Hello and Welcome!
You will find a typical progression is to start small (18-22') then move to something bigger (around 30) and then something even bigger (35-40). Of course not everyone does this, but it makes sense. If you buy an older boat in good condition and keep it that way, you will get most of you money back when you sell.
Used to have a motorhome and did some camping on the north east with my family (wife and 3 young kids). In 2003, after wasting too much time in traffic trying to get back on Long Island after a weekend in PA we decided to give sailing a try. I did some research and in August bought an older Catalina 22. I spent around $3500 for the boat (and trailer) in ready to sail condition. We spent the rest of 2003 learning to sail and having a lot of fun. That first year we trailer sailed the boat - trailer the boat to the marina, rig it, launch it, sail it, recover, un rig and trailer home. Sailing was great, trailering stunk. In 2004 I got a mooring in Mt. Sinai harbor and that made sailing much more fun. We sailed that boat all spring 2004 and I was hooked. By June I (thought I) knew what I was doing and wanted a boat big enough to spend weekends on. The Catalina 22 had a small cabin that the kids (2. 5. 8 at the time) could nap, play, relax in, but was way too small to overnight on. So at the end of June I bought a Newport 28. This was a 'big boat' with inboard diesel, real marine head, pressure hot and cold water, galley, bunks for 5, wheel steering, roller furler, etc. We had a lot fun with that boat and sailed to Milford Ct, Northport NY, Mattituck, Bridgeport, etc. The Newport was great for a night or two, but too small for a week (which was my next plan). Sailed the Newport for 3 years and then bought an O'day 35 at the end of 2006. The 35 had plenty of space for 5 people for up to a week. We sailed that boat from NYC to Block Island and everywhere in between. For my use, a boat around 35' is the perfect size. Small enough to single hand, and maintain myself (mostly). Big enough for 4-6 people to get away for a few days. Capable of sailing in some bad weather, enough tankage, etc. In 2013 I sold the O'day and bought my current boat, a C&C 110. This boat will keep me happy until I retire. Then, with some luck, I will get something around 42' to spend a month or so aboard in places like Maine in summer or the carib in winter.
Some random thoughts:
Sailboats are slow! So a 100 mile trip in a boat is a LONG trip (especially for someone just starting). Gardiners bay in a FANTASTIC place to sail. There are so many places near by you could easily spend a few years and never be more than 100 miles from home.
You should check out the Peconic Bay Sailing Association
Where are you going to keep the boat? Make sure you get that done before you buy anything. Slip? Mooring? Trailer?
Don't get hung on any particular brand. Catalina, Hunter, Beneteau, Jeanneau, O'day, Newport, Pearson, C&C, Tartan, Watkins, Precision, etc. - they are all MOSTLY the same. Some are better, some are worse. My suggestion is to start playing around on yachtworld and look at lots of pictures. Then ask more questions.
Have fund and good luck,
Originally Posted by longislandrookie
everyone seems to agree that handlng a small 22 is very good to learn (and fun) . .if i can steal one for cheap, i get to be on the water. learn from her until i grow out of it. sounds like a plan.
and i can keep looking around for a 30 footer in the same time ,since i did not brake the bank , no rush.
thank you for your valuable input.
bon vent a tous !