# Your Progression of Boats, Learning Curve Questions (Start Big / Start Small)



## superslomo (Jun 16, 2015)

I've been mulling this over, thought about asking in the Learn to Sail forum section, but I thought I'd ask here as more folks would likely have more personal experience to share.

I learned to sail on 16' Bullseyes when I was young, windsurfed a bit, and am getting myself back into it sailing Rainbows at a local school/club membership program. I was talking to a good friend who is eager to sail when he retires, and has decided on buying a 40'-ish multihull (in the $500k range, so he thinks) to take off on and sail the world, after doing some ASA courses.

So, you can guess where I fall on this, but I'm curious whether I'm totally off-base, and he's more sane than I think... I always figured it's best to start small, work your way up, beginning with boats where you can overcome mistakes a bit more easily, in smaller water with smaller forces involved, and work your way up to the big sailing. That all being said, here's what I'm wondering...

How did you all get from starting out from scratch to where you are now? What progression of boats did you sail/own/experience, as owner/skipper, as crew, and what do you think makes sense as a set of steps to take?

I'm enjoying the Rainbows now, and am remembering all manner of things I forgot, and working on singlehanding in relatively controlled, mellow conditions before looking to buy something next year. I was thinking something in the 25-foot range, to take the next step up, with the option to overnight with my small troupe (dog/wife/daughter), before moving up again a few years later to something around 30' for doing cruising down the coast here in the Northeast. Clearly, I like the concept of going small to big, but I know there are folks who've gone in at the deep end with a big boat, headed offshore and survived... I'd like to get into bluewater sailing eventually, shorthanded or singlehanded in all likelihood, but I'm figuring on taking my time to get there.

I know that on a smaller boat, I feel like when a mistake happens, you can more readily muscle your way through it... you can't body-english a 37' heavy displacement boat, but you can still hope to on a 2500 pound rainbow, it seems.

Any input is useful food for thought... what did you do, what would you recommend, what would you do differently, what do you think is ideal, what are you amazed you survived ()?


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## outbound (Dec 3, 2012)

As a teenager crewed on very large boats for a summer. Was a gofer and other than learning what the sea had to offer experiencing different types of weather learned little. After schooling worked my way up
Harpoon
Cape Dory 25
Cape Dory 30
Tatyana 37
South Hants England done as a one off for an Ostar
Monitor 36
Pacific Sea Craft 34
And now my beloved last boat an Outbound 46
Have had crew having done ALL the ASA courses. Have had crew with captain tickets. From experience firmly believe these credentials are useless in judging competency. I would take experienced crew over credentialed crew every day of the week.
Firmly believe you learn by doing. Firmly believe the safest way to learn is to incrementally increase the size of vessel and length of passage. Firmly believe being captain or navigator or crew require three different skill sets.


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## Stu Jackson (Jul 28, 2001)

I started out in Beetle catboats in summer camp in MA. When I moved to SF, wer rented Rhodes 22s and then bought a Catalina 22. Five years later a Catalina 25, 13 years with that boat and now 17 with our Catalina 34. We "skipped" the Catalina 30 stage. 

I agree learning on small baots teaches you to sail, but bigger boats teach you how to deal with boat SYSTEMS.

Like these:

"101" Series - Quick Links to "Popular" Topics includes "Electrical 101"

Your buddy can spend some time to learn to sail while he's figuring out where to spend his half a million. 

If he doesn't, how will he learn what the right thing he wants to spend it on will be?


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## superslomo (Jun 16, 2015)

Stu Jackson said:


> I started out in Beetle catboats in summer camp in MA. When I moved to SF, wer rented Rhodes 22s and then bought a Catalina 22. Five years later a Catalina 25, 13 years with that boat and now 17 with our Catalina 34. We "skipped" the Catalina 30 stage.
> 
> I agree learning on small baots teaches you to sail, but bigger boats teach you how to deal with boat SYSTEMS.


Would you say that you found being on a series of ever larger boats gave you a more gradual learning curve on those systems?

