Postcards & Passports

Put Winter Park on Your Orlando Itinerary

This post was most recently updated on July 9th, 2019

Winter Park was once called “the prettiest place I have seen in Florida” by President Chester A. Arthur. And President Grover Cleveland said that Winter Park was the most pleasant diversion of his Florida trip. After spending half a day in Winter Park on a recent visit to Orlando, I have to agree. I wish I’d had more time to spend there, and I highly recommend making it part of your Orlando itinerary.

Winter Park

Why Winter Park?

Winter Park is a beautiful city, just seven miles from downtown Orlando. It is considered part of the greater metropolitan area of Orlando. In downtown Winter Park, along cobble stoned Park Avenue, there are lots of upscale boutiques and restaurants. Central Park boasts manicured lawns, a fountain, a new train station and the Saturday Farmers’ Market.

Also on Park Avenue is the Charles Hosmer Morse Museum of American Art, which contains the world’s largest collection of Tiffany glass.

Winter Park

Tiffany glass

Another  museum is the Albin Polasek museum and sculpture gardens. It is housed in the late sculptor’s home on Osceola Lake’s shores, at 633 Osceola Avenue. We actually passed this museum and could see it from the Scenic Boat Tour.

Winter Park

Albin Polasek Museum & Sculpture Gardens

Winter Park Scenic Boat Tour

Winter Park is nestled among a chain of seven pristine lakes connected by canals. One of the most interesting attractions is the Scenic Boat Tour. It’s a well-kept secret, but those who have been always spread the word, because it’s such a fun way to see the lakes, the million-dollar homes perched on their shores, and learn more about Winter Park. When I learned about the tour, I knew I just had to make time to fit it in.

Winter Park

What to Expect

The Winter Park Scenic Boat Tour is an hour-long narrated tour. It navigates through three of the seven lakes: Osceola, Virginia, and Maitland. Most of the guides are retirees, and they share humorous anecdotes mixed in with lots of historic and current information about the area. The boats also travel through two of the narrow canals that connect the lakes. It’s a tight squeeze, and you might need to duck when the boat goes under some bridges, but it’s great fun and quite beautiful, too. Spanish moss drapes overhead from the cypress trees, and the canals provide a welcome shady spot, as you travel from lake to lake.

As we passed the many beautiful homes and landmarks, our guide would share stories and trivia, such as the following:

The basketball player, Horace Grant, who measured 6’10”, sold his custom-built Winter Park home. The new owners couldn’t reach the light switches! And they converted the basketball court into a ballroom for 200 people.

Winter Park

Rollins College

Rollins College is fifth in the nation in intercollegiate water skiing and costs $60,000 per year for tuition.When Fred Rogers (of Mister Rogers fame) was a student at Rollins, he needed his own space so he could practice music without noise or interruption. He lived in this home:

Winter Park

Mr. Fred Rogers’ college home

The canals that link the lakes were built in the 1930’s as a public works project.

All alligators are removed from the lakes by the city. (Do they end up at Gatorland?)

Cypress trees give off tannic acid, which turns the water green.

Winter Park

Tree “islands”

One of the owners of a multi-million dollar home on the lake purchased another multi-million dollar home next door to him. He then razed the home…just to have a bigger lawn!

Orange groves used to grow in much of what is now Winter Park.

There’s a lot more I’m not telling you, because I don’t want to ruin all the surprises. Take the tour yourself to learn about all the celebrities and history that are part of Winter Park’s story.

Tips for the tour:

  • You’ll want to use sunscreen.
  • Parking is free at the parking lot at the east end of E. Morse Boulevard. Park and walk down to the boat dock on Lake Osceola.
  • There are restrooms you can use before (or after) the boat tour just above the dock. You can also buy a postcard, sunscreen, or drink at the tiny shop there.
  • Admission for the Winter Park Scenic Boat Tour is very reasonably priced — only $14 for adults and $7 for children 2-11 years. (Under 2 yrs is free). Tours run from 10 am to 4 pm, every day of the year except Christmas.
  • You can request reservations here.

Have I convinced you?

If you’re in Orlando, you’re probably planning to visit a theme park. The crowds and lines will wear you out by the end of the day. On the other hand, if you spend a day or half-day in Winter Park, you’ll leave refreshed and relaxed. It’s a city where you’ll experience the charm of southern hospitality. You can just sit and enjoy the scenery – in a park or on the boat tour…or browse inspiring museums or go shopping. I think you’re going to love it!

  • We enjoyed lunch at the Croissant Gourmet at 120 E Morse Blvd. Their croissant sandwiches and French bakery items are amazing!
  • The Winter Park Farmers’ Market is housed in the old train station. It’s open every Saturday from 7 am to 1 pm. You will find produce, flowers, bakery items, and much more.
  • The Charles Hosmer Morse Museum of American Art is open 9:30-4:00 Tues-Sat, and 1:00-4:00 on Sundays. Admission is $6/adults, $5/seniors, and $1/students (children 11 and under are free). Admission is free on Fridays
  • The Albin Polasek Museum & Sculpture Gardens are open Tues-Sat, from 10 am to 4 pm and on Sundays, from 1 pm to 4 pm. Admission is $5/adults, $4/seniors, $3/students, and children under 12 yrs are free. Parking is free.

Disclosure — My husband and I received complimentary admission to the scenic boat tour in exchange for a review. As always, I only give honest reviews based on my actual experience.

Be sure to let me know what you think of Winter Park or the Scenic Boat Tour in the comments below…

Winter Park



13 thoughts on “Put Winter Park on Your Orlando Itinerary

  1. Michele Peterson

    Winter Park looks gorgeous and full of history and art — something I wouldn’t expect to see around Orlando. The Winter Park scenic boat tour looks like a great escape from the crowds.

  2. Emily

    Looks wonderful! Just what you need as a respite from the busy theme parks – I’m planning on taking the kids there one day so I’ll remember to go to Winter Park too.

  3. Pingback: Four Half-Days in Orlando - Postcards & Passports

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