
Sailing is a weather dependent sport. When I learned to sail, I would head out on Lake Michigan in heavy wind, light wind, rough seas and calm seas—the best conditions always seemed to elude the confines of class. The same is true for regattas and other large trips planed well in advanced. I worked in an office where I could see a sliver of the lake from our office conference room. I’d look out to see if there were ideal conditions—10 to 12 knots and calm seas. During this time, I had access to my yacht club’s fleet of keel boats so I’d look at the reservations for the fleet only to see, unfortunately, that all boats would be in use.
The only way to avoid this and have unfettered access to the water on your own schedule is to purchase your own boat. What is the cost of this perfect access? I’ll discuss that in this article looking at three categories of expenses: the initial acquisition cost, fixed costs to keep and maintain the boat, and the variable costs that are related to how often you use the vessel. This article is specific to the Chicago boating scene but similar costs and considerations can be applied to sailing grounds around the world.
ACQUISITION COSTS
If you are scrolling on your favorite boat listing website or looking at a classified ads at your local club, you’ll see a plethora of boats ranging from new and well cared for, to boats that need a refit. Depending on your budget, you can keep your acquisition costs as low as a dollar or you can buy a new boat right from your local boat broker. That listing price is just the start, with additional costs to be factored in like a boat surveyor, transportation, rigging and launching the vessel.
SURVEYOR
If you’re looking to buy a new boat, you can skip the surveying of the vessel because it is comprised of new components and should come with some sort of warrantee. If you’re buying a used boat, you will want to get it surveyed. A surveyor is a maritime specialist who will look over a potential vessel and give you a report on the vessel’s structural soundness and status of the systems, including electric, plumbing and engine. This is essential to have done prior to purchase of a vessel to know what you are getting. Surveyors will charge 20 to 25 dollars per foot. If you’re looking at a 35-foot boat expect to pay in the range of $700 to $875.
TRANSPORTATION

Once you have found the perfect boat, you’ll need to get it to wherever you plan to sail. This can be as simple as sailing your new boat to a new slip or as complex as trucking a boat across the country, shipping a boat across from Europe or paying a delivery crew to bring the boat across the ocean.
Local. Starting with the easiest and cheapest option, if you’re fortunate enough to sail a boat to your new slip or if the boat is stored on the hard in the general area, you’ll be sailing it, so this cost is negligible. The next scenario is purchasing boat form the surrounding area and you need to transport it. A friend bought a Merit 25 that had been neglected on a farm in upstate Wisconsin. His transportation cost was gas and a rental of a U-haul. He also had to buy a raccoon trap to remove the family of raccoons out of the hull.
Other coast. If you found your dream blue water cruiser but it’s on a different coast, you can look into a marine transport company. Some associated costs with this method will be de-stepping the mast and fully derigging the boat, possibly dropping the keel or removing deck hardware to provide necessary clearance for the vessel en route.
International. If you are buying a boat from further afield, maybe to take advantage of an exchange rate or you found just the right options you were searching for, you will need to sail it or ship it to you. Yacht shipping is common. Boats are hoisted onto a cradle on the deck of a cargo ship and unloaded at a local port. The TP52 SUPER SERIES utilizes this type of transport, specifically the shipping company Peters & May to move their fleet from the Mediterranean to Newport.
If you were to purchase a boat from a European manufacturer, maybe at boot Düsseldorf, one of the world’s premier boat shows, then plan to sail it on the east coast of the United States, you may want to save the boat the 3,000 nautical mile journey and opt to ship it. Conversely, if you are buying a capable boat that has been properly surveyed you may consider sailing the vessel back to port.
I was fortunate enough to jump on such a delivery from Malta to the boat’s final port of San Diego. I joined the vessel from the Canary Islands to Puerto Rico but the owner paid dockage, flew the crew in, provisioned for himself and five crew, and he bought hundreds of gallons of diesel. I did not ask the final cost, but I am sure this far exceeded the cost of shipping the vessel. The owner in this instance was able to have a two-month vacation and sail half way around the world and cross the Panama Canal.
RIGGING SETUP
The final component of acquisition cost is rigging. This is a variable category that ranges from negligible to requiring a large capital investment. In the case of the 25-foot boat from a farm, my friend and I were able to step the mast with all halyards on it and went sailing that day. If you’re buying a larger boat, or need to reassemble a boat after overland shipping, the yard will change out a rigging fee to step the mast. The yard can also set up all running rigging—the fees vary depending on the yard and size of the mast.
FIXED COSTS

