Making the change

Scott T-Bird · Oct 27, 2014

The Basic Keelboat class might be a good idea and it shouldn't cost more than $300 for a 2-day class. If you're willing to spend the money, you could also consider a live-aboard class for maybe 4-5 days which might be more like a vacation on a boat. You might learn more about your preferences if you did that. At least if the class doesn't feel worthwhile, you might enjoy the time anyway.

I think people have very different perceptions about how worthwhile classes are ... that's really hard to recommend. I think the perception of the standard ASA classes can be anything from totally worthwhile to totally worthless ... that's just my take. IIRC, I did an ASA Introduction to Cruising class where I basically passed the Basic Keelboat simply by passing a test. I did this after I owned our boat for at least a year, and I was simply looking for the little certification booklet in case I ever needed to present it for chartering. It's in a drawer and hasn't come out in many years.

capnrick · Oct 27, 2014

Looks like good advice from all. The only thing I can add is the very different and pleasurable experiences you are about to have while sailing. Remember: when you put those big white cloth things up it gets wayyyy cheaper than gas...

Bob J. · Oct 27, 2014

nevertolate said:
I have owned power boats since my early 20's and currently own a 1993 Monterey 242 SEL. I have always enjoyed watching the sailboats while underway and even though I am 52 I want to learn how to sail.

Being a former power boater myself, welcome to the dark side

Sailing, it's peaceful, it's frustrating, but most of all it's awesome!
I didn't learn to sail until I was 54. Take a basic keel boat course, then go for the 28-30 footer & get out there. It makes no sense messing around with a smaller boat @ this point in your life....

Bob

ALNims · Oct 27, 2014

I started at 59 and got my end boat first and am working into my boat. I agree with the poster that you will save money and time with this approach. Keep in mind safety first and become familiar with your on board equipment. Try to sail with a group when possible and learn from their experience. You will be fine.

Daveinet · Oct 27, 2014

Anyone notice the absence of recommendation of either the Hunter Edge, or Mac 26X or M?

Pelicaneer · Oct 27, 2014

Find the largest fleet of the smallest sailboat in your area. El Toro is ideal. Penguin, Snipe, Lido 14, certainly nothing larger than a Lightning. If there is any sort of class offered, enroll. If everyone else is under 18 so much the better - you will be challenged to keep up. (Beware of Lasers however! They are rather specialized)

If there are no club classes, just ask around and offer to crew, or buy one of the class most popular. Your power boat experience might help. Better if you came from a canoe or kayak - those folk develop the most boat sense the fastest.

Saiil in small boats for for a year at least, every time you can. Drift through the tules (or eel grass) watching birds; fly across the waves into a strong wind, balanced on the rail of the boat, and in between sail the lake or the bay chosing marks, destinations, don't just float aimlessly.

If there is racing in your area for your class, study the basic rules and stay out of close confrontations you do not understand. You will be welcomed, helped, tutored, and will learn to handle a sailboat. Anyone can step from a small sailboat to a large one and easily adjust. Going from a large sailboat to a small one will only show you how little you have learned in the large boat.

Jean

wesleysherman · Oct 27, 2014

My experiance

My first thought was to buy a small 20 footer and learn to sail, but I was anxious and impatient. So i cut a few corners and bought right off a 27 footer. I advertised on Craig's List for a experienced sailor for some one to help me learn. A dozen people answered and I found a great 50s age man who has since become a great friend, Who has tremendous knowledge and experience.

I also learned by taking some entry lvl classes and volunteering on some beer can races at the local yacht clubs.

But by far I learned the most and the fastest by being on my boat with a highly experienced sailor. I gave up the beer can and classes. But that was just me.

I am sure if you volunteer for local events and races at Yacht clubs and look for an experienced sailor as a guide, you would be ahead of the game and its much more fun to learn on your own boat.

Just and idea that worked for me.

I got very lucky and bought a 27' 1982 Cherub era hunter at an auction that was in Bristol mint condition belive it or not for less than 2k. But as I said I was extremely lucky... I am going to trade up to a larger boat soon, since I am in my late 40s to my last boat, somthing in the 30-40 range.. which i plan to have till death or alzheimer's takes me.

