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

Today we are breaking down the ultimate retirement list for 2023 in the state of Florida. Through hours of research and thought I'm taking from number 10 to my overall number one option, and we're talking about the location and why that matters. The three absolute most important reasons they're even on this list in general. And then also the number one reason that differentiates everyone on the list from anything else you could choose. I hope this adds to you so much value, and let's hop right in.

  • #10 Vero Beach, Florida
  • #9 New Smyrna Beach, Florida
  • #8 Key West (Marathon), Florida
  • #7 Mount Dora, Florida
  • #6 Cape Coral, Florida
  • #5 Lakewood Ranch, Florida
  • #4 Destin, Florida
  • #3 Naples, Florida
  • #2 St. Pete, Florida
  • #1 Sarasota, Florida

#10 Vero Beach, Florida


 

Number 10 on our list, working our way down, I'm going with a place called Vero Beach, Florida. So, right off the bat locationally, we are going to head to the Atlantic Coast of Florida, and we are going to say about two hours south of Daytona Beach and about an hour and a half north of West Palm Beach, just to give you a general framework. All right, three things I'd really like for retirement here. One, you have all those beautiful beaches, but without the crowds, without the tolls for parking, and without all the bridge crossing and all the minutia you have to deal with there. Number two is building height restrictions. Besides one building that basically snuck through the cracks, you have severe limits of height restrictions on what they can do. I.E. you're not going to have all these luxury high-rise condominiums that pop up like it's happening in a lot of other parts of Florida. And you're not going to have the density of population that brings with 150 to 300 different units packed in a very small piece of land.

And number 3, for Florida's sake and Seaside retirement basis, you still have a lot of relative affordability. So, I think that's an overall win when it comes to picking between the 10 options. Okay, and lastly, for my what's so special about Vero Beach item, I'm calling Sunrises Not High Rises. Because of the way the city very specifically and somewhat old school-wise controls expansion in general. So, someone always prevents some sort of crazy commercial outpouring and kind of preserves what a lot of people think made this town historically great. 

 

#9 New Smyrna Beach, Florida


 

All right, number 9 on my list, I'm going with New Smyrna Beach, Florida. So, this time we're going right back to the Atlantic Coast, but we're heading north and we're much closer to Daytona Beach, just 15 miles one way. And also just one hour to the Disney capital of Orlando, Florida. Okay, three things I like here for retirement.

Number 1, kind of a unique one, surfing. You don't hear surfing synonymous with Florida a ton. But if you're moving from a state or an area in general where surfing's a part of your culture and that's something you would really miss if you moved to Florida, this would actually give you a pretty viable option in my personal opinion. A lot of people think it's the most consistent overall surf break in the entire state of Florida. When there's waves nowhere else, you can find some sort of wave here. So, I think that would add one interesting element.

Okay, number 2 here I'm going with the arts. So, New Smyrna has been ranked on many, many lists over the last few years as one of the top overall small cities in the entire country for this specific category. And that there's quite like a small budding group of very intentional artists and painters and sculptors that have created a cool communal, approachable environment. If you're into this kind of thing and the artistic community in general, this gives you a whole other layer.

All right, and number three on the list, we're rounding it out with one of the fan favorites is a beach that you can actually drive your car on. So, you have that element where you can physically drive your car on the beach or you can go park and open the tailgate, and you got your whole setup right there. But what's cool is you also don't only have that. You have places where if you're not into that or you don't want that environment around whatever you're doing, you have spots where you don't have to do that. You have spots where you can do that. So, I think that does give you a cool option, just on convenience in general.

Okay, and for my, what is so special about New Smyrna Beach, Florida, I'm jumping on the back of what travel and leisure poignantly named Florida's Most Underrated Seaside Destination. Despite all of this crazy Florida boom we've seen over the last couple of years, in my opinion, I still think that New Smyrna Beach, Florida is still somewhat overlooked, which could provide an interesting opportunity for you.

 

#8 Key West, Florida / Marathon Key

 


 

Number eight on the list may be the peacock of the bunch. We're going with Key West, Florida slash a little bit of Marathon Key as well. So, here you are the southernmost point in the entire state of Florida, which is going to roughly put you about three hours, three and a half hours from Miami one way and just 90 miles one way to Cuba. Okay, three things I like here. Number one is just the laid-back charm element. So, kind of cliché to say, but this is a true unicorn, Florida retirement living. Everything a Jimmy Buffett song would describe this place as it is quaint, it is charming, it is old school Florida, it's water-based. It's everything you would picture in a dream of or a lot of people's dream of retiring in Florida.

