for wealthy New Englanders to seek solace from the ice and snow, hence its name, Winter Park.
It has retained that sleepy, upmarket character, despite being only a 15-minute drive from downtown Orlando.
I’m on a 45-minute tour of Winter Park with Scenic Boat Tours, which costs $20 for adults and $10 for children. Skipper Wayne Osley sets the tone: “Our boat tours have been running for 87 years, and today you’re going to see some beautiful places.”
A network of bamboo-lined canals connects three lakes in Winter Park: Osceola, Virginia and Maitland.
Lake Virginia is home to Rollins College, Florida’s oldest university, but with lakeside dorms featuring pools, it’s no ordinary college campus.
Picture: Visit Orlando/Judy Watson Tracy
I spy students taking a break to soak up the Florida sunshine on loungers, or paddleboarding on the water. On Lake Osceola, white-panelled Victorian cottages and 1920s Mediterranean-style mansions dominate.
But as we pass through the Venetian Canal to Lake Maitland, flora and fauna take over.
Two owls sit in the high branches of a 250-year-old southern pine tree, surveying us as we pass, while an anhinga waterbird spreads its giant wings to dry in the sun.
After rounding off the tour at a house with giant sculptures of Mickey and Minnie Mouse – in case we’ve forgotten which city we’re in – I wander to Winter Park’s charming Park Avenue, where clients will find the Charles Hosmer Morse Museum of American Art.
Inside is the world’s largest collection of glass art by Louis Comfort Tiffany, art nouveau extraordinaire and son of the famous jeweller.
Stained-glass windows are the real showstoppers, but lamps, iridescent crockery and even a Byzantine-style chapel Tiffany built for the 1893 Chicago World’s Fair provide plenty for connoisseurs to pore over.
Across the road at Boca restaurant, I find the perfect cocktail for toasting my Winter Park experience – a smoky winter spritz. Here’s to finding unexpected gems in the theme park capital of the world.
Book it: Gold Medal sells a seven-night stay at the Hilton Hotel Orlando Downtown from £989 per person, based on two adults and two children sharing a Queen Room. The price includes breakfast, car hire and flights from Heathrow departing May 25, 2027.
goldmedal.co.uk