A Surprising Art Escape (and More) Near Orlando

Serenity and art in Orlando, that madhouse of theme parks? Yes, it's true. Welcome to Winter Park, Florida.

WINTER PARK, Florida – Even people who love Orlando’s theme parks may want (or need) a change of scene. Winter Park is known for its gentler pace and historic charm, but what wowed me were the cultural treasures less than 45 minutes from the parks.

The Scene

Posh and arty, this city of 30,000 people packs a lot into ten square miles, including a vintage downtown with leafy, brick-paved streets. Locals and visitors shop at indie stores, sip coffee and eat at restaurants both down-home and trendy, and stroll in pretty parks. More unusually for a place this size, they can soak up art spanning styles from Tiffany glass creations to dazzling contemporary works. Students at private liberal-arts Rollins College, founded in 1885, add a youthful buzz.

Winter Park’s distinct sense of place comes from its past, preserved in several historic districts. In 1881, northerners Loring Chase and Oliver Chapman purchased 600 acres and designed a Floridian, slightly Mediterranean version of a New England town. Streets curve around lakes, and Central Park stands in as a town green. The goal was to create a winter escape for wealthy northerners, who built handsome homes and cultural institutions.

Today Winter Park may be a suburb of Orlando, but it’s a reminder that there’s more to Central Florida than the Mouse.

Lay of the Land

Winter Park is fifteen miles and a 30-minute drive north of Orlando International Airport and 30 to 45 minutes from Orlando’s theme parks. The Downtown Historic District is the main hub. Park Avenue, its heart, is a walkable retail and dining center that extends from Canton Avenue south to Comstock Avenue, with low-rise buildings dating between 1882 and the mid-1960s. Tidy lawns and a rose garden fill Central Park on the west side of Park Avenue. Winter Park’s train station is here, too. The Mediterranean-style, lakeside campus of Rollins College lies beyond Park Avenue’s southern end. Just west of the train tracks, Hannibal Square offers shopping and dining and a look at Winter Park’s Black history. East of downtown are the six lakes of the Winter Park Chain of Lakes.

If You Only Do One Thing

The Charles Hosmer Morse Museum of American Art displays a glittering collection of works by Louis Comfort Tiffany, including a chapel and furnishings from Tiffany’s Long Island house. (My suggestion: Pair this Gilded Age bling with a drink at the Alfond Inn and a look at the hotel’s stunning contemporary art.)

What You Should Know on Your First Day

Slowing down is the way to appreciate Winter Park’s mellow vibe, whether by tootling around on the old-timey Scenic Boat Tour or lunching alfresco on Park Avenue.

See All the Art

At the Charles Hosmer Morse Museum of American Art (Morse Museum, for short) downtown, all that glitters is Tiffany: specifically, gallery after gallery of gleaming, jewel-like art glass, leaded-glass windows, pottery, lamps, and more by prolific designer Louis Comfort Tiffany (1848–1933). This unique collection, the world’s most comprehensive, includes the mosaic and glass Tiffany Chapel created in 1893 and the 12,000-square foot Laurelton Hall Wing, with architectural and decorative elements from Tiffany’s Long Island home, Laurelton Hall. It can feel slightly overwhelming, so I focused first on the chapel and Laurelton Hall rooms. Other artists are represented, too. The introductory videos about the museum’s history and the Tiffany Chapel are worth viewing; they’re also on the website.

The 6,000-work collection of the free Rollins Museum of Art (RMA), part of Rollins College, focuses on European Old Masters, American art, and global contemporary art. This teaching museum sees art as a way to encourage lifelong learning and critical thinking and dialog; its varied, stimulating exhibitions change frequently. RMA has been growing its collection and audience, and plans have been approved for a larger building across from the Alfond Inn and a block from Park Avenue.