The next jump I make is going to hopefully be to owning something along the lines of an older catalina or o'day 25, as long as I can afford it and it's in reasonable shape, it'll be fun to have on the Hudson by us. I'm hoping that from the Rainbows that it's not too big a leap, I think it'll be manageable, though, with a year of waking up my skills a bit at a time.

A sailor I worked with told me his strongest recommendation was to just do whatever you can to be on the water in whatever you can afford, and move up as you are able, selling and buying used along the way. I can scrape together the kind of money to buy one of those boats and keep it running, but if I'm waiting even for $20k to show up in the next 12 months, I'm going to be a very disappointed guy 

I've had sketchy experiences even mooring a 20' motorboat with a less than cooperative gearbox on the outboard motor at a tight slip in a closely packed marina. I can't imagine having to do it for the first time with a 40'x24' patch of my life savings, surrounded by boats I couldn't afford to fix if I ran into them... that turns into a bad day pretty quickly, even if there's not much wind and wave action 

I'm just looking now to get my wife into the habit (her first sail was with me last weekend, pretty much perfect day, and it went well), and teach my daughter the ropes as she grows into the ability (she's five now), so smaller -> bigger boats and trips seems like a good fit for budget and all other things as well.


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## Lakepapa (Jul 21, 2015)

I'm at step one. Took an intro to sailing course last month and just bought my first sailboat this week. Will learn how to sail it for the next year on our inland lake. My intention is to move on up to something in the 22-25 ft range after that.

Did some sailing in college (loved it) and 40+ years later, took a bareboat to cruising course last year in the BVI (44ft Cat). Fun, but way too complex (systems, rigging, handling, navigating etc.) for me to feel comfortable with. So, I'm restarting from scratch.


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## Stu Jackson (Jul 28, 2001)

During all this, we took lessons when we got our first, the C22. We took four lessons, three on three other different boats a tad larger and then the last one on our own boat. Learn how to steer and run the boat, it'll all come to you. Don't oversweat/overthink the size thing. You're not going from a puddle jumper to the Queen Mary. A 25 foot boat seemed huge to us after the 22, since it doubled the volume. But that extra volume was sweet! 

Sometimes it's harder to teach your wife or kid to drive. Consider having them take lessons - without you around.

Good luck.


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## superslomo (Jun 16, 2015)

Lakepapa, what'd you end up getting?

Stu Jackson, I'm not overly concerned about the transition upcoming, figured it would be manageable... also, since it'll be from the boats I'm in now, where there is no motor, and I'm tying off to a mooring under sail singlehanded, our own boat when it comes will be on a mooring or a slip with at least an outboard to work with. The running back and forth while shooting a mooring ball is a bit more excitement than I'd like in future on a regular basis 

My kid is doing great with it. My wife will probably have an easier time learning from someone other than me, so if she decides she wants to do more than keep an eye on things, I'm going to see if she wants to just do the ASA 101 course. I'm skipping it for now, as it feels like a repetition of lessons I've done before, and the cert itself doesn't seem to matter all that much, from what I'm gathering from folks.

I was thinking about the bareboat and cruising courses just to get a bit of practice with heads, nav gear, handling larger sails etc., but I'm taking it a step at a time.


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## Lakepapa (Jul 21, 2015)

Oops, sorry about that. I bought a sunfish.


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## Donna_F (Nov 7, 2005)

The OP is going to get all kinds of opinions. Mostly, people think their way is the best way because it worked for them. I suggest that anyone in this position do what feels right to them, their situation, their budget.

Just because the OP's friend's plan is to buy a half mill dollar boat he doesn't know how to sail doesn't mean that's the right path for the OP.


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## superslomo (Jun 16, 2015)

I was just surprised when he mentioned it... I guess it seemed like aside from the sheer question of the money, it'd be a pretty steep curve to learn on something that size, even if you've done a few courses, handling a boat by yourself or with one or two inexperienced friends on board would seem a pretty crazy way to do it.

A sort of "really, you don't want to own something smaller in the meantime and get the hang of it?" "Nah, how hard can it be? I'll figure it out then." Not my dime, I guess...

It just got me wondering what people had experienced, what they thought worked, or didn't, and how they would recommend going about the later phases of owning and learning etc.

