Culture in Orlando: How to Spend a Weekend
Where to Discover Orlando's History, Art and Culture?
Orlando might be the “Theme Park Capital of the World” but it’s also a hotbed of classy cultural attractions that will appeal to the more erudite traveler. Historic Church Street offers a glimpse of The Sunshine State’s old-world architecture while the Orlando Museum of Art showcases one of the finest American art collections in the Southeastern United States, dating between the 18th century and the mid-1940’s.
Meanwhile, the compact coastal city of Mount Dora delights with its antiques shops, annual festivals, and charming cafes, while Downtown Kissimmee draws in the throngs with its lively farmer’s market and eclectic collection of restaurants. There’s plenty more to discover in every corner of the city.
What are the best ways to spend a weekend in cultural Orlando?
1. Church Street
The unofficial heart of Downtown Orlando
Good for: Food, History, Nightlife
If you’re a first time visitor in Orlando, Church Street is the place to go. This historic stretch is home to some of the city’s best restaurants and also boasts a lively nightlife scene. The iconic Railroad Depot was built in 1889 and stands as a reminder of the city’s long-lost past.
Stroll the length of Church Street to marvel at its intriguing architecture before taking a spooky ghost tour of the area’s most haunted buildings. Come evening, dance the night away at Studio 27 or enjoy hearty fare and spirits at the buzzy Delaney’s Tavern. Read more
Location: Church Street, Orlando, FL, USA
Church Street
2. The Albin Polasek Museum & Sculpture Gardens
Pays homage to the internationally acclaimed Czech sculptor
Good for: Couples, Group, History, Photo
The Albin Polasek Museum & Sculpture Gardens can be found in Winter Park, a spirited neighborhood just north of Orlando. The museum is set in the historic home of Czech sculptor Albin Polasek. Though the property is small, it contains a great number of artworks.
The guided tour features a short video which explains the history of the property, giving you a better understanding of the sculptures and why Polasek created them. Each piece represents different eras in the artist’s life, with most focused on religion. Don’t miss the special guest exhibits. Read more
Location: 633 Osceola Ave, Winter Park, FL 32789, USA
Open: Tuesday–Saturday from 10 am to 4 pm, Sunday from 1 pm to 4 pm (closed on Mondays)
Phone: +1 407-647-6294
The Albin Polasek Museum & Sculpture Gardens
3. Rollins Museum of Art
Discover objects ranging from antiquity through to contemporary eras
Good for: Budget, History, Photo
The Rollins Museum of Art is home to over 5,000 exceptional objects, from rare antiques to contemporary works. Located in the grounds of Rollins College, it’s right in the heart of Orlando’s Winter Park neighborhood and overlooks stunning Lake Virginia.
The museum boasts the only European Old Masters collection in the Orlando area, along with contemporary American pieces. Exhibitions change frequently, so there’s always something new to enjoy, along with special events like art presentations. Entry to the venue is free. Read more
Location: Rollins College, 1000 Holt Ave, Winter Park, FL 32789, USA
Open: Tuesday from 10 am to 7 pm, Wednesday–Friday from 10 am to 4 pm, Saturday and Sunday from 12 pm to 5 pm (closed on Monday)
Phone: +1 407-646-2526
Rollins Museum of Art
4. Downtown Kissimmee
Historic Floridian city that’s close to major attractions
Good for: Couples, Families, History
Downtown Kissimmee, in Osceola County, is a typical all-American town. Despite its past as a shipping port, the region now boasts plenty of boutique shops, eclectic art galleries, and ambient restaurants. Hunt for vintage homewares in the many antiques stores before taking part in an art workshop at La Casa Del Artesano or shopping creative pieces at Fragments Art Studio. For a decadent treat, head to Abracadabra Ice Cream Factory.
