Sailboats for Sale

Sailboats are incredible vessels designed to offer its owners and guests the thrill of sailing; the feeling of conducting your own boat on the ocean. Search below for these intriguing boats for sale by location, price, size, brand and more.

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Sailboat Buying Guide

What Is a Sailboat?

A sailboat or sailing boat is a boat propelled partly or entirely by sails and is smaller than a sailing yacht under 79ft (24m). Sailboats can come in different styles including high performance, day sailers, racers, outboard motors, and more. Whether you’re looking to buy your next boat, or want to sell your sailboat, read on for more information.

What Is the Difference Between a Sailboat, a Sailing Yacht and a Motor Yacht?

The primary difference between a sailboat and a motor yacht lies in their propulsion systems. Sailboats or sailing yachts use sails to harness the wind for movement, relying on wind power. In contrast, luxury or low cost motor yachts are equipped with engines for propulsion, allowing them to navigate using motorized power. A sailing yacht is typically a sailboat 79ft (24m) and above. Distinctions between what constitutes a sail boat or sailing yacht vary by region and maritime culture. On there are currently over 1,000 sailing boats and yachts for sale, ranging from 14ft (4m) day sailers to 213ft (65m) luxury sailing yachts located around the world – from the South of France to the US, Indonesia, Australia and more in a wide range of prices.

What are the Different Types of Sailboats?

Although sailboat terminology has varied across history, in general, the type of boat may be distinguished by size, boat hull design, configuration, keel type, purpose, number and configuration of masts, and sail plan.

Below are some popular monohull type of sailboats:


The cutter is similar to a sloop with single mast and mainsail, but generally carries the mast further aft so that a jib and staysail can be attached to the head stay and inner forestay. It used to be a common racing configuration, today it gives versatility to cruising boats.


A catboat has a single mast mounted far forward but doesn’t have a jib. Today’s catboats have only the mainsail; however, a catboat can usually carry multiple sails from the gaff rig.

(Sailing) Dinghy

A dinghy is a type of small open sailboat, more akin to a day sailer. Characterized for their short length overall and light weight, which also makes them very easy to handle, sailing dinghies are used for recreation, youth sailing programs, sail training, and tending a larger vessel.


A ketch is a type of sailing yacht with two masts. They are like sloops in this, but ketches have a second shorter mast astern of the mainmast, forward of the rudder. The second mast is called the mizzen mast and the sail is called the mizzen sail. Originally, ketches were fishing vessels; the term “ketch” comes from the same root word as “catch”. Their versatility and ease of use has made them popular, particularly in Northern European waters, where their sail plan allows them to react quickly to varying wind conditions.


A schooner is a type of sailing vessel with fore-and-aft sails on two or more masts, the foremast being always lower than the foremost main. Such vessels were first used by the Dutch in the 16th or 17th century. Originally schooners were gaff-rigged, but modern schooners may be Bermuda-rigged. (A Bermuda rigged schooner typically has four triangular sails: a mainsail, a mainstay sail, the foremast, a forestaysail, and a jib (or genoa) forward of the foremast. An advantage of the staysail schooner is that it is easily handled and reefed by a small crew, as both staysails can be self-tacking.


A sloop (from Dutch sloep) is a sailboat with a single mast and a fore-and-aft rig. A sloop has only one headsail, nevertheless if a vessel has two or more headsails, she is called a ‘cutter’ and her mast may be set further aft than on a sloop. In the US however, a sloop may have one, two or three headsails forward of the mast – the term cutter not generally being used for sailboats. The most common rig nowadays is the “Bermuda sloop” which carries a mainsail on a boom aft of the mast, with a single loose-footed headsail (a jib or a genoa jib) forward of the mast. This is an optimal rig for upwind sailing; consequently, sloops are popular with sport sailors and yachtsmen, and for racing. This type of boat and rig is simple in its basic form and is maneuverable and fast.

The main disadvantage is the relatively large size of the sails, especially on larger vessels. It is also less successful sailing downwind; the addition of a spinnaker in fact is necessary for faster speed in all but the strongest winds, and the spinnaker is an unstable sail requiring continual trimming.


