Updated July 2nd, 2023
If you are new to sailing and want to get a boat, what should you get? There are tons of sailboats out there on Craigslist, eBay, and Marketplace. Prices can range from free to a hundred thousand or more. What should you get for your first sailboat? Keep reading below to learn a little more about sailboats and what you should look for. I also have my picks for the best small sailboat for beginners.
What makes a sailboat good for beginners?
I learned to sail in middle school and have done it regularly since then. I spent my college summers working as a children’s sailing school instructor at a few yacht clubs around the US. I’ve raced sailboats a ton too on all kinds of boats from collegiate buoy racing too overnight long distance races. After years of doing this, I am way more of a go sailing for fun kind of guy than someone who lives for the competition.
For anyone thinking about learning to sail, it’s not that hard to learn sailing basics. You can teach yourself watching Youtube vidoes but it wouldn’t hurt to take a sailing lesson just to learn the basic sailing terms and see a live hands on demonstration of how to sail.
Here is what I have learned over the years for which boats make learning to sail easier.
Easy to sail
You need a boat that is easy to sail. You don’t want to get a boat that capsizes super easily. You want a stable boat that can tolerate some mistakes without sending you into the drink. You want a boat that isn’t too overpowered so it won’t feel terrifying if the wind picks up while you are out.
Easy to rig
You want a boat you can rig and put together easily. If it’s a trailerable boat you need a mast you can put up and down without hurting your back or needing a bunch of tricks. A racing boat with a lot of sail controls may have a ton of things you need to hook up when rigging it and lots of adjustments depending on wind conditions. A recreational day sailing boat may have very few. As a beginner sailor looking for a boat, less is more. You want something that leans towards, lift the mast, put the sails on, hoist, and go.
Small size
What exactly is a small sailboat anyways? A read an article recently in a popular sailboat cruising magazine. They labeled a 36 footer as a “compact cruising yacht”. There is nothing compact or small about a 36 footer. Bigger sailboats react slower to steering and sail controls. A larger boat will have a lot more momentum when you are trying to get on and off the dock. The bigger the boat, the more load and force on all the lines and sails.
I recommend learning to sail first on something simple like a Sunfish. A little 14 foot sailing dinghy that can hold 1 or 2 adults. If your more ambitious and want to start with a boat you could go cruising in then a Catalina 25 or 27 are good choices. You really should not go any bigger than that for your first boat. A Catalina 30 weighs twice as much as a Catalina 27 and you can’t just easily push it around the dock. A 30 footer should be saved for your second or later boat.
Dinghy vs keelboat
Your first sailboat can be a dinghy without a keel or a keelboat. Small keelboats can make really good learning boats. With most keelboats you don’t need to worry about capsizing. If you go with a dinghy get something that is easy to upright.
Flying Scots are used for learning sailboats in many places including a sailing club I used to belong too. They are big stable and tubby. They are horrible to upright if you do manage to capsize them. You will need help from a powerboat to do it. If you go for a dinghy with no keel, it is better to stick to 15 feet or under so you can upright it without outside help. The 16 to 20 foot dinghy is where it can take some skill to self rescue yourself after a capsize if it’s possible at all.
If you decide to get a 20 to 25 foot keelboat, it is easiest to keep them at a marina with a hoist or preferably in the water. Trailer launching keelboats is a challenge even with a swing keel because of how deep you need to get them in the water to float off the trailer.
Minimal sail controls
When you learn to sail, all you really need are a halyard to hoist the mainsail, a sheet to control the mainsail. You don’t really need anything else to be adjustable. That is all you need to sail upwind, downwind, or any other point of sail. Everything else is extra for a beginner.
1 or 2 sails
When you learn to sail all you need is a mainsail. The near perfect learning sailboat is the Sunfish which has a lateen rig with only 1 sail. It has really simple controls and you can rig it wrong and it will still sail for you.
It is okay to learn to sail on a sloop rigged boat with 2 sails. A mainsail and a headsail or jib. Stop there.
