This blog article is derived directly from our YouTube Video Podcast (featured at the bottom)

Hello everyone, and welcome to the Market Smart video podcast. I am your host Adam Hancock, and in today's episode, I have a guest named Chris Serra. We walked through his very recent journey from Boston, Massachusetts to landing in Southwest Florida. I thought Chris's story was interesting to share because he took such an exhaustive approach to a lifelong dream of leaving Massachusetts and ending up in Florida, that if you're trying to go through that journey now and you're anywhere in those phases, then Chris really covered all the bases where I think he could ease the next person's relocation. You know, comparing the cities versus each other, going macro to micro, picking the suburb within one metro. If you're into lifestyle items like golf, and exiting the winter, and you're considering all the economics of those two states, all of those things that are really, really hot buttons, Chris is one of the most thoughtful, articulate people that I've ever met on communicating this information.

adam hancock


Okay, we are live. As you can see here, I'm with Chris Serra, thanks so much for joining us. I just want to hop right into it. The first question I thought would be interesting is, let's focus on ... The thumbnail suggests you're from the Boston area, and you can tell us more about your background, but let's talk about the exit in a silo. So you come to the decision, "I'm going to leave Boston. I'm going to go somewhere else," wherever that may be. Can you talk to some of the main reasons that kind of spurred that decision and what you went through while making that decision?

chris serra


Yeah. Thanks for having me on, Adam. My name's Chris Serra. I'm a retired Boston firefighter. I worked in the City of Boston for 31 years. I knew at a young age that I was going to be able to retire early because of the position that I had. So A, I was a golfer, mediocre at best, but a golfer, and knew I wanted to retire somewhere I could do that year-round. Had gone on multiple trips as a young guy with my crazy friends and fire guys, to South Carolina, Georgia, and Florida. So the whole Southeast was open to exploration for me.


A few times we had gone down to Myrtle Beach, and it was like March or April, and I had realized that, "You know what? If I'm going to make this kind of huge relocation move, I'm not going to be somewhere where I'm going to be cold ever again in the wintertime." So that kind of made it more of a Florida conversation. Then around 2001, my parents relocated from Boston. My dad was still working at the time, and they relocated to Jacksonville, Florida, the very, very northern part of the state. A lot of people would call it South Georgia.

I would visit them frequently. Golfing there I would go to the Players Championship over at Ponte Vedra Beach every year. Loved it. Really for a long, long time, all my focus was centered on retiring there along that coast, because you had St. Augustine, and Jacksonville, and the beaches, and all kinds of nice golf, and I really thought that was kind of it. Then as I got a little bit older, I had some other friends that retired and snowbird, wintered, however, you'd like to say it, down in the Lauderdale by the Sea-Pompano area.


So I would go there and I'd say, "Wow, this is a little bit more interesting." And just like I alluded to before, it doesn't get really cold here in the wintertime. Jacksonville, sorry, it still does get 30, 40 degrees sometimes in the wintertime. So then I started looking around there and I really liked that. And I always had pictured myself being kind of an East Coast Florida guy. And then we had some other friends that were over in Naples. So I started discovering some of the Naples area and how golf-driven that whole scene is.

And the Gulf Coast, that was my first exposure to the Gulf Coast, and those beaches, and the warm waters, and it was even a little bit further south, and I started seeing sunsets after being a sunrise guy my whole life, and started thinking, "Okay, so I'm kind of all over the place." So probably the last 10 or 15 years before I could retire, I spent a lot of time just thinking, narrowing down what exactly I needed, what were the requirements for where I was going to live next, where I was going to live last really.


I wanted to be in a gated golf community. I wanted an urban area, a city with fine dining and things like that nearby, but I did not want to live in an urban area again. I had come from that for the first 54 years of my life. So when I started doing some more research, I discovered Lakewood Ranch was being built outside of Sarasota.

And I thought, "Wow. This is really kind of ideal as far as some of the golf-deeded communities. They have a lot of social things going on within the community, a lot of fine dining, fun things, and places to go have a few cocktails, and hang out and meet people out here. But also 25 minutes, a half-hour down the road, downtown Sarasota fine arts shows if you want to go to that kind of stuff. And the beach was right there." So all that kind of went into my funnel before I landed in Lakewood Ranch due to finding Adam on YouTube and kind of doing some more research that way. But that's kind of how it all came to be.

Adam hancock


So yeah, and I've said this like a million times to you. But you have a really good background for having this conversation with people finding this also on YouTube is that you, one, just did this. But you had one of the most detailed kinds of ways you went about it. Just like you explained. I mean that was a very short amount of time, four or five minutes you articulated the whole thing of 20 years. But every interaction with you I thought was very detailed. You had really done your due diligence to get your head around the area.

