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Buying a Sailboat: What You Need to Consider

You may have been dreaming of owning a sailboat all of your life. And now is the time to go for it and take the plunge into boat ownership. Or perhaps you’ve owned motorboats before and feel the need for a change and a new challenge? Whatever your reasons, buying a sailboat is an exciting prospect, and the beginning of a whole new journey and lifestyle. 

Starting your search for the perfect sailboat can seem daunting. There are many different types, styles, models, and sizes of sailboats cruising our oceans and lakes, so trying to hone in on the perfect one may be difficult. Where do you start? Our guide to the Different Types of Sailboats offers a good overview if you don’t already have a direction worked out.

Even assuming you already have an idea of what you’re looking for, we can help you look at the factors you should consider when buying a sailboat, decisions you’ll need to make, and top tips for settling on the right choice. 



sailing boat


5 Key Factors to Consider when Buying a Sailboat

Your first step is to sit down and be completely honest with yourself as you consider what exactly you need from your boat. Note that we say ‘need’ and not ‘want.’ Of course there are things you’d like to have, if possible, and by all means add those to your decision-making list, but what you really need from your boat should be at the top of that list and will help you narrow your choices. Things to consider when buying a sailboat include:


What sort of sailing do you plan on doing?

This is the most important question when buying a sailboat and will be the deciding factor in choosing the right style. If it’s day sailing on a lake, you might want a small, affordable sailing dinghy, whereas that obviously won’t work for your coastal and bluewater cruising aspirations. Do you want to stay aboard your boat for long stretches of time? Sail across oceans? Cruise up and down the coast with family and friends onboard? Sail in an occasional race or compete every weekend? Narrow down the options as your first step.


Who will be sailing with you?

This will be part of the decision in what size sailboat you buy (but not the only one, as we’ll see below). Will it be only you and a friend or spouse? Will the kids be coming along as well? Or do you have entertaining groups of friends in mind? You’d be surprised (or perhaps not!) how many friends want to join you for weekends when you own a sailing yacht. Combine how many people will be sailing with you to determine how much cockpit space you’ll need, how many berths, and what size galley. 


What is your budget?

Buying a sailboat is a process of compromise for most people. What we want isn’t always what we can afford, and it’s vital to be realistic about how much you will be ready to spend on a boat. The sale price is only the beginning of boat ownership costs, as you need to factor in annual storage fees, maintenance, insurance, and upkeep. Check out our guide to The Real Costs of Owning a Boat for more information, as well as inspirational ideas of how you can Reduce the Cost of Boat Ownership. It’s very easy to overspend on the boat up front and not leave enough in the budget for a refit on a used boat, a trailer to tow it, new electronics, or sails, etc. A common way to approach buying a used sailboat is to only use half of your budget on the boat itself, and the other half on a refit or upgrades. 


Where will you keep your boat?

You’ll need somewhere to store your boat year round, and you need to weigh up several factors including how accessible or close by your boat will need to be, how much you can afford, and is it suitable for both winter and summer? Smaller sailboats can be trailered and may be kept in your yard for the most accessible and low-cost option, but larger boats will need a mooring or slip and then be hauled and winterized at the end of the season. For more, check out our guide to Storing Your Boat Year Round


Do you have the time and/or experience needed to own a sailboat?

Think first about your free time, and then factor in the preparation and maintenance that a boat needs and halve it. While a lot of maintenance can be done in the off-season, leaving you more time to enjoy your boat in the boating season, it’ll still need cleaning after each outing, which takes up your time. Also, will you be able to sail it by yourself? Or will you have to synchronize your schedule with others? 


You also need to be honest with yourself about your sailing experience and ability. Buying a boat that is too big or too complex to handle is the quickest way to get demoralized about sailing. Always go for a simpler or smaller boat than you think you need and enjoy it. It doesn’t have to be your forever boat, and you can upgrade as your confidence grows in a few years. Check out our guide to Choosing the Best Beginner Sailboat as a good starting point. 


sailboat blue sea


Buying a Sailboat: A Checklist of Decisions to Make

Once you’ve thought about the 5 key factors above, it’s time to start narrowing down boat types and configurations. The list can be long when it comes to detailing everything you may want or need on a boat, but the following checklist offers a good start toward fine-tuning your choices.


  • Do you need a bluewater cruiser, coastal day boat, or inshore dinghy?
  • Do you want a monohull, catamaran, or trimaran?
  • Does the boat need to be light enough to store it on a trailer?
  • Do you want or need a boat with shallow draft, with either a shoal-draft keel, centerboard, or daggerboard?
  • Will the boat have a single rudder on the centerline or twin rudders?
  • Would you like a new or used boat? (See our article on new versus used boats for more on that) 
  • How many cabins should your boat have, if any?
  • Would you prefer an aft or center cockpit?
  • What kind of mast and sails would suit you best? A standard sloop configuration or a specialty set-up such as cat rig, ketch, schooner, yawl, or cutter?
  • To reduce sail area in high winds, will you use roller-furling sails or more traditional reefing systems?
  • Do you want a performance-oriented sail configuration including, for example, a large full-battened mainsail or should you choose a smaller, cheaper, simple-to-handle main with less sail area.


