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What to do in winter park, florida: the perfect weekend itinerary.

By Ana Connery

Winter Park , a city of 25,000 just five miles north of downtown Orlando, has been a tony retreat pretty much since it was first developed in the late 1800s by wealthy northerners who wanted to take advantage of the lakeside setting.

The entrepreneurs drew plans for a city that would embrace the park-like setting and provide opportunities for local businesses to thrive.

Today, Winter Park still feels more town than city , with its walkable grid of brick-paved streets flanked by a European style of architecture that celebrates Gothic arches, clay-barrel roofs and intricate ironwork. Wandering around is a must.

Park Avenue is Winter Park’s main artery, running for eight blocks from Rollins College to the Charles Hosmer Morse Museum of American Art before fading into a residential neighborhood shaded by moss-draped oaks.  

Winter Park feels more town than city, with its walkable grid of brick-paved streets flanked by a European style of architecture that celebrates Gothic arches, clay-barrel roofs and intricate ironwork.

- Julie Fletcher for VISIT FLORIDA

Park Avenue is Winter Park’s main artery, running for eight blocks from Rollins College to the Charles Hosmer Morse Museum of American Art before fading into a neighborhood shaded by moss-draped oaks.

Art and Academia

As you stroll the garden paths and side streets, a sense of collegiate history echoes, but perhaps no more so than at the new Alfond Inn . Long a popular getaway for the nation’s elite, including President and Mrs. Reagan, who celebrated their 25th wedding anniversary here, what was then the legendary Langford Inn sat empty for years.

Eventually a pair of Rollins alumni, Ted and Barbara Alfond, invested millions to rebuild it in part to showcase their extraordinary art collection, the centerpiece of the Cornell Fine Arts Museum on the nearby campus. The renowned art lovers wanted the 112-room hotel to serve as much as a “visual syllabus” as a place for students’ parents and visitors to lay their head.

Check in on a Friday afternoon and the myriad courtyards and conservatory will likely be abuzz with well-heeled locals kicking off the weekend with one of the bar’s happy hour specials. Having a drink in hand is not a bad way to embark on a self-guided tour of the contemporary art collection found primarily on the first and second floors. It's a must-see for an art lovers.

From high-energy video to neon signs that promote the Alfond’s mission with words like, “Language must speak for itself,” the collection’s highlights include “Afghan Girl,” the famous photo by Steve McCurry that graced the cover of National Geographic and is commonly referred to as the Afghan Mona Lisa.

A group of 19 paintings of the covers of famous books comprises a collection that connotes the intellectual curiosity of the Rollins faculty members who chose the works as their fave pieces of literature.

To experience activities rich in culture, walk north on Park Avenue past the many family-owned jewelry shops, cafes and boutiques tucked in between preppy chain stores to the Morse Museum , where admission is free every Friday between 4 and 8 p.m. except during summer.

If you get tired of walking, take a two-wheeled adventure down the city streets.

Winter Park's wide variety of restaurants means there is something for everyone.

The draw here is the exquisite glass art of Louis Comfort Tiffany, the most comprehensive collection of his work in the world. His chapel interior, the original from the 1893 World’s Columbian Exposition in Chicago, is as full of detail and spiritual prowess as any you’d find in Europe.

The galleries featuring the ornate art and furnishings from his famed Laurelton Hall residence on Long Island provides a peek at what an artist can do with enormous wealth (Tiffany’s father was the founder of the famed Fifth Avenue jewelry store in New York).

Stop for dinner at Prato on Park Avenue, where a floor-to-ceiling glass storefront opens to reveal a seamless transition from the inside out.

Ask for a table near the sidewalk so you catch the scent of the Central Park rose garden across the street and watch Amtrak trains shuffle passengers in and out of the town depot. With a setting like this, you’ll be tricked into thinking you’ve gone back in time—with more appropriate clothes.

There are few light dishes at Prato, but the modern Italian cuisine does subscribe to the trendy farm-to-table approach to food with many local farmers highlighted on the menu. Start with the savory meatballs in a roasted tomato pulp before indulging in the Widow Maker pizza from the wood-burning oven in the open kitchen. Topped with fennel, sausage, prosciutto and a sunny-side up egg, it’s a hearty take on a popular dish. You’ll be glad for the walk back to the Alfond Inn.

Natural Wonders

Wake up early to beat the crowds at the Winter Park Farmer’s Market just two blocks west of Park Avenue. Next to produce and plant stands from nearby farms, a lineup of food stalls and trucks serve everything from French croissants to fresh smoothies.

Inside the adjacent brick building that once housed the original Winter Park train depot, you’ll find fresh bagel sandwiches as well as homemade pastas and cheeses. Sit on the breezy patio to enjoy your breakfast before peeking into the Winter Park History Museum at the northern end of the building. Run by volunteers, it features rotating exhibits that showcase the history of the city, including a recent retrospective of the local high school.

