How to Retire on a Sailboat

How to Retire on a Sailboat | Life of Sailing

Last Updated by

Daniel Wade

June 15, 2022

Living on a sailboat is a rewarding and affordable way to enjoy your retirement.

In this article, we'll cover the basics of how to retire on a sailboat, including the typical cost and other considerations. We'll also cover the top destinations for liveaboard retirees, along with how to complete daily tasks while living aboard. We’ll also show you how to find the best sailboat to retire on.

The best way to retire on a sailboat is to purchase a larger boat that's in good condition and to dock it at an affordable marina. Buying a new boat can make retirement easier and safer.

This article is primarily based on the experience of retired people who currently live on sailboats. We also sourced information from organizations such as the AARP.


Table of contents

How Much does it Cost to Retire on a Sailboat?

Cost is a major consideration during retirement. Sailing is commonly perceived as a luxury activity, so many people are surprised to learn just how affordable it can be. Here, we'll break down some of the biggest liveaboard sailing expenses to help you get a general idea of what to expect.

The Boat Itself

Generally speaking, the boat itself is the greatest overall expense. And when you think about it, it makes sense to spend more on a nicer boat initially so you can spend more time enjoying it and less time fixing it.

If you already have a comfortable sailboat, you don't have to worry about the initial cost. So, how much does a sailboat cost? A well-maintained used sailboat that's suitable for retirement costs anywhere from $15,000 to $50,000 depending on the size, type, and age.

Considering that you'll be living aboard, purchasing a comfortable sailboat is considerably more affordable than buying a retirement condo or home pretty much anywhere in the country. To put it into perspective, the cost of a quality liveaboard sailboat is comparable to the cost of a used single-wide mobile home in many places.

If you're considering a brand new sailboat, the costs are considerably higher. The typical cost of a larger new cruising sailboat exceeds $125,000. We'll use a brand new 31-foot Catalina 315 as an example.

The manufacturer's suggested retail price (MSRP) of this sailboat is $163,000, which is about average for a boat of this caliber. The base MSRP is just for the base-model boat itself. In most cases, a well-equipped Catalina 315 leaves the dealership ready-to-sail for about $215,000 to $225,000.

New Sailboat vs. Used Sailboat

Why would anyone consider spending upwards of $200,000 on a liveaboard sailboat? Actually, there are numerous reasons to consider purchasing a new sailboat for retirement. Modern technology has radically transformed sailing, and new sailboats come equipped with the latest comfort, convenience, and labor-saving options.

On many new vessels, almost all of the rigging can be controlled electrically from the cockpit. Everything from raising the sails to lowering the anchor can be automated, which eliminates the laborious and hazardous aspects of sailing.

Additionally, these vessels come with clean and modern cabins and all the necessities, such as spacious bathrooms, electrical outlets, sound systems, lighting, and cooking facilities. And since it's new, you're not likely to have any problems with it for a long time.

Used sailboats have benefits too, the most obvious of which is the price. Fiberglass sailboats between 25 and 45 feet in length have been manufactured since the 1960s, and there are still many well-preserved examples for sale.

A used sailboat from the 1970s or 1980s can save you a significant amount of money, provided you're willing to spend more time maintaining and repairing it. Don't expect too many bells and whistles on these vessels, but many modern convenience and safety features can be retrofitted with relative ease.


Insurance is a factor that a lot of people fail to consider when living aboard a sailboat. Boat insurance isn't usually mandated like car insurance, but it's a valuable thing to have. Thankfully, sailboat insurance is one of the least expensive necessities for liveaboard retirees.

The average price of sailboat insurance is just a few hundred dollars per year. The price varies based on several factors, including the value of your boat. For a typical used sailboat that's worth about $25,000, your annual insurance cost will be about $350.

As a rule of thumb, you can expect insurance to cost 1.5 to 3 percent of the value of your vessel.

The cost of insurance for a brand new boat will obviously be higher, but there are several ways you can reduce your rate. These include bundling your car insurance (if you choose to continue driving), and you can take sailing or boating training courses. Each insurance company has different requirements for discounts, so be sure to shop around.

