Homeowner viewpoints Orlando travel tips

A day trip to Winter Park by Ruth Moriarty

White Rose Property Management homeowner Ruth Moriarty shares her travel tips for a great day out in Winter Park, Florida.

We’re really delighted that our homeowner Ruth Moriarty has kindly shared some more of her Florida travel tips with us. 

Her blogs about Bok Tower Gardens and the Lake Eola farmers’ market were really well received. And it’s so great to hear about day trips beyond the Orlando theme parks.

This time, Ruth tells us all about the wonderful shops, side roads and sightseeing to enjoy in Winter Park.

Winter Park, Florida by Ruth Moriarty

Winter Park is an old city just outside Orlando with lots of history. Its first inhabitants were regional American Indians (Seminole).

Later, the Europeans rocked up in the late 1850s. Today, Winter Park very much retains the feel of a small European town.

The railroad has been here since the 1880s and is still being used. The track runs straight through the central park and a very cute station

There are lots of small, winding brick streets to explore, plenty of trees to shade you from the hot Florida sun and lots to do covering a wide variety of tastes, prices and interests. 

The Saturday Farmers’ Market

When I lived in Florida, I used to do the almost 80-mile round trip from home to Winter Park once a month, mainly to visit the market! It’s bright and vibrant and there is so much to choose from.

There are stalls selling food, baked goods, plants, jewellery, local produce. It’s a very popular place for people to gather.

The unofficial parade of dogs and their humans is a delight for anyone who has a soft spot for our four-legged friends. Be prepared for dogs in buggies, dogs in tee-shirts, dogs in boots and being as or more groomed than their human counterparts.

Currently the Market is located in the West Meadow (150 North New York Ave.) from 8am-1pm.


The town and surrounding area is well worth a visit and there is lots to see. 

At the centre of Downtown Winter Park is Park Avenue, a tree-lined, cobblestoned street full of eateries and some great shops. It is such a pretty place to wander around and there are lots of small boutiques, including one of my favourites, Peterbrooke Chocolatier.

Another great place to stop where you can try before you buy is The Wine Room. No need to say more.

Little cafés and restaurants are hidden away in small arcades, which are well worth exploring. Many eateries have terraces, where you can watch the world go by!

There is something for every taste and price. Winter Park is also one of the dog-friendliest places I have ever been to.  Dogs are welcome in many places and there are always doggy water bowls and people ready to make a fuss of your precious pooch.

If you need more retail therapy, Shops on Park, at the centre of Park Avenue, is an elegant, indoor centre with some big brand shops. 

Kraft Azalea Park

This is a stunning public park bordering on the lakes. It is a gorgeous place to go and take a picnic and sit in the shade on a hot day.

Here you can while away the hours people watching, admiring the boats and deciding which of the mansions that surround the lakefronts you could live in!

It’s one of more than 70 parks in Winter Park, each holding various events, festivals and celebrations throughout the year – so you have plenty of choice.

Scenic Boat Tour – East Morse Boulevard

This is one of my absolute favourite things here.

I suggest you go there first to secure your ticket as they get very busy even out of season.

It’s a fully guided tour, in turn relaxing and exhilarating. The one-hour cruise takes you through the some of the lakes and canals of historic Winter Park.

The boats go from a slow crawl through the tiny canals to whizzing across the open lakes to get from one side to the other.

The canals linking the chain of lakes were man-made by the Seminole hundreds of years ago and it’s easy to imagine them coming through these narrow waterways in their little dug outs – very atmospheric.

At the other extreme, you get to see the many million-dollar mansions (some of them worth $20,000,000). Your guide will have all sorts of local knowledge and information to share.

It costs $14 adult, $7 child (go with cash as they don’t accept cards) and runs from 10 a.m. to 4 p.m. every hour on the hour.  The boats are fine for anyone who is a little shaky on their feet, but I didn’t see anywhere for wheelchairs.

Croissant Gourmet Bakery

We chose not to go back to the main street as we found a little French café just up the road from the Boat Cruise after our hour on the water. 

We had a delicious lunch at Croissant Gourmet Bakery on East Morse Blvd. We did eat some delicious, healthy salads and savoury croissants but had to save ourselves for the beautifully crafted desserts (each cake was fairly divided into three!)

Why you should go

Go to shop, go to explore, go to people watch, go to watch an open-air movie in the Park or go for some culture too (I love the town’s museum – also worth a visit!).

You can find further information about Winter Park on the Visit Florida website.

About Ruth’s home

If you’d like to book your stay to enjoy Winter Park or other Central Florida attractions, please check out our homes here.

Ruth’s home is the very wonderful Sapphire Sky Villa at Orange Tree.  See more – and book – here.

Would you like to share your tips for great days out in Florida?

We’d love to share contributions from our guests and homeowners about great days out in Florida.  If you have tips or ideas you’d like to share on our blog, please reach out to our team. 

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