Making the change

Oct 26, 2014
7
Monterey 242Sel City Island New York
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. Maybe the final straw was reading The Long Way by Bernard Moitessier while I was anchored for 3 days on the Monterey.

I have read that a lot of sailors say to buy your end boat at the start and save yourself the loss of re-selling when you move up. I also think it would be good to learn on my own boat.

I would be single handing most of the time since I can hardly get the wife on my boat (never mind a heeling sailboat lol). I was thinking in the 28-30 foot range, and would eventually (a few years from now) like to make annual runs from NYC to Florida.

I would be in the price range of 25k to 30k. I'm going to take some sailing classes next spring /summer and would also have my friend teach me what he knows about sailing. He has a Captains License and delivers power boats from NYC to Florida BUT he has only sailed for two summers on his buddy's 23 foot sailboat so his sail experience is very limited.

Any and all comments would be greatly appreciated. If I get a response telling me I'm nuts and I am too old to start sailing at my age I will know my wife is on this forum. Thanks!
 
Last edited:
Jul 21, 2013
333
Searching for 1st sailing boat 27-28, 34-36 Channel Islands, Marina Del Rey
Never too late to start anything in life.


Register for sailing courses, study the concepts of sailing and dive in.
Sailing is a bit physically demanding, but you will love it. Very peaceful activity.
 

Sailm8

.
Feb 21, 2008
1,750
Hunter 29.5 Punta Gorda
IMHO you are in the right size for your budget. Florida is a good place to shop, good selection and prices. Don't overlook the accommodations. If you travel from NY to Florida via the ditch, you will be sleeping, eating, showering and pooping for a long time on your boat. Be comfortable at anchor. Although it is a sailboat you will be motoring for long periods (days) at a time so a low hour diesel is a plus unless it's a real old boat and motor has been neglected. Propane over alcohol but not CNG. Refrigeration can be a plus or minus depends on your sailing style. Draft not more than 5 feet, closer to 4 is better.

Others will chime in and these are just my opinions. Every sailor has his own perfect boat, however everyone is still looking.
 
May 11, 2005
3,431
Seidelman S37 Slidell, La.
Small

Many will disagree with me on this, and it is not the way I started and learned. But I would advise that you buy a little bitty boat to learn. A sunfish, or lazer or flying scott, will teach you a lot of lessons that would be very expensive on a larger boat. And they can be had very cheap. Fun to sail too.
 
Jan 22, 2008
1,483
Hunter 37 C sloop Punta Gorda FL
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. Maybe the final straw was reading The Long Way by Bernard Moitessier while I was anchored for 3 days on the Monterey. I have read that a lot of sailors say to buy your end boat at the start and save yourself the money loss of re-selling when you move up. I also think it would be good to learn on my own boat.I would be single handing most of the time since I can hardly get the wife on my boat (never mind a heeling sailboat lol). I was thinking in the 28-30 foot range, and would eventually ( a few years from now) like to make annual runs from NYC to Florida. I would be in the price range of 25k to 30k. I'm going to take some sailing classes next spring /summer and would also have my friend teach what he knows about sailing. He has a Captains Liscense and delivers power boats from NYC to Florida BUT he has only sailed for two summers on his buddy's 23 foot sailboat so his sail experience is very limited. Any and all comments would be greatly appreciated. If I get a response telling me I'm nuts and I am to old to start sailing now at my age I will know my wife is on this forum. Thanks
Keep your money in your pocket for now. Find a sailing school. Learn to sail on their boats. Charter, rent or crew for racers.your tastes will change with experience. Later, ease into ownership. Never say this is my last boat.
 
Mar 20, 2012
3,983
Cal 34-III, MacGregor 25 Salem, Oregon
Many will disagree with me on this, and it is not the way I started and learned. But I would advise that you buy a little bitty boat to learn. A sunfish, or lazer or flying scott, will teach you a lot of lessons that would be very expensive on a larger boat. And they can be had very cheap. Fun to sail too.
I would fully agree with buying a smaller boat first.
As the original poster is going to try and learn everything that his buddy knows, and his buddy only has the experiance of sailing on another friends boat... there is not enoungh experiance there to learn from...

