Best Trailerable Sailboats

If you are interested in buying a boat but want to keep it stored on land, then the best trailerable sailboats are your only choice

This article may contain affiliate links where we earn a commission from qualifying purchases.

If you are interested in buying a boat but want to keep it stored on land, then the best trailerable sailboats are your only choice

The best trailerable sailboats offer excellent performance for their size and can be used as family sailing boats, coastal cruising sailboats, and even fast day-racers. Catalina Yachts, Hunter Marine, Cape Dory, MacGregor Yachts, and Contessa offer the best trailerable sailboats available today.

While we all dream of owning boats which we can keep on our driveways and pull out for weekend races, many of us have to stick to powerboats as they're much easier to manage. However, if you really love sailing, why not consider your holidays in something which can be carried on a trailer or towed behind your car? You might have to use it only once every few weeks, but when you do go out in it, it will be worth it!

This article is a collection of thoughts and ideas from our expert sailor staff on what they feel are some of the best trailerable sailboats out there today. It's written to hopefully inspire you if you're looking for a new boat or just want to dream about what you'd like to have someday.

Table of Contents

1. Catalina 22 Sport

The Catalina 22 Sport Sailboat is a high-quality sailboat that can accommodate up to four individuals. This boat has been designed with the modern sailor in mind, and it makes sailing an enjoyable experience for any level of sailor.

The boat was built by Catalina Yachts, which was founded in 1969. Today, this company has grown into one of the premier sailboat builders worldwide. They build boats ranging from 16 feet long to 60 feet long, and they offer many different types of boats, including yachts and trawlers, as well as fishing boats and powerboats.

It's no surprise then that their products are prized for quality construction and attention to detail: every single part on a Catalina yacht is custom-made to ensure maximum strength, durability, and performance.

The Catalina 22 is a small boat designed for recreational use. The hull of the boat was built to be exceptionally stiff to travel quickly across choppy waters or large waves without feeling unstable or tipping over. The boat's floor is concave, which creates pockets that trap air inside the boat's floor. This makes for an incredibly stable ride in rough conditions, no matter how choppy they may be.

The hull on the Catalina 22 Sport is designed to cut through the water easily, making it easier for you to sail faster and farther. The deck is also designed for performance, with a self-bailing cockpit that will keep you and your crew dry even in the worst weather conditions.

The mast and boom are made of anodized aluminum, which will not corrode or rust even when exposed to saltwater. The rigging is stainless steel, which resists corrosion and rust as well. All of this means that the Catalina 22 Sport will be ready to sail even when you are not prepared for your next outing: simply wipe it down with a damp cloth and let it dry to ensure that it's clean and safe to use again the next time you go out on the water.

The Catalina 22 comes in two different layouts – an aft cabin version and a standard model without any additional sleeping area. Both versions have a V-berth cabin which sleeps one individual comfortably, as well as storage areas both in the cabin and behind it where you can store away personal items for later use.

Along with its sleek design, this boat also offers many features you don't normally find on boats at this price point (see below). Simply put, there are few other boats out there that offer all these features along with excellent performance and stability in such a compact, affordable package. The Catalina 22 boat is designed to be the best family recreational boat out there.

The Catalina 22 Sport is perfect for small families looking to enjoy sailing without spending too much money. This boat is also ideal for novice sailors who are still learning the ropes. With its sturdy construction and dependable performance, this Catalina can make even beginner sailors look like experts on the water.


  • Price: $5000 to $40000
  • Length: 23 ft 10 inches
  • Displacement: 2380 lbs
  • Beam: 7 ft 8 inches
  • Draft: 5 ft


  • Great value for money
  • Durable fiberglass construction
  • Spacious cabin area
  • Built for speed


  • None that we could find

2. Hunter 27

Are you in the market for a boat to enjoy sailing but have never spent time on the water? Or are you an avid sailor looking for something new? If so, then look no further. The Hunter 27 is perfect for both scenarios because of its affordability and simplicity.

The Hunter 27 is an easy-to-manage trailerable sailboat. The hull is made of fiberglass, which makes it extremely durable, but not weighted enough to break your back when pulling closer up to shore. When you are ready to drop the sails and motor again, this boat takes only minutes.