Spend the afternoon partaking in activities at the Alfond Inn’s rooftop pool with its tree-line view of the apartment building across the street. Sir Paul McCartney reportedly bought the top floors for his stepson, who attends Rollins College.

Catch the sunset during the last Winter Park Scenic Boat Tour of the day. From the dock on the east end of Morse Street, this family-owned business has been taking passengers across three of the seven lakes on the tranquil Winter Park chain since 1938. Besides great views of the sprawling backyards of the city’s wealthiest residents, you’ll sneak a peek at the beautiful Rollins campus and might even catch a gator or crane sunbathing along the mangroves as you slide across two narrow canals.

Sunday stroll

Come Sunday, if it hasn’t already, Winter Park makes it clear this is a playground for the upper crust. Stroll west past the cardigans and linen pants toward Hannibal Square , a section of the city originally designed as a separate community for African Americans.

The two blocks here are like a mini Park Avenue of fine restaurants and specialty shops.

On the rare weekend that a festival of some sort is not in full swing, wrap the weekend with a little window shopping at Tuni , a trendy boutique owned by a local mother and daughter. Linger over the baubles at another family-owned biz, Simmons Jewelry , and the handcrafted home accents at Ten Thousand Villages before sliding into a sidewalk cafe for one last taste of the Florida good life.

For more about Winter Park, visit www.cityofwinterpark.org .

Places to Remember

Winter Park

Related content.

The Alfond Inn

• 300 E. New England Avenue
• (407) 998-8090

Winter Park Chamber of Commerce

• 151 W Lyman Avenue
• (407) 644-8281

City of Winter Garden

• 300 W Plant Street
• (407) 656-4111

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25 Things to See & Do

Park Avenue and the surrounding Winter Park community offer residents and visitors a variety of activities. From enjoying one of our local parks and exploring a museum, to dining al fresco and attempting to paddle board, the Park Avenue area is rich in exceptional experiences.

1.  Park Avenue Shopping District

The centerpiece of a lavish winter retreat since 1887, Park Avenue has long been the place for a relaxing stroll in elegant surroundings. Experience a unique destination for fine dining, fashion, and art in one of Florida’s most unique and flourishing communities. Bordered by a shady park that plays host to concerts and art festivals, Park Avenue is home to one-of-a-kind boutiques and well-known shops, sidewalk cafes and fine dining restaurants, as well as world-renowned art collections in the area’s museums.

Downtown Winter Park’s charm is magnified in the truly unique details: hidden gardens and side streets that are home to locally-owned shops, a farmers’ market that attracts both locals and visitors alike each Saturday morning, festive parades that mark the seasons and a scenic boat tour that cruises the canals between the City’s lakes overlooking the area’s most prestigious homes. Often called “Little Europe,” Park Avenue in downtown Winter Park is a year round destination that is sure to charm visitors of all ages. 

2.  Charles Hosmer Morse Museum of American Art

The Charles Hosmer Morse Museum of American Art is home to the world’s most comprehensive collection of works by Louis Comfort Tiffany (1848–1933). The Museum’s Tiffany collection includes jewelry, pottery, paintings, art glass, leaded-glass windows and lamps, and the chapel interior the artist designed for the 1893 World’s Columbian Exposition in Chicago.

The newest wing of the Morse Museum, which opened in February 2011, provides long-term public access to a collection of art and architectural objects from Louis Comfort Tiffany’s celebrated Long Island home, Laurelton Hall. The Museum is open to the public Tuesday through Sunday throughout the year with the exception of some major holidays. To plan your visit and for more information, click  here .

3.  Albin Polasek Museum and Sculpture Gardens

Founded in 1961, the Albin Polasek Museum & Sculpture Gardens is home to a fine art collection focusing primarily on American representational sculpture, with over 200 works by Czech-born American sculptor, Albin Polasek.

The museum also offers guided tours of the historic Polasek residence and chapel, an outdoor sculpture garden and a gift shop.  In addition, the museum hosts cultural events throughout the year, such as the Winter Park Paint Out in the spring and a Chamber Concert Series in the winter. The Museum is open to the public Tuesday through Sunday throughout the year.  To plan your visit and for more information, click  here .

4.  Winter Park Scenic Boat Tour

The Winter Park Scenic Boat Tour is an 18-passenger pontoon boat ride on the pristine Winter Park chain of lakes. The tour offers hour- long, guided cruises through three of the seven lakes and two man made canals on the tranquil Winter Park chain.

Every tour guarantees plenty of swaying palms, towering cypress trees, lush ferns and a variety of flourishing sub-tropical flowers. You will also experience breathtaking views of opulent private homes and exquisite estates sprawling along the shores. Tour guides are sure to point out sights of Rollins College, Albin Polasek Museum & Sculpture Gardens, Kraft Azalea Gardens, and more. Tours are available for individuals, groups and private events throughout the year. To learn more about the Winter Park Scenic Boat Tour, click  here .

