The Best Cities To Retire With A Sailboat

The Best Cities To Retire With A Sailboat | Life of Sailing

Last Updated by

Daniel Wade

June 15, 2022

Deciding where to retire with a sailboat is not an easy decision to make.

Chances are this is the first time in a long time you have truly felt that you can pick up your roots, and move to pastures anew.

This is an exciting time. The promise of little to no work and an abundance of free time is something that many people haven’t enjoyed since they were a carefree teenager. For some people, it has been even longer.

So, that begs the question: What are the best states to retire with a sailboat? This article answers that question, as well as giving you all the information you might need when considering where to retire with or on your sailboat. By the end, you will hopefully have a good idea of whether or not retiring on a sailboat is right for you, and if it is which state would be best.


Table of contents

What do I need to know about retiring with a sailboat?

Retiring with a sailboat can be a lot of fun. But, it is also a lot of responsibility.

Maintaining a boat is not just a matter of pride but safety. If you don’t have the time or money to keep your boat running in tip-top shape you are in for a bad time.

Luckily, when it comes to retirement you will now have an abundance of time. More so, you will likely have a decent amount of money on hand with the combination of your savings and your pension. So, time and money are covered.

Now all that’s left to discuss is sacrifice.

Maintaining a boat requires a lot of sacrifices. It is far easier to just retire to your house. Even if you only planned on retiring to your boat part-time, you need to be sure that its the right choice for you and your family.

These next segments will help you know for certain whether it is indeed for you.

What are the benefits of retiring with a sailboat?

Retiring with a sailboat is amazing. You have the opportunity to spend as much time at sea as you want. Long gone are the days of work commitment.

If you want to go sailing on a Wednesday morning, just go. There is no one but the weather (or perhaps your spouse) to stop you.

You also have far more peace, and quiet, at sea than you do at the land. You only need to sail a couple of hundred feet out to sea and drop anchor to experience the quiet.

Additionally, the cost of living on a sailboat can be a lot less than living in your home. If you choose to live on your sailboat full time and sell your house, the money from selling your house alone will pay for anything and everything you might need.

Maintaining a house is a very time-consuming task; if you chose a boat over a house you would be making your life easier. If you try to do both, you’re just making more work for yourself.

What are the downsides of retiring with a sailboat?

The downsides of retiring with a sailboat are pretty similar to living on a sailboat during your work life.

There is limited space, the weather plays a bigger role in your life, and it can be boring for some people.

If you are retiring to your boat full time you are going to need a decent-sized boat. Space is precious, so you will need things to do around the boat that can entertain you.

If you still worked while living on your boat, you spend 6-10 hours a day away from the boat working. If you don’t have to or want to work you are going to spend much more time on the boat. This can lead to you become very bored.

People who have recently retired tend to spend the first 6-24 months very bored and frustrated. Living on a boat can exaggerate this.

But, on the other hand, you may save a lot of money by retiring to your boat. This could leave you with the finances to spend your day out doing cool things. This is why planning your finances for retirement should include more than just the cost of the marina slip.

Is it cost-effective to retire with a sailboat?

Sure, it can be super cost-effective. If you live on your sailboat full time you are going to save a heck of a lot of money on property tax, home maintenance, power, gas, water, cable, and any other utility bills. All of those can add up to a lot. Not to mention if you are renting, not the owner, of your home.

With a boat, your costs are pretty much marina slip + utilities. Those utilities are less too.

The problems only truly start to arise when you can’t settle on one or the other. A house or a boat. Because then you are having to split your time and your money between two places of residence.

You must consider that, even though you have a pension coming in, you likely don’t have an active income anymore. The money you have now will need to last you for the rest of your life. That’s why many people feel compelled to choose one or the other.

If you have your heart set on both but the finances don’t quite make sense, the best option is to get a smaller boat. Many marinas charge based on the length or size of the boat. Owning a smaller boat, as you might expect, costs less.

How much does it cost to retire to your sailboat?

How much it costs to retire will depend on where you are. Just like how rent and taxes vary from state to state, even from city to city, so does marina costs.

If you are trying to live in New York or Miami Beach your marina slip is going to cost a lot more than, say, Destin Florida.

Budgeting for the maximum amount of money you feel comfortable allocating to marina costs is perhaps the most important thing to consider.

A good rule of thumb is to allow about $1000-$1500 a month for marina costs. This includes the lease, power, water, and perhaps even wifi.

