10 Things to do in Charming Winter Park, Florida

While Orlando receives much of the fanfare, with its numerous theme parks and attractions, there is another small, charming destination nestled along the city’s edge that is well worth a visit. Located just 15 minutes from downtown Orlando and roughly 30 minutes from Walt Disney World Resort, Winter Park, Florida, is a quaint town with a warm ambience. It’s the perfect place to relax, enjoy some shopping, visit green spaces and experience the Old Florida charm.

Let’s take a look at the top ten things to do when you visit Winter Park, Fl.

#1: Shop on Park Avenue

Park Avenue is the central hub of Winter Park. It’s a charming, tree-lined street that spans several blocks and is host to numerous shops, restaurants, cafes and galleries. This street is the perfect place to kick off your visit to Winter Park. Stroll the brick-paved sidewalks and admire the stunning architecture found along this street. Stop to soak in the sight of the Park Plaza Hotel, which features an iconic old European style, or take some time to admire the modern Winter Park Public Library with its sweeping archways.

While there is plenty to take in, the main attraction of Park Avenue is the street’s abundance of high-end shops and boutiques. Shop for jewelry, clothing and home decor. Pop into local art galleries and find something unique to bring home. At night, the avenue twinkles as the elegant street lamps kick on. It’s a picture-worthy moment.

#2: Satiate Your Appetite

With all your strolling down Park Avenue, you’re sure to work up an appetite. Luckily, around nearly every corner is an opportunity to satiate your hunger. Casual cafes with outdoor patios offer fresh and nutritious bites to eat. Upscale dining provides the perfect evening date night. Upscale dining provides the perfect evening date night. Check out AAA Three Diamond Prato if you are in the mood for Italian-fare, or the Three Diamond Umi for sushi lovers.

In between meals, be sure to also take the time to visit one of the area’s numerous chocolatiers and candy shops. Visit Kilwins for classic style ice cream, fudge and others that have been hand-crafted since 1947. Or head to Peterbrooke for fine chocolate made with "the very best ingredients and old-world techniques." Whatever your sweet tooth may be craving, you're sure to find in Winter Park.

#3: Meander through the Mead Botanical Gardens

One of the best parts about visiting Winter Park is the chance to embrace the pleasant climate. Year-round, greenery grows in abundance due to the humid, warm weather. To enjoy the best the area has to offer, plan a visit to the Mead Botanical Gardens.

The entrance is free, and it’s the perfect place to take a leisurely afternoon stroll. Traverse the nature trails and relax among the stunning display of both native and landscaped plants. Then take a quiet walk through the butterfly gardens. Not only will you be greeted by stunning butterflies, but you’ll have the chance to enjoy the colorful array of plants that attract pollinators to the area. It’s a fantastic way to learn more about the critical role that bees, butterflies, wasps and other insects play in our food supply chain.

#4: Attend a Show

Winter Park is home to the only professional musical theater in Central Florida. The Winter Park Playhouse puts on incredible productions, including musicals, revues and cabarets. The Mainstage hosts Broadway and Off-Broadway productions year-round.

The small, intimate setting of this theater makes each show engaging. It’s an up-close and personal experience you won’t soon forget.

#5: Visit the Farmers Market

Discover the array of local produce, plants and baked goods available at the Winter Park Farmers Market. Every Saturday morning, from 7 a.m. to 1 p.m., you’ll find vendors proudly displaying their goods. It’s a wonderful opportunity to engage with the local community and support small farmers and artisans. Sample delectable bread. Sip on a cup of coffee, and fill a bag with fresh fruits and veggies.

#6: See the Area by Boat

All around Winter Park are a chain of lakes connected together by small canals. These lakes provide a stunning backdrop to the city and provide the perfect chance to spend the day on the water.

While many boat tours involve piling onto large vessels with dozens of other people, the Winter Park experience is a little bit different. Here, you’ll board a small pontoon with a handful of others. There’s no awning, no second deck and no crowds.

Why are the tour boats in Winter Park so small? The answer lies in the canals. Aboard a small pontoon, you’ll have a unique opportunity to traverse from lake to lake via the area’s narrow canals. Lush greenery, large trees overhanging the waters and stunningly landscaped lake properties all contribute to the magnificent experience of a scenic boat tour in Winter Park.

#7: Immerse Yourself in the Arts

Art plays a central role in the Winter Park community, and this passion is showcased in the area’s numerous museums. Plan a visit to the Charles Hosmer Morse Museum of American Art, where you’ll stand in awe of the incredible collection of works by Louis Comfort Tiffany. The Morse Museum houses the world’s largest, most comprehensive collection of Tiffany works. Browse the famous leaded glass lamps and windows, stunning designer jewelry, pottery and more.

Another fantastic option for art enthusiasts is the Albin Polasek Museum and Sculpture Garden. Set in the historic home of Czech sculptor Albin Polasek, you’ll have the chance to tour his home, explore galleries of art and stroll through the sculpture gardens.

#8: Take a Collegiate Stroll

Located in Winter Park is the campus of Rollins College. Named the most beautiful college campus in the nation by the Princeton Review, the beautiful grounds of Rollins College invite you to take a leisurely stroll.

Stunning historic buildings crafted in the Mediterranean revival style are surrounded by oversized oak trees. The entire campus overlooks a lake, adding to the lustrous appeal of the property. Walk the half-mile lakeshore path, or head to Dinky Dock Park where you can launch a kayak directly into the waters.

During your visit, be sure to stop into the free Rollins College Museum of Art as well. Though there is no price for admission, this museum repeatedly earns high marks for its quality exhibits and displays.

#9: Have a Picnic in a Scenic Park

With numerous lakes and lush greenery, parks abound in Winter Park. Pack a picnic and spend a day enjoying the sunny weather of central Florida.

Perhaps the crown jewel of all the city parks, Central Park is the perfect location for a lunch al fresco. Located off of Park Avenue downtown, this 11-acre park features sprawling oaks, colorful flowers and beautiful fountains. Be sure to stop and smell the roses at the rose garden in the southern corner of the park.

#10: Play a Round of Golf

With a robust retirement community, Florida is a state well-known for its numerous options to tee off. In Winter Park, golfing enthusiasts will enjoy a challenging game at the Winter Park Golf Course. The second oldest golf club in Central Florida, this course first opened in 1914. Ever since, golfers have enjoyed the area's beautiful landscape while trying their hand at the challenging course. While the course only has nine holes, narrow, tree-lined fairways and postage-stamp greens will still put one’s golf skills to the test. The course is open to the public, but be sure to book a tee time ahead.

Join the over a million AAA members and start planning your trip to Winter Park today. Dream up the perfect trip with our Trip Canvas research tool, and use your membership to get the best discounts on hotels, rental cars, and entertainment tickets.