Making the change

[tzuelke]

I know others will disagree with me on this, but if you really feel that you are a sailboat sailor and you will know the first time you take the wheel or the tiller, buy you last boat first.
I am 56 years old and I bought a 1990 Hunter 27 in January of this year, took US Sailing and ASA sailing courses and 10 month later I love sailing or just working on my boat. However, I am all ready wishing I had bought " my last boat"! Take you time and look around because, boats do grow on trees and there is always going to be a great boat out there for you. Look local because buying a boat and having to put her on a trailer is not a fun way to spend $$$.
Good luck and God's speed

 

[kito]

I would suggest a Catalina 22 to start. Plenty available and easy to sell if you find out sailing isn't really your cup of tea. Trailerable too so can save on slip fees that a larger boat will require. They are easy to single hand if rigged for it. It's a sloop so you can learn tending the jib like a bigger boat. The smaller boats like Sunfish and Force 5's are fun but are very uncomfortable especially on the back.

 

[capta]

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 wholeheartedly agree with this approach. Sailing just isn't rocket science and with a good book like Royce's Sailing Illustrated and a small cheap boat, you'll master the whole thing quite quickly. You really can not learn to sail on a big boat. You can learn to pull strings and things, but you will not understand why you are pulling strings and things until you get into a small boat and feel the changes in motion as you make small adjustments to the sails and rudder. Tipping over a couple of dozen times is also a very important thing to experience, and best done on a very small boat. But unless you are the kind of person that needs to be taught, sailing lessons in the beginning are really a waste of money.
Once you have a good understanding of the mechanics of sailing, it then behooves you to get on as many boats as you can, so that you can make an informed decision when you choose a larger boat to buy. This is when a Caribbean charter with a skipper willing to teach you about cruising can be of value in deciding if that is something you might like to do.
Sailing is all about having fun messing about with boats and very few sailing teachers are that calm and rational about the whole thing. Sailing is probably the safest sport there is and it's a shame when the fun takes a back seat to worry and preparation for disaster. Sure the boom can hit you on the head, but you can drown in 2" of bath water too. Go forth, young man, and have fun.

 

[Gobsmacked]

Nevertolate,
Buy a 16-20 foot daysailer in which to learn. My experience after more than 60 years as a sailor is that people who learn to sail monohull dinghies can quickly learn to sail anything else and make the switch to big boats easily. That's not true the other way around.
Once you learn what makes a sailboat go, and the nuances of the standing and running rigging, there will be literally dozens of good 28-30 footers available in your budget range, many of them in mint condition.
You can learn to sail on a Sunfish or Laser, and they are fun boats. But I think the best way to start is on a small sloop (mainsail and jib), and since most guys your age aren't midgets, preferably on a boat you can sit in comfortably and that weighs more than you do.
I've owned a dozen sailboats from 12-32 feet in my life, both monohulls and multihulls, and I've helmed and crewed aboard other boats up to 60 feet. I spent a lot of years racing, but my wife never enjoyed sailing much (and hated being aboard in a race.)
Last summer one of her friends decided to take a beginner's sailing course at a yacht club, and she talked my wife into doing it with her. They sailed 420 dinghies, a very physical and uncomfortable little 13-footer normally raced by high school and college kids.
She enjoyed it, and what's more, it turns out she's a natural helmsperson. After that class ended I bought an 18-foot daysailer so she could keep sailing. It's fast and fun and much more comfortable than the 420, especially for women of a certain age, as the French say.
Because I travelled so much in my job I hadn't owned a cruising boat for some years, but I also found a 30-footer that I liked a lot and we bought that, too. Her first bigger boat experience was on that 30-footer, and once she figured out that you turn the wheel the opposite way that you would a tiller, she loved sailing it.
We are keeping the bigger boat on the Great Lakes and trailered the daysailer back to Florida, where it's great for puttering around the shallow bays on the southwest coast.
Before you buy a cruising boat, ask yourself what you want to do with it. Remember, most 30-foot sailboats average about 5-6 knots, so you aren't going to go very far if you're just out for the day. Will you mostly daysail or are you planning some extended trips?
You also have to think hard about how much will actually use the accommodations below. I have a friend who owns a beautiful 35-foot cruising boat that he has never spent a single night aboard. He races and daysails and ties it up at its home dock every night. About all he uses the galley for is making Bloody Marys in the marina in the evening.
And what are the sailing conditions where you live? If you have a lot of shallow water, you won't want a deep draft boat. If you mostly experience light air conditions, as in southwest Florida, you'll want a lighter boat with a lot of sail area. If you get nice trade winds, like the east coast of Florida, a heavier, deeper-draft boat might be better.
There's a lot to think about. That's why it won't hurt to spend a year or so learning to sail through a local yacht club or private program before committing to a boat you'll probably keep for some time.
Lots of luck,
Gobsmacked

 

[pateco]

I have been sailing since I was very young, Pram, Sunfish, Hobbie, Prindle, Lazers, 420s. Then in college started sailing offshore on larger boats racing with my college sailing team. With all that sailing, I have never owned my own boat. However at 50 years old, I have just recently picked up a FREE 1983 Hunter 31. It was in somewhat rough shape, but my family and I are having a blast restoring it. If you want to see what is involved in redoing an older boat, please check out our project page The Stargazer Adventure Their are lots of considerations when purchasing a sailboat, and lots of items to look at when making your decision. Keep reading this forum, it has been a great help to us in our adventure.