And you kind of went through all those natural steps of like a mini New York is a lot of times that eastern Florida area, the Boca Ratons of the world, the Deerfield Beaches, and the Vero Beaches, and then you made this migration over here. It seems like when you speak I would immediately say, "I'm done with the winter. I want to golf, so I'm going for a lifestyle that I can do 300+ days a year."


How much did other factors like the difference in politics, the difference in cost, how much did that influence Florida being picked over, or was it just a primary winter thing, or Florida over the Georgias of the world, and the North Carolinas, and all that? Or did it not have as much effect as quality of life to you?

Chris Serra


I mean I think a lot of those things factored into it. I think it was multifaceted. I always knew that where I was from might not necessarily be a perfect fit for my mindset politically, and I'll just kind of leave that there. But it's progressed a little bit to the point where I was starting to really think, "I'm not in a place with a lot of like-minded people," and I knew I'd find a lot of people that kind of thought the same way about being a little bit freer down here in Florida. So that's the reason why I came. It's not the main reason.



As I said, I knew at a young age that I was going to want to winter down here anyway. And then when I started thinking about maintaining homes and that kind of thing, I knew if I just came down here full time, I could enjoy this lifestyle year round. The COVID thing certainly kind of pushed me a little bit earlier than I thought I was going to retire. Originally, I was going to be retiring sometime this year.

As it turned out I talked to some people, I talked to my financial advisor, things like that, I knew I would do well on my home in Boston as far as selling it, and making a decent profit on it, and being able to come down here. So yes, the politics played into it. Obviously the geography and the weather played into it. And I don't know if it was just impatience on my part or if the pandemic and some of the stricter regulations in the Northeast in my part of the world kind of made me take a step quicker than I would have if that hadn't happened.

adam hancock


So I think what's interesting is like ... So based on your experience and really targeting this area for a long time, would you be able to if you were talking to a fireman back home that's 10 years behind you or someone that does a very similar regimented, very similar in infrastructure, government kind of led defined career, how long do you think it takes for someone to get their head around what you did if they were saying like, "When should I start looking? How early is too early?"



I think you'd have a good perspective on if someone wanted to replicate what you did, and they know that barring some wild circumstance they're not going to do it earlier, how many years do you think it takes for someone to get their head around making that final decision in Florida?

chris serra


That's a good question. I think because I had thought about it for so long and I had all those other options, like my vacation experiences in other places, my parents living up in the northern part of the state, and having friends in different parts of the state, I think that all obviously went into my decision. But ultimately when I did as much research as I could, the internet being a wonderful tool to do this, take a deep dive into all these places, nothing checked all my boxes like Lakewood Ranch.


So for me, if I was speaking to one of my colleagues that are still working, that's five, 10 years out, I think I could get them down that funnel a lot quicker because I think like-minded people who wanted to live in a gated golf community, who wanted access to world-class beaches and a wonderful little downtown dining scene like you get in downtown Sarasota, and then like I said, all the fun things, the social aspect of being out in Lakewood Ranch and having Sarasota at your fingertips, I think I could get them down that funnel in a hurry if it fit for them.

The wonderful thing about where I ended up is that it's not ... Nothing against Naples. Naples is lovely, but there are a lot more retirees down there. There are a lot more empty nesters down there. Up where I am it's much more multigen. Right? It's the number one multigen in the country. There are people here with children, the schools are excellent, so you see the whole gamut. You could have a three-generational family, you could have say a younger family with children that brought along like a grandparent or both grandparents, and everybody would always have things to do at their fingertips.


I think that would appeal to most people, where wrapping your head around a Naples where you're in your little gated community, and you really don't have a lot of interaction with a lot of the people from the other communities, is kind of the norm. Or again, I have friends that think that they want to end up in the Carolinas, and the Carolinas are lovely. But when you start really thinking about escaping winter and the cold, and how you want to spend the majority of your time outside, or playing golf, or riding your bike, or whatever you want to do, I think Florida's weather just can't be beaten when it comes to offering you 300+ days of sunshine a year to do all that stuff.

adam hancock


Yeah. No, that's a good point. I was going to go there. So I think if you said ... My experience, is right, I think you hit it on the head, and it depends on where you are on your search, and how early you find this out, but you're not comparing Jacksonville versus Orlando, versus Sarasota, so you haven't made a decision yet. Right? And those are very niche. That's a whole metro. Right?


