Best Small Sailboats With Standing Headroom

Best Small Sailboats With Standing Headroom | Life of Sailing

Last Updated by

Daniel Wade

December 28, 2023

Key Takeaways

  • There are plenty of small sailboats that offer adequate standing headroom
  • Boats that are trailerable are a good start since they are a compact package
  • Many of these boats have a swing keel or other options to make it easier to transport
  • Bigger boats typically have more headroom but will cost more and be difficult to move
  • You many need to compromise space below deck when standing if you find a great boat

Some might think that a smaller boat means there is not full standing headroom. So what small sailboat with standing headroom is out there?

Some examples of small sailboats with standing headroom include the Catalina 25, Grampian 26, and the Beneteau First 27. Keep in mind that some of these might be older boats and are considered trailerable sailboats. Not all small trailerable sailboat brands will have great headroom.

Based on previous experience, there are plenty of family cruiser small boat options out there that have standing headroom to accommodate a lot of sailors out there. Depending on how tall you might be to stand fully upright will also play a role in how much head room you might have.


Table of contents

Top Eight Small Boat Options with Standing Headroom

You might have heard the phrase trailer sailors when it comes to small boats. Indeed, a trailer sailer will use a trailer to haul smaller boats. Trailering your boat offers budget-friendly freedom to explore new sailing destinations without mooring costs and allowing you to sail essentially anywhere you want.

Having good headroom is a widely used term without proper measurement. Assuming you are not over six feet tall, a lot of small sailboats will have decent headroom. Thankfully, there are some small cruising sailboats that you can pull with a trailer with good headroom.

Catalina 25


The Catalina 25 is arguably one of the most popular cruising sailboats of all time. There were around 5,866 built from 1978 up until 1994 and featured various offerings for keels.

One of the more appealing features on the boat was the pop top section to allow standing headroom. These were common after 1987 so make sure to check the year of the boat if you find one, as it should have the pop top.

Grampian 26


From 1967 to 1977, the Grampian had roughly 980 models produced. These Canadian boats featured an enclosed head, had six feet of headroom, and was roomy enough with a full galley.

Depending on which option you might have available, some were built with motors inboard or outboard and others had a centerboard or keel. This made transporting it easier, especially with its low four foot draft.

Beneteau First 27


The First 27 by Beneteau makes the list as a boat that is nearing 30 feet but has headroom adequate for someone 5 '10". These were first built in 1978 and you can likely find many being sailed today.

These boats have plenty of speed and are excellent on the water for accommodating a small family up to six. It also features a galley and fridge to live aboard if you wanted that option.

Westerly Pageant


Westerly Marine built 551 of the Pageant in the 1970’s. This 23 foot cruiser idolized comfort over the total speed, giving you a relaxing ride. They also made some with a fin keel, but these were marketed as the Kendal 23.It was a heavy boat, especially with its bilge keel. This made transferring on a trailer interesting if you could accommodate. It had a solid amount of headroom but you had to keep in mind where you were walking down below.

Telstar 28


There are a few multihull boats out there under 30 feet that offer quality standing headroom and the Telstar 28 is one of them. It showcases good speed up to 15 knots and is narrow for easy transport on a trailer.

It does not have the same living space as a monohull would, but this trimaran offers one of the more headroom than some of the other trailerable boats. A person standing around six feet could easily stand tall in one of these.

Nash 26


The Nash 26 was designed in 1976 and had plenty of boats to choose from. If kept in good condition, there is a good chance that you can still find one today. These were solid boats that had a decent amount of headroom below deck.

Corsair 760


The Corsair 760 is a newer trimaran (2018) and is currently still being built. This is the smallest offering from Corsair, which is a 24 foot multihull that is trailerable.

It has a pop top across the companionway to allow more space for headroom. These are easy to set up (the amas) and you can typically be ready to sail within the hour if you need to put it together after trailering.

MacGregor 26


The MacGregor 26 had various model transformations over the years that they were built, from 1990 to 1995. These boats used water for ballast and were ultimately lightweight all around. These were great for weekend use or day sailing.

The founder retired in 2013 and his daughter took over under a new name, Tattoo Yachts. These are still in production and utilize similar builds comparable to the MacGregor 26, but have upgraded features throughout.

