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Winter Park is a very charming little town that is only 30 minutes away from Orlando. Winter Park preserves all the charm of a small town in central Florida, with tree-lined streets and flower beds everywhere. It is an ideal tour for those who want to escape the hustle and bustle of shopping-parks in Orlando. What makes the tour even more special is that the place is little known by tourists, which allows you to better feel the small town climate of the interior of Florida.

Winter Park Florida - a charming little town near Orlando

Until 1880 the community was called Lakeview, due to the chain of lakes that surround it. With the arrival of the South Florida Railroad, it was renamed Winter Park. In fact, the region was much sought after by wealthy families in the northern United States, who fled the harsh winters of their cities to the milder temperatures of central Florida. To this day, the city is known as the place where “Old Money” (old money) is located in the Orlando area, precisely because it is an old city where wealthy northern families came.

Walk the streets of Winter Park and enjoy shopping, restaurants, cafes, pastry shops and the city’s pleasant climate – Photo:

All the architecture and planning of the avenues and streets were influenced, at the time, by the concepts of the wealthy families of the North of the USA. Today it is still possible to see several mansions in the region of those times, many of them built on the banks of the lakes. Another feature brought from the north are the wide streets, decorated with flower boxes. The city’s architecture and charm are still considerably preserved, even though “Greater Orlando” is pushing its borders. Added to this charm and romantic atmosphere are the historic houses, restaurants, shops, pastry shops and cafes in the city.

Winter Park Orlando Attractions

Winter Park is an excellent tour option and brings attractions and activities for the whole family. Below are some tips on what to do in Winter Park:

Park Avenue Walk

The best thing about Winter Park is walking along Park Avenue and enjoying the shops, cafes, pastry shops and other super charming little establishments on the avenue. Have lunch or dinner in one of the excellent restaurants on the avenue.

Central Park

Here it is also worth a stroll to enjoy the super wooded and peaceful park, with a cozy atmosphere that brings a lot of peace! Central Park in Winter Park features several fountains and gardens. Worth a walk or even a picnic. The place hosts events and festivals at certain times of the year. A traditional event in the region is the Winter Park Sidewal Art Festival, one of the most traditional and important art events in the United States, which receives almost 400 thousand visitors a year.

Scenic Boat Tour – Lake Tour

Scenic Boat Winter Park
Boat trip by the company Scenic Boat Tour. Sail the region’s rivers and lakes and enjoy the lush nature of central Florida

Boat trip by the company Scenic Boat Tour. Sail the region’s rivers and lakes and enjoy the lush nature of central Florida

Winter Park is surrounded by a chain of lakes with lush nature. A traditional tour in the city and very beautiful, besides being fun, is the Scenic Boat Tour. It is a boat trip through rivers and lakes (the boat does not rock) where you can appreciate the natural and wild beauty of the region and also enjoy the wonderful lakefront mansions. The tour lasts about 1 (one) hour.

Farmer’s Market

Farmer's Market Winter Park

As in Winter Garden, a city in Winter Park also offers a market for farmers. It is a fair of local producers in the open sky that runs until the weekends. Take the opportunity to enjoy the local culture and gastronomy, buy souvenirs and enjoy the fair which is very interesting. They can be used by farmers and local residents. Get there early and have breakfast there! Some of the stalls that the Mercado do Agricultor offers are: flower stalls, artisan breads, local sweets, Argentine empanadas, local cheeses, jellies, juices, fruits, ready-to-eat salads and other sweets. For those staying in vacation homes in Orlando, it is legal to buy ready-made things at the fairs to eat at home.

Winter Park Orlando Train Station

Be sure to stop by Winter Park’s charming train station. Very cute with local architecture! It is worth taking a picture and, if you have time, you can take a train to New York if you want. The interesting thing about these small towns and the collaborative atmosphere they offer is that there is an atmosphere where everyone cooperates and helps each other. At the train station there is a wooden house with several books inside for those who want to pick one up, exchange it, read it and return it to the next station… it’s free!


The city also offers a variety of museums, several of which are related to art. One of the most famous and traditional is the Charles Hosme Morse Museum of American Art. It is an American art museum that features a huge Tiffany glass collection. Other museums in the city are: Albin Polasek Museum & Sculpture Gardens, Cornell Fine Arts Museum, Hannibal Square Heritage Center. The latter tells the story of Winter Park.

The Wine Room

The Wine Room Winter Park

The Wine Room is a liquor store that was famous in the region for its different and intelligent method of tasting wines. Upon entering the store, the customer purchases a prepaid card and a glass of wine. The card can be loaded with the value that the customer wants, respecting a minimum not too expensive. With the card loaded and the glass of wine in hand, the fun begins. The innovation is in the middle of acquiring the doses of the wines to be tasted: through machines! The machines are imported from Italy and have the latest technology to preserve the main properties of the wines. There are more than 150 wine labels from all over the world. Doses can be 30 ml, 70 ml or 130 ml. If the customer likes the wine, the bottle is there to buy. It’s a different and smart way to taste wine. Learn more about The Wine Room.

Buy Houses in Winter Park

The charm and tranquility of Winter Park put fate in contention for Orlando’s major neighborhoods and regions to buy a home in Florida.

Many celebrities seek the region to buy houses by the lake and enjoy the quality of life in Winter Park.

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