Things to do in Winter Park to experience its special charm

For 140 years visitors have come to explore the many charms of Winter Park, a tree-filled small city now engulfed by metropolitan Orlando. Originally, they came by train.

I decided Winter Park was the perfect modern-day destination to reach by train, combining a “romantic rail journey” with a walkable town. I was right – except for the “romantic rail journey” part. But more on that later.

While Amtrak left a lot to be desired, Winter Park lived up to expectations. In a three-night stay, we walked everywhere. There were enough things to do in Winter Park that I left wishing I had time to get to one additional museum and one more great park.

Winter Park started as a resort for rich northerners fleeing cold weather in the 1800s. With its chain of six sparkling lakes, it soon became a place where wealthy folks built grand winter homes.

Winter Park Sidewalk Art Festival, Winter Park, March 15-17, 2024. This large show annually earns top ranking among art festivals nationwide. In addition to the draw of high-quality art, it offers activities to entertain various ages and interests. Be aware: It draws a big crowd.

Winter Park has remained decidedly upscale and has benefited from all the resources associated with wealth over the years.

Its rich residents developed a few museums that are real gems, a fabulous nearby botanical garden and Rollins College, a private college with a beautiful campus.

There is even a touristy but fun Scenic Boat Tour, operating since 1938.

It’s all compact and walkable (our grand tour required only one $10 Uber ride). Winter Park still has many red-brick streets and historic homes and buildings. In short, I found lots of things to do in Winter Park to make a great Florida getaway.

We arrived at the very cute retro-looking train depot, also a busy stop for the regional SunRail system. When you reach the town this way, everything that surrounds you is full of Winter Park history and charm.

The center of the city has an attractive Central Park with an arbor of gorgeous purple wisteria blooming profusely in March. There are fountains and benches and open space for families and sweethearts to enjoy.

Paralleling the train tracks is Park Avenue, lined with a wide variety of great restaurants, coffee shops, wine bars, a chocolatier, a fabulous French bakery and trendy shops.

On one end of the shopping district is the Charles Hosmer Morse Museum of American Art, very much worth visiting.

At the other, Park Avenue leads to the lovely campus of Rollins Campus, where you can take a scenic walk along Lake Virginia and visit the free art museum.

Park Avenue has big shady trees and planters bursting with colorful flowers.

Off Park Avenue, you can walk a few blocks on New England Avenue across the tracks to the lively Hannibal Square district, also full of restaurants and cafes along the red-brick road.

On the way, at the side of the train tracks is the small but impressive Winter Park History Museum.

Planning your visit to Winter Park

It’s not every Florida town where you can plan two days of activities on foot, but the heart of Winter Park is compact, developed before cars dominated the city.

We arrived on a Sunday night, which meant our first day in town was a Monday —  actually not a great idea. All the museums are closed on Monday, as well as several restaurants. But our first day was packed full of fun including two botanical gardens and the Scenic Boat Tour.

Enjoying Margarita Mondays ($5 and terrific) at Pepe’s Cantina in the Hannibal Square neighborhood made it all worthwhile. Day two, then, was dominated by museums.

Eight great things to do in Winter Park

1. The Charles Hosmer Morse Museum of American Art

This is the top attraction in Winter Park. The Morse Museum is known for its collection of works by Louis Comfort Tiffany and, as a result, it has eye candy that will appeal to even people who don’t normally like art museums.

The examples of Tiffany glass here are luminous, colorful and easy to appreciate. You can breeze through in 45 minutes or, if you get captivated by Tiffany and his life, you could easily spend two hours.

We particularly enjoyed the several galleries devoted to Tiffany’s Long Island mansion, Laurelton Hall, which burned down. His home there, where his work went far beyond windows and lamps, was one of his masterpieces.

The founders of the Morse Museum, Hugh McKean and Jeannette Genius McKean, had the items that would be salvaged brought to the museum where they are now displayed. This includes parts of several rooms, such as an entire arbor with magnificent daffodil ornamental columns.