 

[dziedzicmj]

I would suggest that how you learn is secondary (buy a smaller boat, charter, sail with friends), but gain some experience before you buy you final boat. At this stage you don't know yet what you like and dislike. And opinions vary. One like a Catalina 22 or a MacGregor 26, another may swear by a 40+ or even a 50+ foot cruiser.

After a season or two you would know what matters to you. Do you want a tiller or a wheel, an outboard on inboard, plenty of cockpit (and a smaller cabin) or vice-versa. Some people swear by hank-on sails, others would never sail without a roller furler.

Others can only offer their opinions and advice, but your preferences are the only things that matter.

So try various things before you buy it. And even after that, you will make some mistakes.

Good luck.

 

[JamesG161]

Go to or join the local yacht club, sailor hang out or marina pubs. Make friend with all size captains and volunteer to be crew. Buy some fuel, beverages or food. You will be surprised at the invites you get. Lessons are fun and you will learn the sailing TERMS faster than book. Also the various parts of the sailing adventure are exposed: Racing, Day Sailing, Cruising (long distance and local), group adventures, therapy, fishing, etc.

TIP: There is no such thing as a ROPE on a sailing vessel and a Sheet is not a bedding material.
Jim...

PS: I found power boats were more work than sailing, except perhaps in a squall.

 

[mrreg]

I have owned and sailed on small boats on and off over the years and crewed for friends on larger boats....but this past June I purchased a 1978 Catalina 30 to celebrate by 71st birthday. It's rigged to sail solo. I am working my way up to local sailing single handed....at bit of a work out, but love it. I say go for it!

 

[mauruuru]

Two pieces of advice I received-but ignored-when purchasing my first sailboat many years ago when I bought a Catalina 23:
1. a bigger boat is easier to learn to sail, get a 30 footer you can afford
2. get a complete survey before buying...in that price range a lot of stuff will need replaced, repaired.
My second boat, an O'day 30 proved both points to be correct. The O'day was much easier to single hand than the Catalina and I owned her far longer for the reason that I replaced virtually everything and rigged her for single handing.
Finally remember in the transition from power to sail, it will no longer be about the destination, rather the journey getting there!

 

[centerline]

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..

I have to disagree with this.... the following statements are true for all types of boats but even more so for a sailboat.

almost everyone that thinks they will purchase their last boat first will regret that path.... unless they have a load of money to make modifications to the boat that for most of us would be unaffordable.
a sailboat, more than any other type of boat, is a compromise. you have to give up one desirable characteristic for another, and until you know what you want and how you want it, and what you can live with and cant do without, you shouldnt "sell the farm" and invest everything in the "dream" boat until you do know that it is "the boat" that you want to build on....

and in addition, I can name many guys, who purchased too much boat, have owned the boat several years or more, and are still afraid of it, still dont know their capabilities, and have no idea of what the boat is even capable of..... these boats dont get used as much as boats where the owners have "earned" the passion for their boat rather than "buying" it.
I honestly cannot recall a single name of someone who started out small and worked their way up to a bigger boat, that is afraid of what they have or unsure of their experience in boat handling...

it seems the experience of starting small gives the opportunity to decide to either learn and to like the lifestyle, or to decide it really isnt for them...

granted, a 30ft boat isnt BIG, but the cost is kinda hefty, and the risks of purchasing the "wrong" first boat without some experience of the particular type of boat, is high.

 

[bffatcat]

new sailor

I have to agree with Benny at 52 I do not see the point in starting small
go to sailing school learn the basics Your Idea of a 27-28 footer is a good Idea One more thing: I would look close to home NY NJ plenty of good boats for sail. Be sure and get it surveyed b4 u buy

Good luck

 

[mikeyairtime]

I'm a powerboat guy and when I retire I'll get a Fischer motorsailer or something similar. For me it's simple, sailboats are good for extended cruising on a budget and they're fun to race. Day sailing, not so much unless it's really blowing. Sailing is simple, you can travel in any direction except for 45 or so degrees (less in most cases) either side of straight into the wind. Go to the local marina that does week night beer can races and offer to split costs. I learned to sail in one summer of beer can regatas. One side note, in racing there will be yelling.

