Winter Park is the Original Florida Vacation Destination

Visit Winter Park for A Break from Tourist Sensory Overload

Just a few miles north of Orlando, Winter Park is a beautiful respite from the sensory overload. Get away from the theme parks, enclosed malls and fast food joints. When you need a break and want to appreciate Florida’s natural beauty, head up to Winter Park for a day.

Thank you for listening to The Orlando Local Show. In this episode, we’re going to share one of the hot spots near Orlando were locals like to relax with some great food, art and shopping.

Winter Park is a city of its own that started out as a vacation town for wealthy northerners who wanted to escape the cold and snow. It’s still the hub of old money in Central Florida.

The Local Getaway

Winter Park grew into a great place for relaxation, dining and shopping. We cover some of our favorite parts of the city in the podcast, and you can find links below to get an idea of what it has to offer.

Hillstone is one of my favorite restaurants. It’s the only place I know inland where seaplanes can (and do) fly in for lunch.

Park Avenue is like an outdoor shopping mall, filled with a combination stores and restaurants, most of which are independent. You can take time to relax in Central Park and catch the occasional concert.

We’re just scratching the surface, though. There’s far more to Winter Park than we had time to cover. Give it a shot on your next visit. Take a break from the theme parks and other tourist attractions.

Related Links

Winter Park Village

Morse Museum of Art

Central Park

Albin Polasek Museum and Sculpture Gardens

Winter Park Sidewalk Art Festival

Hillstone Restaurant

The Coop

4 Rivers Smokehouse

Marlow’s Tavern


Welcome to the Orlando Local Show, episode number twenty-six.

William:   Hi, thank you very much for joining us on the Orlando Local Show. Today we’re going to be talking about Winter Park - Florida’s original vacation destination.

Hi, my name is William Beem.

Lee:         Hi, my name is Lee Beem.

William:   We just want to kind of go over some of the areas besides the theme parks, in case you’re looking for a day trip and you just want to get out and see what’s available around Central Florida.

Today we are going to be talking about Winter Park. The reason I said it’s Florida’s original vacation destination is because for central Florida it kind of was. I mean back in the 1880’s a couple of business magnates came down here – one of them because he had poor health – and he loved the way the area looked.  He decided, you know what? I’m going to build a city here and get all my rich, wealthy friends up north to come down here. That’s why they called it Winter Park. When it’s so miserable and snowing up there, they were going to take the train down and just kind of relax in the middle of Florida.

Lee:         It’s just a wonderful place to hang out and ‘be.’

William:   And honestly, it still is.  I mean if you look at the atmosphere when you’re going around Winter Park, particularly in the area around Park Avenue and just kind of where some of the shops and restaurants are, it’s just a very nice place. You get a lot of oak trees just giving you a canopy over the street.

Winter Park has got a lot of brick road, still.

Lee:         Yes.

William:   It’s just kind of a combination of eclectic and rustic, I think.

Lee:         Absolutely. It’s got so much character.

William:   And it’s a good way to kind of get away from not only the theme parks, but also kind of like a little bit of urban overload.  If you’re in some of the other parts of town. Or maybe suburban overload if you just ...

Lee:         It really is and it still has the energy, even though you feel like you’re taking a mental break from everything and you feel like you’ve got the space, it’s still got a lot of energy. It’s very lively.

William:   It’s got that small town feel, but yet it’s still a busy kind of place. So when you get down in Park Avenue it’s lively because it’s not so much crowded and cars that are jamming you up too much. I mean it can get a little bit – sometimes maybe on the weekends – but the sidewalks are busy.

Lee:         Yes.  And a lot of the restaurants and bars have seating outside and shaded patios, so that kind of adds to the feel of the atmosphere with the energy and the people and the mood. Things are happening.

William:   It’s a little town where you can kind of walk around a bit.

Lee:         It’s got a very distinct personality.

William:   So if you like going to the shopping mall, but you don’t necessarily want to be in there with all the noise that kind of gets caved in with it, walking down Park Avenue I think is really a good escape.

Lee:         Absolutely. I love it.

William:   We were driving down there looking at Christmas lights and they’ve got these little lights that kind of hang over the street that just kind of blink on and off. It was just a peaceful feeling little place.