The museum is closed on Mondays.

Admission is inexpensive, so you have no excuse to miss it. It’s $6 adults; $5 seniors; $1 students (with valid ID) and free for children younger than 12. In addition it is free to all Fridays from 4 p.m. to 8 p.m.!

Charles Hosmer Morse Museum of American Art
445 N. Park Ave., Winter Park, FL 32789
(407) 645-5311

2. Winter Park Scenic Boat Tour

Visitors to Winter Park have been delighting in this boat tour since 1938. The boats only hold 18 people and they do not have canopies because the narrow canals that connect the Winter Park chain of lakes go under bridges that are only inches above your head.

This is your classic Florida tourist experience, complete with the corny guide telling the same groan-worthy jokes on every cruise. But it has been around for more than 80 years for a reason – spectacular scenery you’ll only see this way.  

Who among us does not want to gaze at magnificent mansions with boat houses prettier than our own home?

The highlight, though, is threading through Winter Park’s very narrow canals connecting the lakes, where trees hang overhead and flowers bloom in lushly landscaped yards.

The tour provides interesting history of Winter Park and shows you several notable buildings and the Rollins College campus from the water. We also liked that on this boat tour, the driver hits the gas pedal occasionally, providing a whoosh of speed and a breeze.

The tours are exactly an hour long, which is perfect, and are offered hourly with no reservations (except for large groups). It’s an inexpensive thing to add to your day – tickets are $16 adults; $8 ages 2 to 11.

3. Albin Polasek Museum and Sculpture Garden

I have to admit, I had never heard of Albin Polasek, but the sculptor’s 1949 home and gardens on Lake Osceola is a real hidden gem and worth a stop.

Polasek was a successful and well known 20th Century sculptor who led the Chicago Art Institute’s sculpture program for many years. Born in what is now the Czech Republic, Polasek retired to Winter Park and built a lake home and studio with a magnificent view.

Visitors get a brief tour of the home — it is not huge but the interior is filled with his art and it’s quite interesting to see. The gardens display dozens of sculptures, surrounded by Florida plants, flowers and trees along the shore of Lake Osceola.

Many of the works have a religious character, but many others are nudes. Some have a personal touch, such as the painting where he inserted his face into the Stations of the Cross among the holy people at the foot of the crucifixion.

The museum and grounds can be seen in an hour or two, but you also can linger at the picnic tables in the garden. The museum is closed on Mondays. Admission is $12 for adults.

Albin Polasek Museum and Sculpture Garden
633 Osceola Ave., Winter Park, FL 32789
(407) 647-6294

4. Things to do in Winter Park: Strolling the grounds of Rollins College and visiting its free art museum

In 2015, the campus of Rollins College was named the most beautiful in the nation by the Princeton Review and it makes for a beautiful walk.

You can reach the campus in 10 minutes from downtown. Just go to the southern end of South Park Avenue and cross busy Fairbanks Avenue.

The campus has many handsome historic buildings in the Mediterranean revival style framed by sprawling live oaks and overlooking Lake Virginia.

There is a half mile lakeshore walk through the campus, along which is the free Rollins College Museum of Art. It’s a small museum that gets high marks for its quality, displaying visiting exhibits as well as items from its own collection. (Just like the other two art museums in town, it’s closed on Mondays.)

At the northern end of the campus is a city park called Dinky Dock Park, where you’ll find locals fishing and launching kayaks into Lake Virginia. There is free parking here, but spaces aren’t always easy to get.

Rollins College Museum of Art
1000 Holt Ave., Winter Park, FL 32789
(407) 646-2000

5. Mead Botanical Garden

This free garden is a half hour walk from the heart of downtown. We enjoyed walking along red brick roads through historic neighborhoods to reach it.

Mead Botanical Garden has some beautifully landscaped spaces with colorful planters as well as camellias and azaleas, which were in bloom for our March visit.