The best boat insurance companies are BoatUS (which offers towing and other marine services), United Marine Underwriters, along with traditional auto indemnity companies such as Allstate, Nationwide, Progressive, and Geico. Many liveaboards choose to insure their boats with a marine insurance company such as BoatUS, as these companies offer nation-wide water services such as towing and repair.

Slip Fees

Docking and slip fees are often the highest recurring expenses for liveaboard retirees. These are usually paid monthly, though some marinas work out long-term rates with liveaboards.

Slip fees cover the cost of docking your boat at a marina or yacht club, and they usually don't include club membership fees. Utilities are often included in the price as well, which simplifies monthly bill paying.

On average, the cost to dock a liveaboard sailboat ranges from $600 to $3,000 per year. This is considerably cheaper than rent in most places. That sail, slip fees vary widely between locations and cities. Some marinas charge per foot of length, with prices ranging from $5 per foot to upwards of $300 per foot per year. Next, we'll take a look at the average cost to dock a typical sailboat in five major U.S. coastal cities.

Slip Cost in Miami

Florida is an extremely popular destination for retired liveaboard sailors, and there's an enormous amount of docking infrastructure there. In big cities such as Miami, the cost to get a slip at a decent marina ranges from $1,000 per year to $5,000 per year.

Slip Cost in Cape Cod

The atmosphere in Cape Cod is about as far removed from Miami as you can get. Prices for slips in New England vary widely, but the typical price in Cape Cod starts around $5,000 to $6,000 per year.

Slip Cost in Galveston

The Texas coastline is famous for reasonable docking prices, though costs have increased over the years, and it's not the bargain that it used to be. That said, you can usually find a slip for between $2,000 and $5,000 per year, depending on the marina and how long you stay.

Slip Cost in San Francisco

San Francisco is one of the costliest places to dock in the United States, The most affordable slips in the city rent at an average rate of $18.00 per foot, meaning that a 30-foot sailboat would cost about $6,480 per year. Nevertheless, that's still highly affordable compared to housing costs in the city.

Slip Cost in Chicago

The Great Lakes are an excellent place to live aboard a sailboat, provided you can deal with the cold. The typical cost to dock a sailboat in the city is between $2.00 and $4.00 per foot per month, adding up to between $720 and $1,440 per year.


Utilities are another factor to consider before moving onto a sailboat. Utilities are included in the cost of the slip at some marinas. And while many others don't meter your usage, they may charge an extra monthly fee to allow you to access power and water hookups. Most sailors find that they use much less power and water while living on a boat, which reduces utility expenses significantly.

Property Taxes

Some states and localities charge property taxes for liveaboards. Some states, such as Florida, charge a 6% personal property tax on sailboats. Be sure to check with a local tax attorney to better understand what (if any) tax obligation you could face.


Fuel is an expense to consider even if you don't plan on going anywhere. Sailboats are never hooked up to city gas lines, so you'll need to purchase stove and heater fuel separately. Most sailboats have liquid-fuel stoves and heaters, which run on diesel, kerosene, or alcohol. It's wise to factor in an additional monthly fuel cost of $50 to $150. These figures can double during the winter, especially if you have a large boat.

Repairs and Maintenance

Repairs can quickly increase the cost of living on a sailboat. This is why many people opt to purchase a new boat and ditch the hassle of downtime and repair costs.

Regular maintenance itself is responsible for the majority of these costs. Hauling out, which is necessary to annually scrape the bottom, costs between $20 and $30 per foot. This is without the added cost of scraping or painting the bottom, which costs between $1,000 and $3,000. The total cost of yearly maintenance averages out to about $2,700.


Registering a sailboat is fairly inexpensive in most places. In most states, you can renew your tags for between $100 and $200 if you have a sailboat under 40 feet in length.

Total Cost to Retire on a Sailboat

Based on everything we've covered, the total cost to retire on a sailboat ranges from $5,000 to $10,000 per year, not including the purchase price. Below, we put together a chart of annual sailboat costs along with the initial price of a used and brand new 31-foot sailboat.

