3 Spots Not to Miss in Winter Park, Florida

Spend a Relaxing Day in this Upscale Town Just North of Downtown Orlando

The neighborhoods and small cities that together make up the Greater Orlando area are a diverse mix of cultural offerings. The tourism corridor holds excitement and the promise of make-believe. And Orlando’s many neighborhoods each offer distinctive reasons to visit. But for sheer charm, beauty and cultural opportunities, head north for a 10-minute drive from downtown on Interstate Four to spend the day in Winter Park.

Originally chartered as a resort town for wealthy Northerners in the late 1800s, Winter Park continues to draw visitors today for its beautiful natural setting, quaint cobblestone streets, lovely parks, fantastic shopping and seemingly endless museums. It’s well worth planning a day trip to check out some of its attractions. Here, we offer some of our favorites stops.

Winter Park Scenic Boat Tour

For an opportunity to explore Winter Park’s pristine chain of lakes, consider taking the Winter Park Scenic Boat Tour, which launches from the end of Morse Boulevard on Lake Osceola.

Winter Park Scenic Boat Tour
(Courtesy Brooke Fehr)

Dating to 1938, making it one of Florida’s oldest attractions, the tour offers guests a leisurely trip through three of the seven Winter Park lakes—Lake Osceola, Lake Virginia and Lake Maitland—via two narrow canals that were built by lumber interests in the 19th century to link the lakes together.

Knowledgeable guides make the hour-long tour interesting, as passengers view lush, tropical flora and keep their eyes peeled for swooping cranes and possibly an alligator or two. From their vantage point, guests will also see stately homes, Rollins College and Kraft Azalea Gardens.

Winter Park Scenic Boat Tour
(Courtesy Winter Park Scenic Boat Tour)

Tours depart daily, every hour, from 10 am until 4 pm and are offered every day except Christmas Day. Adult tickets are available for $14, while tickets for children 2-11 are $7; children under 2 are free. 

Charles Hosmer Morse Museum of American Art

Once you return from your boat tour and you have an opportunity to dine al fresco at one of Park Avenue’s fabulous restaurants, head to the Morse Museum for a quiet afternoon among treasures. The Winter Park icon was founded by Jeannette Genius McKean in 1942, and was named for her grandfather, Charles Hosmer Morse, a Chicago businessman and Winter Park philanthropist.

The Morse Museum is home to the largest comprehensive collection of various works by Louis Comfort Tiffany, the prolific artist and designer whose declared his life-long goal was “the pursuit of beauty.” View examples of jewelry created by Tiffany and his designers, but also take in examples of his painting, pottery, art glass and more.

Now through July 8, 2018, visitors also have the opportunity to view The Domes of the Yosemite, the largest existing painting by American artist Albert Bierstadt.

"The Domes of Yosemite" by Albert Bierstadt at the Morse Museum of Art
(Courtesy of The Charles Hosmer Morse Museum of American Art)

The painting recently underwent extensive conservation efforts in Miami, and makes the stop in Orlando en route back to its home at the St. Johnsbury Athenaeum in St. Johnsbury, Vermont, a town with a connection to the Morse: Charles Hosmer Morse was born there.

A self-guided tour of the museum takes about an hour, but allow for another 30 minutes to view two films that offer additional information about the collection as well as the Tiffany Chapel. Docent-led tours are also available. The museum is open Tuesday through Saturday, 9:30 am to 4 pm and on Sunday from 1-4 pm. Admission is $6 for adults, $5 for seniors age 60 and older, $1 for students with a valid ID, and free for children under 12. In addition, if you visit during the winter or spring months, all visitors are admitted free of charge 4-8 pm on Fridays, November through April. For more information on booking tours, please visit the museum’s website. 

Rifle Paper Company

Before leaving the Morse, be sure to visit the museum’s gift shop for exclusive merchandise honoring the work of Tiffany. Then head to New England Avenue, off of Park Avenue’s main shopping district, to stock up on creative paper goods at Rifle Paper Company.

(Courtesy Brooke Fehr)

The brand, which started with a collection of stationary sold from the garage apartment of husband and wife team Nathan and Anna Bond in 2009, has grown exponentially. Visit Rifle’s flagship store to stock up on writing papers, enamel pins, calendars, fabric and much, much more.

It’s the perfect spot to find a unique memento of your time in Orlando. 

Rifle Paper Co. Print
(Courtesy Brooke Fehr)