Lee:         It’s pretty. It’s like stepping back into an era gone by.

William:   That’s not to say that it doesn’t have modern shops there. I mean you’ll find a couple of chains that are still in there, but you are also going to find a lot of independent shops when you go down Park Avenue.

Lee:         I think that’s also what’s nice. If you want something different, that’s a place to get it and it’s just the experience is not just a place; it’s actually an experience.

William:   It is and it’s also an art community. If you look at Winter Park we’ll talk about this later, but there are a number of museums there. They have the Winter Park Sidewalk Art Festival every year and that is one of the biggest and best in the nation.

We’ll get over to that, but I think one of the next things we wanted to talk about is just the fact that there are a lot of really great restaurants that come out of Winter Park.

Lee:         Yes and nice atmospheres there.  I love eating outside. I know the rest of my family don’t care for it, save for a couple of months of the year.

William:   A couple of months of the year, you know, when it’s not too hot and it’s not too cold and the breeze isn’t blowing your napkins all over the place.

Lee:        Yeah, but I’m very much an outdoors person.

William:   Yes you are!

We go to restaurants in Winter Park all the time. Some of them are going to be chain restaurants.  We were just at the Cheesecake Factory this past weekend.

Lee:         Yes.

William:   And that was nice; especially when you have some gift cards to use.

Lee:         That helped.

William:   You will also find that Winter Park is kind of like a good place for independent restaurants to kick up. Now one of the biggest barbecue places in Central Florida is called Four Rivers Smokehouse. It started off as a very small little restaurant right next to a church on Fairbanks Avenue and they quickly outgrew that. They had lines going out the door.

It got to be a safety hazard. The church across the street offered their parking lot to keep people safe until Four Rivers could finally move to a larger space and they’ve got a really nice, big restaurant down the road and they’ve expanded out in Central Florida.  But also another one of their restaurants was kind of a spin-off concept called The Coop, which is about fried chicken and southern cuisine.

Lee:         I like The Coop.

William:   When The Coop started off I wasn’t really that impressed with it when it first opened up because there were extremely long lines going out the door and I thought, you know what? It’s good food but it fried chicken wasn’t worth that kind of a wait.

Barbecue? Maybe yeah.  But fried chicken wasn’t.  And it’s changed quite a bit.

First off the wait isn’t as bad at The Coop and secondly, they’ve also got a chef that – I don’t want to say new chef because she’s been there for a while – but she’s kind of changed the menu too and it is a lot of southern food. They will have special occasions like during the week. They’ll do certain different types of things that are not typically on the menu.

Lee:         Yeah, there was a bit of a menu change-up, almost like a mini overhaul about a year ago maybe.

William:   About a year ago, I would say.

Lee:         I liked it enough. I probably liked it more than anybody else in the family when we went, but it was noticeable. I mean we walked in and I said, “This is different.”

The lines were moving quicker, the food looked better. And it’s not that I didn’t think the food looked good before, but you know what it’s like when it’s all kind of open display and you can watch people serving up. It can start to look a bit sloppy if you get there later in the day. And everything had just changed.

William:   Well they also started doing breakfast. I think until about two in the afternoon.

Lee:         Two in the afternoon. Yes.

William:   I think that was a good concept because as much as I like fried chicken, I also realize that not everybody wants fried chicken so if you are taking a family in there, there is going to be someone who really doesn’t want to eat meat off the bone or they just don’t want something fried.  And they have other dishes there, I think, that are looking pretty good.

Lee:         Yes.

William:   And they’ve got options for you. Again, that’s Winter Park. It was the place where people come around to eat. You can walk there from other places.

Another one of our favorite restaurants there is Dexters.

Lee:         Ahh, Dexters.  Lovely.

William:   And we’ve got a thing for Dexters and Winter Park for two reasons. One, we were married in a small little wedding chapel in Winter Park.

Lee:         Loved it!

William:  It was a beautiful, tiny little place. We didn’t want to have a large wedding, but it was just ...

Lee:         It was perfect for us.

William:   Perfect for us. And then we went out and we had our wedding photos taken right around Winter Park. Everything was in nice walking distance and then we had our dinner before we went off on our honeymoon off at Dexters.

Lee:         Yes we did. I just really enjoyed that meal.