Tips for Buying a Sailboat

  • Charter first. The best way to discover what you like and don’t like is to experience first hand what it’s like to sail it in different wind conditions and simply spend time aboard, on deck and below. Consider chartering different style yachts to see what works best for you and your family. Bareboat charters allow you to be in control of the boat for the duration of your charter, which also gives a more realistic insight into what life would be like—it’s an option to have a paid captain aboard to take the helm while you lounge on deck with a cocktail in hand, but that won’t quite be the reality on your own boat! It also allows your family to see what they think of it. You don’t want to buy a new sailboat to find out the motion makes someone horribly seasick. 
  • Start small and trade up. Your first sailboat doesn’t have to be yours forever, so buy one that suits you now, rather than one you plan to grow into. There are many benefits to keeping your boat as small as is comfortable and practical for your needs; it’s cheaper to buy and cheaper to run, it’s easier to handle, needs fewer crew aboard, plus the upkeep is less, as are the slip fees. In fact, you might not even need a slip if you can trailer it. As a general rule, things start to get more expensive over the 23-foot mark. While it’s possible to buy an easy-to-sail, affordable 30-foot boat, it will cost you more in moorings, insurance, and maintenance.
  • Do your research. Research, research, and research some more. The more you know about sailboats and the current market (both for new and used boats) the better placed you’ll be to make a good purchase and investment. Talk to boat people, head down to your local marina, charter if possible, look online, ask questions on forums. When it comes to purchase prices, knowing what the market value for a boat is will ensure you don’t overpay. You can start by searching through the thousands of sailboats for sale on Rightboat to see what’s in your budget. 
  • Don’t be swayed by a long equipment list. An impressive equipment list is often used as a sales tactic, but try not to be swayed. Replacing or buying new equipment can often be cheaper than the extra they’re asking in the listing price. Navigational electronics get outdated quickly, too. Focus on the condition of the boat itself and not the cosmetics. 
  • Take safety seriously. Don’t scrimp on the safety provisions you need on your boat. Make sure you keep enough in your budget to buy everything you need for the size of the vessel you’ll be sailing, the number of people on board, and your sailing location. That could simply mean good, wearable lifejackets and a robust first-aid kit for a small boat, or an ocean life raft, EPIRBs, SOLAS-rated life jackets, a VHF radio with AIS, bilge pumps, and a satellite phone if you’re heading far offshore. 
  • If it doesn’t feel right, walk away. Trust your gut instincts if something doesn’t feel right. There will always be another boat, and you don’t want your exciting boat-buying dream to end up as a nightmare because your boat needs huge amounts of expensive repairs. Boaters are friendly folk, and the buying process is usually enjoyable. But keep in mind that this is a business transaction and try to stay objective and unemotional. Getting a good marine survey will help reassure you it’s a good investment (read our article Do I Need a Marine Survey? for more). 
  • Consider boat size carefully. Ok, so we’re going to contradict ourselves here. Above we recommended buying a smaller boat and upgrading when you are ready for something bigger, which is sound advice, but you also don’t want to buy a boat that is way too small. Going up 10 feet in length can double the volume of your boat, and if you know you’re going to be spending long periods of time onboard, that space becomes invaluable. To find your sweet spot, this might be a good time to charter a 32-footer with another couple for a week and then decide. 
  • Be wary of buying a super cheap boat. Seeing a rock bottom price tag on a sailboat can be extremely tempting. Who doesn’t want a bargain? But be wary of massively underpriced boats because they could cost you far more in refit and repairs than you can imagine. Yes, there are great bargains to be found, but if it feels too cheap, then it probably is. Have a read of our article Buying a Cheap Boat: Is it a Good Idea? for more. 
  • Discover the best places to buy a sailboat. These days, there are many places to look for a boat for sale.
  • Boat-sales websites: Websites such as Rightboat.com offer you the chance to do a detailed and specific search by entering the type and style of boat you’re looking for along with the length, location, and price bracket. You’ll be able to look through detailed photographs and videos, see full specifications, and make contact with the private seller, dealer, or broker.
  • Boat brokers and dealers: Most brokers and dealers sell both new and used boats, and they may either sell a wide range of brands and models, or specialize with one or two brands. Working with a broker can offer reassurance, as they are experts in their field and often know the boats they’re selling inside out. When buying a new boat, they can also help you to customize it, include extras in your package, such as trailers, and offer boat-finance options.  
  • A local boat show: There are hundreds of boat shows annually across the world, from local and regional shows to famous international events. Visiting a show can be a great way to search for your next boat, and it allows you to climb aboard the latest models, compare similar boats, and sometimes even go for a sea trial.
  • Find out exactly how to buy a sailboat. Before embarking on your boat-buying journey, read our detailed, step-by-step guide to Buying a Boat. Knowing how the process works will give you confidence to go ahead, ensure you don’t miss anything, and ensure you get the best boat for your money. 


sailing boat sunset


Are you ready to start your sailboat-buying journey? Then check out these fabulous Sailboats for Sale in your area on Rightboat and you could be soon be setting sail. 



John Burnham is a marine ​editor and writer with ​decades of journalism experience as ​Chief Editor of​ boats.com,​ Sailing World, Cruising World, and ​other boating websites. As a competitive sailor, he has led teams to world and national titles in the International One-Design, Shields, and other classes. Based in Newport, Rhode Island, John is a​ PCC leadership coach, a member of the ​America’s Cup Hall of Fame Selection Committee​, and a ​past board member of Sail America and US Sailing. For more, see johnsburnham.com.


Samantha Wilson has spent her entire life on and around boats, from tiny sailing dinghies all the way up to superyachts. She writes for many boating and yachting publications, top charter agencies, and some of the largest travel businesses in the industry, combining her knowledge and passion of boating, travel and writing to create topical, useful and engaging content.

More from: John Burnham / Samantha Wilson

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