A yawl is typically a two-masted sailboat, usually rigged with one or more jib sails, a mainsail, and a mizzen. Like the ketch, the forward (main) mast is higher than the mizzenmast, but the mizzenmast of a yawl is placed astern of the rudder post (more for balancing the helm than propulsion) while that of the ketch is closer amidships. Like most modern pleasure boats, yawls are rigged with fore-and-aft sails – the most effective rigging in utilizing manpower. The word yawl is sometimes applied to a dinghy or day sailer and to a light fishing vessel rigged with lugsails.

What Is the Difference Between a Sailing Boat and a Motorsailer?

There are many different types of sailboats, and there are various uses for each type. When it comes to sailboats versus motorsailers, the differences are significant. When making a purchase, you want to make sure you’re getting the best sailboat for your needs.


The main difference between sailboats and motorsailers is that while sailboats are powered and propelled by the force of the wind against the sails, motorsailers are a hybrid and can be powered equally by the wind in its sails, as well as internal engines (the ratio of sail propulsion to power can range from 30% sail / 70% power up to 70% sail / 30% power).


Cost is another element that distinguishes sailboats and motorsailers. Purchasing a sailboat can be relatively convenient, depending of course on the type of sailboat – is it a day sailer or 150-foot sailing yacht? Regular maintenance is performed by skilled professionals, insurance, crew, docking, and more is necessary to enjoy the boat and keep its value. The average cost of motorsailers on the other hand, can be quite high, especially when dealing with sailing yachts (i.e. motorsailers larger than 24m). In addition to maintenance and insurance, the fuel, the crew fees, and the yacht management run by specialized companies are to be considered and can make the running costs of motorsailers considerably more expensive.


In terms of functionality, while sailboats can be very technical to run, and one needs to learn the parts of the boat and how to set up the sails and mast in the ideal positions according to weather and wind patterns (although in the case of sailing yachts you must still count on an expert crew); motorsailers can have the option to propel the boat with just the motors – it is common for sailing yachts to use this mode when doing the ocean crossing for instance.

What are the Different Types of Small Sailboats Available?

Depending on what you want to achieve with your sailboat, there are a few different options available. From the smallest to the largest small sailboats, you can choose from:

  • Dinghies – Often what people learn to sail on, dinghies are small, with no cabins and minimal sails. They are the perfect small sailboat to get used to sailing and maneuvering the boat. Some will also race dinghy sailboats.
  • Daysailers – Larger than dinghies but smaller than cruisers, daysailers may have a small cabin or dinette below but the area will be minimal. You’re likely looking at sailboats around 20ft in the daysailer category – again, very fun to get out and learn the ropes on.
  • Cruisers – Small sailboats for sale like cruisers are one step above daysailers. These are created for overnight trips and have a few different cabins below deck. You will also have a kitchen and dining area, head (toilet and washroom), with ample storage.
  • Racing Sailboats – Racing sailboats or performance sailboats are built to go fast and go far. These are ideal for people looking to enter races or regattas with their racing sailboat.
  • Catamarans – A dual-hulled sailing boat, catamarans have increased stability and a wider beam than most sailboats. They may not be able to gain the same speeds as a monohull, but many people enjoy the socializing areas and wider cabin spaces.
  • Classic Sailboats – Classic wooden sailboats are for those who love the classic design of a wood sailboat and the taste of an era gone by. They will require more maintenance and upkeep than more modern steel or aluminum hulled sailboats, but a classic is a classic for a reason, right?

Why Consider Buying a Used Sailboat?

Looking at used sailboats for sale is an attractive option for many, not only due to the cost comparison to newer models, but also because of the history and proven track record the sailboat has. Some other reasons people consider used sailboats for sale includes:

  • Cost – It’s no secret new sailboats carry a larger price tag than older, used models. Boats by nature tend to depreciate in value, so buying a used sailboat means your budget can be stretched further, while buying a used sailboat with plenty of mileage left.
  • More Choice – Maybe you aren’t completely sold on a used sailboat but may want to consider a catamaran or even a classic wooden sailboat. There are a variety of options of used sailboats for sale on the brokerage market, meaning you may discover a make or model you hadn’t even considered.
  • Track Record – With a used sailboat, you get the full history of the vessel – how she sails, how she moves, anything you need to know about the vessel and even tips on where to cruise (or where to avoid).
  • Upgrades – Most sailboat owners put some love and money into their vessel. This means you’ll get an older model, but perhaps the old owner made some extensive upgrades which means your money is going to stretch even further than if you bought a lower end, brand new model.