I don't doubt there are people who've bought a bigger boat and worked their way up to knowing how to manage one, but I'm more conservative (and definitely more broke) than that would befit, so I'm going to figure on getting something local that's in reasonable shape in about a year and getting the most out of it I can. Obviously, a gigantic, brand-new boat sounds pretty sweet, but I'm pretty sure I'd rather have something cheap I don't have to worry about much, and I don't need to go around the world, just from about Poughkeepsie to NYC at the absolute MOST for the next few years, and mostly just in the stretch of water around Beacon, where we can get a mooring (hopefully.) Present sailing is on Haverstraw Bay and around Croton.


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## Stu Jackson (Jul 28, 2001)

superslomo said:


> be on a mooring or a slip with at least an outboard to work with. The running back and forth while shooting a mooring ball is a bit more excitement than I'd like in future on a regular basis


I hear ya.

What I learned to do is to pick it up from the cockpit.


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## superslomo (Jun 16, 2015)

Any trick to that move (pick up from the cockpit), or any tips you could suggest? I figure you just start a bit closer to the buoy and let it run along the side of the boat, then put the mooring line on a side cleat in the cockpit, drop sails, and finally move the mooring line up to the front cleat around the outside of the shrouds... any risks of splitting the pickup buoy and actual mooring ball with any adverse effects?


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## Don L (Aug 8, 2008)

I had never sailed, but was interested in cruising. So my wife and I took ASA Bareboat lessons on a 36' boat. Then joined a club and we sailed on either a 33 or 34' boat on weekends for 3 months. Then we got our first boat, a 39 footer than we sailed for 2 years. Now we have been sailing a 43' boat for the past 5 years (because that 39' boat was too small to make a good live aboard cruiser).

We had no interest in sailing smaller boats. We were interested in learning to cruise not just sail (sailing is easy really). So I of course believe you should try to learn and sail on boats that match your overall goal.


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## jwing (Jun 20, 2013)

Different strokes for different folks.

Yes, sailing is easy. I went from Sunfish at Boy Scout camp to a Hobie 16 for about a year just after college. After an interlude of no sailing for about 13 years, I started bareboat chartering. No lessons. I loved island hopping, but I realized that I was not a good sailor and those big, heavy charter boats weren't teaching me much.

So I bought a 19' day sailer. I'm learning a lot. A small boat presents the sailor with the joy of sailing for sake of sailing. One doesn't need to learn all the nuances of sailing to enjoy sailing. I'm glad I'm learning them before my mind gets cluttered with all the systems that bigger boats have. 

For those who don't care about those nuances, skipping the small boat is a good option. For me it's not. Different strokes...


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## TomMaine (Dec 21, 2010)

superslomo said:


> I'm just looking now to get my wife into the habit (her first sail was with me last weekend, pretty much perfect day, and it went well), and teach my daughter the ropes as she grows into the ability (she's five now), so smaller -> bigger boats and trips seems like a good fit for budget and all other things as well.


I think you're on the right track. I started very young, on a home built Sailfish. Then a little on Lightnings. The first 'large' boat I bought was 23' swing keel. That's the point I met my wife. Our first date-and her first sail, was on that boat. Then we went to a 28', did a little cruising together. The progression of boats just happens if you start young.

My wife on the other hand, loved to be sailing but never really picked it up starting with a 23'er.

We added a daughter and son to the 28'er(owned for 13 years). When the kids were 2 and 3, I built a sailing dinghy. That dinghy worked magic in our family. They all learned to sail in the dinghy, including my wife.

Had I not added that sailing dinghy, which we have used as a tender for the last 20+ years, I'm not sure what would have happened.

Here's our daughter a couple years ago sailing the dog in our now battle scared Nutshell, on a break from college.


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## Don L (Aug 8, 2008)

jwing said:


> So I bought a 19' day sailer. I'm learning a lot. A small boat presents the sailor with the joy of sailing for sake of sailing. One doesn't need to learn all the nuances of sailing to enjoy sailing. I'm glad I'm learning them before my mind gets cluttered with all the systems that bigger boats have.