Number two, is, which I really, really like, is you don't really need a car. If you get to the right part of the Keys, you don't really need a car. A lot of people will travel by fat tire bike or golf cart or something like that. But I think once you get there, you kind of have everything you need. And if you end up here retiring, that's kind of what you would be seeking for the most part in my opinion. And number three I'm going to throw in lifestyle diversity. There's people from all walks of life. I would say it's a very approachable, inclusive environment overall. So, if you're kind of seeking like-minded people, depending on what you're looking for, I think it would provide that as well.

All right, and what's so special about the Keys and Key West in general here? I'm calling basically the Caribbean. So, kind of straight, no chaser with that, but you are so far off in one direction that if you want to be on a complete island and still be stateside, then this is the destination.

 

 #7 Mount Dora, Florida


 Working our way down to number seven, maybe throwing you for a slight surprise here. I'm going with Mount Dora, Florida. So locationally, this is actually a suburb of Orlando, Florida, about 33 miles to its northwest. Okay, three things I like here because I do feel like I'm always talking about coast, coast, and beach, beach so much. I wanted to give you one inland alternative in case that's not your thing.

So, number one is Mount Dora has actually been ranked on lists as one of the friendliest small towns in the entire country. So, if maybe your point of view is that all this destination relocation that's been created has created a melting pot in the state and community of the way people treat each other maybe is a lost art. This could give you a different version.

Number two, on the back of that you do have very much an old school country living field that they maintain pretty well. So, for being so close to a huge metro, which is cool because you're not in complete isolation, it does give you a chance to live on the outskirts of it without being far removed from it. And if you're retiring without the hustle bustle, maybe that's what you want. Number three, for being a pretty small place, a lot of people consider or coin Mount Dora as the festival city because of the density of fairs and seasonal festivals that they do pretty much year round. So, that'll give you an entertainment aspect as well.

All right, and what is so special about Mount Dora Florida as a takeaway, I'm calling the Central Escape. So, amazing central proximity to the entire state. Just 30 minutes one way to downtown Orlando. You have Lakeland right there, a similar commute to the entire Tampa Bay area. So, great proximity day trip ability, but you live in your own little world when you come back home.

 

#6 Cape Coral, Florida


Number six on the list is Cape Coral, Florida. So, this is our first venture thus far to the southwest Gulf Coast of Florida. So, you're going to be about an hour north of Naples one way and about an hour and a half south of Sarasota.

All right. Three things I think are special here, and number one is even particularly interesting. So, Cape Coral, Florida for being a relatively small city in the grand scheme of that conversation has over 400 separate miles of water canals. So, reference point-wise, that's more than any city of any size in the entire world, including Venice, Italy. So beyond just being a fun fact and flood prevention, think about the provision of your capability of living near the water and a cost-efficient way of living near the water if you have that level of abundance, and it's not in that scarcity. So, I really like that.

Number two is, in my opinion, it's generally going to be a little bit larger lots here by being this close to the water. They're going to be larger in above 10,000 square feet on average for the lot size, which compared to the neighboring cities, that's going the opposite direction. So, if you're looking for a little bit more space, I know that's a hot button, then this might be a place where you can not only get a cost advantage, but you get that.

Number three Because of this place has really been booming. It's always been kind of a hidden gem in my opinion, because you have Sarasota, Naples and border it and then Tampa and all that. Those have always been unanimously popular and this one has kind of snuck in between, and people didn't know industry and where to work and all that kind of stuff.

But it absolutely exploded because the cost. With that is coming growth, and that's what it's been missing a little bit in my opinion. So, you're having a couple projects that are going to add a bunch of mixed use waterfront development of maybe luxury condominiums, luxury homes with commercial districts and restaurants and progressive commercial development like Bimini Basin, Seven Islands, things like that. So, commercial growth I think is a third thing that's going to add to this area's uniqueness.

All right, and what is so special about Cape Coral Florida as a differentiator? I'm calling Affordable Boaters' Paradise. Really, everything's in the name there, but if you try to look and compare these homes on this kind of water in Naples or Sarasota or any of the surrounding areas like that, they're incredibly, incredibly difficult to get into and they do not come at a discount.

#5 Lakewood Ranch, Florida


We have made it to our halfway point, and I'm going with number five of Lakewood Ranch, Florida. So, this is actually a new construction suburb that turned into its own city, but Locationally, you are Sarasota, Florida metro based, that would be the commonality. You're about 30 minutes one way to downtown Sarasota, Florida. Okay, three things I think are special about this one.