It is possible to get marinas that cost far less, but you, of course, won’t be getting as much. Whether that means fewer amenities or an objectively “worse” location.

You also may want to consider the cost of boat maintenance. Your boat should, in truth, be painted at least every two years. If you feel like doing that yourself, great, if not it is going to cost you a few hundred dollars a year on average.

How do people supplement their income when retiring to their sailboat?

$15k a year for your marina is a lot. If you are working even a decent job this might be well out of your price range. That’s why ensuring your pension + savings can cover your marina slip is so important.

If you find that you don’t quite have enough money available to afford this lifestyle, there are some options. Sell your belongings that you no longer need/want (not that they would fit on your boat anyway). Sell your home, so you live full time on your boat. Or, find some ways to supplement your income. Many people who retire choose to work a part-time job, not for the money, but for the social aspects.

If you feel like working a part-time job is something that you would be interested in, it can certainly help with your dream of retiring to a sailboat. The advantage of not needing to work is you can be very selective with where you do work.

Perhaps you want to work part-time at an animal shelter because you love dogs. The pay is poor, it never would have sustained you before retirement. But now, you have the financial security to work there.

If you don’t see the appeal of working a part-time job, that’s fine too. After all, you just retired. Going back to work might sound like a genuine nightmare.

If you fall into that category this leaves you with only two options. Either learn to make money trading stocks/bonds, which can be high risk/high reward, but exciting, or find a way to commoditize your hobby.

If you like knitting scarves, sell those scarves. If you enjoy making small wood carvings, sell them. There are so many hobbies that can be used as a secondary source of income if you are willing to put the work in.

The choice is up to you. Perhaps you’re even lucky enough to not need any extra money. Perhaps you were a very smart saver/investor and nows the time to relax. All of your hard work is finally paying off.

Is it safe to retire primarily to your sailboat?

The risks of making your sailboat your primary place of residence are the same for whether you have retired or not. If there is a bad storm, and your boat becomes badly damaged, your out of luck. You are going to need to shell out for a hotel until your boat is repaired.

Additionally, if there is a tornado, hurricane, cyclone, etc and you have nowhere to go you are going to need to sail your boat to safer waters if possible.

Or, you are going to have to abandon your boat/home. The problem here is if you own boat chances are you don’t own a car. So, how are you going to get to safety? That might be tricky.

You may not wish to think about this, but living on a sailboat can start to become unsafe as you get older. This is, of course, not a problem right now.

If you are planning for retirement or have only just retired this isn’t an issue at all. It only truly becomes problematic when you reach into your 80’s. Which, unless you retired very late in life, is way away in the future. It is not a present issue, but, it is an issue for later in life.

It is important to think about how difficult it can be to live on your boat as you lose mobility. Its a lot harder to get around on a boat than in a one-story home. Additionally, if you need medical assistance it can be very hard for an ambulance to reach you.

They will struggle to get into the marina, find your slip, and get you to the ambulance. It isn’t fun to think that far ahead. It can put a downer on the whole idea of living aboard your sailboat. But, it is something that needs to be thought about.

The best states to retire with a sailboat

Finding the best state to retire can be a little tricky. If you have never lived in, or even visited, a specific state knowing whether it would be a good fit for you is a very expensive guessing game.

Luckily, since boats give you the freedom to move around, you could, in theory, try all of them on this list even if only for a few weeks.

Of course, you would be doing it to ensure you can make an informed decision but it would also be super exciting. The idea of sailing all around the continental United States (and beyond) sounds to me like a grand adventure.

Here are the best states to retire in with your sailboat. The cities mentioned are home to arguably the best marinas in the states. Some of them made the list for their beauty, some for the convenience, and some for the price.

Which state is truly best is highly subjective. What is best for you might not be best for me. This is why the following list is not in any particular order, which state is best for you is a matter of personal preference.

Destin or Tampa Bay Florida:

Florida has a reputation for being a place people go to retire. Of course, most of them don’t retire to their sailboats. But they could. Florida is home to some of the best marinas in the entire country. The weather is beautiful, the people are friendly, and the food is great. More specifically though, you will probably want to move to either Tampa Bay or Destin. You might be surprised to find that no Miami marinas made it to the list, and the reason is simple. This list is for the best places to retire. Miami is very much a party city. Many people like this, many people don’t. I don’t want to make any assumptions, but if you are looking to retire you probably don’t.