So say it's not Jacksonville, it's not South Florida, Orlando's too far inland, and you're going southwest Florida. It's a three-headed monster. Based on beyond it being multigen, which is a fantastic point, what else would you say if someone is realistically looking at a Sarasota versus Naples, looking for kind of what you were looking for?

Maybe even Tampa Bay's in the conversation of those suburbs, beyond multigen what else would you say was a big hitter? Would you say it's the town you were led to? Is it the new construction abundance? If you didn't choose Lakewood, what would've been your plan B or C if you fell in love with the whole idea and Lakewood didn't exist? Can you talk through what other things you'd compare and contrast? Because I think that's a pretty hot button for a lot of people.

chris serra


It depends on your situation. I think some people are looking for different things. They want to be closer to schools. There are some excellent colleges in Southwest Florida, north of here. Again, Naples is lovely, it's just that it doesn't have the social interaction thing built in like this master plan community that I'm in does. We have that, the Wednesday night ranch night, and the first Friday, and they have kids' movie night, and they have the farmer's market every Sunday. That stuff is built in and that's important to me.


It's like, makes you intertwined with your community. And like I said, as nice as it all is, I wanted to be in a gated golf community with that stuff within five, 10 minutes of me and then an urban area at my disposal when I want to go in and do the fine dining, or take in a show, or whatever. The other thing for me was the proximity to a world-class beach. As I said, I think everybody always talks about Siesta Key being the number one-rated beach in the country. I can't see why Lido's not 1A. It's the same beach with to me more access.

I don't know. Just where it sits with St. Armands right there, and how lovely it is to see sunsets out there. I can't get enough of that. So it's just personal preference. I understand why some people want to be in a deeded golf community in Naples. I know of a community down there where I have friends. There are retired fire guys. There are retired cops. It's a great scene. They play matches on Sundays and then they go over to someone's house and cook out or whatever. I could get into all that. I could.



But it just seemed like I was putting myself in a little box and not enjoying all the other things that came with the area that I ended up choosing. So I don't pretend to know all the benefits of say living up in Tampa and having Clearwater and St. Pete at my disposal all the time. I mean they're not that far away. But for me, it was a gated golf community with the kind of proximity that I have to the beach. But it's still like that buffer zone. So when you think about a Hurricane Ian coming ashore, no damage.


I mean there's like a balance that you have to strike, and for me that kind of ticks all the boxes. For somebody else, it might not. But I can't think of too many people that I would not try and direct to this area just because there's so much right here at your disposal. And if you're looking for new construction, we have every kind of new construction for every kind of budget there is. If you're looking for a resale home ... I come from an area where an old home is something that was built in the 1800s. When you come here they'll talk about, "Well, it's kind of an older home. Yeah, it was built in 1998." You know what I mean? It's just a different conversation.

adam hancock


Yeah.

chris serra


So I think there's something for everybody here, and I think you'd be hard-pressed to find somebody that didn't like a lot of what is going on here. I don't pretend to be able to compete with somebody that wants to live in say The Villages. The Village is a very niche community, mostly for older people, empty nesters, want to play golf every single day. That's all they want to do is travel around by golf cart, go to the little concert they have out on the lawn, and do that whole thing. Awesome. Good for them. That's not kind of what I want to do. I want everything at my disposal, and be in a gated golf community, and I think I found it.

adam hancock


Yeah, and I love that. So let me ask you a fun one. What are three favorite golf neighborhoods in Southwest Florida?

chris serra


My three favorites, I mean I live in Lakewood Ranch Golf and Country Club. It is an awesome place. It's got mature trees because it's about 20-something years old now. I walk five and a half miles around that place every day. It looks like heaven. I joke with my wife, I'm like, "Don't you feel like we jumped over a fence to get in here?" It's that beautiful. It's a very, very nice place. I like Azario up the street. It's only got one course, but the amenities that they are building there, and the social scene that I think is going to be available to people there, is going to be special. And we've talked about this with all our teammates. One teammate came up with it, but I think we all kind of use it now to speak to our people when they come to town, is the analogy of being a freshman in college. So I ended up pivoting and buying in a neighborhood that's a little bit older, so it was an established community. So the neighbors that are there they're very friendly, but it's not like we're all in the same social situation where we're trying to get to know everybody at the same time.


When you move into one of these new construction communities like Azario, everybody's kind of getting there at the same time, and they're all looking for the same thing. We came down here because we want to be outside playing pickleball, playing golf, all that stuff. So you get to meet everybody and you're all kind of on the same level making friends. So I think, sorry, that's one of the golf communities that I also like. But bar none, if price tag wasn't an issue, if I could live and play at one place, it would be the Longboat Key Club. I love it out there. You have the best of everything right there.


