7 Best Sailboats Under $20,000

Best Sailboats Under $20,000 | Life of Sailing

Last Updated by

Daniel Wade

December 27, 2023

You can buy a fully-equipped and serviceable sailboat for less than $20,000 on the used market. Most of these vessels are fiberglass sloops.

Used sailboats between 20 and 30 feet in length can be found for between $10,000 and $20,000 nationwide, especially on the coast. Catalina, O'Day, and Islander sailboats are common in this price range and lots of fun to sail.


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What to Look for When Buying a Used Sailboat

When buying a used sailboat, it's essential to carefully inspect the vessel and look for flaws and structural issues. Sailboats in this price range are often ready to sail or just need minor improvements.

For the price, an older fiberglass 20 to 30-foot sailboat should be in good to excellent condition. Here's what to look for when buying a used sailboat and what to expect in the sub-$20,000 range.

Overall Condition

The overall condition of the boat is important, as it gives you an idea of how well the vessel was maintained. A sailboat with a clean, glossy hull, a solid deck, fresh varnish, and polished brass is an excellent sign of a responsible owner.

However, a sailboat with rust, corroded aluminum parts, a filthy hull, and a moldy interior was likely neglected in more ways than one. The first impressions of a sailboat can give you a pretty good idea of what lies below the surface.

Hull and Deck

Fiberglass boats are quite impervious to weather and corrosion, but problems occur when water penetrates the hull. Soft spots form around areas where the fiberglass cracks and water permeates.

Look for 'dented' areas of the deck where water pools up, as deformities can be a sign of something worse going on underneath. Check the bilge for excessive water but be mindful that some boats came with 'wet' bilges.


Does the vessel have all of its standing rigging tightened and maintained? What about sails, halyards, and sheets? If the rigging is present and neatly organized, it's a good sign that you're getting your money's worth.


If the vessel has an inboard motor, check the condition and fire it up. Inboards can be an expensive nightmare if they're neglected, which is often the case on used sailboats. See how it runs and make sure it responds to forward and reverse.


Sailboats are notorious for poor wiring and electrical issues. Much of the time, sailboats were shoddily wired from the factory, and sometimes the issue is related to improper maintenance or water damage.

Check the switchboard and make sure everything works. Try the radio, cabin lights, engine starter, hydraulic systems, and bilge pumps. A few broken lights or dead outlets are acceptable, but an electrically-neglected vessel can be a nightmare and a navigational hazard.

Best Affordable Used Sailboats Under 20k

Owning a used sailboat is a great way to explore local waterways and occupy the weekends. Sailboats made by well-known manufacturers were produced in huge numbers in the 1960s, 1970s, and 1980s.

These vessels are seaworthy and affordable, which makes them an excellent choice for budget-friendly sailing. Here are seven of the best used sailboats for under $20,000.

7. West Wight Potter 19


It's difficult to omit the West Wight Potter 19 from a list of the best affordable sailboats for under $20,000, as this vessel is exceptional by almost every metric. The West Wight Potter 19 is the ultimate small trailer sailboat.

The vessel is a V-bottom sloop with a fiberglass hull and a centerboard. It was introduced in 1971 and has since become very popular from the United States all the way to Australia. It's a hardy coastal and inland cruising vessel that's made occasional offshore trips, including one from San Francisco to Hawaii.

It measures just under 19 feet overall and has a width of 7 feet 6 inches. With the keel up, it has a draft of only 6 inches, making it a beachable and trailerable cruising boat.

For its size, the West Wight Potter 19 has spacious accommodations below. It features a center-mounted split galley with a stove and a sink, along with space for a head below the stove.

A V-berth upfront offers sleeping quarters for two, and two additional berths aft bring the comfortable capacity up to four. The centerboard trunk in the center of the cabin features rigging to raise, lower, and lock the centerboard.