Fixed cost is there every year, no matter if you sail the boat once a year, or if you are the first one in the water and last one in the fall, the cost will remain the same in both instances.
WINTER STORAGE
In Chicago, let’s start looking at these costs at the end of the year. You’ll need to store the boat somewhere when the harbors freeze. You have three options: outside, inside and climate controlled. In fairer parts of the country, you may be able to negate this cost by staying in the water. For outdoor storage, you can leave your boat covered on a trailer or a cradle in a yacht yard. I would recommend winterizing the vessel. In short, winterizing involves covering the vessel, adding stabilizer to the fuel system, draining any water that could expand and adding anti-freeze to plumbing systems. To protect your boat from the harsh winter weather, debris and animals, shrink wrap is a way to seal your boat throughout winter. For smaller vessels, a tarp or canvas cover can work to keep debris out as well.
If you want to avoid the hassle of covering your vessel, yards have a large, unconditioned shed where vessels can stay. These are a great option if you want to take on any large improvement projects like upgrading electronics or replacing deck hardware. The next option is conditioned space which is a heated/ air-conditioned shed. I’ve raced on boats that have been stored in industrial buildings between tenants as well as in air plane hangars, so you can get creative on where to keep a boat. The benefit here is the vessel is not exposed to humidity or temperature swings that can prematurely age a boat. Storage of a 35-ft. boat outside of the city at Manitowoc Marina costs $1,475. If you want indoor heated storage, it costs $9.50 a square foot, so for a 35-ft. boat with a 10-ft. beam, you’re paying around $3,300.

Costs for storage range drastically—if a friend has land, you can park a trailer in exchange for a summer sail and you’re sitting pretty. If you’re trying to store a vessel close to a metro area, expect to pay a premium, but the tradeoff is the vessel is close to you for winter maintenance. Looking at yards further from the city will usually result in saving on cost. If you’re willing to deliver the boat across the lake to southern Michigan or north to Wisconsin, there are yards that do incredible work in Manitowoc and Muskegon at a substantial discount compared to yards south of Chicago. The downside is you could be facing a cold delivery.
SUMMER STORAGE
Sorry to have to talk about the cold! For the warmer months you’ll need a place for the boat to live. If you have a trailer sailor—a vessel you can trailer to a launch ramp or hoist—you will just have to pay a ramp access fee. Most beaches allow vessels to be stored on the beach like catamarans—Gillson Beach in Wilmette is a great beach launch facility for catamarans, as is Lake Forest beach where you can store a catamaran for $519 for residents and $779 for non-residents. Some municipalities offer vessel storage on a pad or parking lot—this requires a crane to launch and retrieve the vessel after every time it is sailed. This system works for boats from 18 feet to the mid-20s, like flying Scotts, Ensigns, and J22s, to name few. These hoists can be found in around the Chicago area in Wilmette Harbor, Montrose Harbor and Belmont Harbor.

This is the harbor in Lake Forest north of Chicago, however these facilities can also be found in Belmont and Montrose Harbor in Chicago, and Wilmette Harbor closer to the city.
The boat on the far left dock with a black sail cover is the formerly raccoon-infested Merit 25 from Wisconsin. (Photo/ Nick Van Antwerp)
Mooring ball. If you’re looking to save some effort and keep your boat in the water, the most economical way is at a mooring ball. This will require a dinghy to access. However, many harbors also offer tenders to take you to and from your vessel around the clock. Fees for moorings are assessed on a per foot basis. Fees are dependent harbor to harbor but are bracketed in five-foot length increments, starting at 25 feet.
Dock. The easiest way to store a vessel is on a dock. Docks allow for the easiest access for crews to load sails and provisions, with the added benefit of having dockside power and water. You will pay a premium for this convenience, but these amenities can be had for varying prices. It’s all about location, location, location. If you want to keep your boat farther from the city center, you can find more affordable rates at harbors like Jackson Park and Montrose, while Burnham and Monroe will be the most expensive.
For comparison, storing the same 35-ft. boat on a mooring in Jackson Park Harbor slightly south of the city will cost a resident of Chicago $1,441.83. While the same boat stored closer to the city in Monroe Harbor would cost $1,887.90, and moving just a few thousand feet north to DuSable, a slip costs $5,146.39 for that same 35-ft. boat.
CLUB MEMBERSHIP

