What You Need to Know Before You Buy a Sailboat - Five steps to prepare for the reality of boat ownership | Modern Sailing

What You Need to Know Before You Buy a Sailboat - Five steps to prepare for the reality of boat ownership

Are you new to sailing and already dreaming about buying your first boat? There’s something so alluring and romantic about the idea of buying a boat, cutting the dock lines, and sailing away. This powerful allure is the fuel for a sailing industry that thrives in spite of sailing being perhaps the most impractical mode of transportation that exists in modern times. The idea of sailing is so alluring, in fact, that we often hear about people buying boats and simply casting off, not letting a lack of experience stand in their way. 

On one hand, we are impressed by their chutzpah and we root for them. On the other hand, we know that the reality of boat ownership will catch up with many of these starry-eyed newbies sooner or later, who may end up walking away (or running) and selling their boat for much less than was invested in its original purchase, repairs, maintenance, cleaning, berthing, insurance, and upgrades.

The truth is that unless you’re financially very comfortable and can afford to pay others to take care of the grittiest aspects, buying a boat can be in some ways like having a baby – it’s a huge responsibility! All those who come aboard your boat are putting their lives into your hands. Boat ownership can be messy, expensive, risky, stressful, exhausting, and will test your patience. The immaterial rewards can be immeasurable and well-worth these challenges – otherwise we wouldn’t pursue this nonsensical endeavor with such ineffable devotion! (A difference between boat ownership and parenthood is that your child won’t ever leave you in the sea to drown. Or so one would hope!)

Many of us who work for Modern Sailing are, or were at one time, boat owners ourselves, or are directly involved in the care of our fleet, so we have some perspective to offer on this subject. We are dreamers too and nothing thrills us more than aiding and witnessing others making their own sailing dreams come true. Our intention is never to scare you away from your big dream, but as a sailing school, one of our core motives is to help others prepare for the real risks and challenges that come with those cherished dreams. We hope you’ll find this article helpful as you prepare to buy a boat of your own.


1. Learn to Sail Before You Buy a Sailboat
2, Learn What Kind of Sailing You Love to Do
3. Learn About Your Preferred Boat Features and Designs
4. Learn About Sailboat Maintenance, Repair, and Troubleshooting
5. Connect to Community to Support Your Goals
6. How Long Does This Process Take?
7. Need Some Advice?

1. Learn to Sail Before You Buy a Sailboat

There’s a huge learning curve involved both with sailing and with boat ownership. Combining the two at the same time can be a recipe for overwhelm. We often hear stories about intrepid souls with little to no sailing experience who buy a sailboat, read books and watch videos to learn how to sail, and figure out how to repair and maintain the boat’s myriad systems along the way. Some have risen to this challenge, and while we are mightily impressed, we don’t recommend it for everyone! We’ve also heard many stories about some of those intrepid souls who eventually discovered that they, their significant other, or their child(ren) actually hate sailing. Or, they realized that owning a boat costs more in terms of time and money than they can afford. Or worse, their lack of experience led to disaster. The reasons sailors bail out of boat ownership are many and can often be avoided with smart planning and preparation.

We recommend to not start everything all at once. A rational, phased-in approach to your sailing dream will invite enough of the rewards to keep you emotionally invested through the challenges as they come.

Start by not only learning to sail, but by learning whether you and anyone you hope to involve actually enjoy the kind of sailing you dream of doing. Take some sailing lessons, join a sailing club, and expose yourself to as many weather conditions as you possibly can – preferably on OPBs (other people’s boats). In the process, you’ll find out how much you actually enjoy sailing and how well you can tolerate it when conditions are less than ideal.

Some might say they don’t want to waste the time and money on sailing lessons. But, considering that those who come aboard your boat are putting their lives in your hands, and anyone attempting to rescue you from a serious mistake may be putting their life on the line too, we tend to think the investment in lessons is well worth it. Also, you’ll learn the common language for boat parts, lines, and maneuvers, which will make you a better crewmate and a more effective skipper and leader for your own crew someday.

While you’re learning to sail, you’ll be very safe with a US Coast Guard licensed captain as your guide. Experienced instructors know a lot about what can go wrong on a boat, and how to prevent, troubleshoot, and manage problems as they arise. A good sailing instructor will allow you to make minor mistakes as a natural part of the learning process, but will quickly step in to prevent errors that could lead to injury or damage. There isn’t one sailor or instructor on the planet who knows everything about sailing, but the more people you sail with and the more often you sail, the more you will learn, and the better you’ll be prepared.

This level of preparation is worth every penny and every minute, and then some. You are laying a solid foundation of safety and seamanship that will serve you well and contribute to your enjoyment of sailing over the years. Eventually you can even become a valued mentor and the dollars you invested in the beginning will also contribute a legacy of sailing enjoyment for many others.

