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DayVenture 26: Winter Park by Train + Boat


🍊 Park Avenue Escape

There’s something magical about a day that doesn’t require a car — just sunshine, good company, and the rhythm of an easy ride. This Dayventure brings you right into the heart of Winter Park using the SunRail, with a cozy French brunch, lakeside breezes, and a sweet ending on iconic Park Avenue.

Perfect for newcomers, longtime locals, couples, families, and anyone craving a simple, soulful Florida day.


🚆 1. Getting There: Ride the SunRail to Winter Park Station

Leave the car at home for a day that starts instantly with a sense of adventure. Pick up the SunRail and relax into the slow, steady glide toward Winter Park.

Why it’s special:

  • It turns the day into an adventure, not just an outing.
  • No parking battles — you step right out onto Park Avenue. In fact, consider the Park Avenue station your first attraction, it’s one of the most beautiful stations on SunRail’s route.
  • Kids love it, couples find it charming, and solo riders get built-in people-watching.

As the train pulls into Winter Park Station, you’re greeted by oak canopies, brick sidewalks, and the hum of main-street life. Step off, stretch, and breathe it in — you’ve arrived somewhere both small-town sweet and quietly luxurious.


🥐 2. First Stop: A Cozy French Café on Park Avenue

From the station, stroll a few steps to your café of choice — like Croissant Gourmet, Briarpatch, or Mon Petit Chéri. Each has that charming “sit-and-stay-awhile” vibe Winter Park does so well.

What makes this stop feel like a Dayventure:

  • Outdoor seating perfect for people-watching.
  • Flaky pastries and buttery aromas that transport you to Paris.
  • A warm latte paired with morning sunshine and the sound of clinking plates.

Order something indulgent — a croissant, a quiche, or a pretty tart — because today is about savoring.


🚤 3. Main Event: The Winter Park Scenic Boat Tour

Once you’re full and happy, walk a leafy ten minutes toward the dock for the Scenic Boat Tour — a Winter Park classic since 1938.

Here’s what makes it magical:

  • You glide through lakes linked by historic, vine-draped canals.
  • Guides share bits of old-Florida charm, Rollins College lore, and megamansion stories.
  • You’ll see herons, cypress trees, and sunlight bouncing on the water.

It’s peaceful, breezy, and perfect for photos.
It also gives newcomers a glimpse of the “real Winter Park” — the older, water-bound version hidden beneath the upscale exterior.


🍨 4. Sweet Ending: Kilwin’s Ice Cream on Park Avenue

After the boat tour, stroll back toward Park Ave and stop at Kilwin’s, where the smell of waffle cones practically pulls you inside.

Best part:

  • Fresh caramel wafting from the back
  • Handmade chocolates and clusters
  • Ice cream that’s cold enough to handle Florida heat

Grab a scoop and sit on a bench under the shade trees. This is your wind-down moment — watching shoppers wander by, hearing the fountain, enjoying the simple joy of a perfect dessert.


🚆 5. Homeward Bound: SunRail, Round Two

As the day winds down, head back to the station for your return ride.
There’s something satisfying about ending a day the same way it began — gently, without stress.

On the SunRail ride home, you get time to reflect.
To watch the city slide past.
To feel rooted, just a little more, in the place you now call home.


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