Winter Park, FL – Orlando’s Hidden Gem

[Winter Park, FL – May 28/29, 2018]

A work conference the week of Memorial Day brought me to Orlando, FL – amusement park capital of the world. The conference started on Tuesday afternoon, May 29th and ended on Friday morning, June 1. This schedule left me some free time before and after to explore. I decided to travel on Monday afternoon to avoid having to take a red-eye (overnight) flight, which meant that I had Tuesday morning free. And for the weekend after the conference, I decided to hop on over to Augusta, GA, which I had not visited since I left in 2009.

By this time, it had been six month since my last big trip. Aside from a day trip to Channel Islands national park in March, I felt like I haven’t traveled in forever! I was getting really antsy, so this trip came at the right time. My flight left LA at 3 pm, and we crossed the Gulf of Mexico right at sunset. From my window seat, I could see tropical storm Alberto, which made landfall in the Florida panhandle earlier that day. You can see my flight’s path and the storm in the map below, courtesy of I also saved a video of the view from my seat in my Instagram highlights, go check it out!

DL1649 Tracking

My half day on Tuesday morning was a hard to plan. I didn’t have a lot of time, and I wasn’t looking forward to having to deal with going back and forth to the airport to pick up and drop off a rental car. I was on my hotel’s website when I noticed a rental car desk listed under its amenities. It had limited hours – 8 am to 12 pm – and I definitely needed a reservation, but it saved me at least an hour and a half of time as I no longer needed to go to the airport just to deal with the car! It was super convenient. I didn’t even know rental car desks at hotels are a thing, but now that I know, I will certainly keep this in mind for when I need a car in a pinch.

I also had a hard time deciding what to do. Cape Canaveral and the Kennedy Space center were a 45-minute drive from where I was staying. While this is a major attraction, it takes a full day to really experience it. Even if I had decided to go, I’d only be able to do the 2-hour bus tour around the center. I didn’t look forward to sitting and being inside on my only free morning given that I was going to be doing that all throughout my conference. Amusement parks would also take a full day, were ridiculously expensive and weren’t my jam anyways.  Between this and the car situation, I was almost ready to throw in the towel and just spend my half day by the pool at the hotel. But I kept googling and googling and finally, I found a blog post about 17 things to do in Orlando besides amusement parks! Two of them were in Winter Park, FL – an easy 20-minute drive from my hotel – and they seemed totally under-rated attractions that would be great to spotlight on my blog. Around the same time, I stumbled upon the hotel car desk and suddenly, it was all settled! And that’s how I found myself driving North on I-4 towards Winter Park on Tuesday morning.

I have to be honest – traffic was a pain! LA gets a bad rep when it comes to that, so I expect everywhere else to be better. But my 20-minute drive to Winter Park turned into 50 minutes due to accidents, which didn’t leave me a lot of time for breakfast. Luckily, I had picked something just a mile from where I needed to be for my first Winter Park attraction. Canopy Cafe had great reviews, one of which mentioned a patio. Sold!


And when I got there, I wasn’t disappointed. It was the first workday after Memorial Day weekend, so I was the only person there. Country music was playing in the background, there were grits and biscuits on the menu and my server kept calling me “honey.” I was definitely in the South!


The first thing I did in Winter park was the Winter Park Scenic Boat Tour, which departed just down the street, on Lake Osceola.


Tours run hourly from 10 am to 4 pm, and I wanted to make it on the 10 am tour for both crowd and heat management. It was a good call – there were only six other people on the boat with me, and the weather was perfect, with temps just breaking 80F/26C.

The tour took us on three of the seven lakes that make up the Winter Park Chain of Lakes and two of the canals that connect them. Admission is $14, cash and check only – no credit cards. The boats are completely open, so come prepared with sunscreen, hats and whatever else you need to shield from the sun. I brought my wide-brimmed hat just for this tour, and I purchased a mini-sized tube of sunscreen at the ticket window.

Here is a little video from the beginning of the boat tour.


Clearly, this place is heaven for the boat enthusiast. Virtually every home had a boat dock.


But the real treat for us came from going through the canals that connect the lakes. They were built during the logging era at the end of the 19th century. At the time, the canals were straight. When homes were built here and boat houses added on, there was a need for extra space for the boats to come in and out of the canal. Therefore, the canals are now slightly curved. Going through them was like going into a completely different world compared to the lakes they connect.


Here is a video of us entering the first canal and exiting on the other side.

The second canal was called The Venice Canal, which made me laugh because it is nothing like the actual Venice canals. Here’s a video of us going through it.