Number one, I'm calling everything but the beach. So, in the last couple of years, especially gone are the days where you go to the suburbs and you get on the outskirts of town, and of course, you get new homes and you get affordability, but you lose what's cool about the town. Lakewood Ranch, Florida may be the best mousetrap in this conversation. Three downtowns were built into the entire suburb and all were built post-1995. You have shopping, you have restaurants, you have boutiques, you have lakes for recreation. Half of the entire acreage of Lakewood Ranch is set aside for green space and a trail system. You have schools of all sorts, highly rated public school districts with multiple options. You have private options like Montessori and Charter, there's coworking, there are commercial spaces for work viability, and there are hospitals and urgent cares built in. And you have everything beyond just coming into the Gulf Coast beaches. And that's not functional for a lot of people day to day.

Number two, I'm calling multi-generational and variety. And what I mean by that quickly is one, Lakewood Ranch, Florida is the number one multi-generational master plan suburb in the entire United States. So, they're at the top of this conversation. But in my experience that a lot of people that are looking to retire, they don't necessarily need to be in the most kid-friendly neighborhood, and they don't want all of that because they might be beyond those years. But they don't necessarily want to be completely isolated from it. They want the energy and they want the texture, and they want all different kinds of age people. They just want the option where maybe they're not all in their neighborhood. So, Lakewood Ranch gives you that. It is multi-generational in that it has a lot of price points and a lot of home types and attractive amenities where it's going to attract families. But it also has 30 plus new construction neighborhoods, all built 1995 and newer, and it has 55 and it has luxury elements and it has golf elements, and it has a lot of communities that won't appeal to families in the same like, but they're still in the general 50,000-acre radius. So, I think those two combined satiate a lot of folks' needs.

Number three, I'm calling community, community, community. And what I simply mean by that is if you move from out of state and you want a lot of environments where you can meet people on your own terms, this has overwhelming amount. I mean, I think there's 600 plus live events of some sort, including farmer's markets and First Fridays, and there's many, many different clubs, and there's bird watching and there's polo grounds and all kinds of stuff. So, whether you're the most social person or you're not, and you want a pickle ball or anything, you want to meet people and you know no one, then there's a lot of forced communal environments that are done in a very, very approachable manner.

Lastly, what is so special about Lakewood Ranch, Florida? As a takeaway, I'm calling Two Towns for The Price of One. So this again, is a huge suburb when I named all those kind of things. But it's also Sarasota Florida base, which is highly regarded to a lot of folks as always, on the top retirement destinations. You have Siesta Key, you have Lido, Longboat, key, downtown, Sarasota, Venice, Anna Maria Island. So, you have all of this and any community in all of Lake Ranch, you'd be hard-pressed to be more than 45 minutes one way, but 20 miles, 25 miles from anything else that this entire metro has to offer.

#4 Destin, Florida


All right, number four on the list, I'm going with Destin, Florida. So, here we're going to head all the way over to the panhandle of Florida, which is going to put you about two and a half hours one way to Tallahassee, which is the home at FSU, and also just two hours one way to Mobile Alabama. Okay, three things I like here about Destin, Florida.

Number one is the crystal clear green water. So, if you're not familiar, this area is actually known as the Emerald Coast because of this fact. But the way the water runs in this location, you have this green tint to this very tropical feeling, clean, clear water, which is very lovely to be around, in my opinion.

Number two, unbelievable fishing. So, this geography puts you in a place where the fishing inshore, offshore so much at your disposal, whether you have a boat or not, charter, glory, you have a ton of options, but right close behind that, golf, shopping, and dining are also right up there. So, because this is a destination location for tours, you have a lot of amenities if you're a full-time resident to use, if you enjoy those.

Three, kind of a unique one to any other one on this list is, and I experienced this because I went to school actually in Pensacola for college. I lived in Gulf Breeze for four years. You have seasons kind of for Florida. If you're from an area that is not Florida and you come here and you're like, God, there's just no break from the heat and the humidity all year around, well this place is a little bit of an anomaly by this location. There's four months on average a year that the high is less than 65 degrees, which that's amazing for Florida if you put it in perspective. And then there's several months of the year where the lows are in the 40s. So at least it gives you some break or some not as big of a gap on your total relocation.

