Well i'm a very recent addition to the Steem community and I figured i'd share a few of my picks for the most bang for your buck to enjoy the boating lifestyle. I'm a huge fan of spending time on the water and there's so many ways to do it , my favorite however are sailboats! Now you might think they're a little old fashioned or slow, and in all honesty those are some pretty valid points, but on the other hand they often have a ton of usable space for their size, are super cheap to operate, and you can actually learn something while relaxing... the art of sailing!
Catalina 22
The Catalina 22 is perhaps the most iconic trailer sailor in existence. First produced in 1969 the 22 has seen some face-lifts over the years but is still basically as 50 years ago! The Catalina 22 is known for being robustly built and capable as a daysailer or weekender, its rigging is designed to be beginner friendly yet is capable enough to keep experienced sailors interested. Additionally, these boats can be had for a very reasonable price with a late 70's model in solid condition costing around 3,000 USD, and due to almost 15,000 22's being produced there is no shortage of spare parts or knowledge on their upkeep.
O'Day 222
O'day, although they no longer make boats, are known as some of the robust boats you can buy for the money. Built with thick fiberglass hulls, heavy duty sailing hardware, and efficient sail plans these boats are a hell of a deal. The 222 in particular is one of the better known small boats produced by O'day, and for good reason, you get a lot of big boat features, such as a well appointed cabin and stable handling characteristics. Also unlike most O'day boats they were meant to be trailered which means easy rigging of the mast and a swing keel for easy trailering and easy beaching. Among sailors these are viewed as some of the best small boats out there.
Macgregor 22 / Venture 222
Macgregor began building boats in the early 1960's and has produced a wide range of trailerable sailboats to this day (now being known as Tattoo Yachts) ranging from 17 to 26 feet. Here we have the Macgregor Venture or as it was later known the Macgregor 22. These boats were designed for the weekend sailor or the family looking to get out on sheltered waters for a few days. Not the most robustly built, they make up for it by being ultra easy to maintain, very easy to handle on the water, and with an elegantly simple sail plan and rigging they are a beginners delight. Don't write them off too quickly however because they offer great interior space (enough for a couple to weekend on it ), are very competitively priced, and with so many boats still out there sailing there are huge communities online offering support and knowledge for their modification and upkeep.
O'Day Mariner
No surprise here that a second O'day made my list. This is the O'day Mariner, coming in as the smallest of the list at 19 feet, but don't let its small size deceive you, this is perhaps the most true to form sailboat of the bunch being designed from a one-design race boat. The Mariner is designed to be a fast and efficient craft, yet compared to the race boat it was designed from the mariner is set up with either a two or four place cabin for extended cruises. Again the Mariner has all the O'day brand benefits described above, but the Mariner is designed for someone who may already have some sailing knowledge or someone looking to push sailing a little bit farther than strictly recreation. Lastly, the Mariner has become one of the most sought after small sailboats on the market and often fetch much higher prices than the other boats in this list.
Precision 21
Rounding out the end of the list is the Precision 21, this robust shoal keel (shallow water) with centerboard pocket cruiser is one of the lesser known but competitive options for a trailerable sailboat. The 21 has all that you could ask for in a small boat, great handling characteristics, a generous beam width creating a large cockpit and cabin, and many boats even include a 10 gallon water supply and alcohol stove for extended weekend trips in protected or coastal waters. Not nearly as well known as the others and appearing in lesser numbers the Precision 21 should not be overlooked if one is available near you.