5.   Culinary Excursion: Dining on Park Avenue

Park Avenue’s eateries offer something to suit every taste, especially foodies! This culinary utopia is home to over 40 restaurants, including everything from ice cream shops to award-winning fine dining. It also boasts a variety of gourmet food stores where you can find everything from savory spices to sweet treats.

Whether you are looking for brunch, lunch while shopping the Park Avenue District, or a special dinner with family and friends, Park Avenue provides a diverse mixture of cuisines. You’ll discover traditional French, Italian, Thai, Tex-Mex, Turkish and American dishes, as well as everything in between. There is even something to satisfy the vegan and vegetarian palate. Visiting later in the day? The area’s active culinary scene carries on late into the evening. Be sure to plan a stop at an upscale wine bar. For more information and to view a listing of Park Avenue dining options, click  here .

6.  Central   Park

Central Park is the crown jewel of all the city’s parks. Conveniently located on Park Avenue in the heart of the downtown shopping district, this 11-acre park boasts shady oak trees, landscaped planters, sitting areas, open space and three beautiful fountains. There is even a rose garden at the southern corner of Central Park. The lush foliage and relaxing atmosphere make it the perfect environment for a picnic.

The park welcomes visitors to the city that arrive by train and hosts numerous events and activities throughout the year, including the Winter Park Sidewalk Art Festival, Winter Park Autumn Art Festival , Winter on the Avenue , the annual Pancake Breakfast before the Christmas Parade , and the Olde Fashioned 4th of July Celebration. Enjoy this oasis of nature in the heart of Winter Park.  To learn more information about Central Park, click  here .

7.  Winter Park Farmers’ Market

The Winter Park Farmers’ Market is now held every Saturday morning at the West Meadow at the corner of New York and Morse Avenues. 

The market takes place every Saturday morning from 7 a.m. to 1 p.m. and is a popular community-gathering place that provides fine produce, plants, baked goods and so much more. For more information about the Winter Park Farmers’ Market, click  here .

8.  Rollins College

Located along the banks of Lake Virginia in the heart of Central Florida, the beautiful Rollins College campus encourages visitors to take advantage of Florida’s natural beauty and Winter Park’s history and charm. With its Spanish-Mediterranean architecture, lush grounds and gorgeous setting, Rollins was named one of the 50 Most Amazing College Campuses in 2011 by The Best Colleges, and the number one regional university in the South in 2021 by U.S. News & World Report .

Feel free to stroll across the lush landscaped 80-acre campus through the beautiful rose garden or along the Walk of Fame containing more than 200 stones gathered from the birthplaces of influential cultural and historical figures. You'll also find a bronze statue of legendary television host Mr. Fred Rodgers, one of Rollins' most famous graduates. Take a relaxing walk on the lakeside walking trail, visit the Rollins Musem of Art or attend one of the many  cultural ,  sporting  or educational events offered by Rollins College throughout the year. For more information and to plan your visit to Rollins College, click  here .

9.  R ollins Museum of Art

Set like a jewel on the Rollins College campus overlooking  beautiful Lake Virginia, the Rollins Museum of Art offers  visitors a sophisticated, intimate viewing experience in one of  the  nation’s most innovative college art museums. The richly  diverse art collection of the museum boasts more than 5,000  works and  is recognized as one of the largest and most  distinguished  collections in Florida.

Original and traveling exhibitions change seasonally and feature outstanding works of art for all tastes, from the early Renaissance to cutting-edge contemporary. The museum’s original exhibitions are drawn from a broad range of paintings, prints, drawing and sculpture. The museum is open to the public Tuesday through Sunday throughout the year. To learn more about the museum and to plan your visit, click  here .

10.   Casa Feliz Historic Home Museum

Overlooking the golf course in the heart of Winter Park lies the historic Casa Feliz, beautifully restored Spanish farmhouse designed by acclaimed architect James Gamble Rogers II. The exterior of the house and grounds provide a picture-perfect backdrop for weddings and parties. The rich textures of original Spanish roof tiles and whitewashed century-old bricks, a turret, a bell tower and a heavy timber balcony detailed in colors of the Mediterranean. The lush landscaping—courtyards, sweeping oaks, and native plants contained by ancient clay amphorae add to the historic beauty if the restored farmhouse.

The rich detail of the interior of the house include the living room’s vaulted ceiling of massive hand-hewn beams; the heavily carved European antiques accenting each room; a Majolica-tiled interior courtyard and fountain; arched doorways and a circular staircase, all evoking 19th century Spain.  Casa Feliz offers tours on Tuesday and Thursday from 10 a.m. – 2 p.m. and an open house on Sunday from 12 – 3 p.m. Other special events include Art at the Casa, Christmas at the Casa and the annual James Gamble Rogers Colloquium on Historic Preservation. For more information about Casa Feliz including upcoming events, click  here .

11.  Winter Park History Museum

Explore the interesting history of Winter Park at the Winter Park History Museum. The museum collects, preserves, promotes and researches the history of Winter Park and its surrounding area, and shares that history with the public through educational programs and the operation the museum. The museum is home to many collections of historical items relevant to the Winter Park community and also curates interesting exhibitions of Winter Park history. The museum is open to the public Tuesday through Saturday, throughout the year. For more information about the Winter Park History Museum, click  here .

