Howdy Scott! Welcome to
posting in the forum.
You mentioned a few key desires in your original post. You want something that would
work on some of the many smaller lakes in your area and
you want to "entertain" and you want the boat to be small enough to enjoy etc.
Reading that,
I consider "guest comfort" to be an important thing, IF you wish to take friends sailing with you (if that is what you mean by "entertain").
Comfort for Guests on a Small Boat?
For many people who are not yet "sailors" the act of getting stuck for hours on a sailboat that leans, with hard seats, cramped conditions, and no
toilet, can be less than desirable way to spend their leisure time. Many people I have talked with might enjoy an hour daysail on a big boat, but smaller
boats are not so "inviting." Some complain about the lack of comfort and amenities, even for a day sail. This is compared to the typical
power boat (of similar or a bit larger length) experience that has nice soft seating, mostly upright movement, goes faster, and usually has some kind of head/toilet aboard.
The brand of
boats that have caught my eye are made by Compac Yachts and their catboats especially. They do make a range of boats, but the 20 foot
LOA catboats most appeal to me, and look like they would be very nice for a couple or small
family (or with friends) for daysails and/or for "pocket cruising."
Com-Pac Yachts: Trailerable Cat Boats, Trailerable Cruisers, and Cruising Sailboats
I think the catboats they make look great. By "catboat" I don't mean a
catamaran. The catboats have a
mast located near the bow of the boat. It is a distinctive design, and known as one that is easy to sail (one larger sail).
They make some catboat models for
day sailing (big open cockpits that can hold a lot of people) and some with a small
cabin that allows one to use it for cruising (a few berths, portapotty, small
galley, etc.).
If you want to do some "pocket cruising" and overnight on the boat.
My favorite model, the Horizon Cat has a small but surprisingly roomy and very comfortable looking cabin.
The Horizon Cat Week-end Cruiser from Com-Pac Yachts
If you only want to do daysailing with friends.
Check out their "Horizon Day Cat" (20' LOA) as it looks like a lot of fun to me. It has the simple to learn and use "catboat" rig, and it has a very roomy
cockpit for a
small boat (the
cockpit is 10 feet long on a 20 foot long boat), has swing (lifting)
keel,
shallow draft, and
is trailerable. Look at the photos below and see the one the shows that large cockpit. To me, THAT is the feature that will matter for "entertaining" on a day-sailor. The roomy cockpit also has a built-in ice chest/cooler. In addition, it has a small cabin where a porta-potty can be kept private, another thing that is important if you are taking out guests.
For Trailerable Boats: How will you raise the mast?
One of the most appealing things to me about the Compac boats is their method of raising (stepping) the mast when you arrive at your sailing
destination by trailer. You can read about their method on their site. It appears that anyone could do it and looks very easy. That is something to consider as one gets older like me, especially those who must
single hand or don't use a big crew. In my opinion, having a mast that is easy to step (raise or install for sailing) is a MUST for a trailer sailor (for me) and as I would want to be able to "single hand" the boat whenever I want, I would really want a mast that is easy for ONE person to raise safely. I was impressed by thee photos at the following link:
The Mastendr Quick-Rig Sailing System from Com-Pac Yachts
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Note: I have no connection to this brand or sellers. I am simply
posting information about a boat I admire and would consider as a nice day sailor or pocket cruiser.