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Orlando's leafy north side

Winter Park

Brick streets, oak shade and the city's most civilized afternoon: Park Avenue's shops and cafes, a museum full of Tiffany glass, and a boat tour gliding past lakefront mansions just ten minutes north of downtown Orlando.

ORLANDOWINTER PARK · FL

If the theme parks are Orlando's big, bright voice, Winter Park is its quiet, well-read older sibling. This is the leafy, moneyed town just north of downtown, founded in the 1880s as a winter resort for Northerners and still wearing it well: brick-paved streets, cobbled sidewalks, towering live oaks dripping with Spanish moss, and a chain of glassy lakes threaded together by hand-dug canals. The pace here is a full gear slower than the resort corridor, and that is precisely the point.

It is the easy answer to "what is there to do in Orlando besides the parks?" Couples, art lovers, ladies who brunch and anyone craving a non-Disney afternoon will feel right at home. Spend a morning on Park Avenue, an hour on the water, and the rest of the day wandering between a Tiffany-glass museum and a college campus on the lake. For more in this vein, see our gardens & museums guide and the dining roundup on Park Avenue.

The highlights

What to see & do

A handful of walkable blocks and a string of lakes with one of the best non-park lineups in greater Orlando.

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THE MAIN STREET · PARK AVE

Park Avenue & Central Park

Winter Park's heart is a few brick blocks of independent boutiques, galleries and sidewalk cafes facing the green lawns and rose garden of Central Park. Browse spots like the Writer's Block Bookstore, then settle in for a coffee and watch the town drift by. On Saturday mornings the Winter Park Farmers' Market sets up in and around Central Park near the historic train depot; check the city's site for the current spot and hours.

Free to stroll
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TIFFANY GLASS · 445 N PARK AVE

The Morse Museum

The Charles Hosmer Morse Museum of American Art holds the most comprehensive collection of Louis Comfort Tiffany anywhere, from glowing leaded-glass windows and lamps to jewelry and Favrile glass. The showstopper is the reconstructed Tiffany Chapel built for the 1893 World's Columbian Exposition in Chicago. Admission is modest; check the museum's site for current hours and pricing before you go.

Small fee
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ON THE WATER · LAKE OSCEOLA

Winter Park Scenic Boat Tour

Running since 1938, this narrated hour-long cruise leaves from a little dock at the east end of Morse Boulevard and glides through three of Winter Park's lakes and two slim, jungle-shaded canals. You will pass swaying palms, towering cypress, lakefront mansions and the Rollins campus, with the odd alligator sunning on the bank. The pontoons hold about 18 and run on the hour; check the official site for current times and rates.

Cruise
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CAMPUS & ART · 1000 HOLT AVE

Rollins College & the Rollins Museum of Art

Two blocks off Park Avenue, the 70-acre Rollins College campus sits on the shore of Lake Virginia, all Spanish-Mediterranean architecture, mossy oaks and a pretty lakeside chapel. It is a lovely walk, and on campus you will find the Rollins Museum of Art (the former Cornell Fine Arts Museum), home to the Orlando area's only European Old Masters collection. Check current days and admission before visiting.

Often free
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THE WEST SIDE · NEW ENGLAND AVE

Hannibal Square

Just west of Park Avenue, Hannibal Square is one of Winter Park's oldest neighborhoods and the historic heart of its Black community, dating to the town's founding in the 1880s. Today it is a relaxed cluster of restaurants and shops along New England Avenue, including the flagship Rifle Paper Co. store; stop into the Hannibal Square Heritage Center, whose photographs and oral histories tell the West Side's story.

Free
Tables we like

Where to eat & brunch

Park Avenue does the slow, civilized meal as well as anywhere in Orlando.

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PASTRY & BRUNCH · PARK AVE

The Glass Knife

A polished bakery-cafe that doubles as a prime brunch stop: dazzling pastry case up front, a full kitchen turning out breakfast, lunch and weekend brunch in back. It is the natural first or last stop on a Park Avenue stroll.

Brunch
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ITALIAN & TAPAS · PARK AVE

Prato & Bulla Gastrobar

For dinner on Park Avenue, Prato turns out wood-fired modern Italian. A short hop away on nearby Orlando Avenue, Bulla Gastrobar runs a lively Spanish tapas room. Both are Winter Park mainstays and good places to land when the shops close. Reservations are wise on weekends.

Dinner
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SWEETS · PARK AVE

Peterbrooke Chocolatier

A Park Avenue institution for hand-dipped chocolates and their famous chocolate-covered popcorn. Grab a bag for the walk to the boat tour or the museum; it is the kind of small, old-fashioned pleasure Winter Park does so well.

Treat
Getting around: Winter Park is roughly ten minutes north of downtown Orlando and easy to reach by car; there is also a SunRail commuter-train station right off Park Avenue. Once you arrive, leave the car and walk. Look for the city garage and side-street parking near Park Avenue, which fills up on Saturday mornings during the Farmers' Market, so come early.
Do it like a local

A perfect Winter Park day

Coffee, glass, water and a slow dinner, all within a few oak-shaded blocks.

  1. Start with pastry and coffee at The Glass Knife, then browse the boutiques along Park Avenue and Central Park.
  2. Spend an hour with the Tiffany glass at the Morse Museum, ending at the reconstructed chapel.
  3. Head down Morse Boulevard for the Scenic Boat Tour and a lazy lap of the lakes.
  4. Walk the Rollins College lakefront, then wander west to Hannibal Square and the Heritage Center.
  5. Settle in for dinner at Prato or Bulla, or chase the sunset on a campus bench by the water.
Good to know

Common questions

Where is Winter Park in relation to Orlando?

Winter Park is an independent city directly north of downtown Orlando, only about ten minutes away by car. It sits within greater Orlando and is easy to combine with a downtown visit, and a SunRail commuter-train station drops you a short walk from Park Avenue.

What is there to do in Winter Park?

Stroll the shops and cafes of Park Avenue along Central Park, see the world's largest Tiffany glass collection at the Morse Museum, take the hour-long Scenic Boat Tour across the lakes, walk the lakefront Rollins College campus and its art museum, and explore the historic Hannibal Square neighborhood on the West Side.

What is the Morse Museum known for?

The Charles Hosmer Morse Museum of American Art on Park Avenue holds the most comprehensive collection of works by Louis Comfort Tiffany in the world, including leaded-glass windows, lamps and jewelry. Its centerpiece is the reconstructed Tiffany Chapel from the 1893 World's Columbian Exposition. Check the museum's site for current hours and admission.

How does the Winter Park Scenic Boat Tour work?

It is a narrated hour-long pontoon cruise that has run since 1938, leaving from a dock at the east end of Morse Boulevard on Lake Osceola. The route winds through three lakes and two hand-dug canals past mansions, cypress and palms. Tours generally run on the hour during the day, but check the official site for current times and prices.

Is Winter Park a good non-theme-park day in Orlando?

Yes. Winter Park is one of the best answers to wanting a slower, grown-up day away from the parks, with art, a boat tour, an old college campus and excellent brunch and dinner all packed into a few walkable, oak-shaded blocks. It pairs well with Leu Gardens and downtown Orlando.

Where should I park in Winter Park?

Aim for the city parking garage near Park Avenue or the metered side streets, then explore on foot since the core is very walkable. Parking fills quickly on Saturday mornings when the Farmers' Market is on, so arrive early or take SunRail in.