You don’t need a spinnaker. Ask anyone who has raced sailboats and they will have stories about what went wrong with a spinnaker. Spinnakers are responsible for breaking more stuff on a sailboat than anything else.
There are boats out there with 2 or more masts such as a ketch or yawl. The second mast is called a mizzen mast. Don’t even think of getting one of these either. It’s just more distraction and things that can break or go wrong. You don’t want a cutter rigged sloop. These have 2 headsails which you again don’t need or want.
Tiller steering
Your first boat should have tiller steering. Don’t get a boat with wheel steering. The wheel mechanism has a lot of drag and slop in it and you won’t feel how the boat is reacting. A tiller lets you immediately feel the boat is out of balance. A tiller is easier to learn to sail upwind with by learning to push it towards or away from the sail. Wheel steering is less intuitive. Stay away from that big cruise with a wheel.
Trailerable boats vs marinas
I grew up in central Pennsylvania where we had small lakes to sail on. This meant a trailerable small boat when we got our first sailboat. I currently live in Michigan near the Great Lakes. Most boats I’ve had as an adult have lived at a marina and not at my house.
If you want to sail more often, keep it rigged at a marina so you have to do the very least possible to get it out on the water. I use my sailboats way more often when I don’t have to hook it up to a car, drag it to the lake, rig it and do the reverse to go home. The downside is cost. Keeping even a Sunfish at a marina or yacht club can cost a lot.
If you want to experience sailing on a low budget, trailering smaller boats is a fine way to go. If you want more convenience and your willing to pay for it consider keeping your boat rigged at a marina.
Portable boats (multi-section hull or inflatable)
There are a few new entries in the boating world that focus on making the boat easier to store and transport. These involve either inflatable hulls or a folding or multi-section hull. These let you store the boat in your garage, large closet or spare room. You can fit them in the back of a small SUV for transport without roof racks or a trailer. 2 great examples of these are the Tiwal inflatable sailboat and Minicat inflatable catamaran.
Commonly available and easy to get parts
Stuff will break on your sailboat if you use it enough. Some parts on a boat are really generic such as pullies, blocks and lines. Other parts are not such as boom or mast end fittings, rudders, etc… There are a lot of cheap boats out on Craigslist. There are a million old 15 foot 2 person sloop rigged sailing dinghies out there in people’s yards. Before buying any of these make sure that all the parts are there. Do not buy one without seeing it rigged with sails up first.
If your not sure find an experienced sailor friend who sails to go look at it with you. If anything is broken look up to see if you can get a replacement part. For many of these old boats, replacement parts are impossible to find which is why they are being given away for not much or free.
If a boat has an active racing class still, there is a good chance replacement parts are available. Racers go out in high winds and push the boat which means they break stuff. Boats like a Sunfish or Laser that are still produced and raced all over are easy to get sails and spare parts.
Keep it inexpensive
When you are buying your starter boat, know that it won’t be your last boat. You will learn what you like and don’t like and you’ll want another boat. There is a disease among sailors called “Threefootitis”. No matter how big a boat you buy, you will always want one at least a 3 feet bigger boat. Don’t spend a ton on your first sailboat. There are tons of Sunfish out there for under $1000 and even under $500. I once got one for free that was still in racing condition. The biggest boat you should consider, something like a Catalina 27, can be had for well under $5000. Under $10,000 for a fully optioned one with wheel steering and a diesel inboard.
See our guide to how much does a small sailboat cost to learn more about what it costs to buy a sailboat.
My top 8 picks for the best small sailboat for beginners
1 – Minicat Inflatable Catamaran
Minicat makes a line of inflatable catamarans. They are available in a few sizes and suitable for children up to a few adults. Minicat’s use an inflatable hulls with a multi-piece mast and trampoline. The whole thing can be put away in 1 to 2 bags that are 6ft x 1ft x 1ft. They will easily fit in the back of an SUV with the rear seats folded or easily tied to a roof rack.=
The Minicat can hit high speeds just like a solid hulled catamaran. They have a full length fin down each hull to generate power. They are as fun to sail as any traditional hobie cat or other beach catameran but much easier to transport and store.