The 47-acre garden has plenty of wilder terrain too, and offers hiking trails, picturesque bridges, a pond and a creek. I particularly liked the small creek lined with cypress knees. There are mansions across the water.

Mead Botanical Garden
1300 S Denning Drive, Winter Park, FL 32789
(407) 622-6323

6. Harry P. Leu Botanical Gardens

While technically not in Winter Park, Leu Botanical Garden is so close to Winter Park that we walked there from Mead Botanical Garden. Most people would drive or Uber, I suspect; it’s a long but scenic walk. By the time we’d explored the garden, we were foot-sore and took an Uber back to our hotel for a reasonable $10. It’s a 3-mile walk.

This 50-acre botanical garden could be the most beautiful place in Orlando.

With towering mature trees giving shade and Lake Rowena providing a beautiful backdrop, the gardens unveil beauty at every turn – and there are many turns in the winding walkways.

You’ll find different favorites at different times of year. There is a big rose garden, which was not flowering much on our visit, but we enjoyed the camellias in its extensive collection.

A favorite year ‘round is the tropical stream, lush with fascinating specimens, all of which are carefully labeled.

The garden has an Old Florida feel and contains the Leu House Museum, a restored 19th Century home listed on the National Register of Historic Places that has been owned by only four families.

Birds and wildlife abound. On one visit, we saw otters in Lake Rowena.

Admission is $15 adults; $10 for children 4 to 17.

Harry P. Leu Botanical Gardens
1920 N. Forest Ave., Orlando, FL 32803
(407) 246-2620

7. Take a walk to Kraft Azalea Park

A mile north of the Morse Museum and downtown Winter Park is another special park. It’s a half hour walk through some of the beautiful residential streets of Winter Park.

A few highlights of the walk: Be sure to stop to gaze at Casa Feliz Historic Home at 656 Park Ave. This special-event venue is not currently open for tours, but the 1932 “Andalusian farmhouse” is a beauty to admire from outside.

Plan your route so you cross the Venetian Canal at Alabama Drive and Palmer Avenue. This is one of the picturesque canals the Scenic Boat Tour takes visitors through.

You can stop and grab a bench at Kraft Azalea Park. It’s only five acres, but this free public garden packs in a lot of beauty. The park occupies a peninsula in Lake Maitland and is full of gorgeous shading trees hanging with Spanish moss. It includes one of the largest banyan trees you’ll find this far north.

It is also home to a great egret rookery. (Details are here.) Every year between February and early June, about 50 nesting pairs take up residence here.

The park has benches, a dock and its Exedra Monument, in the style of ancient Greece, is popular for weddings.

Kraft Azalea Gardens
1365 Alabama Drive, Winter Park, FL 32789
(407) 599-3334

8. Things to do in Winter Park: Dine, drink, sample wine, chocolates, coffee, pastries and more

The downtown Winter Park area is full of culinary treats.

There are adorable coffee shops — CFS Coffee in Hannibal Square smelled divine with cute outdoor seating and folks rave about New General just off Park Avenue.

For wine bars, you’ll pass two highly rated ones on Park Avenue — The Wine Room on Park Avenue and the Parkview.

The chocolates and cookies were so tempting in Peterbrooke Chocolatier on Park Avenue and Croissant Gourmet, just off Park Avenue at 120 E. Morse Blvd., is full of treats, as well as being a good place to buy a sandwich for the train.

And the restaurants? You’ll find every kind of place to dine, many within walking distance. Consult Yelp and TripAdvisor for tips.

Here are three perennial favorites on Park Avenue:

Prato, 124 N Park Ave., Winter Park, 32789. It’s the downtown spot for all things Italian, from pizza to meatballs to the salads and soups. It also gets high marks for its view of Park Avenue and the ambiance.

The Parkview, 136 S Park Ave., Winter Park, 32789. While primarily a wine and beer bar, the dinner menu has a nice selection of sandwiches, salads, flatbreads and a few special entrees.