If a bigger sailboat is purchased by someone without sailing experiance, i would highly recommend formal sailing lessons.

My opinion here comes from my experance..
When a person is going to teach themselves how to sail, which isnt difficult if your a quick learner, There will be a much better learning curve by owning a small daysailor and pushing it to its limits so you can learn how to handle the wind.
once you know the wind and how to use it to your advantage, and once you know where the dangers are and how to avoid them, then is the time to move up to a bigger boat... then you only have to learn how to handle the bigger boat in the same wind...

Too much boat too soon can easily take the fun out of sailing, especially if you dont know how to handle the wind that comes your way... and if you invest that much money in a larger boat, only to find it quickly becomes no fun, that would be a very expensive lesson about sailing and sailboats.

Age has nothing to do with it at all... how nimble you are and how sharp your mind is has everything to do with it... and if you want to sail in the cold wet months, how hearty and tough you are will be a big factor.
 
Apr 1, 2010
398
Cal 33 and Sea Pearl 21 . Crystal River, FL
i would definitely agree with starting out small. I am self taught and sailed my rk 20 (not big by any stretch of the imagination, but not a dingy either). several months back a bought a sunfish. first of all it is a BLAST. second, I went sailing this past weekend on my (new to me) c22 and noticed ALOT of differences in how I sailed SINCE having the sunfish. the most minute changes are hardly noticed in a big boat unless you are watching your speed on a gps, but those same changes will set you back a little while you FEEL the speed increase on a sunfish.
 

Tim R.

.
May 27, 2004
3,626
Caliber 40 Long Range Cruiser Portland, Maine
Many will disagree with me on this, and it is not the way I started and learned. But I would advise that you buy a little bitty boat to learn. A sunfish, or lazer or flying scott, will teach you a lot of lessons that would be very expensive on a larger boat. And they can be had very cheap. Fun to sail too.
I would not disagree with this. I have seen many give up or make very costly mistakes because their first boat was too big and/or complex. Remember, owning a sailboat is only partly about sailing. Maintenance also factors in from a cost and experience standpoint. Generally, smaller is simpler and cheaper.
 
May 11, 2005
3,431
Seidelman S37 Slidell, La.
Besides the cost

As a p-revious poster noted. You notice small mistakes much easier in a smaller boat, and you learn much easier and quicker to feel what the boat is doing. And like I said, they are FUN.
 
May 24, 2004
7,164
CC 30 South Florida
That is the right approach; purchase your last boat first. Learning how to sail is easier on a big boat as they are more stable and a lot more forgiving than the smaller vessels. If you were in your twenties and perhaps interested in racing I would say learn in a small boat but being in your 50's and looking forward to cruising I would say do not waste time and learn in what you are going to be sailing. Operating a sailboat in close quarters is very different than operating a powerboat. First learn how to leave and return to the dock in varying conditions. Use the boat as a powerboat for a while until you become comfortable on how a displacement hull moves thru the water. You can take classes or find an experienced sailor to go out with you a couple of time and teach you the basics. Then it will be up to you to practice and practice. Boat handling is just one of the skills that will help you to get to Florida, then you have a steep learning curve starting with navigation, boat systems, anchoring, provisioning, rules of the road, communications, weather etc.
 
Apr 27, 2014
27
Catalina 30 1986 MkI Newington Nh
In my youth I sailed sunfish, Force-5s and Hobbies, then the kids came along and had nothing until I reached 66. This spring bought a C 30 and spent the summer sailing and working on her. So I don't think your nuts. I sailed a lot single handed, and haven't had this much fun in a long long time.
My requirements for my new toy where
all lines leading to the cockpit.
Furling head-sail and lazy Jacks on the Main. (got lucky and found Both Furling Gen and Main)
No larger than 30 feet.
My like to have list was
Pressure hot/cold water
LPG over CNG
Anchor windless
I got lucky and got everything except the windless for under $25,000.00.
You have owned boats for a long time and know how much work they are. So go for it!
 