The Minicat 420 is their most popular design. It is about the same size as a Hobie 14 and good for up to 4 adults. You can learn more about or get one from Great Lakes Watercraft.
2 – Tiwal Inflatable Sailboats
Tiwal makes a line of 3 inflatable sailboats. They range from a basic dinghy to a performance racer. They are capable of sailing with 1-3 adults and children depending on the model. They break down into bags that will fit in the back of most people’s cars.
They use modern rigs with furling or reefing options so you can use them in a variety of winds. They use drop-stich construction to be able to create a v-hull that gives good performance on the water. The Tiwal 3R has hiking racks for even more performance.
Tiwal sailboats have been seen on Below Deck Sailing Yacht. They are one of the favorite water toys for people cruising on big boats. They let anyone try sailing with a small, easy to transport, and affordable package.
Visit Tiwal.com to learn more about their sailboats.
3 – Sunfish
I personally learned to sail on a Sunfish. It is still one of the best sailboats to learn sailing on. It is a super simple boat design that is easy and fun to sail and virtually anyone can rig or launch it.
Sunfish are small, 14 foot sailboats with a lateen rig that only has a main sail. They are sometimes referred to as board boats. They have a flat deck you sit on top of. These are common at beach resorts around the world so almost everyone has seen one at one point or another.
They are extremely simple to rig. You put the mast through the sail/booms and into the hull. There is one halyard to raise the sail. They have one sheet to control the sail. Racers have figured out ways to rig more controls but chances are, any boat you buy used won’t have them. 2 adults can easily fit on a Sunfish for sailing around.
Sunfish are very forgiving and easy to sail. The square sided hard chined hull makes them feel stable in the water even in a lot of wind. If you do capsize they are easy to upright and self bailing.
New Sunfish are still being built and they are raced in many places so parts are sails are easy to get. If you do feel like giving racing a try, chances are there is somewhere you can do it. The boats are sturdy and durable.
To learn more about Sunfish go here.
4 – Laser
A Laser is another 14 foot 1 or 2 person sailboat that falls under the board boat category. They are very common and raced all over the place. It is the most popular racing sailboat in the history of sailing. They are currently an Olympic class boat as well. They have been raced at the Olympics in every summer games since 1996.
Lasers are less stable and capsize easier than Sunfish. They are a bit faster and higher performance for those wanting a little more oomph. They are still manageable for beginners. They are one of the easiest boats out there to upright after a capsize. If you choose one, take it out on lighter wind days until you get the hang of it. Don’t start out on a day with lots of wind and white caps or you will probably spend the whole day capsizing over and over.
Lasers are available with different sized sails. The most common version is the standard laser. The next most common is called the “Laser Radial” which has a smaller sail and mast. Some boats will have both. If it’s your first boat I strongly recommend looking for a boat with a Radial rig.
The thing to watch for with Lasers is their mast step. This is where the mast goes into the hull. If you are looking for one, pour a glass of water into the hole and see if it stays there or drains into the hull. If it drains into the hull, walk away from that boat. The weakness of these boats is the mast to hull joint which weakens with time and lots of use. If the mast step holds water it is fine.
To learn more about Lasers go here.
5 – West Wight Potter 15/19
West Wight Potters are very small cruising keelboats. They come in 15 and 19 foot versions. The 15 footer can be towed behind almost any car. The 19 footer needs a good sized SUV like an Explorer. They are very simple sloop rigged boats without any extra racing controls. They have keels and are stable. There are lots of them out there and they are still being made.
These aren’t the fastest or flashiest boats out there. They are easy to rig, easy to sail and you can do trailer cruising on them. These are for sail regularly on Craigslist and Marketplace. They are known to be solidly built without any common failure points.
If you are looking for a small keelboat you can learn to sail with and tow around these are a great choice.
To learn more about West Wight Potters go here.