Boca, 358 N Park Ave, Winter Park. This is a hopping spot that can get loud. It offers an eclectic menu and is popular for lunch.

Hotels in Winter Park FL: Two good choices downtown

We stayed in the historic Park Plaza Hotel, which has a perfect location in the center of downtown, a block from the train station overlooking both Central Park and Park Avenue.

We love historic hotels, and flaws that others note  – tiny bathrooms, small rooms – are fine by us. They come with staying in what I consider a charming one-of-a-kind hotel with character. This one turned 100 in 2022!

Two things I particularly loved about the Park Plaza Hotel: its ancient elevator with the metal grate you manually close before the elevator moves and the tasty continental breakfast brought to the room on a wooden tray when you call the front desk.

The fresh croissant and container of coffee were ideal, though the rooms are so small there was barely a place to sit and enjoy it.

Next time I’ll try to book the more expensive balcony rooms, which have plant-filled balconies where such a breakfast could be best enjoyed. As it is, during high season in March 2022, our room was $159 thanks to the “Florida resident” rate – reasonable for its outstanding location.

There is another downtown hotel that is newer, fancier and a bit more expensive – the Alphond Inn, operated by Rollins College. Profits help support the college and it offers some great sounding packages. The Alphond is four blocks from the train station, so it also has an excellent location.

Park Plaza Hotel
307 S. Park Ave., Winter Park, FL 32789
 (407) 647-1072

Alphond Inn
300 E. New England Ave., Winter Park, FL 32789
(407) 998-8090

Hotels in Winter Park on Hotels.com

Vacation rentals in Winter Park on VRBO

Taking Amtrak to Winter Park

I had long wanted to take Amtrak on a Florida Rambler trip, and I knew Winter Park was ideal because of its charming downtown built around the railroad station.

So when I heard that Amtrak was having a BOGO sale, which was about to end, I quickly booked a round-trip ticket for my husband and me. What a deal! Only $48 roundtrip from our Fort Lauderdale home for both of us!

The problem is: I didn’t look at the route or the length of the journey. It was only when we were waiting ….and waiting….and waiting for the train to arrive in Fort Lauderdale – only its third stop from its starting location! – that I learned that the train goes to Winter Park via Tampa. And it was more than a seven hour trip, IF it was on time, which it was not, and maybe never is.

The only train available is a daily trip on the Silver Star. A shorter route, skipping the side trip to Tampa, is offered on the Silver Meteor, which is currently out of service, returning perhaps at some point in 2022.

As it turns out, our journey started 90 minutes late and we lost time as we travelled. The Silver Star’s route goes through Lakeland twice, as it veers off to Tampa and back.

The seating is large and feels luxurious compared to airplane travel, and we enjoyed looking out the windows. But the food was abysmal. (A variety of plastic wrapped sandwiches heated in a microwave.)

On our return from Winter Park, the train was not very clean, which is not surprising since it was on its last few hours of a 1,522-mile route between New York City and Miami via Washington, D.C. At least one of the bathrooms was unusable as a result.

I have to admit: I’ll do better research if I ever do it again. I do love train travel, though, and I believe in finding alternatives to cars.

So I think it might work from Tampa or Jacksonville as a way to visit Winter Park. Also: Within the greater Orlando area, you could use the SunRail system to have a weekend getaway by rail in Winter Park.

From the minute I stepped off the train to the moment I boarded for our return, I loved Winter Park. But in this case, getting there was not half the fun.

More things to do in Orlando area

• Eight natural places to enjoy in Orlando area
• Moss Park offers great camping near Disney
• Winter Garden: Old Florida town thrives around great bike trail
• West Orange Trail: Impressive bike trail in Central Florida
• Van Fleet Trail: 29 miles of beauty by bike near Orlando
• Wekiva River Basin’s stunning beauty invites paddlers, campers, hikers and bikers