"Abandon Land" (name of my boat and my motto)

Gobsmacked · Oct 27, 2014

nevertolate said:
Well, first off I want to say thanks to all those who took the time to respond. My next question is can anyone recommend a very good sailing school that would best prepare me for what I have planned ( cruising). I talked to a guy in my marina who knew of a sailing course I was considering and he said (don't know if he was right or wrong) I would be disappointed with what I would get for my $700- $ 800. I live in Nassau County Long Island NY, and I boat out of City Island NY. If anyone can recommend a good school for next spring/summer that will start me off on the right foot I would greatly appreciate it.

Nevertolate,
I suspect that there are a lot of small yacht clubs and sailing clubs in your area where you can become a member for under $1,000 a year and get to sail on a whole bunch of boats over the summer. And if you buy a boat you'll be able to find people to crew for you.
The key to becoming a good sailor isn't taking a half-dozen lessons through a commercial course but spending a lot of hours on a sailboat, learning to tack and jibe and what a well-trimed sail looks like. You'll also probably scare the crap out of yourself a few times, which is all part of the process.
As one respondent pointed out, sailing isn't rocket science. But neither is plumbing, and all the good plumbers I've ever hired have mostly learned their trade through years of on the job training.

geek_guy · Oct 28, 2014

I have made the switch sail to power to sail, and now have both. Which must qualify me for some sort of dufus award.

First on getting your final boat. I've owned a Catalina 22, 25, Newport 30, Regal 20, Sea Ray 25, and several other small power boats. I really believed everyone to be my 'final' boat. I learned and discovered all along the way. All had reason to love, and reason to want more. But frankly it was great fun all along the way.

I think it's more about what you want/like. We actually use our sailboat as a cabin as much as a sailboat. You can get around on a sailboat with pretty limited sailing skills. If you pick things reasonably easily, you can function after reading a book, and getting some basic help for a couple hours. You aren't going to be the greatest or fastest sailor on the water. But you may not care. After all a sailboat at best only goes about 6 knots. So from best to worst you aren't screaming into the ozone layer, nor being the worst that you are not moving. After some time on the water you may decide you want to be the screamer. You may be happy just lazing around. Or something in between. There might even be a chance for your wife. My wife hates the bouncy frantic feel of the power boat, but loves the smooth quiet of the sailboat. The heel is a very odd sensation, but you can reduce or let out the sail to reduce that too.

The big difference in working a sailboat over power is just the hp to weight/size ratio. In the power boat you have enough power to immediately go in reverse or gun it to get out of the way or change directions. Not so much on the sailboat. So you just have to anticipate much more in advance that you will need to change direction. But then you are also gong much slower, so it doesn't take the power to stop. Somewhat.

The sailboat is more of a travel trailer too. With that comes systems that you probably don't have on the power boat. Pressure water, water heater, full galley, etc.... With that comes learning and the opportunity to fix broken things.

You can find tremendous options in your price range. I am in North Florida and commonly see nice older sailboats from 30 to 37 foot in your price. They will not be perfect. But would be functional. Part of the fun may be finding, learning about the different boats. Poking around boats is great fun - at least for me.

Good luck and like sailors like to say 'enjoy the journey' not just getting to the end. To include looking at boats, trying them out, and getting your 'final' one.

stevewitt1 · Oct 28, 2014

Nevertolate:

I'm also one of the few AC/DC (BOATERS!!!) Years ago '74-75 just out of college two years a friend and myself wanted to sail. We had no money and could borrow even less. Scraped together down and built a Lugar 26 Tradewinds. Sailed it for 12 years then went to 27 Catalina. Started hearing "My idea of boating is ""hit the throttle and go""" and marriage being a sport of compromise put me in a 30' SeaRay Sedan Bridge. After the divorce I went back to sailing with a 31" Allmand (still one of the best boats ever made in it's class for overall comfort) Then time constraints put me back in Stinkpotting with a 3270 Bayliner MotorYacht. Well three years ago I woke up out of the fog I was living in and bought my retirement boat 34' Catalina 1989 Mk1 and love it. Still need the windless (next spring). Will book my 2015 upgrades, windless, new electronics at Strictly Sail this Jan in Chicago then hope to live long enough to enjoy it.