William:   Dexters is ... I’m stumbling over how to explain this.

Lee:         The food is art.  I think it’s trending that way. It’s not on the extreme where you go somewhere and things kind of look like you don’t know how to disassemble them to eat. But the food is art. However it’s not to the extreme that you are not satisfied when you leave. We had a lovely meal and we ... I don’t recall if we had an appetizer that evening? I think we planned on dessert and we were actually more than satisfied. We weren’t able to manage dessert that evening.

So I think they do feed you properly. I think that’s the best way to describe it.

William:   I think you’re right when you say the food is art, because I had a few years where I worked at a Culinary Academy and I’m not a chef by any means. I was there supporting IT.  But I got to see how the French cooking style comes around and they definitely use that technique at Dexters. But the food is not like ‘fufu stuff’ that nobody knows what it is trying to eat it.  They take common items and they dress it up in such a way ... it’s not even dressing I would say – they prepare it in such a way that it looks beautiful, it tastes wonderful and yet you can still have comfort food there.

Lee:         I really enjoyed it. I mean I love my rare tuna steaks and I had some form of that. It was sliced up and prepared that evening. It was absolutely wonderful and it was prepared to perfection for me. I am very, very particular about tuna steak. Do not overcook it! I expect it to have a very thin outer crust that’s been seared and the inside must still be alive. I mean I will eat my raw tuna!

William:   Yes you will!  We really love Dexters and we have no problem recommending it.

Another one that’s one of my favorites is Hillstone and that’s right on 17-92, just off of Fairbanks. Maybe a block or so north of it.

Hillstone is not an inexpensive restaurant, but it’s probably what I would call the best kitchen in town.  And by that, I mean everything is prepared wonderfully. They will do a different soup every day. Mondays they do a red bean soup that I just absolutely adore. And I hardly ever get Mondays off where I can go over there and have it.

Saturday they do a wonderful firehouse chili with some nachos to go with it. They’ve got a black bean soup, I think on Thursday. But it’s not just about the soups.  I mean they will do everything from steaks and chops to fish.

Lee:         Wonderful salads as well.

William:   But in order to keep things fresh, I mean they’ve got a bakery that makes bread fresh for them every day. They have their own herb garden just right outside the restaurant so they go out there and they can pick their herbs fresh.

Lee:         Yes.

William:   So they are growing things and they’ve chosen their vendors who provide food for them very carefully. Even the ice cream! I asked them once, “Who makes this?”

They told me international-something or other. I don’t know who that is, but it tastes delicious.  Everything is fresh. It’s very well prepared. The staff is extremely well trained.

Lee:         They are. And they are also very well presented. You are not getting people in jeans and T shirts. These people are dressed.

William:   Yeah and it’s not to say that you can’t walk in there with jeans; certainly you can! But it is a bit more of an upscale kind of restaurant. I don’t know what else to call it, but upscale casual.

Lee:         It’s upscale and comfortable.

William:   Yes. And it’s one of my favorite places.  It’s a little on the higher priced side. It’s well worth it. I really enjoy that.

And of course we also talked about some of the chain restaurants that are around there.  One of the ones that we really enjoy is Chuy’s. They just recently opened up just right across the street from Hillstone.

Cheesecake Factory is one we went to a number of times; that’s in the Winter Park Village and so is another one called Brio. I just took you there for the first time a couple of weeks ago.

Lee:         I thoroughly enjoyed Brio. Usually with Italian food I am quite picky.  I don’t really care for pasta, I’m not one who does the garlic bread thing so it’s a little bit more difficult to satisfy me. That was absolutely wonderful.

They had enough variety on the menu, but it wasn’t an overwhelming menu and everything was prepared just so.

William:   It’s not the kind of place where they’re bringing out pizza and garlic knots or things like that. The bread that comes out is kind of a sourdough with also some flatbread and the presentation is almost like a fan in the background.

Lee:         It was lovely. I really enjoyed that flatbread. It was seeded and lightly seasoned.

William:   I know I had a grilled salmon there with roasted sweet potatoes and some peppers and it’s an unusual combination, but it had a wonderful flavour to it.

Lee:         It was lovely. It just worked together.

