what to do?

[Champlain94]

Im ready to purchase my first sailboat. Im only ASA 101 certified. But I have been on many different sailboats. Colgate 27, Cabo Rico 37, Alberg 30, Tayana, CSY 44. None mine. Nothing long term. I have never had an over night trip or stay. What I want Is your opinion. Should I buy for example;
25' Oday, Balboa, Hunter, Catalina, etc. with a trailer to learn on and save money, Which will be cheaper all around.

Or a 27-34' boat. Cape dory, Alberg, Yankee, Bristol, Tartan, Allied etc. We have a location here with free year round mooring and public docks for access.
Money is a factor. I can afford to purchase the boat(loan) and do a few upgrades. Mostly learning and playing on the ICW/ Waccamaw River with shallow bays that have access to the open ocean. Little river and Winyah Bay.
Thank You.

[SailFastTri]

Size matters. Are you single, a couple, or a family? Small kids or grown? You want to day-sail or do weekends/vacations?

[Champlain94]

Married 19 year old daughter. Both dislike boats. Maybe I can get them in one if im tied to a dock or cruising slow down the ICW for a short distance. I want to camp out on the boat, improve what little sailing skills I have, push my luck, heel the boat, fish off it, Most of the time I feel I will be by my self. With occasional guest. One maybe two. Family or friend.

[sandy stone]

If you have access to free mooring, I think it is a no-brainer. I used to have a 16' dinghy (Windmill) on a trailer, and that got to be a pain to rig and derig every time I wanted to go sailing. I later owned a 23' trailer-sailer (Paceship) which I thankfully was able to keep in the water. Looking at the size of the boat and the rig, I didn't care to even think about what it would have been like launching from a trailer.
Now, some people like the mobility that a trailered boat gives you, access to different cruising areas and such, but for me the ease of use of a moored boat is a much bigger advantage.

[Randyonr3]

one of the downsides of owning a larger boat is SAILING IT.. when we had our 22, we sailed it every weekend, different lake or bay.. always on the go and SAILING..
We finally moved up and on or 42 foot and sail seldom .. uasally its between anchorages or marinas.. could be due to us living on the boat for the last 10 years but I know I miss the small boat sailing..

[SailFastTri]

Most females require privacy when they need to relieve themselves, so you'll need an enclosed head (bathroom) if you want the wife and daughter to join you as crew. That was the one requiremtn my wife had when I first shopped for boats and it pushes you into the larger sizes. Otherwise for single-handing the smaller boat will be easier to handle and probably more fun to sail.

[GordMay]

Greetings and welcome aboard the CF, Champlain94.

[tdoster]

My rule of thumb has always been to buy the smallest boat you can be comfortable on for at least a week for anything that you are talking about 25+

I love the Yankee's. They were great boats and after they went out of business, pretty much saved Catalina and gave them something other than the great Butler Designs. Robert Finch did the 24-28 and the 30 and 38 were SS designs. Cape Dory's are great boats as well, we currently own one. Remember the draft for where you are planning on sailing.

From what I heard you say, you may want to look into a Compac or Seaward 25. These are both trailerable and setup for thin water sailing. The Seaward 25 holds it's value well, but plan on spending ~ 15-25K for a good one on a trailer and be careful with boats made prior to 1995. It is a good boat to get the wife into sailing as there is a full head and fairly decent galley. If you are 6' tall or over, you will not be happy with a trailer sailor. Catalina 25's are good choices as well. I like having a diesel and the ability to put a high amp alternator and extend the cruising if I choose, so that was a big factor for us when I got my current wife into sailing.

If you have USAA, then age is less of a factor for loans, but the other banks require the boat be 25 years or less and loan on nada (which is far below market). You will find that if you are financing that you are limited and not able to get as good of a deal. Boat values are really based on the ability to finance where you see them really drop in value once that magic 25 years sets in and the next owner must pay cash, or a substantial down payment. Again, USAA can't be beat if you qualify for membership.

Beam is important if you want a trailer sailor or even a boat that can be cheaply moved out of the water. 8' 6" is the magic number for not requiring a permit to move in most states.

I brought up the idea of getting my current wife into sailing. We stated with a Seaward 25 and she enjoyed it enough to move up from there, so it was a wise choice that cost a little more up front, but held it's value and made a good stepping stone to get her excited about moving up and sailing to further destinations.

[JeffDPT]

I second tdoster. My '87 seaward 24 is my second boat after a 19' trailerable daysailer. My wife and I can stay up to 3 nights without a little claustrophobia. 3 people can overnight. It has a nice size cockpit for another couple for daysails. Best of all, I bought it for $9 grand a few years ago. Needed an 10 hp O/B to get going, added a mainsail last year. The 24s, 25s, and newer 26s are all close in layout with the newer ones having an enclosed head. Good Luck

[Unkle Toad]

seems to me like there are two basic schools of sailboat buying.(ignoring those with the money to just do whatever the feel like at the time)

1. get a smaller boat sail it for a year or two .. upgrade sail it for a year or two. lather rinse repeat until you get to the size that is right for you.
this has a couple of points to it. you get to learn maintenence on a boat that you will be passing on so you are better at it by the time you get your forever boat. most small to smallish sailboats retain value pretty well if you take care of them so its not like your tossing the money away when you upgrade.

2. dive in both feet first and buy the boat you think you will want forever(me)

from what you said you seem to have been on a lot of boats. so you should be starting to get a feel for what feels good to you. if the lady's really will not be doing anything more then hanging out for a coctail at the docs that shouldnt play in too much but the idea of something in the 25ish range with an enclosed head might just be enough to coax them out for an over night a time or two.

i have been on a few of the boats on your list and many of them seem a little big(== more money to keep in good shape) for what you have planned. I like the idea of one in the 25' range. it seems like it would fit your plan well.