There are a couple significant and perhaps contraditory pieces to your question. As a beginner sailor, you will greatly benefit from getting a boat that comparatively small, 25 to 30 feet (or smaller), and that is light and responsive enough that you cna really learn how to properly trim (adjust) the sails for the conditions and also that won''t overpower your abilities. That is slightly in conflict with your goal to be able to sail to New York which involves a little outside work. Still, if you picked your weather window right a 30 footer would have a relatively easy time of it.
Under no circumstances would I ever recommend a wheel steering in a boat this size for a beginner sailer. Even with the advances in wheel steering, the increased drag and lack of feel of a wheel steering makes it hard to really learn to sail well. I know that there are people out there who have learned to sail on wheel steering, meaning they have learned enough to get from place to place mostly under sail. They may even have sailed for a lifetime, but they have never learned how to trim the sails properly and really finesse the boat. (Its a bit like the difference in skiing between a guy how does ''carves a turn'' vs the guy doing ''gorilla turns''.) I see these people out on the water all of the time. If they learned to adjust their sails properly they would be Heel less, roll less, be faster in most conditions and more comfortable in most conditions and not have to motor as much. It really does make a big difference in how much you get to enjoy your boat.
If you are only sailing in Boston Harbor you probably could get by with an outboard. If you are going to be sailing to New York, you would be far better served by a boat with an inboard. Inboards tend to be far more reliable and more significanlty, outboards are really useless if you end up in really awful weather or even a short slop left after a bad storm.
I think that we are talking about a boat that is probably too big to trailer and so will probably be at a dock. Here''s the deal. Trailering offers a number of advantages over docking, lower storage costs being a big one, and the ability to trailer the boat to distant locations being another. But trailering comes at a big price. Rigging
and unrigging a trailerable is a major time consuming operation. When I had a trailerable the quickest I could get from the parking lot to the water was about 45 minutes and it took about the same amount of time the other way. That means you better have half a day if you are going to ''slip out for a couple hours''. My current boat, a 28 footer, can literally be underway in 5-7 minutes from the time that I hit the dock, covers off, lines
run and ready to sail. It makes it much easier to grab a quick evening sail.
I don''t know how things are in Boston, but around here you can often get a slip at a private dock for very little money. (I have only paid for a slip 1 year out the 18 years that I have owned boats in Annapolis.) When I lived in Savannah, I had a slip at a small private marina owned by a shrimp boat operator that was about a quarter of the going rates at a ''real marina'' and in Miami I joined a small yacht club and kept my boat there for next to nothing. in the Northeast, moorings are often a real bargain and the boats take less abuse on a mooring.
In terms of make, there are a lot of good boats out there for your purpose. (This is my standard response. You actually have less experience than most people looking for a first boat today so I would not necessarily suggest that you look at the higher performance designs (noted with an *))
"There is no more controversial a question than what is a perfect first boat. To begin with all boats are compromises. They are compromises between optimum sailing ability and the need for accommodations or shoal draft. If a boat gets wider it gets more stable up to a point but then it has less reserve stability to right itself if it goes over. If a boat is too wide and blunt, it has a lot of drag but lots of room down below. If a boat is too narrow it has less drag but if too narrow won''t have much stability or room down below. Too much weight and the boat is slow and hard to handle, too little weight the boat is fast, fun, and easy to handle up to a point but at some point takes greater skills and athletic ability.
If you ask some sailors, they will recommend a traditional design because they are a bit harder to get into trouble with. I somewhat disagree. I really think that the boat you buy should be responsive enough that you can learn proper sail trim and boat handling. I have taught a lot of people to sail and I firmly believe that to really learn to sail the boat should be light and responsive enough that you can experiment with sail trim and sailing angles and see and feel the results. I recommend a boat with a reasonably easily driven hull and reasonably modern rig
and underbody. I find that fractional rigged sloops are really the easiest to learn proper sail trim on. Much of this depends on your own priorities. There are a lot people out on the water who really only understand the rudimentary aspects of sail trim and boat handling. That works for them and I am not judging them. If you really want to learn the fine points of sailing then I would stick to sloop 30 feet or less in length and of light to moderate displacement and a fin keel and spade rudder. Beginners sometimes think they prefer wheel steering, but on the size boats you are talking about a tiller is far and away better both to learn on and to sail with.