See as much of Downtown Kissimmee as possible by taking a self-guided walking tour, starting from the Kissimmee Street Office. Easily reachable by car or taxi, the town is a 30-minute drive south of Orlando. Read more
Location: Kissimmee, FL, USA
Downtown Kissimmee
5. Dr. Phillips Center for the Performing Arts
State-of-the-art theater complex
Good for: Couples, Families, Nightlife
The Dr. Phillips Center for the Performing Arts is a sprawling entertainment complex in Downtown Orlando which hosts numerous shows and events. The venue features a 2,700-seat theater hall for spectacular Broadway plays and musicals. There’s also a 1,700-seat venue for smaller events such as ballet recitals, orchestral performances, and awards ceremonies.
If you’re wanting to grace the stage yourself, take a Broadway masterclass or enroll the kids in a camp to learn the ins and ours of the theater industry. Read more
Location: 445 S Magnolia Ave, Orlando, FL 32801, USA
Open: Show times vary
Phone: +1 407-358-6603
Dr. Phillips Center for the Performing Arts
6. Mennello Museum of American Art
A charming folk art museum
Good for: Couples, Families, History
The Mennello Museum of American Art is home to a permanent collection of paintings by self-taught artist Earl Cunningham. His vivid landscapes with mismatched details feature alongside special exhibitions and events, including an annual Folk Art Festival. Family days take place every second Sunday of the month with free admission.
Just outside the Mennello Museum of American Art is The Sculpture Garden. It’s where you can find “The Mayor,” a 350-year-old live oak tree draped with Spanish moss. On selected days of the week, enjoy a peaceful yoga session by the lake. Your yoga ticket also includes entrance into the museum. Read more
Location: 900 E Princeton St, Orlando, FL 32803, USA
Open: Tuesday–Saturday from 10.30 am to 4.30 pm, Sunday from 12 pm to 4.30 pm (closed on Mondays)
Phone: +1 407-246-4278
Mennello Museum of American Art
7. Mount Dora
A culturally rich city in Central Florida
Good for: Couples, Families, Shoppers
The charismatic city of Mount Dora is surrounded by beautiful lakes and offers charming attractions all year round. With a population of around 12,000 people, this relatively small community boasts a unique charm that’s punctuated by its active arts community. Known as the “The New England of the South” and “The Festival City,” Mount Dora sees outdoor celebrations take place throughout the year, including the Mount Dora Arts Festival.
Downtown is full of boutiques selling hand-crafted art, clothing, and gifts. Antique lovers should check out the more than 60 vendors in the Village Antique Mall for rare collectibles and jewelry. Read more
Location: Mt Dora, FL 32757, USA
Mount Dora
8. Orlando Museum of Art
A beloved community art museum
Good for: Couples, Families, History
The Orlando Museum of Art is a non-profit visual arts space. Founded in 1924, it’s one of the oldest and most renowned museums in the Central Florida area, featuring a wide array of nationally recognized exhibits. Permanent collections include historic and contemporary works, African art, and pieces spanning the ancient Americas (long considered the best of its kind in the Southeastern USA).
Exhibitions rotate frequently, so there’s always something new to discover, alongside docent-led tours, workshops, and yoga classes. Every third Thursday of the month, opening hours are extended so you can peruse works by local artists and enjoy live music performances. Read more
Location: 2416 N Mills Ave, Orlando, FL 32803, USA
Open: Tuesday–Friday from 10 am to 4 pm, Saturday–Sunday from 12 pm to 4 pm (closed on Mondays)
Phone: +1 407-896-4231
Orlando Museum of Art
9. Winter Park
A scenic small town in Central Florida
Good for: Food, Nightlife, Shoppers
The upscale village of Winter Park is full of historical and cultural attractions, a little north of Downtown Orlando. From its 9-hole golf course and sophisticated shopping boutiques to its fine-dining restaurants, there so much to do along its peaceful leafy streets.
You can visit this quaint area during the day for a spot of lunch and shopping, or head there come evening when the main street is lit up and bustling with activity. Its pleasant vibe sees many couples head out for a stroll after dinner and drinks. For a touch of culture, visit the Charles Hosmer Morse Museum of American Art or swing by Central Park for a walk amongst nature. Read more
Location: Winter Park, FL, USA
Winter Park
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