Sailboat Type New 30-Foot Sailboat Used 30-Foot Sailboat
Purchase Price $215,000 $20,000
Registration $110 $110
Insurance $3,225 $300
Slip Fees $2,000 $2,000
Utilities $360 $360
Fuel (Heating, Cooking) $450 $450
Total With Purchase $221,145 $23,220
Annual Total $6,145 $3,220

Health and Mobility

Health and mobility are essential factors to consider before moving onto a sailboat. Even the largest sailboats have tight passageways in some places, and the majority of boats have one or two steep steps in the entryway.

If you're still able to perform normal tasks such as climbing stairs and driving, you should have no trouble getting around on a sailboat. Living aboard on the dock is a relatively easy and low-risk proposition.

Embarking on long sailing trips, on the other hand, requires more careful consideration. The best thing to do is to get regular physical evaluations and to talk to your doctor prior to embarking on an extended voyage.

Oxygen tanks and similar long-term treatment devices can be extremely hazardous to use on a sailboat, so those needing long-term daily treatment may want to consider a more spacious powerboat or limiting their boating to occasional excursions. Again, each case is different, so check with your doctor to evaluate your specific circumstances.

Extended Retirement Voyages

Many retirees choose to make extended passages on their sailboats. Everything from local island-hopping to circumnavigation is well within the realm of possibilities to an experienced sailor or retired couple, and numerous groups exist related to this topic.

Recently, Ronna Benjamin and her husband Mike published their sailing chronicles in the AARP "Disrupt Aging" column. Mike, an experienced sailor in his 60s, bought a 49-foot sailboat with his wife and sold their home of 30 years to pursue their dreams of sailing the world.

At one point, Ronna recalled meeting a retired liveaboard couple in the 1990s who lived aboard their boat and enjoyed the tropical environment. Ronna and Mike aren't alone, as the Internet is full of thousands of stories about retirees making long offshore passages and exploring the world on their sailboats.

The most popular destinations for retired sailboat owners are the Bahamas, Hawaii, and various remote Pacific islands such as Fiji. With proper planning, any experienced sailor in generally good health can safely mate these passages, provided they have a well-kept boat that's up to the task.

Keeping Up with Family and Friends

Many retired people worry about giving up-close contact with family and friends if they move onto a sailboat. But in reality, there's no reason why you have to sacrifice relationships to move onto a boat.

This is especially true if you choose a sailboat with a spacious interior. Sailing itself is an excellent way to spend time with friend9, kids, and grandkids. Retirees who live aboard can use it as an opportunity to move even closer to family members, provided that they live near the coast, a river, or a large navigable waterway.

How to Perform Daily Tasks when Retiring on a Sailboat

Retiring aboard a sailboat can make daily tasks such as cooking and doing laundry a bit more challenging. However, where there's a will, there's a way, and malty sailors have already cracked the code. Here's how to make daily tasks easier when retiring on a sailboat.


Here's a great opportunity to simplify your cleaning supplies. On a sailboat, limited space means it's best to find cleaning equipment that serves multiple purposes. A high-quality dust-buster vacuum can replace a large broom, and it can also keep pet hair under control. When finding cleaning supplies for your boat, think small and utilize products that make the most out of limited space.


Cooking aboard a sailboat is much like cooking in a house, except everything is scaled down. Most sailboat galleys have a stove, az oven, a sink, and a refrigerator, but you'll have to downsize your meals and silverware collections. The upside is that it encourages healthy portion sizes, and it's much easier to stay clean and organized.


Laundry can be challenging aboard a sailboat. Some liveaboards do their laundry manually and dry it on the rigging, but this is much too laborious for most people to consider. Thankfully, most full-service marinas offer laundry facilities for a reasonable price. And if your marina doesn't, you can always drop your clothes off at a laundromat or dry cleaning shop.


Bathing is one activity that you won't have to make too much of a sacrifice with, as most modern sailboats come with spacious heads (bathrooms) and on-demand hot water.

Some larger sailboats have more than one head, and others feature a master bathroom with a shower and bathtub combination. You probably won't find a full-sized bathtub aboard a typical sailboat, but tubs are available on many sailboat models today.