The key is to figure out where you are going to sail, what your abilities are and what your real needs are. Different sailing venues favor different types of boats. Boats such as the: (These should all be under 25K, most have inboards which I think is preferable for cruising.)
-Albin Ballad (30 feet (1973-1978) $12-20K)
These are reasonably fast and very well built and finished boats. They are not especially roomy but are good boats for short handing. They are beautiful looking boats. Most have a Volvo 10 hp diesel.
Albin Cumulus (28 feet-(early 1980''s) $15-18K)
These fractional rigged sloops would be a ideal first boat. They are reasonably fast (although 60 sec''s a mile slower than my Laser 28) and easy to handle. They are nicely finished and typically have diesels. The interiors on these boats are not exactly plush but is reasonable for the kind of stuff we do here on the Chesapeake and on much of the Atlantic Coast.
Beneteau First 30 or 30E (30 feet (early 1980''s) $18-22K)
Fairly modern design that should sail reasonably well. Not the most solid boats but fine for most venues. They had diesels and pretty good hardware. The 30E might be a fractional rig
, I don''t recall.
-C&C Corvette (31 feet (1967- 1970) $15-22K) and -C&C Redwing (30 footer ( 1965-1970) $12K- 20K)
Attractive and reasonably venerable designs; they are not especially fast but OK for the era. The Corvettes are moderately long keel/ centerboard boats and so are great for poking around the shallower areas of the Bay. The Redwings are fin keel/space rudder boats. They are really not competitive racers any longer.
Cal 2-30 and Cal 2-29''s (just under 30 feet (mid 1960-early 1970''s) $10-18K)
These are reasonably built racer cruisers that have reasonable accommodations and pretty fair sailing ability. Like the Cal 25, the design is a dated and if the gear has not been updated will be less convenient than a more modern design.
Catalina 27''s: Venerable, common and cheap to buy. I have been sailing on these boats for several summers now. They are not especially well built and tend to blow up hardware but then again I am sailing on a 15 year old boat that has been raced hard for much of its life.
Dehler 31 (31 feet (Mid to late 1980''s) under $20K to mid-20K range)*
These are really neat little boats. They are not as fast as my Laser for example but are quite fast and look easy to sail and single-hand. They are fractional rigged and have a very nice interior plan. They would one of my favorites on this list for a first boat that can be both cruised and raced.
Dufour 2800 (28 feet (mid 1980''s) mid $20K)
These are OK boats with a reasonably solid following. They are not my favorite but they would not be a bad boat if the price were right.
Farr 1020''s (34 feet (Late 1980''s)
These are really nice 34 footers that have a reasonably complete interior for more extended cruising and are quite fast and should be easy to handle.
Late 70''s/ early 80''s Hunter 30''s, (30feet (15-20K)
These are under appreciated boats. We have had two in my family and again it is a matter of finding one that has been upgraded and is in good clean shape. My Dad raced his in PHRF and went for a couple years without finishing lower than a first or second. They are roomy and surprisingly fast.
Irwin Competition 30 (30 feet(mid 1970''s) $12-16K)
These were well rounded little boats that sailed well and had reasonably nice interiors. There was one that dominated its class in PHRF for years. Irwin''s were not the most solidly built boats and so you are looking for a well maintained example in reasonably good shape.
These were part of J-boats ''cruising series'' along with the J-34c, J-35c, J-37, and J-40. These are nice little boats and would be a good choice in a windier cruising ground. They have a nice layout and seemed to be nicely finished.
J-30''s (30 feet(Late 1970''s on) $20-35K)*
These were originally built as ''hot'' race boats and in their day they were really quite fast. Today they are seen as heavy and under canvassed. There are a number of model changes over the years and some resulted in a pretty nice cruising layout. These are good sailing boats but somewhat brutish to sail compared to soem later high performance boats. Ergonomically they are far from my favorite boats, BUT they have a strong following. Their perenial one design status have held their value up quite nicely. They have diesel auxillaries and are pretty easy to find. Be careful of problems with their coring as the Balsa cored and some of these boats have had a very tough life.