I go out sailing on my "big boat" just to sail most of the time just for the fun of it. My mind is rarely cluttered with all the "systems". In fact about the only "system" that could clutter my mind is the refrigerator that is always on, because that means the beer is cold and sandwich meat isn't spoiled. :wink

Most of those days when I'm sailing it seems that half the small boats are sailing on just their head sails because it is too much trouble to take the mainsail cover off. Don't understand the joy of that.


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## outbound (Dec 3, 2012)

Going up gradually teaches many things beyond how to handle a big boat.
First teaches you the elements of seamanship. Big boats are much more forgiving and actually in many ways easier to sail.
Second to learn what each line does to sail shape, speed and comfort. For instance when you just have halyard tension, sheets and out haul you learn what they do. Then adding travelers, sheet angle, cunning hams etc. makes sense.
Before getting AC, wind generators, gensets, watermakers and the like it makes sense to have a simple boat where mistakes aren't so expensive so doing your own work isn't so scary and understanding the basic physics of the system is easier to learn. That way on your big boat you'll know if things are functioning optimally and even if you pay for work you'll know if if was done correctly at reasonable cost.
Similarly, there is a steep learning curve in dealing with weather and mishap management. Things are very different when you are outside BoatUS tow range or can just call the charter company if in a jam. Things are different outside the 200m helicopter range. Things are different with no WM or Budget Marine around.
I've read the above posts and respect the fact people learn in different ways. Still, firmly believe only experience teaches the complete skill set to successfully cruise. I honor those who have the courage to jump right in and trust their experiences will gradually increase in risk and complexity but continue to believe:
There are old sailors
And bold sailors
But no old bold sailors


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## capta (Jun 27, 2011)

Started out in Sausalito on a 9' pram rowing dinghy, rowing all over SF Bay and as far out as Point Bonita. Some days the current was so strong I'd have to leave the boat in the city and take a bus home and return the next day to return the boat to Sausalito.
Then came an 11' Moth where I found it much easier letting the wind do the work. Spent many hours doing scut work on numerous sailboats (to 65') in exchange for sailing time, about 50 hours work for every hour sailing, ugh.
After some years of commercial fishing from Mexico to Alaska (king crab at 15) and a few years in the music business business, I retired at 22, bought a 49' Rhodes ocean racer and sailed to Hawaii (NOT a good cruising boat for two).
There I was hired as sailing master on the 125' ketch Araner and worked on a few day charter boats. 
Traded the Rhodes for a 65' Wm. Hand gaff ketch, became intimately familiar with Hawaiian waters and then continued my circumnavigation from there. Still voyaging on the seas.
IMO one can only learn to pull strings and things on bigger boats (the mechanics of sailing), it takes a smaller boat (under 20') to really understand the feeling of sailing.


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## BarryL (Aug 21, 2003)

Hey,

My 'story' and my opinions.

Sailed a little bit in high school on friends parents boats. Got married, had kids, drove race cars and RV camped with family. After one too many traffic nightmares trying to get back onto Long Island after a weekend away, my wife said 'we live on an island, we should have a boat.' I remembered the fun times in high school, did some research, and bought a Catalina 22. Trailer sailed that boat for the rest of the season, then put it on a mooring. Sailing was great fun, way more than I expected, and I was hooked. The C 22 was a great boat for a young family (kids were 9, 6, 3) to spend the day on the water, but I wanted more, the ability to spend a weekend aboard. Bought a Newport 28, the smallest 'big boat' I could find. This boat had a steering wheel, inboard diesel engine, alternator to charge 2 batteries, real marine head, hot and cold pressure water, AC an DC electrical systems, galley, and berths for 5. We did a number of weekend trips, but a 28' boat with 5 people gets real small. So after 3 years with the Newport (and a nice bonus from work) I bought an O'day 35. The 35 had the space, speed, and tankage for use to go on longer trips, like for 5 days, and to places like New York City (79th boat basin), Montauk, Block Island, etc. Had the O'day for 6 years. Kids got older, wife didn't like spending nights on board, I wanted something newer and faster. Bought a C&C 110 in 2013 and that's where I am today.