 

[bdc1]

I agree start small but maybe not sunfish etc except as a lark along with a deep water boat
I would look to trailer sailors like Hunter Catalina etc. I just bought a Hunter 260 in the range you listed you would pay for your end boat price
(inserted as an example NOT AS AN ADD) I have a McGregor 25 foot swing keel sailboat rigged for single Handling with motor and trailer for $4300 so for a small amount you can find good boats that will get you up and going then sell and move up

 

[LuzSD]

I think you will consider this one of the best decisions you make in your life! We started sailing at 50 something and it is now what defines much of what makes us happy and satisfied. It’s relaxing, beautiful, quiet, scary, fun, exhilarating, crazy, frustrating, and a never ending learning experience. What could beat a breeze in your face, quiet time if you want it, without crowds of people and a great chance to see some wildlife up close?

We got a Catalina 30 and have worked to make it perfect for us over the past 8 years. Though we have thought about getting a bigger boat, she is so important to us as a part of our family I doubt we'd ever be able to part with her. Maybe give her to our kids and move up to bigger but I doubt that even. We will likely just stick with a 30... Its a great size for single handing and still has lots of room for comfort and slip fees are still somewhat reasonable.

Sounds like your plan is a perfect one and what doesn't work will force you to make adjustments. Go for it and enjoy a new chapter in your life.

 

[Daveinet]

Learning how to sail is easier on a big boat as they are more stable and a lot more forgiving than the smaller vessels.

But if the boat is stable and forgiving, you don't learn anything.

 

[Gerald Tibbo]

I was a Power Boater for many years and loved it but really wanted to get into sailing. I have sailed a bit in the past but limited amounts. Last year I bought a Beneteau 343 and Im the happiest sailor ever. By the way......I'm 71 and look at you as a very young fellow. Go for it, its amazing.

GT

 

[zengirl]

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!

Hey, You have plenty of time. I'm a 71yr old lady and I just bought my first boat. Bristol 30' which I hope to sail singlehanded within the next two years. I, like you, have never sailed. With other people, but not on my own. Am taking classes also, I think for me the hardest will be learning to set a course, chart plotting and all. I have also been on big power boats and I feel sailing is an art and a challenge that doesn't come with powerboats. And that is what draws me into the world of sailing. Go for it, sailing by your own wits is such an accomplishment. Wishing you and yours the best.

 

[Pura Vida 85]

Your wife might surprise you. My wife didn't like flying, power boats, motorcycles, but loves to sail. If you are going to do the length of the East coast, you may want to get a slightly bigger boat than what you mentioned.

 

[Scott T-Bird]

nevertolate, there is a lot of variable advise, so I'll add mine. I think you can learn how to sail just fine by starting out with a cruising sailboat in that size. Many sailors say that learning to sail with a dinghy is the only way to go, and I think those are the folks who learned that way, so it's a natural preference. I learned to sail small boats starting at a young age, too, but I don't think it really matters when you're 52 and you know what you want. Actually, when I was in my late 40's and looking for my first cruising sailboat, my experience sailing all sorts of small boats didn't prepare me one iota for what I needed to know in making my purchase of a boat with completely different systems.

What you do have going for you is your expected purchase price is a very nice solid budget for used boats up to 30'. Heck, you could probably find some larger boats that are worthwhile for your budget, so I would narrow down your search by eliminating less than 30'. It sounds like you are set on the idea of anchoring out and cruising the ICW with some excursions outside. A 28' boat may be a tad too tight (for you) for that kind of experience. I have a 27' boat, and I know that for the purpose you are thinking about, more room would be much better.

With the money you are willing to spend, take your time shopping and really focus on the condition of the boat, and the upgraded equipment that comes with the boat. Money spent up-front for superior condition and upgrades WILL save you money in the long run, if you are the sort of person who likes to make upgrades. Sellers NEVER make money on the upgrades, so when the boat comes with upgrades, the seller is selling at a loss ... take advantage of that concept, because when you buy upgrades yourself, you are paying retail. You basically pay wholesale (or nothing at all) for upgrades that come with the boat. Just be sure to not overlook condition defects when you see a boat with all the wishlist items, because poor condition, particularly in the area of diesel mechanics, will bite you on the a$$ if you don't pay attention!

The biggest challenge you will find is learning about your personal preferences and needs. Not many people can describe that for you. Take your time and look at a LOT of boats. Don't worry too much about missing out, the next best thing is always around the corner.

 

[Pura Vida 85]

You might want to take a multi-day 'live-a-board" sailing lesson. This will let you know how you like sailing. I had a hobbie which I only sailed 3-4 times. Took a live-a-board class, purchased my O'day '39 in Lighthouse Point and sailed it to NY. No regrets.