12.  The Bach Festival Society of Winter Park

The auditioned all-volunteer Bach Festival Choir is the nucleus of the Bach Festival Society, with a membership of over 160 singers from all walks of life who share a love of great music.  Many members of the choir have music degrees or advanced musical training, serve as educators in the Central Florida area, or maintain active schedules as soloists in churches and other venues throughout the community. Others are simply brought to the choir by their love of music. To learn more about Bach Festival Society and upcoming performances, click  here .

13.  Popcorn Flicks in the Park

The City of Winter Park and Enzian Theater  collaborate to produce the “Popcorn Flicks” cinema series in Winter Park. The series features classic films for the whole family to enjoy. Popcorn Flicks are usually held on the second Thursday of each month at 8 p.m. (but may not start until sunset to provide an optimal viewing experience). The films are shown in Winter Park’s beautiful Central Park and are free and open to the public. Bring a blanket and picnic or stop by one of our fabulous Winter Park restaurants to grab some snacks to go! To learn more information and to see a list of upcoming flicks, click  here .

14.  Mead Botanical Garden

It has been described as “an urban oasis, a refuge for wildlife, a  botanical garden emphasizing nature, sustainability and  environmental learning, and a place for contemplation,  celebration, and recreation." Mead Botanical Garden is located  just a few miles from the downtown business district. It is a  beautiful place to enjoy a lazy afternoon traversing the nature  trails or dipping your feet in the freshwater ponds. It is also an  excellent venue for intimate gatherings to celebrate special occasions or as a pleasant setting for any group collaboration. For more information about upcoming events, programs scheduled in the garden or to make reservations click  here .

15.  Kraft Azalea Garden

Kraft Azalea Garden is a serene 11-acre park just minutes from  the Park Avenue shopping district. The park is bordered by  beautiful Lake Maitland and offers benches for reading,  picnicking, or for simply enjoying a quiet relaxing time. There  are trails for short walks and a small dock that is ideal for  fishing. The garden is beautiful year round, but be sure to visit  in the months of January through March when the namesake  flowers are in bloom. Find out more about Kraft Azalea Garden by clicking  here .

16.  Winter Park Golf Course

The Winter Park Golf Course is the second oldest golf club in the Central Florida area. The golf course opened in 1914. It stretches through the downtown Winter Park area and provides a challenge to even the most experienced golfer. With its narrow, tree-lined fairways and postage stamp, bunker guarded greens, this course will provide a test for every shot in a golfers arsenal. Daily fees start at $15 to walk 9 holes for Winter Park residents and $18 to walk 9 holes for non-residents. For further information, call 407-599-3419 or click  here .

17.  Shady Park

Shady Park, centrally located in historical Hannibal Square next to the community center, features park benches and a tranquil sidewalk pathway. It is perfect for reading a book or hosting a special community event. Restrooms are located in the adjacent Community Center. To read more information about Shady Park, click  here .

18.  The Alfond Inn

The Alfond Inn contributes to Winter Park’s cultural and artistic reputation by housing a eclectic collection of contemporary art available for  viewing by the public. The collection is an extension of the Rollins Museum of Art and features over 240 paintings, photographs, sculptures and mixed media works commemorating various impacting points in history. On Fridays, be sure to take advantage of the free  docent-led tours  available at 1 p.m.

While experiencing these artistic proofs, feel free to indulge in the additional luxuries offered at the inn. Residents and visitors alike can dine in Hamilton’s Kitchen for holidays brunches and chef-inspired dinners or, attend special  events  like “Get Your Jazz On”. For more information about The Alfond Inn or to make a reservation, click  here .

19. Hannibal Square

Visit Hannibal Square, a historic neighborhood located along New England Avenue two blocks west of Park Avenue, between Virginia and Pennsylvania avenues. Enjoy al fresco dining, stylish home furnishings, exciting boutiques, and unique gifts. While in the area, be sure to pamper yourself at some of the area’s top skin care spas and hair salons. For more information about historic Hannibal Square, click  here .

20. Cultural Walking Tour

Take a self-guided walking tour of the City’s historical treasures, including more than a dozen different sites. The route begins near the historic  Winter Park Golf Club and heads south along Park Avenue calling attention to a  variety of museums and landmarks along the way. The map indicates  opportunities  to head west to Hannibal Square, east to the public library and  south to Rollins  College, home to the Annie Russell Theatre, Knowles Memorial  Chapel and Cornell  Fine Arts Museum. Download your guide by clicking  here .

21.   Alfond Boat House and Dinky Dock

Dinky Dock sits on Lake Virginia, a 224-acre lake in the Winter Park Chain of Lakes.  Now a public park, the area used to be the site of the depot for the Winter Park-Orlando Railroad. Nicknamed the “Dinky Line” for its fragility, the railroad opened on January 2, 1889. The fare from Winter Park to Orlando was 15 cents, and the trip measured six miles and took half an hour. The depot was removed in 1967. But look for a monument, a little to the west of Dinky Dock on Lake Virginia, that marks where the train station once stood.