Moving from small simple boats to progressively larger and more complicated boats allowed me to take my time an adjust. I remember the first time I had to take the Newport 28 out of slip, make a tight turn to starboard, and motor down a narrow fairway. I'm glad the boat was relatively small and light and could be pushed around by hand. I got to learn about headsail furlers, anchoring, using self tailing winches, lighting alcohol stoves, diesel engine maintenance, and all that 'fun' stuff on a fairly simple boat. Going from a 28' boat to a 35' boat was a jump, and the O'day felt huge when i first had to back out of a slip, but I learned alright. 

I would not want to be anywhere near a new sailor with a new, large boat. Too many things can go wrong when docking, anchoring, reefing, etc. 

IMHO, start small and work your way up. You will be able to have cheap fun, learn, experience, and grow. There is a nice older couple who bought a new, beautiful, 38' boat. They keep their boat in a slip near me. The boat almost never leaves the slip. I found out that they are frequently afraid to leave the slip because they fear damaging their boat or a neighbor boat. What a shame!


Barry


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## travlin-easy (Dec 24, 2010)

Go big! Easy to sail, and a lot more comfortable.

Gary


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## Donna_F (Nov 7, 2005)

travlineasy said:


> Go big! Easy to sail, and a lot more comfortable.
> 
> Gary


Sailing isn't the hard part, it's the docking that will mess up your day.


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## PnJ (Sep 24, 2015)

I'm a Noob myself after 30 years of not being on a boat. I started with US sailing lessons on the base as that really cut the price down as well as the rental cost. Flying Scot 19" is what we got certified on and I've already moved up to the Catalina 22'. Amazing what a difference 3' is. LOL
I'm planning to by next spring in the 30' to 35' range. So I'm guessing I'm in the start small category and move on up. I'll be living aboard in St. Augustine come March is the plan.


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## JimsCAL (May 23, 2007)

My progression was a follows:
Jet 14 daysailor - trailered to local lakes
ODay 22 - on Barnegat Bay. Two foot draft was ideal.
Pearson 26 - Traded in the ODay when I moved to Long Island
Cal 9.2 - wanted more of a racer
Cal 33-2 - done with racing, wanted more of a performance cruiser

I was happy with my choices at each step. It fit my needs at the time. If I were you, I would go for something closer to 30 foot as you indicate you want to cruise with wife, kid and dog. Much smaller is going to be tight.


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## aelkin (Feb 3, 2013)

Lots of good advice so far.
SOOO much of this depends on the type of person you are. 
I think at some point, the OP made a statement about being 'conservative'. BINGO - then the start small and work your way up is going to be, by far, the more comfortable route for him/her.
It sounds like the friend with the $500K cat is a bit more of a risk-taker, or has extremely high self confidence. maybe he's been a natural athlete, or a natural learner all his life. That's great, too! There are all types out there. I have guys join my race crew, and within a few races, I trust them in various positions. Conversely, I have guys on the boat for 2-3 years at a time, and they still struggle with the difference between 'down' (traveler) and 'out' (mainsheet)! It's easy to imagine the first guy buying a 40-footer and figuring it out in no time. I would definitely advise the second guy to buy an Optimist.

I progressed from a Tanzer 22 to a S2 26, to a C&C 35 in about 4 years. It was great, from the point of view of reduced costs, risks, potential damage, etc....but on the flip side, I lost my shirt on each of the subsequent sales when it was time to move up. For that reason, I wish I had had the courage and foresight to buy the 35 right up front. It really isn't any more difficult to sail than the 22. But putting up $25K up front for a toy that you're not sure you're going to like is quite a bit more risky than putting up the $4500 the Tanzer cost me.

Bottom line? My opinion is that boat buying and ownership is an intensely individual experience, and you should not worry about what the guy next to you is doing. Do some research, and then do what feels right for you, giving consideration to your unique circumstances - there is no 'right' or 'wrong'.

Andy


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## TQA (Apr 4, 2009)

As a kid we had a heavy clinker built 16 ft CB gunter rigged day sailor which we used mostly on an inland lake.

Went karting, racing, stock car racing, hang gliding.

Aged 40 bought a Catalina[Jaguar] 22 and sailed it on the East coast of Scotland one summer then the Adriatic next. Really learned to sail with this boat.