Oct 26, 2014
7
Monterey 242Sel City Island New York
I appreciate all the responses. I will be going to a sailing school for starters and learn the basics. I have a lot to learn about sailing and I will be an eager student. As far as navigation, anchoring and rules of the road I have been boating for 30 years so that's not a problem and I am in good shape so the physical demands of sailing aren't a problem either. I have the same mindset as Benny stated, if I was in my 20's I'd start out on the small boats and work my way up but not in my situation. I still think its a good idea to spend next season taking classes and sailing lessons while still using my power boat. Then in the 2016 season sell my Monterey and get a 28-30' sailboat and find an experienced sailor to teach me how to handle her in as many different types of situations as we can. I will also keep reading this forum because there is a lot of useful knowledge being dispensed in here that will help me choose the right boat when the time comes. And Nashuasteve I am tired of pulling up my muddy smelly anchor by hand so I too will have a windless on my list.
 

Apex

.
Jun 19, 2013
1,211
C&C 30 Elk Rapids
In my youth I sailed sunfish, Force-5s and Hobbies, then the kids came along and had nothing until I reached 66. This spring bought a C 30 and spent the summer sailing and working on her. So I don't think your nuts. I sailed a lot single handed, and haven't had this much fun in a long long time.
My requirements for my new toy where
all lines leading to the cockpit.
Furling head-sail and lazy Jacks on the Main. (got lucky and found Both Furling Gen and Main)
No larger than 30 feet.
My like to have list was
Pressure hot/cold water
LPG over CNG
Anchor windless
I got lucky and got everything except the windless for under $25,000.00.
You have owned boats for a long time and know how much work they are. So go for it!
a Catalina 30 is a boat that can be carry you through a long time. A good overall choice. I noticed you DID learn to sail on a small boat. I did the same and wholeheartedly endorse that prevailing opinion. You really do learn the feel for sailing and again it IS fun. An older sunfish in good shape can be had for several hundred dollars, and would have no depreciation. Better yet, KEEP the sunfish after for when you feel like playing out on the water.
 

WyattK

.
Oct 27, 2014
3
Grand Banks Trawler 36 Classic Buffalo NY
We have been sailors for over thirty years and I still own an 18' Hobie Cat with wings for fun during the summer. But, after getting serious about cruising we switched to a Grand Banks Trawler to get where we want to and enjoy the ride and the cruising; less physical work and more comfort. True, it's a little more expensive (buying fuel vs. buying sails), but it is a lot less stressful when you get sixty-five plus. We have stayed on the boat for over six months, and next fall we expect to be gone about 9 months.
 
Jun 1, 2013
14
Hunter 306 Treasure Island
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. Maybe the final straw was reading The Long Way by Bernard Moitessier while I was anchored for 3 days on the Monterey.

I have read that a lot of sailors say to buy your end boat at the start and save yourself the loss of re-selling when you move up. I also think it would be good to learn on my own boat.

I would be single handing most of the time since I can hardly get the wife on my boat (never mind a heeling sailboat lol). I was thinking in the 28-30 foot range, and would eventually (a few years from now) like to make annual runs from NYC to Florida.

I would be in the price range of 25k to 30k. I'm going to take some sailing classes next spring /summer and would also have my friend teach me what he knows about sailing. He has a Captains License and delivers power boats from NYC to Florida BUT he has only sailed for two summers on his buddy's 23 foot sailboat so his sail experience is very limited.

Any and all comments would be greatly appreciated. If I get a response telling me I'm nuts and I am too old to start sailing at my age I will know my wife is on this forum. Thanks!
I think the Catalina 30 is an excellent boat. I would suggest looking into a program like "Sailtime". Most locations have certified instructors and you have access to a variety of sailboats to try out. It will also get you involved with like minded individuals in a social setting that might even appeal to your spouse. Just a thought. Great post. Thank you.

J
 
Sep 20, 2014
1,328
Rob Legg RL24 Chain O'Lakes
My recommendation would to buy cheap the first time around. While many will say buy your last boat first, it is very difficult to make an acurate choice until you get your feet wet.