While considering a used sailboat for sale, weigh your preferences. Although used boats offer benefits, you might prefer the safety and enjoyment of a new sailboat.

What are the Key Factors to consider When Buying a Used Sailboat?

Now that we know why some people prefer to look at the brokerage market for a used sailboat for sale, you’ll want to keep a few things in mind when purchasing a used sailboat:

  • Budget – The right place to start before any boat purchase is to determine your budget. What is the maximum you can afford and how much wiggle room is there? Don’t forget, the sale price is only the beginning – you’ll have to consider annual maintenance costs, storing or mooring fees, insurance and other emergency funds needed should something go wrong.
  • Use – Do you want a performance sailboat you can take to the races, or a larger sailboat you can sleep friends and family onboard?
  • Length – Will it just be yourself using the sailboat, or do you want something that could comfortably fit a family of five for long trips at sea?
  • Condition – Are you willing to do some work if needed? Or do you want a used sailboat in near perfect condition?
  • Sails and Equipment – Be sure to examine all aspects of the sailboat before you purchase, and this includes the sails and rigging. It may be a lot of work unrolling all the stored sails, but you’ll be happy you did in case anything comes up as these can be pricey to replace.
  • Engine – Most sailboats will come with at least a small engine to help power you back to shore should something happen. Inspect the engine and determine hours of use to ensure it’s still in good working order.
  • Electronics – Sailboats are prone to water damage from heeling so inspect all electronics and navigation equipment.
  • History – Especially important if the sailboat spent any time in salt water – as this can be especially damaging to a vessel. Your used sailboat should come with a full history of the vessel, including completed works and cruising history.
  • Survey – You’ll want to entrust a reputable marine surveyor to complete a full review of the sailboat before purchase. This is where anything and everything should be flagged, and you can either negotiate the sale price based on this or decide to walk away.
  • Test Run – An honest owner will offer you the ability to take their sailboat out for a test sail so you can really feel how the vessel moves and operates.

What are the Uses and Passengers of a Sailboat?

A sailboat is normally perfect for cruising, sailing alone and/or racing with a few passengers, however, it usually does not provide the same volume and therefore comfort for living aboard motorsailers. Depending on the size of the motorsailer you can invite a lot more people for the cruise as many motorsailers – 100% of motorsailers above 98ft (30m) – come with cabins to live in.

When deciding whether to purchase a traditional sailboat or a motorsailer, one must consider what the goals are with sailing and cruising; what type of boat is best suited for you?

This list of questions that can help narrowing down the search:

  • Are you a beginner at sailing?
  • What is your budget?
  • Do you plan on traveling long distances?
  • Do you want to have passengers with you, or do you prefer to sail alone?
  • Do you plan on living aboard the boat?
  • What do you plan on using your boat for?
  • Is high performance racing important to you?
  • Do you want an outboard motor to help power you across greater distances?

What are Sailboats’ Pros & Cons?

Traditional sailboats today are used most often for recreation. Cruising and racing are some of the most popular hobbies of sailboat owners. Small dinghies tend to be better for racing.

There are pros and cons for this type of boat:


A sailboat can cruise in lakes, rivers, canals, coastal waters, and, of course, oceans. Many people choose sailboats for quick daytime sailing or weekend getaways, or even small day sailers to play around with on the lake.

Manufacturers use advanced technology to make sailboats sturdier, but light at the same time. This allows them to move swiftly with little wind but remain durable cruise after cruise. Sailboats are the most environmentally friendly water vehicles you can imagine! If you are adventurous and like a solo cruise, sailboats are a great option to experience nature firsthand but also for people who want to learn the process of manual sailing.


Sailboats rely on environmental factors, so unless you are blessed with ideal weather and wind conditions, you may have to wait before hitting the water. Sailboats don’t roll very much; they reach an angle of heel and pretty much remain there. The heel will depend on how much wind you get and how much sail you have. And the sail will depend on how hard you want to push the boat to get to your destination. This process will require some packing up, often more than what is required for cruising in a motorsailer. Also considering sailing boats are propelled partly or entirely by sails, they can be at the mercy of the weather more than a motorsailer.

What are Motorsailer’s Pros & Cons?