Age 43 Bought a 38 ft steel ketch and went cruising for 7 years.

Age 62 bought a 44 ft cutter and went cruising again.

At 68 still cruising.


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## travlin-easy (Dec 24, 2010)

DRFerron said:


> Sailing isn't the hard part, it's the docking that will mess up your day.


Docking was easy when I had a fin keel boat, but with a full keel boat, the boat just seems to do weird things. That's why they make bow thrusters, I guess. 

Gary :2 boat:


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## Ajax_MD (Nov 24, 2009)

I really don't see a benefit in increasing boat size by 2 feet every few years. In similar boat types, there really isn't that big of a difference in performance between say, a Catalina 25 and a 27. I can't imagine buying a slightly larger boat every few years and going through the mechanical refresh process and costs over and over again. It seems like a big waste of time and money.

One way to avoid this needless cycle of expense time lost in maintenance, is to buy the larger boat now and belong to a sailing club and learn to sail on small boats and different styles of boats to broaden your palate and range of experiences. Let the club bear the expense and burden of maintenance while you get the educational benefit.

If you're going to cycle through boat ownership, at least make 5-foot increases.
I jumped from a shoal draft, Coronado 25 to a Pearson 30, and bought a Hobie 16 on the side. The Pearson 30 is an old design, but it's still much faster than the Coronado. The increase in size and loads was significant enough to make a difference. The Hobie is very different, very fast and responsive by comparison.


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## superslomo (Jun 16, 2015)

I'm figuring after a year of club boats at 24', something heavier displacement, broader and deeper at 25' seems about right. I'm not looking for big personally, it's not really needed for my current anticipated uses, though in a few years they may become more involved. I'm not expecting to go offshore at this point, and sleeping on board will be more of a night here/night there prospect.

I'd also like to avoid anything (just for me, now) that's too time consuming to get ready for getting underway, as a lot of the time it's likely to be a matter of having a few hours in the evening after getting home to take a sail around the Hudson right at the foot of the hills in town, and it would seem like the bigger the boat, the more work goes into just getting yourself on the water.

Forgetting all of that, I'm on a budget that isn't considering this as a replacement for my house, but as a diversion, so paying cash for something older (new not as imperative, given that it'll be used for the time being within reach of assistance or shore, so the odd bit of breakage and repair isn't life threatening), and means I can work my way in.

Again, I wasn't thinking about "what should I do?" or "what's the RIGHT ANSWER?" as I was wondering what the paths were that people had taken, and what they had found about them... I don't think there's a right answer, though I'd say jumping in big is more likely to be manageable if you aren't in a lot of narrow, skinny water, with a lot of traffic, where the stress level for me of being on a boat worth more than everything I own would make it less fun for me.

No dinghies, though... my wife doesn't care for even the hypothetical possibility of capsizing


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## JimsCAL (May 23, 2007)

That makes sense superslomo. I find little difference in getting my current 33 footer ready for a daysail versus the Pearson 26 I had 25 years ago. In some ways its easier due to the roller furling, inboard engine, etc. I suspect if you get a 25 footer you will be looking to move up in a few years. Seriously think about something in the 27-30 foot range. Small enough to easily daysail but big enough to take the family out for an overnight or for a week-long cruise.


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## dinosdad (Nov 19, 2010)