There are art hotels, and then there’s Alfond Inn, the country’s only hotel that functions as part of an art museum. More than 100 works (with in-depth, museum-style labels) by emerging and well-known global contemporary artists working in different media are displayed in the hotel’s public areas, including the café and bar. The works are part of the Alfond Collection of Contemporary Art, an exciting, thought-provoking 600-piece collection conceived by Rollins alumni Barbara and Ted Alfond and owned by the hotel’s neighbor, Rollins College. The art in the hotel rotates and includes works by Jeffrey Gibson, Carmen Herrera, David Hockney, Gordon Parks, Vik Muniz, Mohammed Sami, Tomás Saraceno, Kay Walkingstick, and Kara Walker.

I love visiting artists’ homes and studios for the insights the spaces yield about each artist. At the Albin Polasek Museum & Sculpture Gardens, on a few serene acres overlooking Lake Osceola, I learned about Czech-born figurative sculptor Albin Polasek (1879–1965), who designed the building in 1950 after a successful career that included heading the Art Institute of Chicago’s sculpture department. The colorful, quirky spaces and the lush sculpture garden’s three dozen pieces tell the inspirational story of a man who overcame many hardships, including learning to sculpt with one hand after a stroke.

Visit Lakes, Parks, and Gardens

A classic since 1938, the Scenic Boat Tour glides around three of the six lakes in the Winter Park Chain of Lakes during a narrated, hour-long ride on an 18-person pontoon boat. My skipper-guide highlighted interesting history – the fun, narrow canals connecting the lakes were constructed for the logging industry – and commented on the lavish houses (some old, some newer) on the shores.

Winter Park is proud of its green spaces, such as manicured Central Park opposite Park Avenue’s shops, the site of the popular Saturday Farmers’ Market, art festivals, and other events. Also worth a look are the five-acre lakeside Kraft Azalea Garden (blooming January through March) and the 47-acre Mead Botanical Garden, with several different ecosystems.

Stroll the Shops

Even for someone who’s not a recreational shopper (guilty as charged!), window-shopping or browsing the mostly independent boutiques and stores along Park Avenue is a Winter Park pleasure. A coffee or lunch stop enhances the experience.

While stores tend to the upscale, there’s something for everyone, from jewelry to shoes. Clothing boutiques stocking colorful, Florida-focused styles at different price points abound, including mother-and-daughter-run Tuni. Stores like preppy Lily Pulitzer and the girly, Barbie-pink Gasp both fit into the scene. The avenue has several chocolate stores such as Peterbrooke and the chocolate restaurant AJ Chocolate House, and other food-focused shops like The Ancient Olive Gourmet, with olive oils, vinegars, and culinary gifts. The Morse Museum’s store stocks Tiffany-related items like jewelry and decorative home items.

Lifestyle brand Rifle Paper Co. is headquartered in Winter Park, and its store in Hannibal Square sells flowery, whimsical cards, journals, wrapping paper, clothing, and more. Fans flock to the large sale room.

Hannibal Square Heritage Center

The Hannibal Square neighborhood was planned from Winter Park’s beginning for African Americans, some of whom worked for the railroad or for wealthy residents and visitors. The area has diversified and gentrified, but Hannibal Square Heritage Center, established by the localCrealdé School of Art in 2007, preserves the history of the segregation era and later. It has special exhibits, but I most appreciated the illustrated neighborhood timeline and archival photos and oral histories from individuals describing life in what was a vibrant community despite challenging circumstances.

Where to Stay

Owned by Rollins College, the upscale, art-filled Alfond Inn at Rollins is a block from Park Avenue and the best choice when Winter Park is more than a day trip. Built in 2013, the hotel added a new wing in 2023, bringing the room count to 183. It also gained a second pool deck and a wellness facility including The Spa, with seven treatment rooms and hydrotherapy amenities. The spacious, comfortable public areas, restaurant, and café are gathering places for locals as well as guests. Everyone gets to appreciate the hotel’s most unique feature, the world-class contemporary art filling its public areas. Guest rooms in white, neutral hues, and plenty of sunny yellow and turquoise have thoughtful amenities, such as excellent, stylish lighting and William Roam toiletries. Rooms in the new wing, where I stayed, are particularly nice. The peacocks on the rugs pay homage to Winter Park’s symbol; the few birds originally brought to the town have multiplied over the decades. A hotel stay benefits a Rollins College student: The net operating income goes to scholarships.