Let's first address what has changed since its previous model. After years of customer input, Hunter Marine completely redesigned this vessel into something that was much more suitable for novice sailors or fishing hobbyists; they modified the keel depth, added a mid-bow entry-level (more like the front), which increases interior space significantly, moved all live wells/storage below deck for improved stability and added a less complicated drop-sail, that helps beginners avoid common mistakes.

As for the interior of the boat, the seating arrangement is perfect for fishing or just lounging around on an afternoon with friends. The 9.25 ft beam offers space to stretch out after spending hours on the water. However, we must recommend adding more storage because there isn't enough below deck. The table in front of the bow does not come with this boat, so if you want one, you will need to buy it separately

We also suggest that you get some type of cushion for your butt when sitting at the table; it can get very uncomfortable without one. However, Hunter Marine has made the boat very easy to customize. They have left a large space in the back of the cabin that is not sealed, letting you run wires or other options as you see fit. The majority of this space is above deck, but if you prefer something below deck, be our guest!

All in all, this is a fantastic boat at an excellent price. The amount of research that Hunter Marine has put into redesigning this model truly speaks to their dedication to customer satisfaction. If you are looking for the perfect vessel to enjoy the water, then look no further than the Hunter 27.


  • Price: $19,000 to $45,000
  • Length: 27 ft
  • Displacement: 7000 lbs
  • Beam: 9.25 ft
  • Draft: 3.50 ft


  • Easy to manage for beginners
  • Good amount of room, especially in the front (keel)
  • Price! What you get for what you pay is simply unbeatable


  • Poor cushioning on table and seats(add some foam and problem solved!)

3. Cape Dory 28

Cape Dory 28 is the perfect example of what the best trailerable sailboats should look like. Built-in Bridgewater, Massachusetts, the Cape Dory 28 is an American-made full keelboat. The design of this boat is based on the brilliant work of Carl Alberg, who was a well-renowned naval architect and engineer.

This boat has a waterline length of 22 ft and a beam of 8 ft 7 in, giving it plenty of space inside without weighing it down with too many materials, making it stable afloat. The Cape Dory 28 also includes an anchor locker, which keeps your heavy fishing equipment out of sight but still easily accessible. The height from the deck to the hull measures only 21 inches, so this boat can still pull up extremely close to shore despite its size.

Cape Dory 28 construction starts with the frames. The frames are then joined together to make the stringers, bulkheads, and hull plating. The inner skin is then fitted with side-by-side longitudinal battens. Fiberglass cloth is then laid over this inner skin, and resin is used for adhesion. The exterior of the boat is then trimmed with fiberglass for protection against seawater corrosion. This type of construction has been done on Cape Dory boats since 1965.

Onboard sleeping accommodations are comfortable enough for 3 to 4 people at one time. Sleeping arrangements include two V-berths under the main salon, two-quarter berths in the main salon, and a convertible dinette located on its port side. The dinette can be converted into a double berth overnight. This boat also includes an enclosed head located on the starboard side and a galley equipped with a propane stove, oven, and refrigerator.

In addition, the cockpit storage areas contain water compartments for storing fishing gear during inclement weather conditions. In this type of vessel, there are two separate self-draining fish wells in which one can store fat fish you may come across while out at sea. There are twin fuel tanks and watertight bulkheads to prevent leaks in the middle of the ocean.

The only downside to this boat is that it can be a bit pricey if you are on a budget. Despite this, the overall value of this vessel is well worth the price.

Overall, if you are looking for the perfect boat to get away from nature for a few days, then look no further than the Cape Dory 28. This vessel won't let you down, whether you are searching for shallow waters or simply sitting back and relaxing with your friends while at sea.


  • Price: $26000-$45,000
  • Length: 28 ft
  • Displacement: 9000 lbs
  • Beam: 8 ft 7 in
  • Draft: 4 ft


  • Built of durable materials
  • Excellent woodwork by American craftsmen
  • Can sleep up to four people comfortably.
  • Spacious for a 28-foot vessel


  • Pricey--but only if you don't know how to look for deals online or at other retailers

4. Contessa 26

The Contessa 26 is a high-quality cruising-style sloop. This boat was originally made in Canada, but you can find it at various retailers.