The cost of a marina slip in Florida (Destin / Tampa Bay) ranges from $3 per foot to $10.

Seattle Washington:

Seattle, Washington, is a great location to retire to if you plan to spend your time sailing. This may sound like a silly statement, “I’m retiring to a sailboat, of course, I’m going to be sailing”. But, you aren’t. You aren’t likely going to be sailing every day, or even every week. Unless you are a very enthusiastic sailor, in which case you need to consider. How much time am I going to spend sailing? If the answer is a lot, choose Seattle. The reason being it has access to some of the best sailing in the country. You can freely sail from saltwater to freshwater exploring all the lakes and rivers of the state. A state such as Florida doesn’t offer this kind of opportunity. You cant sail through a Floridian swamp.

The cost of a marina slip in Washington (Seattle) is going to be about $8 per foot.

Corpus Christi Texas:

Corpus Christi, Texas, is an up and coming area. It has only recently begun to transform into a very boat friendly community. It has steadily gentrified and became cleaner, safer, and better equipped. But, the price hasn’t quite caught up to the city yet. You can afford to live in Corpus Christi. It doesn’t matter your budget, there will be somewhere you can afford. Besides the price, Corpus Christi is home to some of the most square miles of open water in any city in the country. Texas as a whole is a great place to live. The economy is doing great, the food is incredible, and the people are down to earth.

The cost of a marina slip in Texas (Corpus Christi) is going to be anywhere from $5 a foot to $15. Maybe more, if you have a huge sailboat.

Hampton Roads Virginia:

If you decide to live in Hampton Roads, Virginia, you will have amazing access to the Chesapeake Bay. This gives you access to beautiful sailing and the countryside but costs a little less than staying right in the Bay. Or, a lot less. You have great access to the Atlantic ocean, if you want to test yourself and sail beyond the waters of America you can do just that. Easily. Additionally, Virginia’s waterways have some surprisingly good scuba diving. If you haven’t tried scuba before, nows the time. It is a very easy pass time. It doesn’t require great fitness or lots of energy. You can just sit on the ocean floor and watch the world go by.

The cost of a marina in Virginia (Hampton Roads) is going to cost as little as $1.50 per foot in some places. The closer to Chesapeake bay you are, the more it will cost. It can be as much as $15 per foot.

Traverse City Michigan:

If you aren’t the most confident sailor, the idea of facing the rough seas sounds awful and you would rather sail around in peace. Then Traverse might be the place for you. Traverse City offers great access to Lake Michigan, which is great for fishing or just lounging around. Traverse City is very much a tourist city, so it offers plenty of exciting things to do and affordable amenities. If you are going to be living on your boat full time, this might be the one for you. When you give up the amenities of a normal home to retire to your boat, you may find yourself frustrated. If you are staying in Traverse those amenities (Laundry, Gym, etc) are all within walking distance of the marinas.

The cost of these marinas can be a little tricky to calculate. Some are given at a monthly rate, in which case you can expect to pay about $250-$300 per month. If you are trying to live full time at one of the touristy marinas, it can cost closer to $600 per month.

Lake of the Ozarks Missouri:

Lake of the Ozarks is one of the most beautiful places to live not just in Missouri or America, but the world. It is a calm, quaint, lake that has slowly become more tourist. This doesn’t mean it is going to be overrun with tourists, it just means that there is lots to do and lots to see. The towns surrounding the lake are very seasonal. The summer months are busy, the winter ones are less so. This can be either good or bad depending on your perspective of it. Missouri is a very relaxed state to live in, the people are real salt of the earth types. Whether you have visited before or not, you will quickly feel right at home.

The cost of living at the Lake of the Ozarks is quite a lot. You are better off buying a marina slip rather than renting. It becomes more cost-effective to buy after just a couple of years. You can expect to pay anywhere from $30k-$40k.


Hopefully, you now have a better idea about whether or not retiring on your sailboat full time (or even part-time) is right for you. If it is right for you, hopefully, this article has helped you decide where. The US offers a huge array of places for you to live. They all come with their pros and cons, which is best for you is purely personal. It is a good idea to think long and hard about which is right for you. If you feel confident enough to sail from state to state to find the best one for you, great. If you don’t, well you better do your research. Committing to a marina long term can be expensive. Especially if you have to buy your way out of your lease. Whatever you choose, best of luck and happy sailing!

The Best Cities To Retire With A Sailboat
Daniel Wade

Daniel Wade

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

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