Let me be the 400th to welcome you back to "the Force" from "the Darkside"

"The wind is always in the favor of the able sailor"

Steve

visit us at www.ocontoyachtclub.com and www.warbirdsix.com

nashuasteve · Oct 28, 2014

there is a freedom 29 for sale on sailboatlistings.com this is a very easy boat to sail and the right size Its even in NY.

rotzoll · Oct 28, 2014

Go big or go home. I am 53 and started sailing Lake Michigan when I was 50. I started with an O'Day 31 and am now looking to move up to a Catalina 350 or bigger.

rardiH36 · Oct 28, 2014

My take on this:

You have owned power boats for many years. As such, you already have much knowledge of boats, of marinas, of DIY maintenance, and of the boating life ... just being around boats.

Yes, sailing a sailboat is different. But with all your experience, only a variation on the theme. Put your mind to it and you will be a good sailboat owner and sailor in no time.

If your budget will allow, go bigger rather than smaller. As long as your new boat has most lines lead back to the cockpit, sailing (say) a 36' boat really is much the same as (say) a 27'. The bigger boat however is more likely to be comfortable for living on. And is more likely to be the boat you will be happy with and hence continue to own for many many years.

I am opining on this because of my experience. I sailed every once in a while in the 1960's as a teenager on a Lido 14' with friends. Next sailing was a week long ASA course in 2007 which I signed up for after I purchased my 1980 Cheribuni Hunter. Several times I have have been out on new and larger (up to 42 ft) sailboats. Yes, they are impressive. But I never have felt the urge to go bigger. I consider that 36' is the "sweet spot" between all the creature comforts most people need and also to comfortably/safely single hand -- or if one mostly mostly goes out with people (say a spouse) that enjoy the adventure but prefer to be passengers rather than a crew members.

geek_guy · Oct 30, 2014

One further comment that I don't think I saw referenced in the thread is Boat Brokers.

They have been a tremendous resource for me. They are usually very accomplished sailors, and most are very generous with their time. They can help you find your perfect boat. And just give you lots of basic information about boats, the time on the water, your goals. etc.

kenackerman · Oct 30, 2014

I think the others here have pretty well covered the waterfront. However there is something else you might keep in the back of your mind and that is what cruising areas you intend to eventually cover and the conditions you might experience on those.

Smaller boats (in my book under 30') are a lot of fun in bays when the sun is shining and you only want to go out for a day sail or an occasional over night if there is a convenient anchorage or marina as a destination. Lots of fun! Even though some might say they would brave the open ocean in them for long periods or during inclement weather, that is not prudent IMO for several reasons.

While the open ocean can be relatively calm and sunny, mother nature has a way of sneaking up on the best of us. Smaller sail boats have lower freeboard and tend to take more water over the rail when seas increase. If you don't have far to go to make landfall when it is blowing link stink you'll probably be OK. Wet sailors tire more easily however, and if you are fighting both the wind (having to tack & shorten sail) and if the seas are running over 6 feet and current is against you too, you may find that it takes a lot longer to get back than you ever expected and that you are more than likely exhausted.

Almost all small boats under 26 feet also use an outboard that are not really rated to provide the torque to drive through contrary seas even after you drop sails and exhaustion goes up as time expands.

My point to this is, if you want to run back & forth to FL in a boat under 30' you most likely want to use the ditch both ways as another suggested earlier OR if you want to go offshore instead, you might want to consider a boat larger than 30'.

I'm not saying you need to start off that way, but it's how some of us end up with larger vessels. Besides, it's a well known fact that all boats start to shrink shortly after their maiden voyage.

Daveinet · Oct 30, 2014

buy a Mega 30 or a Hobie 33 and you can trailer it from NewYork to Florida.

colinhulse · Nov 1, 2014

Do It!!!

I worked up from a 19 foot power boat to a 34 footer. Took sailing lessons 5 years ago at 48. I went straight to a 30 O'day and had no problems. Sailors told me that was too big, but I just took it slow. I motored out in 5 knots of wind and goofed around until I got the hang of it. I moved up to 10 knots by the end of summer. Today I think nothing of 25 knots (fun). I see all the Sea-Rays tied to the dock, reduced to floating cottages. We call the owners 'Dock Potatoes'..they always ask "How is it out there?" Sailing is great! Don't listen to the over the top stuff about how hard it is to master, it isn't. Just take it slow and easy.