Was sitting on a beach in St. John, saw a sailboat at anchor and said to my wife , "that looks like a great way to live". Fast forward a few months back home in Connecticut we take a Asa 101 class, instructor sucked, no other way to put it, never returned for day 2. Dropped the whole idea, spring comes we take a casual lesson with a wonderful woman who charters day sails and lessons out of Westbrook . That was a great day, learned more than I could in a month with the official class
( I know there are great Asa instructors out and about , but he wasn't one of them). Next day we decided look for a boat we wouldn't outgrow in a few seasons and cheap enough that if we decided this wasn't for us we could dump( donate as storage fees quickly can outstrip the value of a old boat). Found a c&c 30 reasonably priced , in a great location , and a awesome owner who became a good friend. Mind you we had never owned a rowboat. Four seasons in we still enjoy it , still have much to learn , due to life we use it mostly for daysailing , summer cottage , and escape from life. Though buying a smaller daysailor like a Pearson ensign would have been a better choice from a confidence standpoint , the c&c 30 has served us well, has provided a baseline for things we would like in our next boat, ( you don't know what you want until you don't have it! ) . The one thing I would say about going bigger from the start is if your planning for possible cruising , learning maintance on a boat with some systems will serve you well. My background of tool and die, and vintage auto restoration skills carried over to boating, but some of the materials and techniques are a bit different ( you haven't lived till you replace a holding tank and lines! Fun stuff!). 
Our path with buying a larger boat worked for us from a standpoint of not wanting to deal with selling a boat and move up two or three times,
Not so mint I would cry bumping off a dock, but nice enough it brings a smile to my face. If I had been in my twenties instead of my mid forties when I started on this journey I might have started smaller , but at 47 I'm pretty certain I've witnessed more sunsets than I have ones to see,
So Bigger is better for us.


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## Siamese (May 9, 2007)

Me?...Grumman 16, Holder 20, Grampian 26, Prindle 15, Cal 21, O'day 20, Catalina 309, Precision 23, Catalina 28. 

Some of my boats were kept for many years, others not. My current vessel, the Catalina 28, is going to be around a long time. 

It was only my finances that kept me from going from my first boat, the Grumman 16, to a 30 footer. 

But...bigger boats aren't necessarily better boats. The best boat is the one that fits your situation and needs. We daysail 90% and travel up the Lake Michigan coast for a few days at a time the other 10%. The C28 is ideal for us (couple). 

Quick story: My wife decided she wanted to be able to dock the boat. She had never handled a boat, and seldom assisted me in sailing. She's 58, and had zero aptitude for boat handling. I PATIENTLY instructed her and she took it out and back in the slip, I would guess, for a total of 30 times over a 4 week period before she was competent on a relatively windless day. Then she was ready to solo. She just takes her friends out under power. 

Moral of the story: She managed to do it. Docking is where bad stuff is likely to happen, and I won't say she has mastered it, but she knows her limits and stays within them. 

And...if you should go ahead and get a 30 footer, remember, it's not just a sailboat, it's also a slow powerboat. Nothing wrong with mastering the handling of it under power before worrying too much about the sailing part. 

Based on my observations at several marinas, many owners never make a solid effort at practicing basic boat handling. In my wife's case, a half dozen one to two hour sessions made a huge difference. 

So, practice and get competent. No reason why you can't get the 30.


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## capecodda (Oct 6, 2009)

When we met, my wife had a 22 foot keel boat. We still talk about how much fun we had, and how much we learned on that boat. We bought a 28, then a 36, then a 52, and then got smart (and older) and downsized to a 38 we sail now.

At each point in your life, there is the right boat. IMHO, if you're going to do this for 40 or more years, it's hard to pick one that spans that time period and meets your needs at each phase of your life. How many people want to sail with you, where do you want to go, how much comfort do you want?

Small boats teach you to sail, because they react to conditions quickly to changes is sail configuration and rudder. Larger boats teach you about systems, weather, and navigation as you tend to venture further. You can be sailing a big boat poorly, and it doesn't "talk to you" as much, but you aren't staying overnight and voyaging on a small open boat, or at least I'm not.

If you buy a big boat right away, and find out you don't like it, you have more to unravel. If you love it, more power to you. No one right answer, but on balance, I'd start small to learn and make sure I wanted to make the commitment involved in operating and paying the operating costs of a bigger boat. And if no one's said it here, the cheap part is buying it. None of us like to add up our annual operating costs, because they are higher than we'd like to admit. 

But if you are crazy like me, they are worth it.


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## Don L (Aug 8, 2008)

capecodda said:


> You can be sailing a big boat poorly, and it doesn't "talk to you" as much, but you aren't staying overnight and voyaging on a small open boat, or at least I'm not.


People say this like with time you wouldn't learn to the sail the big boat better, which isn't true. But sailing a big boat poorly might mean you are doing 6 knots instead of the 6.5 knots you could do if you wanted to active steer all the time. I think most fo the time you see a big boat sailing "poorly" it isn't they don't know how, it's that they don't really care.