How to Find the Best Retirement Marina

How do you choose the best marina for retirement? There isn't a huge number of retired liveaboards, so there aren't any marinas specifically oriented towards retirees. That said, there are many excellent marinas that cater to liveaboards of all kinds.

The first thing to do when choosing a marina is to make sure that they allow liveaboards in the first place. High-end yacht clubs usually discourage the practice due to aesthetic concerns. That said, regular marinas are split about 50/50, and many welcome liveaboards. The easiest way to find out is to call ahead.

The next factor to consider is location. Is the marina within a reasonable distance of shops and medical facilities? Also, it's a good idea to check out the marina and the surrounding area in person to make sure you don't end up in a bad part of town.

Another factor to consider is the condition of the marina and how it's designed. Accessibility is important, as is the condition and safety of the docks. Run-down marinas and docks filled with derelict boats are common and should be avoided. If you like the marina, see if you can talk with some of the residents to get their opinions on the management.

The residents themselves are the final consideration. What kind of people occupy the marina, and do they seem friendly? It's important to gauge the neighbors before renting a slip, just to make sure you'll get along with the people you'll see every day.

How to Choose the Best Sailboat for Retirement

Choosing a boat is one of the most important and exciting parts of the process. Before you begin searching, it's helpful to decide what you're going to do with the boat, how much space you need, and how much you're willing to spend.

Sailboat Size  

Most people would agree that the smallest practical liveaboard sailboats are around 30 feet in length. Many people live on smaller boats, but cramped conditions can become a serious hassle over time. When it comes to retirement, bigger is almost always better.

When it comes to sailboat length, 35 to 40 feet seems to be ideal for most people. Additionally, a boat between 30 and 60 feet in length will fit in most marina slips, and it will likely be seaworthy enough for any reasonable passage.


Unless you're looking for a project boat, it's usually best to spend a little more upfront on a nicer boat that doesn't need any major repairs. It's pretty easy to tell if a vessel has been cared for, so avoid used boats with any signs of mold, rot, or neglect.


Sailboat configuration is another factor to consider before purchasing a boat. Configuration covers things like sail plan, cabin layout, and hull type. Here are a few examples of sailboat configurations.

Most sailboats are fiberglass Bermuda-rigged sloops with a single cabin forward of the cockpit. These vessels are common because they work very well, and most people enjoy their practicality and sailing characteristics.

Traditional sailboats have more complex rigging and require more maintenance, but some of them are more seaworthy and elegant. It all comes down to personal preference.

If retiring and living aboard is the goal, it's essential to consider the layout of the cabin. The best way to judge a sailboat cabin is to actually go inside of it and try to picture yourself living in it long-term. Niche vessels such as catamarans of aft-cabin monohulls are often more trouble than they're worth, as facilities are often separated and require going up on deck to reach.

Features and Comfort

Modern sailboats come packed with modern technology, which adds an enormous amount of features and improves comfort. But virtually all sailboats sold on the consumer market prior to 2000 seem spartan in comparison. Here's a list of helpful features that many newer boats offer.

  • Automatic power control systems
  • Automatic and dimmable lights
  • Automatic climate control
  • Air conditioning
  • Integrated WiFi
  • Integrated navigation
  • Sound systems
  • Dimmable windows
  • Power winches
  • Power halyards
  • Bathtubs
  • Autopilot
  • Solar or wind power generators
  • TV hookups

Some people prefer simpler systems, as they're easy to use and maintain. But by doing so, you may sacrifice comfort and miss out on many of the great labor-saving devices that are available on sailboats today.

Sailing Characteristics

The final major consideration when choosing a sailboat is its sailing characteristics. Factors that affect how a boat sails are its size, hull shape, rig, and displacement. For example, a heavy-displacement sailboat with a full keel and a wide beam will sail slower than most vessels.

However, this type of sailboat will also be more forgiving and offer superior comfort and safety in rough weather.

On the other hand, a lighter sailboat with a fin keel and a narrow beam has characteristics more aligned with a racing vessel. This boat will be fast and agile, and it offers great responsiveness, but it will probably be less comfortable in rough weather.

How to Retire on 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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