One final fixed cost is a club membership. You don’t need to join a yacht club to sail and many locations don’t have a club. However, if you are planning to use a vessel, the ability to have reciprocity at other clubs is an extremely fun way to explore the lake. I have been fortunate enough to take advantage of neighboring yacht clubs in Milwaukee, St. Joseph Michigan, and Holland Michigan.
Another benefit to belonging to a club is the community of sailors and events you can immerse yourself in. Without a membership, you will still meet amazing people on your dock, taking the tender to your mooring or hanging on the beach rigging your boat. The sailing community will welcome you in.
INSURANCE
Boats can represent a large amount of capital so make sure they are protected. Chicago can be a calm area to sail only during extremely early and late season, but in the heat of summer, especially around events like the Air and Water Show, it feels like all harbors empty in to a congested washing machine of boat wake along Chicago’s shoreline. As the operator of a vessel, you also want to make sure you are protected from damage, any liabilities and incidents that my occur on your boat.
There are some nuances for getting insured outside of the Chicago area. For the Atlantic crossing, the passage was insured by Lloyds of London, it was a tricky policy outside Progressive’s wheelhouse. Many of the large insurers also have exclusionary zones, such as specific latitude exclusionary zones, during historically stormy times of the year. Shop around to find which policy would give you the best coverage. Factors that will affect the cost are the year of vessel, value of the vessel, any financing on the vessel, years of experience operating vessel, paying via a monthly plan or in a lump sum and what your intended use is—pleasure, racing, commercial or some mix of the three.
Registration with the state is another annual fee to account for. In Illinois, this is administered by the Illinois Department of Natural Resources.
REGULAR MAINTENANCE
General upkeep or basic maintenance on systems can include upgrading electronics and rebuilding or replacing deck hardware like cleats, clutches, winches and blocks. Preventative engine maintenance, resealing leaky hatches or any other areas of water infiltration are also common costs. This will vary wildly boat to boat, but you should be prepared to set aside money for whatever may come up. This can be a minor fix, like replacing the pawls in your winch—a Harken winch maintenance kit costs $165.45. Or to replace a Spinlock clutch costs $179.50. Something will always need maintenance and repair.

VARIABLE COSTS
Once you have paid the yacht yard for storage and paid the harbor for the slip, you’re not free and clear yet. Let’s discuss variable costs that you should account for in your budget.
MAINTENANCE
This includes cleaning, system maintenance and engine maintenance. Depending on how often you run your engine will determine your fuel consumption and fuel cost, as well as the frequency of your oil changes—most yacht yards are happy to do this in the winter.
Depending on your standards, you’re going to want to have a cleaning schedule for the boat. Race boats with epoxy bottoms should be done by a diver weekly. If you have anti-fouling bottom paint, you’ll save on hull-cleaning costs, but you need to factor in replacing the bottom paint every five to 10 years. The price of these jobs all depends on your appetite for work and how much you are willing to take on yourself.
RIGGING AND SAILS
In addition to maintenance, you’ll need to factor in replacing standing and running rigging. A set of robust Dacron sails will last about five years before they start to lose their shape. In addition to sails wearing out, running rigging is not immortal—it will eventually need to be replaced. If you keep sheets out of harsh UV light and dry them after every use, you can extend their life, but the more you sail, which means trimming and tacking, you consume the running rigging quicker. Many fleets have classified forums where you can buy lightly used sails that give you a substantial saving over buying brand new sails from the sail maker.
TRAVEL

If your sailing calendar means reaching out into the lake and reaching back with favorable wind, you’ll incur no additional expenses. If you start entering the Wednesday night races, cruising to the amazing harbor towns around southern Lake Michigan and entering the fabulous racing scene—some regattas like the Chicago to Mackinac offer cruising divisions—you will accrue a good bit of expenses.
Also add in transit docking fees to your trip—transit dockage is a few dollars a foot based on the club you visit. Smaller boats will have gasoline engines that are not quite as efficient as diesel but have cheaper fuel, while heavier vessels, 35 feet and are manufactured with smaller diesel engines. These engines consume around a gallon of diesel per hour you run them. If you wanted to sail to Michigan for the weekend and there is no wind for the return, you would be facing an eight to 12 hour motor depending on your vessel.
TRAINING
Please don’t look at the purchase of a boat as the culmination of your growth in sailing but the start. I would strongly encourage you to invest in education. Whether it is going to a racing clinic or hiring a professional to help you find polars and how to shape the sails for your boat. This is, in my opinion, the best money you can spend to increase your aptitude as a sailor and shorten the learning curve on a new boat. You can also pursue your USCG captain’s license. The captain qualifications will allow you work commercially and use your vessel for charter.
CATALINA 32 COSTS VERSUS J/105 COSTS
To illustrate how these fixed and variable cost differ depending on how you want to maintain your vessel, let’s examine two different vessels. Based on the mooring costs discussed earlier, let’s compare the costs to own two 35-ft. sailboats—a Catalina 32 and a J/105. Both are boats I would be confident sailing anywhere in the Great Lakes and are produced by well-respected builders and designers. I broke these costs down as well as links to the boat listings in the chart below.
CATALINA 32