Where to Eat

Orlando’s dining scene has heated up, and Winter Park’s restaurants reflect this, with longtime favorites and hip newcomers serving comfort classics and global fare. Helping jumpstart the scene in 2007 was The Ravenous Pig, a half-mile west of downtown, an industrial-looking gastropub, brewery, and beer garden known for using sustainable local produce. Its design may feel familiar to places you’ve been before, but the menu is freshly creative. The ten-seat, Michelin-starred Soseki, also west of downtown on Fairbanks Avenue, is a multi-course omakase experience using Florida’s produce inventively; advance reservations are essential. Chef Michael Collantes has just opened Bar Kada, a 30-seat sake lounge with an à la carte menu, next door.

The always-hopping AVA MediterrAegean downtown is an airy, see-and-be-seen newcomer focused on authentic Greek seafood dishes and flavors from around the Med. A good prix-fixe menu is offered Sunday to Thursday. Well-executed Italian favorites such as pizzas, panini, and pastas bring the Park Avenue crowds to Prato, with its tall windows, patio, and contemporary rustic look. Park Avenue Tavern in Hannibal Square is a good stop for a drink or hearty fare such as burgers or steak frites; the warm chocolate chip cookie in a skillet is dangerously delicious.

Friendly and bright, the yellow-awninged Briarpatch on Park Avenue has dished up comforting (and not cheap) breakfasts and lunches since 1980. Everyone – me included – seems to pass through for lemon raspberry pancakes, heavenly biscuits, a shrimp po’boy, or a slice of house-made cake. A stop at the Alfond Inn gives time to take in the hotel’s contemporary art and have a satisfying breakfast and lunch (omelets and Benedicts are good) at Hamilton’s Kitchen; The Café has coffee and lighter fare.

A retail store, wine bar, and dining spot since 2006, The Wine Room on Park Avenue offers more than 150 wines in different-size pours from Enomatic dispensing machines (drinkers buy a wine card). Cheeses (a vast list), charcuterie, flatbreads, and small plates appear on the menu, and the casual vibe is welcoming.

Plan Your Trip

How to Get There
Orlando International Airport (MCO) is 15 miles, or a 30-minute drive, south of Winter Park. The city is northeast of the theme parks: about 15 miles, or a 30-minute drive, from Universal Studios Florida and about 30 miles, or a 45-minute drive, from Disney’s Magic Kingdom. Winter Park is six miles, or a 15-minute drive, from downtown Orlando.

Winter Park’s train station is served by Amtrak and SunRail, Greater Orlando’s commuter rail system. Florida’s new high-speed Brightline, with six stops between Miami and Orlando, has a station at Orlando International Airport.

Getting Around
Downtown’s walkability is part of the pleasure of seeing Park Avenue and the main sights. If the distance is greater, a car or ride-hailing service is useful.

When to Go
Orlando and Central Florida are hot and humid in summer, with more rainy days June through September than at other times. Still, vacation time and schedules bring plenty of people here during this season. Fall and winter are comfortable, and early spring is often less humid.

Insider Local Intel
Fred Rogers of Mister Rogers’ Neighborhood graduated from Rollins College. He majored in music composition.

What to Pack
Winter temperatures range from lows in the 50s to highs in the 70s, so layers are useful. Summer temperatures start in the 70s and rise into the 90s, with humidity that makes light attire a requirement. A sweater or wrap is handy for Florida’s ample air-conditioning. Window-shopping and museum-going are easier with good walking shoes, and an umbrella is always useful.