I am looking for a sailboat that I will be using just on weekends at first and to learn more about sailing. I know how to sail but only know the basics. Okay that is just a little back round about me. My budget is low, I am looking at spending a max of 25,000. I do not mind a fixer upper but that said I don't wont a boat I am going to have to completely redo.
I hope to travel longer ways in several years.
1. What type of boat? (sloop, crusier, etc)
2. age of the boat? (does it matter if the boat is older than myself)
3. Size? (I would be using it will one or two other people)
Remember, the dream is to one day sail across the atlantic! (A dream I hope I can make come true)
I would recommend you save your money and start small, maybe even a trailer sailer. You can get a great used boat in the 22' to 25' foot range for less than $10K, and save the rest of the cash for later. 25' is plenty big enough for a weekend for two, (but pretty cramped if you are using it for three days or three people). Small boats are cheaper to dock, cheaper to operate, and cheaper to sell when you want to upgrade.
If you think this is good advice, then look for the common names. Catalina, Hunter, Oday, Precision, Pearson, Seaward, Colgate, and MacGregor. Pick one, or go to the small names if you want. This is not a complete list, this is just the guys that I see out sailing. Oh, and Com-pac. I chose a Catalina because it is rugged and easy to fix, but honestly, so are almost all of the day cruisers. These companies did not make money by building bad boats.
Where I live (landlocked in Florida!) all the best places to sail require a shoal draft. The best places to gunkhole on the intercoastal are in 5 feet of water or less. My friend with his Pearson 35 has to take a kayak to get to places where I could just pull up my Catalina 22, tie it off to a log, and walk to shore. The Pearson is faster, of course, but that doesn't matter unless you are racing. (My friend is not completely insane, by the way, he has the '79 Pearson 35 with the centerboard. It has less than a 4' draft with the board up.)
(If you want a boat for racing, by the way, that is a different question. Just get a J/92 and get it over with. You can use it as a 27' day cruiser, but that is not what it does best. What it does best is scream by boats that are five feet longer. Even used, it is $25K, so a pristine copy will definitely blow your budget, but who cares? It has a 6' draft, so it is a little deep for the muddy places I like to sail, but even the slowest J29 has a PHRF of less than 120. That's not a typo. My friend's Pearson 35 is nearly 180, and my Cat 22 is about 240.)
Anyway, the materials have changed a bit, but the basic design of sailboats has not seen much change in the last 100 years. So don't worry about the age of the sailboat, as long as it was built well to start with, and properly maintained. There are some checklists online to let you know what to look for, but it is different from boat to boat.
If you are looking at a wood-core boat, look for bubbles under the fiberglass skin, which almost always indicate rot. Even if it is a fiberglass core, the bubbles are still a problem. If it is metal core, then look for rust, obviously. Look for any water damage inside the cabin. Rain from above is actually a more common issue than water from below. Look for anything that leaks: chainplates are the worst, but really anything that leaks is a red flag.
Look at the sails carefully (laid out on the ground) and look at the rigging carefully. If someone neglected their rigging, then they neglected the rest of the boat as well. If you don't know how to examine the wiring and the engine, bring someone along who does. Write down a list of all the work it needs, so that you have a pice of paper to look at instead of just a bunch of cell-phone pictures.
Now is a very good time to buy a used boat, so if you shop carefully, you can get a great deal. If you really have your heart set on a bigger boat, then look at Hunter, Pearson, Beneteau, C&C, Columbia, or Catalina. You really don't want (or need) anything longer than a 35-footer, but these days you can get a great used deepwater boat for less than $20K. Make sure you have a little in your pocket for professional repairs, so that you can sail it within a month or two of buying it. Unless you really love working on a boat, don't buy a boat that needs a thousand hours of repairs.