I found a Catalina 32 north of Chicago for $41,000. While there are cheaper options in Annapolis, MD and coastal California, to save money on delivery and shipping let’s go with this local option. This boat does not come with a trailer so it needs to be stored in a yard. If I were to store it outside at Manitowoc, WI, 150 miles north of Chicago, it would cost $1,475. In addition, the yard charges $30 per foot to shrink wrap the vessel prior to outdoor storage.
Assuming this is more of a cruising boat with the occasional regatta entry, there’s no need to dive the bottom so antifouling paint is a great option here. New Dacron sails can be had for $6,000, which includes a genoa main and asymmetric spinnaker, and could last the better part of a decade. Amortized out that’s $500 a year. If you’re looking to improve your skills, Columbia Yacht Club’s learn to race program would improve boat handling and confident shaping sails for the cost of $800 for a six-week class. To maintain the vessel, a bucket soap and boar brush will do the job to keep the deck free of bird droppings.
J/105

To show the variable costs here I also found a J/105 in Milwaukee for sale for $60,000. The vessel would cost the same to launch and survey but let’s look at maintenance and upkeep. The cost to own these two vessels could diverge in the fixed costs and variable costs. If you wanted to store this vessel inside and keep it locally in a Chicago yard for convince, I was quoted $6,700 to drop the mast and get the boat into a shed or $2,415 to keep the boat on the hard—this cost did not factor in winterizing the boat.
New sails. If racing this boat, you are allowed to carry two jibs and two spinnakers. For a sail maker to make two jibs, one main and two spinnakers, it would cost $29,940. Additionally, you should expect to replace the sails periodically, depending on how hard you use them. When spending this kind of money, a sail maker will come on board for a day and help get the boat and sails dialed in. After that, a professional sailor’s day rate can be as low as $300 for someone looking to break in to the industry fresh out of college racing or upwards of $1,400 for someone who has won worlds in a fleet or national championships, especially in a competitive fleet.
Insurance comes at a slight premium because the vessel is an additional two feet longer and if the intended use is racing, $3,187. If this boat was to be kept in Belmont, the same harbor as the above example, but in a slip, the annual cost would be $4,481. Without antifouling bottom paint, you’ll want a diver to scrub the hull semi-regularly. That’s a per foot cost so expect to pay $3 per foot—for a 34-ft. vessel that’s $102 a week, over fifteen weeks in the water that sum totals $1,530.
BOTTOM LINE
In comparing these two theoretical vessels of similar size, the Catalina would cost an owner close to $53,000 the first year and then $11,000 every subsequent year. Whereas the J/105 would cost $91,000 the first year and $30,000 every subsequent year. If you wanted to crunch the numbers, a smaller boat would save you some money and as vessels get bigger, many of the costs associated with the boat’s length will start to compound.
While sailing presents some significant financial hurdles, you can make strategic choices to match your financial means with your sailing dreams. In comparing these two boats, you can have a similar-sized vessel and maintain it for one third the annual operating cost, without sacrificing anything in the way of safety.
CONCLUSION

I have been on a boat that was purchased for $1, where the owner was simply done paying all the fixed costs and wanted the boat gone. This particular boat was stored out of the city on a trailer—the boat required little in the way of winterizing as it had no cabin or fragile systems to protect. The outboard could be taken off and left in a shed or garage. The vessel required little maintenance other than a tarp for storage and new sheets and halyards—it was a great sea worthy vessel. I would not try to cross the lake in it but I was happy sailing it on the coast.
On the other end of the spectrum, I have been on race boats that were stored in heated sheds, docked at a slip in the heart of Chicago, outfitted with the class limit of new sails every year, cleaned weekly by a diver and had a boat captain to replace or maintain anything that may go wrong. A program like that requires a good bit of capital to fund it. All that to say, I had fantastic days on the lake on both programs.
I hope this article and the specific cost breakdown gives you an idea on how to acquire and maintain a vessel with in whatever your budget is. I was fortunate enough to be introduced sailing catamarans off the beach north of the city. This forever instilled the love of the water and has set me on my sailing journey.
Are the cost for winter storage per month or for the season ? It is not specified