William:   And the salmon was prepared just perfectly. I don’t really care for salmon if it’s still raw in the middle. I know some places do it that way and I was bringing that up to the waiter and he said, “Don’t worry. It will be perfect.”  And he was right!

Lee:         He was!

William:   There are a number of other restaurants there. We won’t go through all of them. Some of the ones that you may want to look for are called The Ravenous Pig, The Winter Park Fish Company and Marlow’s Tavern.

And there are plenty of restaurants in the Winter Park area, all within a few blocks of each other, I’d say.

You’re looking probably 17-92 over towards Park Avenue and that will include The Coop and a number of restaurants there and of course going down Fairbanks Avenue you’ll see plenty of them there.

If you get off I-4 at Fairbanks Avenue you’ll drive past Four Rivers Smokehouse that we talked about; it would be on your right and then if you get to 17-92 you could either go straight or turn left and still run into a number of restaurants and head down towards Park Avenue.

It’s just easy to navigate, it’s easy to get around and it can be kind of busy at times. I know they put a Shake Shack restaurant in the shopping plaza right next to where Hillstone is and it drew such a crowd that none of the people who were trying to shop there could really find a place to park because everybody was going to Shake Shack.

It settled down a little bit now.

Some of the other things to do as I said, Winter Park is a bit of an art town so there are a number of shops with creative things and crafts, but there is also a number of museums there, one of which is the Morse Museum of Art which is primarily kind of like a stained glass museum.

If you’re into stained glass or you just want to look at something different, it’s a good place to visit. There’s another one that’s called Polasek Museum and Sculpture Garden so basically you’re walking around through gardens with plenty of sculptures there so you’ll see statues of kids picking oranges from a tree and a number of other things. So it’s something different, it’s interesting, but mostly it’s peaceful. It’s kind of a way to go and appreciate some art without really having to run around a busy gallery like the Art of Disney or something like that.

Central Park is right on Park Avenue. It’s basically a nice wide open area. There’s a Sun Rail station to drop you off right there and then you can walk wherever you want to go down on Park Avenue. They will have free concerts there from time to time, but it’s mostly just like a peaceful are to relax.

And finally I mentioned the Winter Park Sidewalk Art Festival. I’ll put a link to that in the show notes. It’s one of the largest ones in the nation and when it comes around then it’s not quite so peaceful in Winter Park anymore.

Lee:         Well, that’s OK. That’s an event and you expect it to be busy. Actually, if it’s not you kind of feel like maybe you wasted your time if it’s not that popular.

William:   It is extremely popular. People come from all over the country to exhibit there and if you like buying art it is a wonderful way to go in a nice outdoor environment and just look at the art. And then if you appreciate something, go ahead and buy it.

If you’re looking to decorate your house, that’s a good way to find some art for it.

OK we talked about shopping on Park Avenue.  Instead of going to a mall this is kind of like just walking down the sidewalk into a nice peaceful area.  You’re going to find little tiny book stores. There’s going to be a California Closet store there if you’re looking for home renovations.

This is a store I haven’t been to but I really want to go now because it says Filthy Rich of Winter Park.

Lee:         We need to check that out.

William:   I need to find out what is Filthy Rich of Winter Park. Living Morocco, Lucky Brand Jeans, Max & Marley and Shoooz. I love the spelling of this one.

Lee:         Oh, well there you have it!

William:   Someone’s definitely into their shoes.

Lee:         You go to the wine bar first and then that’s how you spell shoes.

William:   Oh there’s definitely wine there. And there are restaurants along the way so if you’re shopping and you get tired of carrying your bags don’t worry. You’ll see some tables, sit down and someone will bring you something to drink.

Lee:         Like wine.

William:   Definitely wine.

Alright so we talked about shopping on Park Avenue. There are a number of other little spots. There’s Winter Park Village and that’s the place where we enjoy. We go in there and there’s a Regal movie theatre, there’s Brio and Cheesecake Factory there and believe it or not we’ve done most of our shopping there at the Guitar Center.

Lee:         Yes!

William:   Podcast stuff has to come from somewhere. We were getting some of that at Guitar Center and also we were looking around because our daughter is playing piano and I used to shop there years ago for my guitars, which are sitting helplessly in the back here never being used!

Lee:         We’d better change that.

William:   I need to change that. I need to start playing my guitars a bit more again.