Typically, our list consists of boats that are built for fishing and/or living off the grid. However, this time we have included a boat that is capable of taking its crew out into the open seas without fear of breaking down or getting lost.

This boat can be found in both fiberglass and aluminum, ranging from 26 to 27 feet long. Despite its size, it is extremely efficient in fuel consumption. It is also extremely lightweight with a displacement of 5600 pounds, so no need to worry about whether or not your car will be able to haul this vessel around with ease.

The Contessa 26 can cruise at speeds of up to 12 knots. This means it is fast enough for coastal trips but still slow enough for fishing.

In terms of design, the Contessa 26 features an efficient hull shape with a masthead sloop. This is crucial in keeping it afloat if there are any leaks.

The Contessa 26 also includes a drop keel that can be deployed to keep this boat stable when at anchorages. This vessel is aesthetically pleasing and highly functional for any family or group of friends who wants to spend some time out on the open seas.

Another great feature of the Contessa 26 is its self-tacking jib and solid fiberglass construction, along with a foam-cored deck, bulkheads, and hull.

This boat doesn't carry too much weight, either. It has a maximum capacity of 5 people plus its captain--but you'll probably want more room than that if your crew includes more than two people. Its fuel tank capacity is 11 gallons, which is ideal for overnight or weekend trips, though longer trips may require refueling along the way.

The only downside to this vessel is that it may be too small for some purposes. Also, the narrow beam might result in heeling. Additionally, you cannot customize it much in terms of power or materials used.

Before setting out on your next voyage, consider purchasing the Contessa 26 as your vessel. With this boat, you will be able to store enough equipment and supplies without worrying about running out of space. You will also be able to bring all members of your crew along with you without worrying about making them feel claustrophobic.


  • Price Range: $6000-$25000
  • Length: 26 ft
  • Beam: 7 ft 8 in
  • Draft: 4 ft
  • Displacement (lbs): 5600 lbs


  • Lightweight and fast on fuel consumption .
  • Ideal for coastal trips but still slow enough to do some fishing along the way.
  • Can be purchased in both fiberglass or aluminum, depending on your preferences .
  • High-quality cruising vessel that is also perfect for short trips out at sea.
  • Capable of taking up to 5 people
  • Budget-friendly


  • Narrow beam might cause heeling
  • Small capacity
  • Less customizable features compared to its competitors

5. MacGregor Venture 25

The Venture 25 is a great boat for both novice and experienced sailors. This boat features a sloop configuration with a cutter rig, which means it's fast, but it can also hold its ground in relatively rough waters.

Out of all the boats on our list, the Venture 25 has one of the smalled capacities for people onboard--it can hold up to 3 people! That being said, it isn't too small that you are sacrificing comfort or features. It can even reach speeds of 10 knots when at optimal conditions.

The Venture 25 comes with standard tackle, including mast hoops which are crucial for hanging sails effectively. It also includes adjustable backstays. Additionally, this vessel has five opening ports with screens, allowing for good ventilation.

The Venture 25 is made out of fiberglass, which means it can resist some damage that other boats cannot. That being said, the more you use this boat, the more likely it is to scuff or scratch. It is advised that you always keep this boat covered when not in use. The floorboards are aluminum, which is prone to corrosion after a significant amount of time in contact with water and sun exposure.

This vessel weighs a total of 2,300 pounds and has a draft of 15 inches when fully loaded with supplies and equipment. Overall, this boat is one of the most well-rounded vessels on our list. While it's not as fast as other larger boats, its capacity for people and comfortability make up for the lack of speed.


  • Price: $9000 to $30000
  • Length: 25 ft
  • Displacement: 2380 lbs
  • Beam: 7 ft 8 inches
  • Draft: 5 ft


  • High strength-to-weight ratio
  • Low draft
  • Extremely lightweight and maneuverable
  • Fast and agile


  • Small capacity
  • floorboards can corrode quickly if they are not taken care of properly

Recent Articles

Subscribe To Our Newsletter

Thank you! You're signed up for our free newsletter!

Oops! Something went wrong while submitting the form