In a previous post I highlighted the fact that you need to look at what your sailing ambitions are and how you plan to utilise the boat.
Living Boatlife
If your boat is going to take you on an adventure, it needs to be capable of withstanding the rigors of a long voyage, as well as providing all of the creature comforts you would expect, even if you are living aboard for a long time. It should have plenty of space, and be well equipped with all of the amenities you could want. And, it should match your budget and suit your sailing style and purpose. The best advice here is to research what other sailors with similar goals are doing, and then copy them (for better or worse) when you start your own project.
Catamarans

The best kind of boat for cruising or touring is the double-hulled one. They don’t heel as much as single hulls, and often you get a lot of livable space in them. It’s another way of sailing, and maybe the right one for you. You should test sailing a catamaran in different weather conditions before going for the buy – which is of course relevant for any boat you are getting.
Holiday Get Aways

I expect most people would set their ambitions in this category. With modern boat design and the aid of electronic equipment you can get a good sailboat easily handled by one or two persons and therefore the perfect family boat. However, if you are looking for a larger boat, you should also consider a race boat disguised as a touring boat. Quite often, you will find that race boat is more stable, as they often have a deeper keel, which you should of course calculate in if you are surrounded by very shallow waters.
Day or week-end sailing

You can enjoy sailing at all levels. If you cannot see yourself crossing oceans or living weeks on a boat, you might want to look into smaller boats. I will argue, that the sailing itself can be more fun, when being close to the water in a smaller boat, maybe even a dinghy. And with a smaller boat, there is also the option of being able to hook it up after the car and be more flexible as to where you are sailing. You don’t need an ocean, a lake will do. With a powerful car, you should be able to transport a boat up to about 24-26 feet in length.
Yacht Racing
If you are serious about yacht racing, you need to look for boats that are classified as such – for racing. But really, the race boats you see in Volvo/The Ocean Race and other high-end racing competitions, are only in reach for the very few. Designing boats for these races is extremely expensive. However, boats exceeding 32-35 feet are often pretty good sailers, simply because there is a financial need to build race boats that can also work as a touring boat, in order to get enough sales.

Acquiring a sailboat, or any boat for that matter is often and for many a big investment. And you don’t want to limit yourself in terms of what direction you are going with your sailing ambition. Of course, you can start small – and less expensive – and then trade up later. Another great option, especially if you want to test yourself and the family aboard, is to rent a sailboat for one and two weeks. If you believe racing is of interest, try to locate local sailers and see if you can join as crew. Not only can you test yourself, but probably also get some good guidance and some fun along the way.
Good luck !
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