As you progress in your sailing education, if it turns out you feel less enthusiastic about the realities than you first imagined, you will only be out the cost of lessons and not the cost of an entire boat plus everything you spent on it after buying it. If you enjoy sailing but decide to downsize your goals, you can always continue sailing on OPBs as a member of a sailing club, racing team, or social group. 

2. Learn What Kind of Sailing You Love to Do

There are many types of sailboats built for different purposes and waterways, and to know which type is right for you, you’ll need to find out the answers to these questions:

  • What kind of sailing do you love to do? Are you interested in performance sailing and racing, casual day sailing, extended cruising, or maybe all three?
  • Will you stick to sheltered inland waters or do you want to explore the coast? Will you ever want to cross an ocean?
  • What is the biggest sailing goal that you hope to achieve with your boat?

To explore these questions, join a race clinic and try out racing. Go on a few overnight and multi-day charters in the Bay. Join a Pacific Coast Expedition or a Global Destinations Flotilla to get a feel for the ocean. Once you have your ASA 104 certification, take your closest companions on a bareboat sailing charter somewhere exotic and beautiful for a taste of the cruising lifestyle. These are the best ways to find out what kind of sailing you love to do – and therefore what type of sailboat will be best for you.

With prudent weather planning, just about any kind of sailboat is up for the job of crossing an ocean, so we won’t delve into the topic of bluewater boats versus coastal cruisers. However, know that due to weight, ballast, and hull shape, some boats' motion will be more comfortable in a seaway than others. Simply know that it takes time to learn about all the different sailboat models, configurations, and builds, and which are ideal for which purposes.

Take the time to learn what kind of sailor you are so you will know what kind of sailboat you want. There’s also nothing wrong with starting with a boat that’s not well-suited for your biggest sailing goal, as long as you understand and intend before you sign on the dotted line that that this will be your “stepping stone” boat.

3. Learn About Your Preferred Boat Features and Designs

In-mast furling mainsail or lazy jacks and stack pack? Dual helm or single? Monohull or catamaran? Pullman berth or centerline? In-line or U-shaped galley? Do all lines lead to the cockpit, or will crew need to go the mast? The possible configurations of boat features are endless. How will you know what your preferences are until you have sailed a variety of boats and experienced for yourself?

This is one of the best advantages of membership with a sailing school or club. You’ll get to try out a wide variety of boats and learn what features and layouts you like and dislike. This will greatly help inform a wise choice of boat for your purchase.

Take your time learning about different sailboat types and designs. One fun way to learn is to simply hop onto YachtWorld.com and look at boats in your price range. When you see something that catches your interest, do some Internet research on the model. Look for a model “owners’ forum” to see what kind of sailing the model’s owners do and what kinds of common complaints they may have. You’ll learn a lot about boat models on the market this way. When you’re seriously shopping for a boat, you’ll know more about what you’re looking for and what you'd prefer to avoid.

4. Learn About Sailboat Maintenance, Repair, and Troubleshooting

There are thousands of parts and pieces on a sailboat, and all of them are continually embattled by the sun, wind, and saltwater. Only your constant care will keep your boat shiny, safe, and seaworthy.

You may have heard some of these bleak euphemisms about boat ownership:

  • "BOAT stands for Break Out Another Thousand."
  • "A boat is a hole in the water that you pour your money into."
  • "Cruising is mostly just repairing boats in exotic places."
  • "The two best days in a boat owner’s life: the day you buy the boat and the day you sell it."

As you learn to sail with others, you will inherently begin to learn about some of the common (and uncommon) problems that crop up on sailboats. In the process, you will begin learning from your instructor(s) and fellow sailors about boat systems and how to keep them running. 

In addition to the mechanical skills you’ll need to develop for self-sufficiency on the water, be prepared for the costs. It’s a common belief that a boat’s annual maintenance and repairs will cost 10-20% its purchase price – every year. Sometimes it ends up being less than that, sometimes more. Our advice is to always budget for more.

For example, the standing rigging will need to be replaced every 10 to 15 years, and depending on the size of the boat, it can cost $2,000 to $20,000 or more. (Costs increase exponentially with every foot of length.) If you buy an older $20,000 boat and the engine croaks, you can wind up spending another $10-15k or more on a repower alone. An unfortunate incident like wrapping a line around a propeller or a grounding can cost thousands to repair. That’s only three small examples of the countless costly repairs that boats can need. (At Modern, we’ve seen it all!) Don’t forget about the costs of berthing and insurance too.

Don’t let all this scare you off, but give you pause to slow down. Strategize your sailing goals carefully. When you are prepared for the costs and technical challenges, it’s possible to own a boat and go cruising even on a shoestring budget.

