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11 Best Small Sailboat Brands: How to Choose Your Next Daysailer or Pocket Cruiser

12th oct 2023 by samantha wilson.

Sailing is a relaxing, invigorating pastime that allows you to harness wind and waves in a unique and historic way without requiring a 50-foot yacht to enjoy what’s special about the experience. In fact, small sailboats allow a delightful back-to-basics experience that often gets lost on larger, systems-heavy sailboats.

On a small sailboat you can connect with the sea, feeling the boat move beneath you. The boat is typically easy to rig, simple to sail, and can even be sailed solo. Small sailboats give you the freedom to trailer your or car-top your boat and go anywhere, and they’re perfect for learning the nuances of sailing. There are many excellent brands and models of small sailboat, each with their own appeal, and here we narrow down some of our favorite in the daysailer and pocket cruiser categories under 30 feet. 

Difference Between a Daysailer and a Pocket Cruiser

While there are many different types of sailboat on the market and there is no single definition of either a daysailer or a pocket cruiser, they are used in a particular way, as the names imply. The term daysailer covers a huge array of sailboats, smaller and sometimes larger, and is generally defined as any day boat used for local sailing, with a simple rig, and easy to get underway. A pocket cruiser typically offers a cabin and head, and adequate accommodations for an overnight stay and sometimes longer cruises. Having said that, there is a large overlap between the two in many instances, so the lines may become blurred. 

What Size is a Small Sailboat?

Small is a relative term of course, but in general—and for the purposes of this article—a small sailboat is one that could be sailed by a small crew, often with one or two people aboard. It will have a simple rig and be trailerable, and it might be either a daysailer or pocket-cruiser style vessel as above. Within those categories, there are many models and styles, but when it comes to length we consider a sailboat as small when it’s under 30 feet in overall length. 

The Best Sailboats Under 30 Feet

Pocket cruiser: Beneteau First 27.  The Beneteau First 27 is a modern example of a pocket cruiser, earning Cruising World ’s Boat of the Year award in the Pocket Cruiser category in 2022. With space for up to six people accommodated in a separated bow-cabin and open saloon, it offers families the chance to go farther, explore more, and cruise in comfort. There is a galley with freshwater and a head, adding to the interior home comforts. The sailboat itself is modern, fast, and stable, designed by Sam Manuard, and has been designed to be incredibly safe and almost unsinkable thanks to its three watertight chambers. The handling is also refreshingly intuitive, with a well-designed cockpit, simple deck controls, and double winches allowing it to be sailed solo, by two people, or a small crew. 

Beneteau sailboats for sale

Photo credit: Beneteau

Daysailer: Alerion 28.  You’ll certainly turn heads cruising along in an Alerion 28, a daysailer whose forerunner by the same name was designed by Nathanael Herreshoff in 1912 and then updated with a modern underbody for fiberglass production by Carl Schumacher in the late 1980s. This pretty daysailer manages to combine a traditional silhouette and classic feel, with very modern engineering creating an excellent package. Over 470 of these sailboats were built and sold in the past 30 years, making it one of the most popular modern daysailers on the water. With a small cabin and saloon, complete with miniature galley area, it offers respite from the sun or wind and the option for a night aboard. The cockpit offers a beautiful sailing experience, with plenty of space for the whole family. 

Alerion boats for sale

Photo credit: Alerion Yachts

The Best Sailboats Under 25 Feet

Pocket cruiser: Cornish Crabber 24.  British manufacturer Cornish Crabber has been producing beautiful, traditional style small sailboats for decades, ensuring they honor their heritage both in the construction style and appearance of their boats. The Cornish Crabber 24 is the most iconic of their range and dates back to the 1980s. It offers a simple yet surprisingly spacious interior layout with cabin, galley, and head, and a good sized cockpit, as well as seating for up to six people. It’s the perfect family sailboat, with clever use of storage as well as just under 5000 pounds of displacement providing stability and easy tacking. Aesthetically the 24 is simply beautiful, with a traditional silhouette (combined with modern engineering), finished in hardwood trims. 

Cornish Crabber boats for sale

Photo credit: Cornish Crabber

Daysailer: Catalina 22 Capri.  Catalina sailboats need little introduction, and are one of the world’s best-known, most-respected brands building small sailboats. The Catalina 22 Capri (also available in a sport model) is a great example of what Catalina does so well. While we’ve classified it as a daysailer, it could easily cross into the pocket cruiser category, as it offers excellent sailing performance in almost all conditions as well as having a small cabin, galley, and head. Loved for its safety, stability, ease of handling and simple maintenance, it makes for a good first family boat for getting out onto the bay or lake. 