But overall if you’re looking for a day trip away from Disney World, away from Universal or Sea World or some of the tourist areas, I recommend Winter Park.

Getting there going straight up I-4 is pretty easy. I mean you are literally going to drive eastbound on I-4 until you come to Fairbanks. And if you miss it on Fairbanks, don’t worry. Take the next exit on Lee Road.  And those are the two exits that you’re looking for. You can take those and just turn right and it will take you right down into the heart of the area that we’re talking about.

And those are kind of like the boundaries: Fairbanks and Lee Road so everything in between there is the part that we are recommending. So you can see Park Avenue, you can go do some shopping, go check out a movie, go check out the museums. Just kind of have a nice, peaceful relaxing day.

Lee:         When I’ve been here in the past for a vacation there’s always at least one day, maybe a few more where the theme parks are just sensory overload and that will happen whether you have kids or you are a group of adults.  And I just have to get out, just for the day; not because I don’t like it, but because my brain needs some breathing space.  And this is just a perfect place to go if you want a break from it all because it changes the pace completely, without being dull and boring.

I mean you can have an active day, which is relatively, I would say stress free.

William:   So if you’re going to take a day away from the theme parks and head to Winter Park, how would you break up your day?

Do you sleep in and relax and enjoy for a little bit first and then head up there?

Lee:         I think that depends on you. Some people are early risers and they prefer not to stay out too late at night. Especially if you have got small children or if that’s just part of your routine. In that case I’d try and head out there and start off with a good breakfast while waiting for everything to open up and then spend the day around there.

Because you’re probably then want to get out shortly after sunset or at least after dinner time. But if you’re wanting to sleep in and have an easy day, show up for an early lunch, eat something, spend the day walking around, go and have a drink late afternoon, do some more shopping, go see a movie if you’d like to do that and then go and have dinner.

William:   I’m thinking that one of the things you need to be careful of if you are coming from the visitor and attraction areas is the fact that it is still business time for other people in Orlando so rush hour on I-4 both in the morning and the evening can be pretty heavy.

So you want to plan either .... Most of the shops I’d say probably open up at 10 o’ clock, the restaurants maybe at 11 o’ clock. So if you’re going to go there for breakfast I would really want to get there earlier, ahead of the rush in the morning.

Otherwise if you’re not going to go there for breakfast I would say wait until 8:30 or 9:00 when most people have already gotten to work.  And then start to head up so that way you kind of miss the morning big rush.

Now again in the evening between four and six you’re going to hit a heavy rush going back towards I-4 and back down towards Disney or Universal or something like that.

Lee:         Yes. So you want to be home by then or still in Winter Park doing something at that time.

William:   I would still be in Winter Park enjoying one of the nice restaurants.

Lee:         You really want to see it lit up in the evenings.

William:   It is beautiful in the evening and it’s nice, it’s peaceful and it’s just a nice place to have your sunset and have a nice dinner too.

Alright, we hope that helped. If you’ve got any questions, please let us know. You can find show notes available at

Thank you so much for joining us on the Orlando Local Show. We hope you enjoyed this episode about Winter Park, Florida. It really is a beautiful area and I’d really recommend that you go there and hang out and just kind of relax and enjoy  yourself without too much of the sensory overload that we were talking about.

Show notes are going to be available at

There is a free transcript of the show there. And of course there are going to be links to subscribe to the podcast. We would really appreciate it if you do that.

Go ahead and click the link, subscribe on iTunes, Google Play and we’ll get the show delivered to you directly for free.

Thanks so much.  We’ll see you next week.

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  1. I haven’t heard of Flagler Beach before, but now i want to go there. I am trying to plan a trip around stops from Red Coach luxury bus lines. Hopefully there is a close stop so I can check it out.

    1. Lee and I were in Flagler Beach about a month ago, since she had an endurance race there. We stopped for dinner at the Flagler Fish Company. Really great seafood. It’s larger than the Winter Park Fish Company and I don’t think they’re related. The fish dip at Winter Park is more of a paté where in Flagler it’s an actual dip.

      They also had a Colossal Shrimp Cocktail that I loved. Big, wonderful shrimp. Great quality stuff. Flagler Beach is north of Ormond Beach & Daytona, but not too far.

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