You have a world-class beach, you have drink and food service out on the sand if you're sitting there. You have 45 holes of golf along the coast. You're watching million-dollar luxury yachts go by. You're watching the sunset every night out there. You have St. Armands at your fingertips which has some of the best dining in the area. Any kind of little discussions that you hear about people saying anything about traffic, you don't care about, you're already where everybody wants to get to. So if I could pick one place that I would be, it would probably be around Longboat Key, a member of the Longboat Key Club.

adam hancock


Okay, so I like to ask one finisher question. And you alluded to it a little bit, so let me ask it in a different way. A two-part question. It's May 2023 as we sit here, and you're just doing the move now, you had the same amount of money you had then, and you know what you know now, where would you go? And you kind of alluded to it in the last one. If money was not an issue at all, where would you go? And if Longboat Key is your number one, what's your number two?

chris serra


If I had the same amount of money that I had when I came, and I was going to do this whole thing again, I'm not sure I would end up anywhere different. So that makes me feel pretty good about my choice. But I would say Azario it was actually, as you know, my first choice. And things just got crazy price-wise building in there, so I kind of got out-priced. But I would still consider it. But I have to say, having three golf courses at my place is kind of a trump card, if you will. And the other question, as far as if it wasn't going to be Longboat Key Club, I'm not really-

adam hancock


Say you still want to golf at Longboat Key Club. You're still a member.

chris serra


Sure.

adam hancock


You can't live there on the grounds. Where would you live?

chris serra


And money's no object?

adam hancock


Money's no object.

Chris serra


I am going to be moving into a building that is yet to be constructed called the Rosewood. That is right down the street. Best of everything. Concierge level. Everything like Lifestyles of the Rich and Famous, right on Lido, looking at the sunset every day, just getting on my bike and going down and playing golf, and maybe taking the wife out to St. Armands for dinner, or having them make dinner for me and bringing it into my luxury condo. I mean, it's really going to be something special, and it's right there. So yeah, that would probably be that.

adam hancock


Awesome. Well, thanks so much for the time. I think super valuable stuff. So I hope you articulated that well enough. And thanks so much, Chris, for joining me on this one, and we'll see you on the next one.


All right, my friends that is a wrap for today's video on Market Smart. Really hope you enjoyed it. Once again, my name is Adam Hancock. If you did enjoy it, the best way to see what's going to be released, we have a ton planned for this avenue, is to subscribe and even hit the bell notification just so you get that notification when we release new videos. Please check out the other videos that are already posted if you haven't already done so. If you are actually actively in the real estate market, even if you've seen someone on video that's a realtor on my team that you'd like to work with individually, we'll put all of our contact information here. Full service real estate brokerage called the Sunshine State Company. We do a ton of relocation, a ton of new construction, but we can do everything in between, pretty much cover the entire state really.


Categories

Free Relocation Guides

The YouTube Channel

Watch The Latest With Adam Hancock

Each week I'll give my view on everything from the best neighborhoods around Southwest Florida and new construction communities.

Subscribe on YouTube

One of the most unique things about our brokerage is how we view the real estate experience!


When you work with The Sunshine State Co team you get Adam, the broker, & your own dedicated agent. This formula provides clients with a full-time market researcher (aka - the best info possible), read more...

👇Like it? Share it! 👇

LIke Free stuff?

Florida guides, tools & more!

The absolute SMARTEST way to relocate and/or invest in the entire state of Florida. We create an abundance of original, value-based and economics-first resources to equip our clients for the real estate market ahead. Smarter buyers are more savvy buyers!

SEE ALL FREE GUIDES & TOOLS

Sunshine State Company

Ready to take the next step?

Let's schedule a meting! During this initial consultation, we'll learn more about your situation and what you're seeking in a home. We'll provide advice and address any concerns you may have, in order to determine the best approach to achieving your goals. By the end of our conversation, we'll have a solid plan of action and next steps for moving forward.

941-263-2613

info@TheSunshineStateCo.com

Explore More Blogs

By Adam Hancock April 4, 2025
10 Best New Communities FOR AMENITIES | Sarasota Florida 2025
By Adam Hancock April 1, 2025
Top 7 New Communities in Southwest Florida Near the Beach [2025]
By Adam Hancock March 24, 2025
Top 5 BEST PLACES TO BUY In Florida's Cooling Housing Market
More Posts