Kirby 30: (30 feet(Late 1970''s-early 1980''s)$12 to $25K)*
These were really intended as race boats but they do have an interior that can be cruised for limited periosds of time. They are one of my favorite boats from that era. (I owned a Kirby 25 which was a smaller version of the 30).
Laser 28''s (28 feet(Early to mid 1980''s) $16to24K)*
What can I say, I love these boats. I have owned mine for 13 years and she has been great as a racer, daysailor, weekender and cruiser for periods up to 11 or so days. They were boats that were a decade ahead of their time. Many are Kevlar/Vinylester construction which is a really tough act to beat in terms of durability and light weight. They had a clever interior with a nice galley and head. Many have pressure water and a shower and a few have hot water heaters even. They have a nice little Buhk diesel. After 13 years Ihave no doubt that this was the right boat for me.
MG27 (27 foot (Mid 1980''s) under $20K)
Nice little fractional rigged English boats. They seem to be well mannered and have an interior layout similar to my Laser 28. They have a diesel aux. They have tiny tanks that will need to get upgraded.
Oday 28 & 30 (28 feet and 30 feet(late 1970''s and early 1980''s) $12-20K)
These were not the best built boats or the fastest boats in their day but are common and sail reasonably well.
1970''s vintage Tartan 30''s, (30 feet( 1970''s) under $20K)
These are my favorite masthead sloops of that era. They are good all around boats. Most still atomic 4''s but you can find them with diesels.
Tartan 26''s: Quite rare little boats. They are nice to sail and have reasonably comfortable interiors.
(Other Tartans to look for are the Tartan Piper and Tartan 31 but these are more expensive boats)
70''s vintage Pearson 30''s (Not Flyers)*
These are very venerable racer/cruisers on the Chesapeake. They have an active one-design class and are also good boats for cruising the Bay. Of course they come in all kinds of condition from really well maintained and up graded with good racing hardware and a diesel engine to stripped and trashed. You can buy them from under $10K (but you would not want any in that price range) to something approaching $20K. You should find good boats in the high teens.
Pearson Flyers: (30(late 1970''s early 1980''s) $12-20K)*
These were intended as competition to the J-30. They were reasonably good boats pretty much on a par with the J-30 in many ways. They have not done as well in racing since they do not have a one design class to help perfect the Breed.
Ranger 29 (29 (early 1970''s) 10-18K)
These are good sailing and nice cruising little boats. They should be adequate for club racing and are certainly good boats. They were not the best built boats and so you should be looking for a clean and updated version. Still they offer a lot of bang for the buck.
Sabre 28 (28 feet(1971 to 1986) $12-30K)
They have a reasonably high quality build, and are still supported by factory, with over 500 made The S-28 is one of the few boats which meets the ORC capsize screen under 30 feet. Nice teak interior and somewhat classic lines
Shockwave (also called Schockwave 30, or Wavelength 30 )*
Pretty stipped out racers but really neat boats. They are quite fast and should be a lot of fun to own. They did have a sort of high tech interior that lacked elegance but worked reasonably well.
Wylie 28 and Wylie 30 (28 and 30 respectively(late 1970''s to early 1980''s) 10-15K)
These are neat little boats that sail well and are really pretty interesting. The few that I have seen have good hardware and have had simple but workable interiors. They came in fractional and masthead rig
versions. There was a masthead version that did quite well on the Bay. There was a one design version called a Hawkfarm. They never caught on the Chesapeake but are still raced in S.F. Bay.
If you want some thing more traditional
C&C Redwings and Corvettes
Pearson Coasters, and Wanderer''s
You will find that these traditional boats have less room and will have older equipment but they should be less money and may be better sailing boats than some of the newer boats on the market today."
Feel free to email me as your search continues and to kick around ideas.