6 – Catalina 25 and Catalina 27
Dinghy sailing isn’t for everyone. Some people are more interested in a cruising boat they can go places with and stay over night. If that is you then a Catalina 25 or 27 is a great choice. Catalina 25 and Catalina 27s are 2 of the most common small cruising keelboats out there. They were built from the 1970’s through late 1980’s. There were thousands of both of them built. I have owned 2 Catalina 27’s and had a ton of fun on both of them. They are easy to sail, dock and take care of. They are at the large end of what you should consider for a beginner sailboat but still manageable.
Both boats were available with lots of options. Catalina 27’s can be simple with tiller steering and outboards. They can be more decked out with wheel steering and diesel of gas inboards. Catalina 25’s are the same although they are all tiller steering. Catalina 25s have either a fixed feel or a retractable keel for trailering. As a trailer boat they are huge and you’ll need something like an F350 to tow it.
For your first sailboat, look for a tiller steering, outboard motor, fixed keel version. Look for a boat with a roller furling headsail. This makes the boat much more easy to manage. You can reduce sail area by partially rolling up the headsail if it gets too windy. This is much better for your first boat then buying one with multiple sails that hank onto the headstay that need changed as the wind changes.
Do some more research into the boat for problem areas such as deck core rot or “Catalina smile” before buying one. Price wise, you can find them for $1000 to $10,000 depending on options and conditions.
To learn more about Catalina 25’s go here. To learn more about Catalina 27’s go here.
7 – Hobie 16/14
Hobie 16’s are the most popular beach catamaran in the world. They are common at beach resorts all over the world. I have owned one of these before too. They are also actively raced so parts and sails are easy to get. The Hobie 14 is the slightly smaller and less popular little brother. Both are available used all over the place for cheap.
Hobies are a ton of fun to sail. You can go really fast flying a hull in one. If you get one of your first sailboat use a bit of caution on when you take it out until you get used to it. Don’t start out on a day the wind is nuking and hope it will go okay because it won’t.
These are fairly easy to rig. This is the most complex boat I would ever recommend to a beginner. The mast can be challenging to raise and lower but there are easy ways Macguyver it and make it not so bad.
They do not tack easily upwind. Like all multihulls they can get stuck in irons easily when pointed into the wind. Sometimes you have to give it a little backwind and opposite rudder to get spun through the wind. It’s easy with a little bit of practice. It won’t tack as easily as a monohull.
To learn more about Hobie cats go here.
8 – The 2 person 14 foot sloop rigged sailing dinghy
There are tons of this type of boat available used everywhere. There isn’t any single one that is widespread around the US to mention a particular design. There are tons of 420’s and Flying Juniors, Capri 14’s, JY15’s, Islander 14’s, etc… out there. They are all meant for 2 people. They all have a sloop rig with main and jib and a retractable centerboard. They all aren’t that hard to rig. They all can be trailered behind any car.
They can be sailed by one person in light winds or 2 people in almost any wind condition. They can be self rescued by 2 people after a capsize without help. Keep this in mind if you think about sailing it alone on a windy day.
As mentioned earlier in the article. The thing to watch out for with this type of boat is making sure all the parts are there. Make sure it is in sailing condition before you buy it. If something is broken make sure you can replace it before buying it.
You might also like:
- How Much Does A Small Sailboat Cost? Big Fun For Small Money
- How To Pick The Best Windsurfing Equipment For Beginners
Doug Ryan
Co-Founder & Chief Editor
I grew up back east in Pennsylvania and learned to ski on a family trip to Killington, Vermont when I was 6. I immediately fell in love with the mountains and outdoors and have been skiing across the US and Canada ever since. I went to school for Mechanical Engineering, and have a Master’s Degree in Material Science and Reliability.
I am a total gear nerd and love learning how things work and thinking about how they could be improved. Nothing excites me more than trying out new gear. I’d rather spend 3 hours taking my bike apart and learning how to change something than go to a bike shop. These days I reside in Michigan by the Great Lakes and go skiing, biking, and boating as much as possible.
doug@adventuregearinsider.com