Today, the dock offers boat access to the beautiful Lake Virginia and the Winter Park chain of lakes. Boaters launching at Dinky Dock may navigate through canals connecting five lakes: Lake Virginia, Lake Osceola, Lake Maitland, Lake Mizell and Lake Minneola.  Learn more information about Dinky Dock by clicking  here .

22.   Winter Park Library

The new Winter Park Library, designed by world-renowned artist and architect Sir David Adjaye, opened in 2021 next to Martin Luther King Jr. Park. This new landmark offers a variety of amenities to residents and visitors, including a studio for audio and video production, a library commons, private study rooms, a computer lab, a 3D printer, arts and crafts room, bikes you can check out, and much more.  A collection of over 280,000 books, audiobooks, music cassettes and CDs, videos, DVDs, and eBooks are available, including the newest large-print books, fiction, and non-fiction books, and audiovisual titles which are displayed on the first floor. The Children’s Library offers a good selection of books, audiotapes, music, computer software, videos, and DVDs for young children, kids, and teenagers. The library offers a wide range of story times and special events for kids of all ages.

Winter Park Chamber of Commerce President and CEO Betsy Gardner Eckbert interviewed Sir Adjaye. To watch this interview, click here . The library is open to the public Monday to Saturday, and closed on Sundays. For more information about Winter Park Library, click  here .

23.  Winter Park Playhouse

The Winter Park Playhouse is Central Florida’s only professional musical theater dedicated to producing musical comedies, revues and cabarets. Located just blocks from Park Avenue, an evening at the Winter Park Playhouse provides quality entertainment in an intimate setting.  Performances are offered year-round. The Mainstage series features seven light-hearted musical comedies and revues that are from Broadway or Off-Broadway. The Spotlight Cabaret Series is a monthly series featuring a different professional singer in an intimate setting. Visit the online box office to view what’s playing and to book your seat by clicking  here .

24.  Central Florida Community Arts

After years of music-making, the founders of Central Florida Community Arts, Joshua Vickery and Jonathan Cole, came to the realization that Central Florida does not offer many cultural platforms for ALL musicians to use their talents. Therefore, in September of 2010, they decided to begin the journey of creating an incredible community arts program. They began reaching out to influential people in the Central Florida area and every one of them responded with overwhelming support – thus, Central Florida Community Arts was born. Since then, many people have been working hard to make this dream become a reality.

After a successful kick off in February 2011, CFCArts performed their inaugural concert to over 1,200 people in May of 2011, with a choir of over 130 singers and an orchestra of over 35 players. That community choir has since grown into several separately-themed choirs with over 500 members total and their per-concert audience has grown to upwards of 5,000 patrons. To learn more about upcoming performances and events,  click here.

25.  Special Events

Winter Park and its downtown area offers a robust events calendar, ensuring there is always something happening on the Avenue! Signature events like the  Autumn Art Festival , the spring Sidewalk Art Festival , Sip, Shop & Stroll, and Best of Winter Park celebration delight both residents and visitors alike. Traditional memories are made during the holiday season with events including the annual Christmas tree lighting during  Winter on the Avenue , the annual Christmas Parade , and the lighting of the Tiffany windows in Central Park hosted by the Charles Hosmer Morse Museum. Your experience in Winter Park is not complete without joining in on the fun! To learn more about upcoming Winter Park events,  click here.

Self-Parking Options ( see parking map ):

On-street parking is available for up to 3 hours.

Free 4-hour parking is available in municipal parking lots within one block of Park Avenue.

North Park Avenue garage offers complimentary parking on 4th & 5th floors only (4-hour parking).

South Park Avenue garage (Truist Parking Garage) offers paid parking by the hour.

Valet Parking Options: Complimentary valet available at New England & Park avenues. Additional valet locations available across from Cocina 214 (along Welbourne Avenue) and at Prato (North Park Avenue).

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The City of Winter Park

Park Avenue in Winter Park Near Orlando

The City of Winter Park & Park Avenue District

Throughout the Orlando area, unique neighborhoods, towns and cities offer outstanding dining, vibrant arts and culture, bespoke retailers, and outdoor adventures. The City of Winter Park is one of the best thanks in large part to the acclaimed restaurants, shopping, arts and more in the upscale Park Avenue District. If you haven’t been there yet, you owe yourself a visit — here’s why.

Discover: A Perfect Day in Winter Park

Approximately 20 minutes northeast of downtown Orlando, and not to be confused with Winter Garden to the west, Winter Park gained its name after the arrival of the South Florida Railroad in 1880. The highly rated Rollins College — Florida’s first four-year university — opened shortly thereafter, heralding the city’s refined future.