There are also alternatives that can help minimize the costs of boat ownership. Sharing ownership (partnership) is one alternative, but ensure you have a legally enforceable agreement with someone you mutually like, respect, and trust. 

Placing your boat in a charter fleet under a Yacht Management Services agreement can help ease the burdens of ownership substantially. When you are not sailing your boat, vetted sailors can pay the charter company to sail her, and you will receive a share of the revenue to help offset the costs. The charter company will also manage the details of berthing, cleaning, maintenance, etc. A disadvantage is that it might not be easy to go sailing spontaneously. You'll have to place an advance reservation on your boat if you want to take her out. Other than that, keeping your boat in a charter fleet means that she will contribute to the learning and enjoyment of others while helping to earn her keep. 

5. Connect to Community to Support Your Goals

There’s an international maritime rule that requires all mariners to give aid to other mariners in distress, as long as doing so doesn’t jeopardize their own vessel and crew. And as diverse a community as we are, those who are drawn or addicted to sailing automatically share something compelling in common. Stemming from this rule and our shared passion is a general spirit of helpfulness and supportiveness among sailors.

If you jump right in and buy a boat, chances are you will soon connect with a neighbor or neighbors in your marina. Favorite topics of conversation among boat owners is about their biggest mistakes (and commonly other people's mistakes) and their boat’s most vexing issues, so it’s quite possible to pick up knowledge just by talking to other boat owners. Not all, but some sailors will even volunteer to come to your boat and help you troubleshoot. You’ll find this spirit of comraderie and helpfulness in marinas, yacht clubs, anchorages, and seaways worldwide.

A sailing school that is also a charter club offers more than just sailing lessons and certifications. It provides ample opportunities for sailors to practice and learn with and from each other. If you sail frequently, your skills, confidence, and community will grow quickly. Using social sailing forums and tools like the GoSailing app and attending sailing seminars and workshops, boat shows, and other social events for sailors like Latitude 38’s Crew List Party can also help you get connected. Modern Sailing’s weekly newsletter email also helps keep you informed about opportunities in the Bay Area for sailors to connect with and learn from others. Remarkably, when you express genuine enthusiasm and passion for sailing, you will attract others who will feel inspired to help you learn and get connected to the resources you need.

While we all have a responsibility to be as self-sufficient as possible, it’s great to know you always have a community to fall back on when you need a sounding board or get into trouble. One day, you will come across a sailor in need, and remembering all those who helped you on your journey, you will be glad to take your turn as a helper or mentor in your community.

6. How Long Does This Process Take?

In our experience, we have seen sailors go from absolute beginners to boat owners in about 1.5 to 3 years. Of course, you can go faster or slower depending on your schedule, budget, and goals.

The photo featured at the top of this article is of a former student and member, Koren Leslie Cohen, seated on the deck of her very own boat, Sugar. Click on the names to learn about how Koren, Warren HolybeeScott Corder, and Ken and Linda Hargreaves went from beginners to boat owners in only three years.

7. Need Some Advice?

Are you still feeling unsure about where to begin? Give us a call at (415) 331-8250 or send us an email. Our friendly office team can help you build a sailing education plan to prepare you with the skills and confidence you'll need to get underway.

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  • Steve Hood, Basic Coastal Cruising

    I would definitely recommend Modern Sailing to anyone who is interested in learning to sail the right way.

  • Rolf Zingg

    Since many, many years, I had the dream to sail underneath the Golden Gate bridge. On October 14th last year, my dream became true. Thanks to our dear friend Aaron Fritz who made it possible and organized this cruise for us. With this adventure I was able to achieve one more milestone on my sailing career.

    Finally on the water, it was great! Full moon made the flows even stronger and it was like sailing in a washing machine.

    I did my sailing education in the English Channel, where the situation with the wind and flows is comparable to the San Francisco Bay. So I felt pretty much "at home" being on the helm in the Bay.

    I hope our skipper Stan Lander enjoyed this day cruise too. We, definitely did! It was an unforgettable experience for all of us.

    A very big thank you to all of you who made it possible, that my dream became reality! Also thank you for the MSC flag I got at the end of the day. It found it's place in my study, where I can see it daily.

    Rolf Zingg
  • Alisa Driscoll, Dual Site Member

    Here are some snaps of Our Saturday, August 20, 2022 Modern Sailing Expedition with Captain Robert Bivin, who was outstanding. Please convey photos and thanks to him. He is an outstanding individual, leader and sailing instructor. His knowledge and experience made us all feel safe and our Farallones Day Trip educational and just amazing. 

    Alisa Driscoll

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Modern Sailing School & Club

Sausalito Location
2310 Marinship Way, Sausalito, CA 94965
(415) 331-8250
(800) 995-1668

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1 Spinnaker Way, Berkeley, CA 94710
(415) 331-8250
(800) 995-1668

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