Find out how to have the perfect day in walkable Winter Park.

Updated Nov. 13, 2025

Part of what makes Orlando so authentic are the striking neighborhoods and communities scattered across Central Florida. Renowned architecture, tree-lined streets and community art are only a handful of features that make neighborhoods like Winter Park so much fun to explore.

Discover: Things to Do in Winter Park

So, leave your car keys behind and slip on some comfortable shoes, because today we will walk you through the easily accessible streets of Winter Park — no gas needed.

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Start Your Breezy Morning With Breakfast and Fun

The Alfond Inn / Hamilton’s Kitchen

They say breakfast is the most important meal, so why not begin your day at Hamilton’s Kitchen, The Alfond Inn’s premier restaurant? Chow down on a nice Farmhouse Platter or grab a matcha from their comfy cafe to get the day going.

Discover: Orlando Brunch Spots

But before you head out, take a minute to stroll through the massive luxury hotel and check out The Alfond Collection of Contemporary Art, which is displayed around the property courtesy of Rollins Museum of Art. Speaking of Rollins…

Rollins College & Rollins Museum of Art

Just an 8-minute walk from The Alfond Inn, you’ll find yourself strolling through the Rollins College campus, a scenic private university that rests on the edge of Lake Virginia. Walk towards the center of the school and you’ll reach the Rollins Museum of Art, a premier teaching museum with rotating exhibits, exciting programming and no cost for admission.

Discover: Orlando Museums & Galleries

If you check out the back lawn of the museum, you’ll be greeted by outdoor sculptures and a breezy view of the lake. Take a moment in the lakeside gazebo to absorb the scenery, because you’re about to get an even closer look at Orlando’s luscious landscape.

Winter Park Scenic Boat Tour

Now you get to put on your sea legs and relax on the Winter Park Scenic Boat Tour, an hour-long leisure ride through the winding canals of Winter Park that’s just a 10-minute walk from Rollins. Once you’ve grabbed your $20 ticket off the small port in Lake Osceola, jump onboard and enjoy a guided trip through a section of the Winter Park Chain of Lakes.

Discover: Experiences on the Water

The tour guides are long-time Winter Park residents who love to share their knowledge about the local flora and fauna, celebrity residents from past and present, and historical tidbits about how the community came to be.

Find Retail Therapy on Park Avenue

Now back on land, the day has just begun because you are just a 9-minute walk from pristine Park Avenue, Winter Park’s charming main street that is overflowing with boutique shops, art galleries and restaurants for you to discover.

Gasp

If pink defines your personality, then our first stop is to shop for all things pink and cute at Gasp. This adorable boutique gift shop is ideal for home decor, traveling trinkets, or simple gifts that won’t weigh you down as you walk through the neighborhood.

Discover: Unique Orlando Gifts

This is also the perfect moment to catch a few snapshots for social media! Take a selfie with their giant kitschy mirror or show off what you got in front of their viral pink “SHOP” stop sign that decorates the entrance. It’s midday now; if we’re feeling peckish, then it’s time for a snack.

The Ancient Olive Gourmet

Right next door to Gasp, if you look closely, you’ll notice a secret treasure tucked away within the Hidden Garden called The Ancient Olive Gourmet. This one-of-a-kind shop specializes in premium extra virgin olive oils and aged balsamic vinegars that come in a variety of diverse flavors.

Discover: 24 Hours for Foodies

Wander through their tasting room and enjoy a unique culinary experience as you try out their various flavors, some of which are made fresh in-store. You can also shop for breads, crackers, soups, snacks and other great pairings to go with your favorite oil.

Now that you have got gifts for loved ones, it’s your turn to get a little something for yourself at our next stop: a pleasant bookstore named Writer’s Block.

Writer’s Block Bookstore

Writer’s Block is a lovable bookstore that’s right around the corner from Ancient Olive and the only independent bookstore in Winter Park. This is one of those snug, home-like bookstores with books and bags that spill out of their shelves, inviting you to settle in and get lost between the pages.

Discover: Orlando Bookstores

If you’re walking with your little ones, you can take them upstairs to their brand-new children’s corridor, where they can pick out a fun read or frolic and play with educational toys. Once you’re done, we’re ready for our next big meal of the day.

End the Night Right With Dinner and Dessert

Luca Turci

After a long day of exploring and shopping, it’s time to wind down with dinner at Luca Turci, a 2-minute walk from Writer’s Block. This chic Italian eatery stuns in the nighttime as you enter through a warmly lit archway and into a cozy, refined dining room inspired by the European countryside.

Discover: Orlando Food & Dining

Savor your dinner the Italian way, complete with carpaccio, bruschetta, and homemade pasta that is made fresh tableside. Nothing compares to cutting into a steaming bowl of toasty lasagna that’s filled with fresh mozzarella, homemade Bolognese and bechamel sauce … so good!

Feel free to peruse their delicious desserts, but we have one last stop in Winter Park for you to end the day on a sweet note.

Gelato-Go Orlando

Our final stop for the day takes us to a colorful dessert shop called Gelato-Go Orlando, a 4-minute walk away from Luca Turci. Known for their authentic Italian gelato, this spot has all the offerings that will satisfy your sweet tooth.

Discover: Orlando Desserts

If you haven’t had the chance to try the latest craze in the dessert world, you need to try their Pistachio Explosion! It’s their own iteration of the famous Persian-style chocolate gelato that mixes creamy pistachio and crunchy kataifi into a delicious treat.

Discover: Where to Get Pistachio Chocolate

Whether you choose to walk or cruise through Winter Park, it makes no difference to the pleasure you’ll have when you experience the wealth of leisure and relaxation that awaits in this charming city.

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