Discover: Winter Park Virtual Tour

Today, Winter Park’s epicenter is Park Avenue, a tree-lined, cobblestoned street bursting with acclaimed eateries, museums and some of the Orlando area’s best shopping. The city also has much for outdoor enthusiasts, including a robust parks system and the gorgeous Winter Park Chain of Lakes.

To really experience Winter Park, you’ll want to stick around for a few days. One of the best places to do so is The Alfond Inn . Owned by Rollins College, the recently renovated, AAA Four Diamond property boasts 112 guest rooms, a full range of amenities (including a pool) and a riveting art collection. What’s more, all of the hotel’s profits endow a scholarship program at Rollins.

Discover:  Orlando's Top Hotels & Resorts

Some of Orlando's top culinary artists ply their trade in Winter Park, including James Beard-nominated Chef Brandon McGlamery. He has one of Winter Park’s MICHELIN Guide Recommended restaurants, Prato , as well as Luke’s Kitchen in nearby Maitland. They specialize in innovative Italian and classic American cuisine, respectively.

Discover: Orlando’s MICHELIN Guide Restaurants

Also nominated for James Beard Award honors, Chefs James and Julie Petrakis operate The Ravenous Pig , a seasonal gastropub that ranked as a MICHELIN Bib Gourmand eatery. You can also try the Petrakises’ fare at another MICHELIN Recommended eatery, The Polite Pig at Disney Springs ®, offering shopping, dining and entertainment at Walt Disney World ® Resort.

Discover: Orlando’s Top Chefs

In addition to being a One-MICHELIN-Star eatery, Soseki Modern Omakase has earned a MICHELIN Sommelier Award for Beverage Director Benjamin Coutts. Also rated as a MICHELIN Bib Gourmand is Swine & Sons, while AVA MediterrAegean , Kai Asian Street Fare and Doshi are MICHELIN Recommended.

Discover: Winter Park Dining

Other local favorites in the Park Avenue area include steaks and seafood at BoVine Steakhouse and blu on the avenue , Umi Sushi , French cuisine at Chez Vincent , New American at 310 Park South , Bosphorous Turkish Cuisine , Italian at VINIA Wine & Kitchen , and farm-to-table goodness at Boca Winter Park and The Alfond Inn’s fresh-focused Hamilton’s Kitchen .

Just a short drive from the city’s core, enjoy Spanish cuisine at Bulla Gastrobar , seafood at Reel Fish Coastal Kitchen , an authentic taste of Italy at Rocco’s Italian Grille & Bar or Bar Italia, world-class desserts at The Glass Knife, Southern cooking at The Coop and 4 Rivers Smokehouse , and choice cuts at Christner’s Prime Steak & Lobster , Fleming’s Prime Steakhouse & Wine Bar , Ruth’s Chris Steak House , and The Tap Room at Dubsdread , among many other options.

Shopaholics will adore Winter Park’s exquisite array of retailers , many of which are on and near Park Avenue. For instance, homegrown boutiques like Tuni Trendy + Chic and John Craig Clothier will have adults looking their best, while Tugboat & The Bird and Bebe’s and Liz’s will do the same for children.

Discover: Winter Park Shopping

You’ll also find outposts from nationally recognized retailers Lilly Pulitzer and J. McLaughlin. Both are part of the lineup at Shops on Park, which offers 20,000 square feet of shopping and dining on Park Avenue.

And yes, you can buy more than clothes in Winter Park. Specialty merchants include The Ancient Olive Gourmet , Bang & Olufsen Winter Park , The Farmacy , Peterbrooke Chocolatier, Williams-Sonoma and Writer’s Block Bookstore, to name a few. On Saturdays, the city offers even more unique shopping at the Winter Park Farmers’ Market.

For still more retail opportunities, make the short drive from Park Avenue to Winter Park Village. The outdoor shopping center has a host of stores and restaurants, plus one of the area's best movie theaters.

Feed your inner artist at Winter Park’s galleries and museums, including Rollins Museum of Art , which offers free admission. This facility’s collection — more than 5,700 pieces from the ancient to modern periods — is so expansive that a portion is displayed as the Alfond Collection of Contemporary Art at The Alfond Inn.

Discover: Orlando Arts, Culture & History

Nearby, you can peruse the world's most comprehensive collection of Louis Comfort Tiffany's creations at The Charles Hosmer Morse Museum of American Art . Similarly, the Albin Polasek Museum & Sculpture Gardens is devoted to the work of its titular sculptor. Or, develop your own artistic talents with a course or two at the Crealdé School of Art.

The latter is adjacent to the Hannibal Square Heritage Center, where you can learn about its namesake Hannibal Square district’s origins as an important African American community. Officially founded in 1881, Hannibal Square was the site of one of the country’s earliest Civil Rights marches in 1887 and is now one of Winter Park’s most expensive sections.

Discover: Things to Do at the Hannibal Square Heritage Center

Winter Park also hosts two annual, outdoor art shows. In March, the Winter Park Sidewalk Art Festival attracts more than 200 artists to Park Avenue and adjacent Central Park, while October's Winter Park Autumn Art Festival exclusively features Florida artists. Admission to both is free.