Being more comfortable, coming with a lot more space than traditional sailboats, motorsailers are great for long cruises. This type of boat can be customized fully or partially, and usually benefit from a high performance output thanks to the added engine power. You can also decide how you want your own interiors to look and have them as welcoming as your home on land – especially on sailing yachts. You can reach offshore areas comfortably and quickly. It all depends on the boat’s fuel tanks, its rate of consumption and propulsion from the outboard motor. You can get a net gain in speed over what would be possible by just using one method of propulsion. With the right motorsailer, you could also decide to circumnavigate the globe!


Motorsailers allow more comfort and lazy days when you don’t feel like setting up your sails. Rolling on motorsailers can be minimal – you just need to make sure you have ideal bilge keels or gyro-driven stabilizers. Motorsailers can tackle a wide range of weather and sea conditions without damage or discomfort. They’re able to keep up a decent speed even if there is little to no wind. Being bulkier and heavier allows motorsailers to offer more space for accommodation inside the boat.


The wide stern and heavy displacement are not ideal for sailing. The big keels tend to slow down a bit, but many sailors can cruise at a reasonable speed. Some sailors tend to think that because they are built half for sailing and half for powering, motorsailers are only half as good at each. While there may be some truth to this statement, many owners of motorsailers enjoy their power and sailing a great deal. There are many benefits to purchasing (or even renting and/or chartering) a sailboat or motorsailer. Consider the facts and features of each of these boats when you’re choosing which boat to purchase or rent. It’s all about your preferences, your style, your budget, and your needs.

What is the Cost of Buying a New Sailboat?

Besides all the typical mooring, fuel and other certifications, new sailboat buyers will encounter some potential hidden charges:

  • Sailboat survey cost – Whether you’re buying privately or through a boat broker.
  • Add-ons – Does the boat come with essentials like anchors, sails and rigging?
  • Depreciation – Like a car, the value of a new boat sinks quickly after purchase. You’ll want to keep this in mind when the time comes to sell your sailboat.

What is the Cost of Buying a Second-Hand Sailboat?

While you may not be able to customize the boat exactly as you wish, there are often fewer hidden costs to buying a used sailboat. Nonetheless, you will want to account for:

  • Broker’s fee – Choose a brokerage based on positive reviews, if you can find them. You could get a great deal on a bargain fixer-upper, or even an ex-charter boat that looks and sails as good as new.
  • Surveyor’s fee – Recommended for boats already accustomed to the high seas.
  • Maintenance – Examine the boat carefully for signs of wear and tear, as fixing any damage can be costly.

Why are Sailing Boats Popular?

Sailing has been around for centuries for travel and fishing, but it’s only become a sport since the early 17th century. The Dutch are said to be the first nation who raced yachts for fun. They gave a ship to Charles II and the sport quickly became popular in England before being taken up in America. Today, it is a pastime enjoyed by millions of people worldwide – both competitively and non-competitively on lakes and rivers to the open ocean – on day sailers and those that can sleep 12 guests in luxurious cabins.

Living on the ocean sounds romantic, and it can be. Sailing for many is about exploring the far flung reaches of the world and discovering places they don’t yet know exist, all while onboard boats propelled partly by or entirely by sails. Sailing is also an invigorating sport that offers many rewards, not the least of which is that it’s simply so much fun. Those who love the environment, live adventurously and want to enjoy the brisk feel of the breeze on their face, the gentle motions of the boat as it cleanly slices through the water are the perfect sailboat buyers.

Nothing compares to the lifestyle on a sailing boat, the freedom that comes with it and the closeness to the sea this type of boat offers. Not to mention the allure of such yachts in films like the James Bond “Casino Royale”, Daniel Craig sails into Venice on the Spirit 54, a classic British yacht that’s celebrated for its elegance; the 54-foot boat was handcrafted in Suffolk, incorporating mahogany topsides and teak decks. By being featured in these James Bond scenes, the yacht not only shot to international fame, but it also became the first sailing yacht to travel along the Grand Canal in around 300 years.

How Much Is Sailboat Insurance?

The cost of sailboat insurance will depend on a few different factors; however, it’s important to preface this by saying that it is usually much cheaper than car insurance (since generally it isn’t getting as much use or mileage); and usually less than motorboat insurance since sailboats don’t reach the same speeds or danger levels. On average, most won’t spend more than $1,500 a year on comprehensive coverage, but here are a few things that can affect your sailboat insurance premiums:

  • Age of boat
  • Type of coverage
  • Use
  • Sailboat value
  • Operator age and experience

Whether you’re looking to purchase or sell your sailboat, working with a trusted broker is a great place to start.