I was surprised to learn that there is a highly rated liberal arts college here in Winter Park. Being employed at a college campus that is considered one the prettiest in the nation, I was intrigued by Rollins College’s scenic location on the lake shore. Would it be prettier than LMU? I didn’t have time to see for myself, but a stroll through campus seemed like a good way to spend a few more hours in the area. We only caught glimpse of some campus buildings from our boat.

Rollins College Campus

Rollins College Campus

I learned a lot about Florida and Winter Park on the boat tour. A major question I had was how anything in Florida could have “winter” in its name. It turns out, Winter Park was a seasonal destination until the 1950s, when the advent of air conditioning made the entire peninsula livable during the summer. But before that, people would come down to Winter Park only in the winter. Most of the homes down here were second homes for rich businessmen in the North East. Even though Winter Park is now inhabited year-round, the presence of that wealth is still evident by the size of the homes we saw from the boat.

My second stop in Winter Park was the Charles Homer Morse Museum of American Art. I’d read that it hosts the largest collection of Tiffany glass in the world, which sounded rather intriguing.

The museum exists thanks to Jeannette and Hugh McKean. Jeannette founded the museum in 1942 and named it after her grandfather, Charles Homer Morse. Hugh McKean was its director from its inception until his death. Besides the Tiffany collection, the museum also holds American art pottery and 18th and 19th century American paintings. Upon hearing I am from California, the woman at the ticket counter told me to not miss Albert Bierstadt’s “The Domes of Yosemite” from 1867. It’s a massive painting!


The collection of Tiffany glass was absolutely amazing. Louis Comfort Tiffany (1848-1933) was the son of the founder of  the famous jewelry house Tiffany & Co. I was surprised to learn that Tiffany & Co started out as a dry goods store, a “stationary and fancy goods emporium”. It was co-founded in 1837 by Charles Lewis Tiffany, Louis’ father, and John B.  Young. Charles Tiffany took control of the entire company in 1853 and established the emphasis on jewelry.

His son Louis became an interior designer and an artist focusing on glass-making. Unfortunately, very few of his interior designs survive; most we only know about from photos. His most famous interior designs were several rooms in the White House, which he renovated in 1882 before president Chester Allan took office. He started adding glass to light fixtures as part of his interior designs.


By 1885, Tiffany wanted to focus on glass-making and even built his own glass factory. I got to enjoy many of his masterpieces in this museum, including:

  • The Tree of Life

The complete tree of life


Creation & Entombment


Geology & Astronomy


Science & Religion

  • A set of stained glass windows depicting the four seasons, autumn pictured below


IMG_0044 (2018-06-06T14_12_06.016).JPG

This is all glass. Tiffany manipulated glass in ways it hadn’t been before, which allowed him to create the designs above without using additional materials.

  • Feeding the Flamingos, leaded glass window
  • The Tiffany Chapel, which he created for the 1893 World Fair in Chicago

So how did all these items end up in a small museum in an Orlando suburb? Hugh McKean, the director and husband of the founder, had met Tiffany when he spent several months at Laurelton Hall, Tiffany’s New York estate, in 1930. At the time, Tiffany had a foundation that sponsored aspiring artists at Laurelton Hall, and Hugh was one of them. He and his wife had acquired several pieces for the museum when it was established but had not yet taken a keen interest in Tiffany’s work. Laurelton Hall and the foundation continued to exist after Tiffany’s death in 1933. In 1957, a devastating fire erupted in Laurelton Hall and destroyed the main house. Tiffany’s daughter wrote to Hugh McKean and suggested that the current owner of the estate might be willing to sell what’s left. Hugh and Jeannette bought everything they could, including furniture, architectural elements, leaded-glass windows and more. With their interest in saving Tiffany’s legacy for posterity ignited, they didn’t stop at Laurelton Hall. They tracked down and acquired whatever Tiffany works they could get their hands on, together with archival and documentary material. Eventually, their collection became the most comprehensive one of his works anywhere. Below are photos of some of the furniture and architectural items they saved from Laurelton Hall, including an entire terrace.


Reception fountain from Laurelton Hall


Daffodil Terrace from Laurelton Hall


Daffodil Terrace from Laurelton Hall


Laurelton Hall doors

I was back on the road shortly after noon. I had spent about 3 hours total in Winter Park at that point, and I had just enough time to get back to my hotel for my first conference session, which started at 1 pm. I could have easily spent more time walking around the cute downtown area and taking a tour of Rollins College. If you find yourself in Central Florida and want to escape the tourist traps, Winter Park is the place to be.



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