Catalina boats for sale

Photo credit: Catalina

The Best Sailboats Under 20 Feet

Pocket cruiser: CapeCutter 19.  This is another model that combines the beauty of the traditional silhouettes with modern-day advancements. The design originates from the classic gaff cutter work boats, but today offers excellent performance—in fact it’s one of the fastest small gaffers in the world. The interior is cleverly spacious, with four berths, two of which convert into a saloon, as well as a simple galley area. With quick rigging, it can be sailed solo, but is also able to accommodate small groups, making it a capable and hugely versatile pocket cruiser. 

CapeCutter boats for sale

Photo credit: Cape Cutter 19

Daysailer: Swallow Yachts’ BayRaider 20.  Classic looks with modern performance are combined in Swallow Yachts’ beautiful BayRaider 20. This is one of the most capable and safest daysailers we’ve seen, but also incredibly versatile thanks to the choices of ballast. Keep the ballast tank empty and it’s light and fast. Fill the tank up and you’ve got a stable and safe boat perfect for beginners and families. While it’s got an eye-catching traditional style, the engineering is modern, with a strong carbon mast and construction. While this is a true daysailer, you can use the optional spray hood and camping accessories to create an overnight adventure. 

Swallow Yachts for sale

Photo credit: Swallow Yachts

The Best Sailboats Under 15 Feet

Pocket Cruiser: NorseBoat 12.5.  Can we truly call the NorseBoat 12.5 a pocket cruiser? Yes we can! The sheer versatility of this excellent little sailboat has convinced us. These beautiful hand-crafted sailboats offer exceptional performance and are described by the manufacturer as ‘the Swiss Army Knives of sailboats’. The traditionally styled 12.5 can be sailed, rowed, and motored. It can be trailered, easily beached, and even used as a camp cruiser, allowing for overnight adventures. There is no end to the fun that can be had with this easy-to-sail and easy-to-handle boat, which makes it a dream to learn in. With positive flotation, lots of clever storage, and a full-size double berth for camp cruising, it really is the perfect mini pocket cruiser. 

NorseBoat for sale

Photo credit: NorseBoats

Daysailer: Original Beetle Cat Boat 12: All across the bays of the US east coast cat boats have long been part of the ocean landscape. Able to access shallow rocky coves yet also withstand the strong coastal winds, these traditional New England fishing boats have an iconic shape and gaff-rigged mainsails. Beetle Cat have been producing elegant wooden cat boats for over 100 years – in fact they’ve made and sold over 4,000 boats to date. Their 12 foot Cat Boat 12 is one of their finest models, offering lovely daysailing opportunities. It has a wide beam and centerboard that lifts up, allowing it to access shallow waters, as well as a forward mast and single sail gaff rig in keeping with the traditional cat boats. To sail one of these is to be part of the heritage of New England and Cape Cod, and to honor the ancient art of hand-made boat building. 

Beetle Cat official website

Photo credit: Beetle Cat

The Best Small Sailboats for Beginners

When it comes to learning to sail, it’s important to have a boat that is easy to handle. There’s no quicker way to put yourself or your family off sailing than to start off with a boat that is either too big or too complicated. When choosing your first boat we recommend the following characteristics:

• Small: The benefits of starting off with a small boat are many, as we’ve seen above. They’re easier to control as well as to moor, and they react more quickly to steering and sails. They can be trailered and launched easily, and the loads generated are much lower than on bigger, heavier boats.
• Easy to sail: You want a boat that is stable and forgiving of mistakes, doesn’t capsize easily, and isn’t too overpowered in a stronger breeze. Keep things simple and learn as you go.
• Simple sail configuration: Choosing a boat that can be rigged by one person in a few minutes, and easily sailed solo, makes it easier to take along inexperienced crews. With regards to the rig, all you need are a halyard to hoist the mainsail and a sheet to control the mainsail.
• Tiller steering: We recommend boats with tiller steering over wheel steering when starting out. The tiller allows you to get a real feel for the boat and how the rudder works as it moves through the water. 

For more information on choosing the best beginner sailboat check out our full guide. There are many popular brands of beginner boats including Sunfish, Laser, and Hunter Marlow. Some of our favorites include;

Hobie 16: The classic Hobie catamaran has been a well-loved beginner sailboat for years, and the Hobie 16 started life back in 1969. Since then they’ve made and sold over a staggering 100,000 of the 16s. It has twin fiberglass and foam hulls, a large trampoline, and a pull-up rudder so it can be sailed straight onto the beach. The basic package comes with an easy to handle main and jib with plenty of extras available too such as a spinnaker and trailer. The Hobie 16 promises a great learning experience and lots of fun in a very nifty and inexpensive package. 

Hobie boats for sale

Photo credit: Hobie

Paine 14: You’ll immediately fall in love with sailing when you step into a beautiful Paine 14. Made from seamless epoxy cold-molded wood, the P-14 is simply beautiful and offers the classic sailing experience with the design and innovation of a more modern hull and rig. Two people will be able to enjoy getting out on the water together and learning the ropes. The Paine 14 has a lead ballast keel that accounts for nearly half her weight, giving her the feel of a much larger boat, but is still trailerable and easy to manage offering the best of both worlds. 