One of the things that stuck out to me was when shopping used boats, prices were all over the place for identical model boats. Other than age, I knew that I had no clue what made a good boat good, and a bad boat bad. So I decided that I should jump in cheap and use that as a learning experience. That way my mistakes would not cost me a lot of money. Some of what I learned is how to look for rot in a fiberglass boat. (and also how much trouble it is to fix it) I learned what good fixtures look like, and why some stuff doesn't work well. The boat did not sail well, and even though it had ballast, it was still tender. The weaknesses of that boat tout me to be a much better skipper, because I had to anticipate problems before they got out of hand. The boat had a flat blade rudder, which didn't do much, so I learned to steer with the sails. (I kept singing "I need a rudder that won't drive me crazy") As bad as the boat was, it was the right thing to do, as I learned what I wanted in a boat without spending much money. I sold the boat for more than I paid for it, but slightly less than I had into it. My net loss over a 3 year period was 150 bucks. Good deal for what I learned. One thing you learn is that if you sail on an OK boat, you never learn what not to buy. The boat had a lot of issues, so the learning experience was invalueble.

So, when you do go to buy that final boat, one thing I would recommend is looking for speed. Even though you may not race, fast boats must be built right and sail well in order to be fast. One other consideration is to look at a used trimaran, such as a Farrier. While the accommodations may not be as big, the boat will sail well. Not only that, but a tri sails FLAT. Knowing the boat is stable and no heeling, you may be able to convince DW to sail with you. Good sense of motion (speed) in light airs, and perfect quite, except for the noise of the water may be able to hook her into loving sailing. There is nothing like it.

Oh, and I should mention, I love the boat I have now. It is perfect for what I wanted in a boat.
 
May 13, 2009
17
Ericson 28 Hingham
thing small

1. Go small to begin with. Keep the power boat for a while and see if you do LOVE sailing. If not you still have your options.

2. asking this site if you should switch from power to sail is like asking Jim Perdue if you should switch from beef to chicken!!!!
 
Jul 21, 2014
1
Hunter 30 Jefferson City
Buy small charter BIG

I would fully agree with buying a smaller boat first.
As the original poster is going to try and learn everything that his buddy knows, and his buddy only has the experiance of sailing on another friends boat... there is not enoungh experiance there to learn from...

If a bigger sailboat is purchased by someone without sailing experiance, i would highly recommend formal sailing lessons.

My opinion here comes from my experance..
When a person is going to teach themselves how to sail, which isnt difficult if your a quick learner, There will be a much better learning curve by owning a small daysailor and pushing it to its limits so you can learn how to handle the wind.
once you know the wind and how to use it to your advantage, and once you know where the dangers are and how to avoid them, then is the time to move up to a bigger boat... then you only have to learn how to handle the bigger boat in the same wind...

Too much boat too soon can easily take the fun out of sailing, especially if you dont know how to handle the wind that comes your way... and if you invest that much money in a larger boat, only to find it quickly becomes no fun, that would be a very expensive lesson about sailing and sailboats.

Age has nothing to do with it at all... how nimble you are and how sharp your mind is has everything to do with it... and if you want to sail in the cold wet months, how hearty and tough you are will be a big factor.
I was a power boater into my 50s. Hard to water ski behind a sailboat. My wife and I enjoy the sailboat now into our 60s. I started with a 22 footer, then a 25 footer and now own a 1979 30 foot Hunter. That is a nice size.

If I make it into my 70s I will probably switch to a Trawler. All the class of a sailboat with the ease of a power boat.

I would agree take some lesions and charter some boats. Check around, chartering sailboats is a real bargin if you shop around and pick the right locations.

BTW I am also a pilot and flight instructor. Airplanes and sailboats both ride on the wind. Works for me
 
Feb 10, 2004
4,099
Hunter 40.5 Warwick, RI
Lots of good thoughts here. I would add my own opinion that a small boat on a local lake is a great way to learn to sail. It is easy to scale up from there and there will be minimal investment loss with a small boat.

All that aside, let me welcome you to sailing from the dark side! :D
 

tbsiii

.
Jun 28, 2011
2
Flying Scot 19 Ft Deep Creek Lake
P-21

Unless you really want the aggravation of sailing all the way to FL from NY, why not buy something that can be trailed to start off with? I trail my 21 ft Precision to Rhode Island and Florida from Pittsburgh with no difficulty with a Toyota Highlander. You can get into the live aboard later if you like it. The Precision 21 is forgiving and easy to handle with a 5HP outboard, shoal keel w/centerboard. Minimal draw is less than 3 feet. Cheap way to get started that is a step up from a one design boat. Have fun!