Sailing on a Budget: How to Have Fun, Save Money, and Fly Like the Wind!

When I was a kid I used to hang out at the marinas in East Norwalk, CT. I was amazed that even on the nicest summer weekends, most of the sailboats never left their slips. They were such beautiful boats -- beautiful but neglected. Not that they were in bad condition -- most looked perfect from a maintenance standpoint. However, the owners rarely seemed to have time to actually sail them. What a shame!

The advantage of thinking small when it comes to sailing is that you will spend less time and money on maintenance. You won't need a large crew to go out on the water. And you'll be less concerned about repairs because there is less to go wrong. Of course, you also won't have a boat loan to pay or an expensive boat slip to worry about every month.

How small is small?

Many beginning sailors get their start in what I call "wet boats" like the Sunfish or Laser. They're an excellent way to get out on the water and learn the basics of sailing. I call them wet boats because you can always count on getting pretty wet when you sail one. They tend to capsize more often and you, the skipper, are more exposed to the water. For some people, that's the fun of it. I say more power to them!

As for me, I wanted a small sailboat that was still large enough to bring a few friends along. I also wanted a small cuddy where I could store a cooler and some other gear. And while I was prepared to do some unscheduled swimming if the need arose, I basically did not want to end up soaking wet on every trip. Being able to sail alone was also an important consideration. With a small budget to work with and a few preferences to guide me, I found that boats we call "daysailers" fit the bill perfectly.

There are many boats that are called daysailers. Most are in the 16' to 22' range. They have a small cuddy and sometimes even a small cabin. Most are trailerable, designed to be easy to sail, are rather quick and perky on the water, and have enough sail control and ballast (usually a centerboard) to keep things right-side up.

After a two month search, I ended up buying an O'Day Daysailor with a trailer in excellent condition for $1,800. (That's my boat, "Hejira," in the photo at the very top of the page.) I spent about another $100 on miscellaneous gear like extra lines, a compass, binoculars, and a first aid kit. A year later I spent another $110 for a tiller extension and a few other items so it would be easier to sail single-handedly.

After trailering Hejira from my house down to the lake for a while, I decided to rent a spot in an open field near a boat ramp for $100 per month. Although the rent was admittedly an unnecessary luxury, I could leave the mast up and quickly transform myself from landlubber to Pirate of Lake Winnipesaukee.

If your goal is to get on a lake or ocean bay and feel connected to the wind and water, nothing beats a small sailboat.

Unless you're planning to buy a new Sunfish or Laser, chances are your "under $2,500" small sailboat will be a used one.

There are literally hundreds of small, inexpensive used sailboats on the market all across the U.S. In my "resources" section, I have listed Internet links to several websites where you can search for used sailboats. Most of the websites for sailboat owners have listings of boats for sale, as well as lots of fascinating information about the boats, repair issues, how to improve performance, and social events for members.

I recently visited "Sailboatlistings.com" and did a search for sailboats priced under $2,500. There were more than two dozen boats for sale, most of them with trailers. There are many more websites with boat classifieds that you can check into. Craigslist is also a place where people sell boats, so take a look there as well.

What are the top candidates for "sailing on a budget"? This is my personal list. It should get you pointed in the right direction. In the Resources section on this page, I list several owners associations and sailboat companies where you can find more detailed information.

O'Day Daysailor - This is the boat that I own and I love it! (Can you tell???) There are several versions of the daysailer, but they are all 16'9" long and 6'3" wide. They are easy to sail, fit nicely on a trailer, and can really take off in a strong wind. Perhaps I am just lucky, but I find this boat very stable. I have yet to capsize!

O'Day Mariner -- The Mariner is about a foot longer than its Daysailer sister and is 7' wide. Below you can find a short video of a Mariner sailing.

MacGregor Weekender 21 -- This is a small, trailerable boat with a big feel. It has a cabin that can sleep up to four people and is known as a very stable ship.

Com-Pac 16/19 Daysailer -- I seriously considered buying a Com-Pac before eventually purchasing the O'Day Daysailer. Com-Pacs are classic-looking boats that have endured very well over several decades. They are still in production.

Catalina 22 Pop-Top -- Catalinas are like the Chevrolets of the sailing crowd. Although newer and larger ships can cost more than your house, there is a plentiful supply of sea-worthy older boats that are on the used boat market. The Catalina 22 in various configurations is one of the most popular. The "pop-top" means that the "ceiling" or top for the enclosed cabin can be pushed up to provide more headroom down below.

Catalina Capri 14.2 -- At just over 14', the Capri is somewhat smaller than the other daysailer boats featured here. It is a good choice, however, for someone who does not need a cabin and who wants to buy something a little newer. If you're interested in sailboat racing, there are numerous fleets of boats around the country that organize races for this class of boat.

Hunter 25 Daysailer -- The Hunter is a bit larger and more expensive than most of the boats listed here, but you can find older sailboats that will fit your budget. At 25' long they are trailerable boats with large cabins. There are several other smaller Hunter sailboats that are worth researching online such as the Hunter 22.

West Wight Potter 15 -- I love just looking at Potters! They are a little ungainly in design, sit high in the water, and probably remind some people (me) of a floating bathtub with sails. But take another look and they might even seem cute! They are incredibly practical boats and offer a great deal of space and sailing fun for their size. It even has a small cabin below. Potter also makes a larger model, the Potter 19.