What is so special about Destin, Florida overall? I'm calling Small Town Feel With Big Town Appeal.For a relatively conservative-sized place, once you get here, you should have everything you need, some of the best of what Florida has to offer, amenities, housing, et cetera. I don't think you're going to be wanting anything else. 

#3 Naples, Florida


Okay, onto number three. We're getting to our shortlist here, Naples, Florida. So, this is back on the Gulf Coast, and it's about the southernmost point beyond Marco Island until you fall off into the Everglades on the Gulf Coast itself. So, that puts you two hours south of Sarasota, Florida, and depending on traffic also just about two hours one way to Miami. All right, three things I like here for this particular retirement list.

Number one is the overall abundance of beach variety. So, because there's so many beaches from south of Marco Island that run straight up to basically Captiva Island, you have kind of something, depending on what you're into or even that mood that day, that'll satiate most people's needs. You want to be more social, you could go the pier and Naples Beach, you could family friendly, you could look at going adjacent to Bonita and Barefoot Beach and Vanderbilt. You're into shelling, they have these very unique pastel colored shells on the Sanibel Captiva, it's like world renowned. Marco Island's, its own little world, and you have a lot in between there.

Number two, this is unanimously considered a golfer's dream. There are a lot of places in Florida that are similar like you have Jacksonville and parts of the Atlantic coast too. But there are over a hundred courses within a 30-mile radius of the city center of Naples, and it's a pretty small geographic area.

And three, I think is a really unique one to just the Gulf Coast conversation that maybe similar cities don't have. I think where Naples really excels is luxury living. There's a strip of neighborhoods from Aqualane Shores and the Moorings and Park Shore that are waterfront, that offer a unique, exclusive, luxurious environment that you have amazing water frontage, unbelievably beautiful homes on a lot of times, big pieces of land, a lot of water access, sometimes custom homes, sometimes renovated, and very, very proximity driven to the downtown Naples area with third and fifth and very historic and very quaint. The level of luxury that you can get here and how exclusive and isolated it feels is at a different tier than I would say a Sarasota and a Tampa offer.

Then what is so special about Naples, Florida as a takeaway here? On the back of point number three, I'm calling Southern Exclusivity because of the mix of very, very high-end residential homes, and waterfront proximity, and it all sits right in front of a quaint southern feel of downtown.

#2 St. Petersburg, Florida


All right, our final two on the list, we are onto St. Petersburg, Florida. So, St. Pete is actually part of the Tampa Bay Florida metro, which puts you back on the Gulf Coast of Florida, kind of the most meaningful northern location. So, you're about an hour north of Sarasota, Florida, about three hours north of Naples, and then also just two-ish hours from Orlando. Okay, three things I like particular here about the coastal part of Tampa Bay.

So, number one, kind of weird to say for Florida, but St. Petersburg is literally the sunniest city in the Sunshine State. No joke. 361 average days of sunshine a year. And it literally had the longest consecutive streak in the Guinness Book of World Records for sunny days. So, if that matters to you in particular, and you're coming to Florida for this reason, then this is the best mouse trip.

Okay, the second thing I really like here if I can articulate this, is I feel like the resident base of this area is generally eclectic, intellectual, and intentional. Because you have the same Gulf Coast proximity as Sarasota, Naples does, but a very, very different city. Right off the bat, the artistic environment of just not artistic like Sarasota's culture too. But this is an eclectic artistic environment with street art and the museum culture. It's a way more youthful feeling. And the other thing is this city is way more urban designed in an urban field than any of the neighboring surrounding cities. So, if you don't feel like you fall into a Naples or a Sarasota bucket, but you like the location as far as water proximity, then I would say this one is a unicorn in that conversation.

Okay, and the third one I wanted to touch on before we move on, similar to Naples, overall beach variety and housing variety. So beaches, you have unanimously popular Clearwater Beach, St. Pete, if you're seeking where people travel to. You also have desolate quaint options like Indian Rocks I really like, Redington, Inbetweeners, Madeira Beach, and Johns Pas Fisherman Village. You have Treasure Island, family-friendly tourist destination, even Tierra Verde, like island-based Fort De Soto Park, and kayaking and fishing, there's a dog park. So, plenty of options there. And then housing you have the most popular probably is. This is a place you go to for family-friendly, historic bungalow housing. So the northeast of downtown is the most popular on the Bayside, probably. Some hitter neighborhoods, old Northeast Woodlawn, and St. Paul Euclid, but you also have Snell Isle, you have quaint retirements like Dunedin and Safety Harbor to your north. So, I think options never hurt the buyer.