Discover: Orlando Events

If live theater is more your thing, book a date at The Winter Park Playhouse . Just blocks from Park Avenue, the 123-seat venue is one of the few professional musical theaters in Florida. And at Casa Feliz, you can enjoy a tour of the historic home on Tuesdays and Thursdays.

The Winter Park Chain of Lakes — 12 in all — includes 2,781 acres of pristine waterways, and the Winter Park Scenic Boat Tour is a fun, relaxing way to experience it. You’ll see all manner of wildlife, not to mention multimillion-dollar mansions, during the narrated, one-hour excursions, which also go past Rollins College and Kraft Azalea Gardens.

Discover: Orlando Ecotourism

The latter is one of 11 amenity-laden public parks maintained by the city, with other standouts including Mead Botanical Garden, Lake Baldwin Park, Phelps Park and Ward Park. If seeing so much green has you aching for a tee time, don't worry: You can get your golf on at the Winter Park Golf Course, a 9-hole, public course that's on the U.S. National Registry of Historic Places.

Naturally — no pun intended — Winter Park’s lakes provide plenty of aquatic adventures beyond the Scenic Boat Tour. Look into paddleboard and kayaking rentals while you’re in the area and explore it all at your own pace.

With so much to see and do, it’s no wonder why locals adore Winter Park — and why you should make it part of your travel plans the next time you’re in Orlando.

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Things to Do in Winter Park, FL - Winter Park Attractions

Things to do in winter park, explore popular experiences, tours in and around winter park.

Winter Park Chain of Lakes Day Time Clear Kayak Paddle

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• Charles Hosmer Morse Museum of American Art
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• Scenic Boat Tour

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This Charming Florida City Near Orlando Is the Perfect Break From the Theme Park Crowds

Even though Winter Park is near Orlando's theme parks, it feels leaps and bounds away.

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Cobblestone streets dotted with Michelin-recognized restaurants and locally owned shops, lakes with boat tours, and grassy areas for kids to play tag and fly kites: This is Winter Park, Florida. A hop, skip, and a jump from Orlando’s theme park scene, this town chartered in 1887 thrills in other ways. Its original purpose still holds true: New Englanders founded it as an escape from cold weather. But since that time, the 10-square-mile city has become a year-round destination. Orlando residents love the place, but they can’t keep it a secret anymore. No matter why you’re in the Orlando area, a few days in Winter Park would provide a welcome respite before heading home. In fact, the town has so much going for it, we’d argue that it merits a trip on its own.

Downtown, Park Avenue — where stand-out restaurants and local boutiques dot the brick streets — is the place to be. Just off Park Avenue, Rollins, a small liberal arts college founded 135 years ago, contributes to the town’s robust array of cultural activities. A short walk from downtown lies the waterfront, where six lakes are connected by navigable canals. Ready to plan a trip to this charming city? Here's what you need to know.

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Best Things to Do in Winter Park

If you like culture, nature, and shopping, Winter Park will be a new favorite. With a rose garden and beautiful fountains, 11-acre Central Park on Park Avenue hosts many of the city’s festivals and events, including holiday festivities and the Olde Fashioned Fourth of July Celebration. It’s also the perfect place to take the kids to burn off steam in between visiting stores or before going back to the hotel.

More spectacular than you’d imagine, the Morse Museum , located on Park Avenue, features a large collection of Tiffany works as well as other American art. The stunning chapel, which was crafted for the Chicago World’s Fair, is a must-see.

When you’re ready for a break from walking, take the hour-long Scenic Boat Tour around Winter Park’s many lakes, where you'll spot beautiful homes while you learn more about the city's history. Kids of all ages are welcome (even encouraged) to join the fun on the 18-passenger pontoon boats. Water sports, like paddleboarding and kayaking, are also popular around the lakes.

On Saturday mornings, dozens of vendors sell their produce, bread, sweets, and more at the Saturday Farmers’ Market . It's the perfect place to grab ingredients before heading to a park for a picnic lunch.

Save room in your suitcase to treat yourself to an item from one of the many one-of-a-kind shops in Winter Park. You’ll swoon over the stationary and artsy decorative items at Rifle Paper Co’s own store (the brand is based in Winter Park).

Local teens and college students shop at Avalon Exchange , a thrift shop that’s clean, organized, and budget friendly with a mix of retro and popular brands. Stop by Loving Thyself Rocks if for nothing else than to get a selfie sitting on the winged crystal chair at the entrance. Writer’s Block bookstore offers a well-curated selection for kids and adults (plus a fantastic name).

Winter Park Hotels

While visitors only have a handful of lodging options in Winter Park, the surrounding area opens up a multitude of possibilities.