The West Wight Potter 19 features a fast-rigging system that allows one person to raise and rig the mast in just a few minutes. It's easy to sail, safe, and plenty of fun. Plus, the hull features positive floatation foam, which makes it quite literally unsinkable.

6. Contessa 26


The Contessa 26 is a unique and capable mid-sized sailboat. It's a fast boat and a common sight at long-range regattas like the singlehanded TransPac race from San Francisco to Hawaii.

The Contessa 26 was produced starting in 1966, but the design dates much further back. The basic hull shape of the Contessa 26 was based on a Nordic Folkboat designed in the late 1930s for speed and agility at sea. As it turned out, the design also proved to be quite seaworthy.

The Contessa 26 was produced up until the end of the 1970s. She measures 25.5 feet overall, with a waterline length of 20 feet. The Contessa 26 has a reasonable beam of 7.5 feet, giving it good stability and seakeeping characteristics without sacrificing speed or handling.

The Contessa 26 is not a trailerable sailboat by most definitions, as it weighs 5,400 lbs and has a 4-foot draft. It has a full ballast keel, which makes it a stout offshore sailing platform. That said, its relatively small draft makes it safe to operate in shallow inland waters.

The accommodations of the Contessa 26 are excellent for its size, and it comfortably sleeps between one and five adults. It features standing headroom, a basic galley, a head with shower, and a standard V-berth upfront.

Space below leaves much to be desired, as vessels like the Catalina 30 outshine it significantly. But overall, the Contessa 26 is an excellent cruising sailboat with a classic design and sharp performance.

5. Catalina 30


The Catalina 30 is one of the best used sailboats available for coastal and offshore cruising. If spacious accommodations are important to you, then you can't go wrong with this 30-foot Catalina sloop.

The vessel features a tall and stout Bermuda rig with an aluminum mast and standard rigging. The Catalina 30 measures 29.92 feet overall, with a length of 25 feet at the waterline. With a beam of 10.83 feet, the Catalina 30 is a wide and stable vessel.

Catalina 30 sailboats feature a long fin keel and a relatively deep 5.25-foot draft, which requires care when operating in shallow water. However, offshore the Catalina 30 has proven to be a seaworthy and well-handling vessel.

Overall, the Catalina 30 weighs just over 10,200 lbs. She's not exactly trailerable, but most marinas can haul out a Catalina 30 without too much trouble.

Interior accommodations on board are stellar. With sleeping room for seven adults, the Catalina 30 is a fantastic family boat. It features a full galley, a head and shower, a chart table, and a spacious dinette.

Over 6,000 Catalina 30 sailboats have been produced since 1972, making it one of the most popular sailboats ever built. A decent used Catalina 30 can be had for around $10,000 to $15,000 on the used market.

4. Islander 28


Another popular and classic 1970s fiberglass sloop is the Islander 28. Launched in 1975, the Islander 28 is an affordable and well-handling sailboat with a reputation for durability and seaworthiness.

The Islander 28 is a masthead sloop with a spade rudder and a fin keel. It displaces 7,000 lbs and has a relatively wide 9.83-foot beam. The Islander 28 measures 27.92 feet overall with a waterline length of 23.08 feet.

Islander sailboats are some of the most common vessels of the 1970s and 1980s. And though not as numerous as the Catalina 30, the Islander 28 is still a popular boat on the used market.

Islander 28 sailboats aren't exactly shoal draft, but their moderate 5-foot draft means they're safe to operate in most harbors. And while not technically trailerable, the Islander 28 is small and light enough to be hauled out and repaired in most boatyards.

The Islander 28 sleeps six adults comfortably and features full accommodations below. These include two seats, a galley, a table, a head with shower, and a V-berth forward.

An Islander 28 is a wise choice for coastal and offshore cruising. It's a stout, safe, and fun boat for the family, and it's easy for moderately experienced sailors to handle. A decent used fully-equipped Islander 28 can be found for less than $20,000 on the used market.