Finally, what is so special about St. Petersburg, Florida? As a takeaway, I'm calling my Best Overall Happy Medium on the Entire List because of a three-headed value monster. Number one, I think the best location in the entire state of Florida, is the Gulf Coast waters in this central proximity. Number two you are flanked by a large metro. Not everyone can live around no industry or doesn't want to live around no industry. Someone might work, you just might want more at your disposal than a quaint sleepy beach town. But number three is you are in a large metro, but because of the three-county Tampa Bay area, you're the coastal county that is basically like a sleepy beach town built within a large metro, which kind of gives you the best of both worlds.

#1 Sarasota, Florida


All right, number one on the list, our grand finale. I'm going with my hometown of Sarasota, Florida. So geography-wise, Sarasota is on the Gulf Coast. You are an hour south of Tampa, you are two hours north of Naples, you're three hours to Miami, three and a half to West Palm, and four and a half to Jacksonville and Saint Augustine. About two, one way to Orlando and about six hours one way to Savannah, Georgia. Okay, three things I like about Sarasota for this particular list. And just a quick caveat to cover the I'm biased because I live here and I'm from here conversation, it's a valid point. But also my brokerage covers the entire state of Florida, so it's not that different to me. But I also believe what I'm going to say here, and if this is about making me pick one, and if I had to put my anchor somewhere and I was of retirement age, I would probably have to put it here still in 2023 for the reasons I'm about to list.

One of those being number one being geography. I had rattled off previously all the proximity of how close it was to all these things, right? Pretty ridiculous, three and a half hours to everything. And for Florida, if you made me put my homestead in one place, I'm very transient and I've lived in a lot of places, I would want feasible access to the rest. And I don't think there's a better location in the state for that conversation because most of what the state has to offer beyond the panhandle, which is like an island on its own, is on the southwest coast and the south coast. And I'd want to be on Gulf Coast waters and even Tampa, Naples are great locations, but you lose the other one. This one sits in between, but it's still three and a half hours to everything you'd want.

Number two something that I probably value even more now that I moved away and come back and have a little bit more perspective, is Sarasota, Florida is very much a play-first and work-second culture. So, if you are of retirement age and you're not contingent on being in place because of industry, then there are a lot of perks to the kind of places you can live and the pace of life that you can live. Sarasota is a place where most people that came here historically are more than the average, made their money elsewhere, and then they brought it here. And what they're seeking now is hospitable environments, like entertainment, and what they need is hospitality-based and then the support of the time you are in your life. Real estate, insurance, financial services, and healthcare. So, the perks to that are our downtown major districts aren't overwhelmed by the average place of a bunch of people bustling in for work, and then they don't live there. So, leaving and creating all this minutia of traffic patterns and nonsense. And like downtown Tampa for instance, most of its work culture, most of its businesses and commercial spaces, and very few restaurants, Sarasota's the opposite. It's art galleries every third step, it's bars and restaurants and Zagat-rated stuff and culture and theater districts and all this kind of stuff. And even on the busiest of times and the busiest times of the year, everybody's coming there to visit. So, it just doesn't create the same nonsense. It feels unbelievably peaceful at all times of the year stuff. Even when it's busy, if everyone's not getting up and trying to do the same thing at the same times, and it's more random because its leisure based, that always creates something hard to replicate in larger metros.

The third one on the list, just to round this thing out for Sarasota, is you have to talk about arts and the beaches. This is the origin of how this place became in Vogue in the first place it was identified. John Ringling thought it was special, came here and it became a popular destination. And Sarasota's known as the cultural coast because of the pure density of art galleries and theaters and music venues and all of that at your disposal in a small geographic region. And then on top of that, it gets we have Siesta Key Beach and Longboat Key and Anna Maria Island and Lido Beach and Venice Island of all that stuff that people like in their minds are seeking out when they relocate. Because we have this magical triangle when you go west here, as I digress here, when we go west here, our downtown is two and a half miles to the beach. The bays are in between, and you're six miles also to Siesta Key. And most of what is happening is all in these same districts. So, beach village, beach Village, and downtown. So, once you get over here, you got everything. So, I think that abundance in general is if you settle down for retirement and you could live leisurely and you didn't have to go to work, there's a lot at your disposal.

What is so special about Sarasota Florida as a takeaway? This might be an obvious one, but this one, I am naming my Number One Best Overall Retirement Destination for 2023. 

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