Chuck Paine boats for sale

Photo credit: Chuck Paine

High-Performance Small Sailboats

Small sailboats generally become high performers if they are light, have a lot of sail area, or they have more than one hull. More recently, some of have been designed with foiling surfaces, as well. For the purposes of this article, we’d like to close by pointing out one model that is super fast and has versatile pocket-cruising capabilities.

Corsair 880 trimaran : The Corsair 880 trimaran is the grandchild of the company’s F27, a model that launched the popularity of trailerable leisure trimarans about 40 years ago. The 880 has taken the model to new heights and exemplifies the incredible space benefits you can achieve in a 29-foot sailboat. We’re talking an aft cabin, room to sleep 5 people, an enclosed head, and standing headroom in the galley and main saloon. It brings many of the opportunities that a much larger yacht plus the ability to cruise in extremely shallow water. Whether you want to cruise to the Bahamas or enjoy a high-adrenaline race, the Corsair 880 offers incredible performance and unlimited adventures in a truly pocket size. 

Corsair boats for sale

Photo credit: Corsair

Written By: Samantha Wilson

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: Samantha Wilson

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Ultimate Guide to the Best Small Sailboats [2023 Reviews]

When I first started looking into buying a small sailboat I found it all very confusing.

I had learned to sail in the San Francisco bay on fairly large keelboats. (J-22, J-105s, Beneteau tktks, etc.)

But I didn’t nessarilly have the money or time to justify the investment in a big yacht like that.

ANd when I started looking at the different classes of small boats out there, it took me some time to try to understand the different kinds.

So I put together this post to try to organize that information.

So if you’re in the market for a small sailboat keep reading and I promise you’ll get a better understanding of everything out there. Tk

Advantages of Buying a Small Sailboat

There’s nothing wrong with owning a large sailboat (if you have endless time, money, and patience.) But there are some advantages to going with a smaller boat. Here are a few of the big ones:

• Cost to Buy – You can purchase a nice used dinghy for under a grand. Or you could get yourself a trailerable weekender for a lot less than you might think.
• Cost to Own – Owning a larger boat can get expensive fast. Just add up the costs of financing, docking, maintenance, insurance, fuel, etc. A small sailboat may allow you to fulfill your dream of being a boat owner without going broke.
• More Options Available – Another nice thing about small sailboats is that there are a ton of different options available. I list over 100 down below along with their size, and an estimate of the purchase cost. You’re sure to find something you like.
• Easier to move – Getting a large keelboat in and out of the water is no easy task. Trailering it around on land is a huge pain and can get expensive. Most of the dinghies and day sailers listed below can be moved by just a couple of people and a good trailer. And you won’t need to go out an buy a dedicated vehicle just to hull the thing around.
• Easier to Sail – Do you plan to race, cruise, or live on this boat? You may find that small sailboats are surprisingly better than larger options.

100+ Small Sailboats Compared

5 questions to answer before buying a small sailboat.

Before you run off and buy one of these boats, take a second to answer the following 5 questions. These aren’t difficult but this simple step will ensure you get the right sailboat for your needs

1. How many people will be using this boat? Small sailboats are obviously not designed to carry a ton of people. So you should buy the size that will best fit your needs. If you plan on being the only person to sail in your sailboat, then you can opt for a smaller sized personal dinghy. If your plan is for two, three, or four people to be on the sailboat at once, then you’re going to need a bigger boat

2. Where do you plan to sail? What kind of sailing do you want to do? The sailboat you buy will need to be appropriate for the environment you’ll be sailing in. Open ocean sailing is different from sailing on a small lake. The style of sailing you want to do matters as well. Do you want to race your sail boat or are you just looking to cruise around? These are things that you have to consider before you buy your small sailboat. If you’re planning to sleep overnight on the boat you will want to look at weekenders. If you get a boat that is not fit for the environment you are in, then you could wind up in a dangerous situation. Or at the very least, have a bad time on the water.

3. How will you be transporting your new sailboat? You also need to think about how you are going to get your new boat to the water. You can haul a small dinghy in almost any trailer or truck. But for other boats you’re going to need to get a specialized trailer. You can look into private professional boat shipping companies. They will handle transport for you but will generally be more expensive.

4. Where will you store your boat? Now you need to think about where you will store the small sailboat. Will you be docking at a marina? Be sure to include docking fees in your budget below. Or do you have space to keep the boat in storage in your garage? Make sure your spouse is okay with this first!

5. How big is your budget? (time and money!) Your budget will also help you narrow down which size and model boat is right for you. New sailboats are more expensive than used. Bigger boats are generally more expensive than smaller boats. Don’t forget to factor in all the extra costs of owning a sailboat. Be sure to consider things like insurance, docking fees, repairs, and transportation. Finally, make sure you have enough time to make owning a boat worthwhile. Often it’s better to make friends with a boat owner, than to become one yourself!

Mike Sellers