3. Compac 23


Compac is a well-known sailboat manufacturer with a long history of producing swift compact cruising boats. The Compac 23 is a large sailboat in a miniature package.

This vessel is ideal for those looking for a small and easy to handle sailboat with spacious accommodations. It features a fiberglass hull, an extensive cabin, and a shallow draft of just over 2 feet.

The Compac 23 has an overall length of just an inch shy of 24 feet, and a beam of 8 feet. Its dimensions make it stable and easy to handle, and it doesn't heel excessively. Overall, the Compac 23 displaces 3,000 lbs.

The interior accommodations of the Compac 23 set it apart from other vessels in its size category. The interior features a separated galley with a sink and a stove, seats, and a V-berth upfront. It also has plenty of well-thought-out storage space throughout the cabin.

The Compac 23 is also available with a pilothouse configuration, which features standing headroom and a clever table arrangement aft. The vessel features a skeg rudder and a long fixed fin keel, which removes the cumbersome centerboard trunk from the cabin.

2. Cal 25


The Cal 25 is a formidable cruiser for its size. While technically a fin-keel sailboat, the Cal 25 features a long ballast keel that offers superior stability and windward performance.

Some would consider the Cal 25 a "flush-deck" sailboat, as the top section of the cabin runs flush with the bow to the cockpit. This design increases cabin space and improves the lines of the boat.

The Cal 25 was produced between 1965 and 1976, making it one of the older fiberglass sloops on our list. That said, Cal Yachts build quality is excellent, and many serviceable examples of the 1,848 original Cal 25 sailboats still exist.

The vessel measures 25 feet overall, with a waterline length of 20 feet. She has a beam of exactly 8 feet and a relatively shallow draft of just 4 feet. The Cal 25 has a modest displacement of 4,000 lbs, making it a relatively practical trailer-sailer option.

The Cal 25 usually came with an outboard motor instead of an inboard to save space. The helm is controlled by a tiller, which maneuvers a skeg rudder located underneath the cockpit. With the mast collapsed, the Cal 25 is a great sailboat for winter storage and summer use.

The level of fit and finish varies between boats, as some were outfitted with finer wood and more premium features than others. The cockpit is spacious for its size, and the cabin headroom is excellent. The Compac 23 is an ideal used shoal-draft cruising sailboat in the sub-$20,000 category, and it's still produced today.

1. Catalina 22


The Catalina 22 was the first sailboat of countless families across the United States. This sleek 22-foot vessel was designed to be the perfect 'starter boat' for sailors who wanted to explore inland waterways and coastal areas.

The Catalina 22 was first introduced in 1969. It has an overall length of 21.5 feet and a beam of 7.67 feet. Catalina 22 sailboats are truly trailerable, as most come with a retractable swing keel. With the keel or centerboard down, the Catalina 22 has a draft of 5 feet.

The Catalina 22 is the most popular sailboat ever produced in its class. With over 15,000 built, this vessel is common on the used market, and parts are abundant. Overall, a standard Catalina 22 sloop weighs around 2,490 lbs, making it practical to tow behind most half-ton pickup trucks or V8 SUVs.

Fiberglass boats like the Catalina 22 are an excellent choice for first-time sailors looking for a fun and capable family boat with overnight accommodations. The Catalina 22 sleeps four adults comfortably, but five can fit if the crew are comfortable with a tighter arrangement.

The most unique feature of the Catalina 22 is its camper-like pop top. The top of the cabin, which normally provides sitting headroom, can be popped up several inches past the original height. This is an excellent feature for cooking at anchor, as it provides standing headroom over the galley and part of the settee.

Pre-owned Catalina 22 sailboats in ready-to-sail configuration run anywhere from $5,000 to $15,000. Fiberglass sailboats like the Catalina 22 make excellent freshwater or saltwater daysailers, and some have completed lengthier offshore voyages.

7 Best Sailboats Under $20,000
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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