Established more than 130 years ago, The Alfond Inn at Rollins is getting better with age. Sprinkled with incredible paintings from the Rollins Art Museum, the recently renovated lobby is a design masterpiece and fosters family togetherness thanks to a variety of seating arrangements and a corner chess set. An expansion, which will add a new spa and a wing to the inn’s current 112 guest rooms, is expected to wrap up by the end of the year. The location, just a few blocks from Park Avenue, is stellar.

With 28 guest rooms — some with original brick walls — the Park Plaza Hotel is the only place to stay on the city’s famed Park Avenue. There are balcony rooms and suites for people-watching.

About eight miles from Winter Park, Sonder Wellborn is located in the oldest house in the Orlando area. Suites are well priced and spacious, plus the property includes a Victorian garden.

If you’re combining a business trip to the Orlando Convention Center with a visit to Winter Park, the AC Hotel Marriott Downtown Orlando is a great choice. The eight-floor, 180-room property boasts a SkyBar Rooftop Terrace with incredible city views. It’s just eight miles from Winter Park.

Visit Florida

Best Time to Visit Winter Park

While you’ll have fun no matter when you go to Winter Park, shifts in weather and special programming favor certain months.

Despite its name, the most comfortable season to visit Winter Park is spring — and the earlier, the better. March feels glorious with average high temperatures reaching about 76 degrees Fahrenheit and the lowest humidity of the year. It’s no coincidence that the organizers of the city’s annual Sidewalk Art Festival, which attracts 350,000 visitors, schedule it for March. It’s a little cooler in February and warmer in April, but still pleasant. You won’t find many April showers in Winter Park — April is the second-least rainy month.

The holidays usher in another magical time to explore Winter Park, especially if you’re bringing children. Two big events take place during the first weekend of December. On Friday, “Winter on the Avenue” transforms Central Park into a holiday wonderland, complete with snow slides, s’mores, and strolling carolers. Everyone gathers around for the lighting of the Christmas tree and menorah. The next day, music fills the streets for the Ye Olde Hometown Christmas Parade. A tradition for more than 70 years, the parade’s headliners include marching bands, fire trucks, and Santa Claus. Winter Park’s weather by far outshines the North Pole, with average December highs in the mid-70s.

Families who have to plan their vacations around school calendars and practice schedules may not be able to avoid a summertime visit. Although it’s typically hot, humid, and rainy, scheduling outdoor activities for the morning or evening will make it less likely that Florida’s temperamental summer weather will interfere with your fun.

Where to Eat and Drink

Orlando locals flock to Winter Park for memorable meals — whether they’re bringing the entire family or looking for a romantic table for two. Winter Park serves up a variety of cuisines and vibes at its top food establishments.

At Briarpatch , the most iconic eatery on Park Avenue, locals line up for mimosas and delicious brunch offerings (think: brown butter Belgian waffles and raspberry lemon cream pancakes.) The housemade cakes — carrot, chocolate layer, and red velvet — are as Instagrammable as they are tasty. You can dine al fresco on the outdoor tables overlooking Central Park or opt for the indoor seating; the dining room oozes Southern charm.

Fresh from earning a Michelin star, Soseki , a 10-seat Japanese restaurant, specializes in a divine multi-course dining experience based on the best ingredients that its farmers, fishermen, and cheese purveyors offer.

With husband-and-wife, James Beard-nominated chefs in the kitchen, The Ravenous Pig hits the spot with a variety of apps, hand-helds, innovative cocktails, and other gastropub fare.

If the kids want pizza, Prato is the place for your family. Request a table on the patio (isn’t there something about eating outside that makes kids less wiggly?) and order them a margarita pie to share while you pick one of the other modern Italian dishes made with locally sourced ingredients.

Getting There

Winter Park is easily accessible by car and airplane. You probably won’t use your car much once you’re in town.

If you’re coming from one of Orlando’s theme parks, the ride will be relatively short. Winter Park is about 30 miles north of Disney’s Magic Kingdom and 15 miles north of Universal Florida on I-4. Tampa, Jacksonville, and Melbourne, Florida are all within two hours or so.

The closest airport is Orlando International Airport, which is about a 30-minute drive to Winter Park. Later in 2023, the Brightline Train’ s airport station will connect the city with Miami, Boca Raton, West Palm Beach, and Fort Lauderdale. If you can fly into the smaller (and far less crowded) Orlando Sanford International Airport, you’d still only have about a half-hour drive.

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Top Things to Do in Winter Park, FL

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Winter Park Chain of Lakes Day Time Clear Kayak Paddle

ICONic City Tour Of Orlando

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Walking tours.

Top Attractions in Winter Park

Other Top Attractions around Winter Park

Cruises, Sailing & Water Tours

Water sports.

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Luxury & Special Occasions

What travellers are saying.

• Charles Hosmer Morse Museum of American Art
• Central Park
• Albin Polasek Museum & Sculpture Gardens
• Kraft Azalea Gardens
• Rollins College
• Lake Virginia
• Winter Park
• Mead Botanical Garden
• Get Up And Go Kayaking - Winter Park
• Scenic Boat Tour