How to Narrow Your Search for a Small Sailboat with Standing Headroom

Finding a smaller boat, which is typically easier on the East coast of the United States, with an adequate amount of headroom may be a challenge. A big boat should be easier to stand below deck but that is not always the case either. Your sailing goals may also come into play on what boat works best for you.

Consider the terms “standing headroom” and trailberable”, as both of these do not mean the same thing, nor do you have to have a small trailerable boat to have enough headroom. For enough headroom, you need to be able to stand upright and this could vary since your height will likely be different based on another customer looking for headroom as well. Many boats were not designed with standing room in mind below deck, so do not be surprised if older ones are not as compatible.

Any boat that is trailerable needs to have the capability to move or hauled on a trailer. However, just because it can fit on a trailer does not make it legal to take on roads. Consider any permits you might need or what you can do to make the boat travel efficiently.

Where to Look for Cruising Sailboats with Good Standing Room

Finding a sailboat should not be hard if you live near a body of water that provides good sailing conditions. However, finding the perfect boat or a similar boat for your sailing goals might be a little more difficult depending on a variety of factors.

Consider your options and make sure you do not rush into purchasing a boat that does not meet most of your requirements. Adjusting your sailing goals might be something you need to do in order to have good standing room below deck.

Your Height

Before you attempt to find the small sailboat of your dreams with the perfect amount of standing room, you need to think about your own height. A lot of boats were made for the average height of a human, which is 69 inches for males in the United States (5 ‘9”).

You will either have to compromise with bending your head a little when walking through the galley or consider a big boat that can accommodate your height. If you are over six feet, then these will likely not fit your requirements for standing room, unless you really overlook this feature altogether. Of course if you are well over six feet, there is not a small sailboat that will accommodate your height below deck.

Online Searches

Searching online is going to be the best resource you have at narrowing down your options. Your sailing goals might only need a boat under 30 feet, but that does not guarantee that this boat will have enough headroom to stand in.

Searching online will allow you to find boats all over the world or within a specific region. You can narrow down your results by certain aspects and potentially even find exact specifications for head room below deck.

This will save you the most time and money, as you will not be jumping around from place to place nor will you be spending money on gas trying to see unnecessary boats in person. This will also give you an opportunity to see boats before someone else and make the buying process simpler.

Local Sources

If you live near coastal waters or by small lakes, you have a great opportunity to check out more boat options. This could be narrowed down further to local newspaper ads, a boatyard, or even a marina.

A newspaper or something similar to reach a larger audience could have ads posted about smaller sailboats with good standing room. These will typically have a number featured to call or an address to take a look at the boat in person.

Boatyards typically have a little bit of everything, but be sure you are ready for the challenge of fixing one up if you go this route. These are sometimes boats that are beyond repair or have been abandoned.

As for marinas or boat clubs, there is a good chance you will see someone with a boat that you like and they may even potentially have one for sale. If not, you might have a chat with the owner to see where they got theirs from and if they know of anyone selling one just like it.


Budget is usually a deciding factor to own a boat, no matter what other features come with it. Simply put, if you do not have enough money to buy it then you will not be sailing it.

Thankfully, a lot of smaller and older boats will be at an affordable price range. This makes it easier to narrow down your searches and find one that fits your budget. Also, a “cheap” price does not always mean a low quality boat, so be sure to do your research on the brand and the condition of the boat.

Keep in mind that a lot of the older ones might need some work done and that will eat into your budget a bit. Preventative maintenance is key to preserving your boat and your bankroll will thank you later.

Are Small Sailboats with Good Standing Room Right for You?

Every person that attempts to buy a boat will have different reasons for purchasing that boat. If standing room is the main one, there are likely many boats that will not fit that criteria. You will either need to change your perspective on the boat buying process or continue to wait until the perfect opportunity comes along.

Other boats typically prioritize the sail experience in light air versus if you can stand up in the galley all the way. But, some have made that a big selling point so that you can remain comfortable at all times. Comfort is attractive to have on long voyages, but if you are using it for the weekend only, you may opt to skip on the convenience factor.

Your budget and specific height will linger in your search results and be quite specific to your own sailing needs. Finding a boat with quality standing room is not difficult but you might need to compromise in a few areas. Do not be afraid to do some dirty work in repairs or other aspects if your budget allows you to make due with the boat that you find.

Best Small Sailboats With Standing Headroom
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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