But it is kind of a useless discussion because it always seems to me that half the boats I see when out day sailing are sailing poorly no matter what size they are (pretty easy to tell by looking at the sails).

Meanwhile once you get there on a small boat you are always in a small boat, but once you get there in a bigger boat you have the comforts of it.


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## gbgreen59 (Aug 20, 2013)

My progression into sailing started with kiteboarding. Once I felt the excitement of using wind to power you, I was hooked. In moving closer to life without a paying job, I decided I wanted to kite and surf in remote parts of the world including the southern Pacific Ocean and the Indian Ocean. So, a sailboat became the means to an end. I jumped straight to a sizable sailboat (35') and am fitting it to sustain "off-the-grid" living.

A series of ASA course work through 104, reading forums and books, along with practice/Practice have been the foundation for spinning up a sailing toolset as fast as possible. After two seasons, my wife and I are now working together as a team. We've been out in winds up to 30 knots, and 4' - 6' seas. We were proud to see that our maximum Speed over Ground showed up at 10 knots when on a beam reach in sizable waves. We've been able to sustain over 7 knots Speed over Water on a close reach. Each of these accomplishments are steps in our journey to become proficient sailors.

I do believe that having a surfing background has benefitted being out in sizable waves (admittedly, 4' - 6' isn't that sizable). I understand where the power of the wave is and where it has less power. I found steering the boat in waves was pretty intuitive whether going up or down wind. Being out in waves (only 4' - 6' is biggest so far) is sooooo!!! much fun. The tops of approaching waves were staring us in the face when we were heeled about 15 degrees. My wife and I were both hooting like kids. 

Last season we were fodder to the other sailors as I watch them all pass me. This year, not as many pass. But, we are still fodder to the racers. They are a point of reference to my progression. :boat :


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## Faster (Sep 13, 2005)

We're with capecodda.... started 35 years ago with a 24, to a 28, to 40 and now back to 35. Sailing with less crew now (kids have their own boat). We do appreciate the amenities we have on our smaller, more easily managed boat that we didn't even have with the 40 footer.. like refrigeration, good battery bank, cabin heat etc.

But each boat was the 'right one' for the time.


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## gbgreen59 (Aug 20, 2013)

A corollary to my experience was keeping the boat on course at night while in waves with no land horizon in view. We did this during the ASA 104 class. It forced us to steer to the compass with no other point of reference, except maybe the wind instrument. This was challenging and very beneficial to growing the toolset for the future. Good stuff.


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## Sinister (Dec 29, 2014)

I am currently on my first boat, a 30 footer, named Learning Curve. She was named that when I got her and it seemed perfectly suited to me.

I had crewed in a small regatta a few times and sailed my friends 30 footer a couple of dozen times. 

I might not sail her perfectly, but I enjoy every minute on the water, wether under sail or motor.

I've learned a lot this year and the learning curve is still pretty steep, but I wanted to make some memories and not wait so long the chance passed me by.


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## jiffy97 (Jun 30, 2015)

Guess this is as good a place as any for my first post on here. I had never touched a line before this summer. Had always been fascinated by sailing and loved the couple harbor sails I went on in Newport RI. After years of making up excuses on why I should do the responsible thing and not own a boat I had enough slaps in the face that life is too short. I signed up for sailing classes in June. Started on Hunter 15s. Progressed up through O'Day 20 and O'Day 22. 

I have been poking around boatyards and online listings all year as well. After actually being on a 22 I realized it would be too small for what I wanted. Which was something to go out with my kids (12 and 15- My son and I are both over 6' tall) and some friends for daysails and for the kids and I to do overnights on weekends. After much research I settled on a really nice Catalina 25. Will be picking it up Columbus day weekend. It may be a bit cramped for weekends with the kids but it has the pop top for more headroom and air. Basic systems to learn on. Came with a nice trailer so I don't have to pay winter storage fees. I think it will suit us nicely as a first boat.

Plan is to upgrade to a 40' when my daughter graduates from HS and sail off..... Having that conversation with new women I date is interesting. But I figure the right boat woman is out there somewhere!


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## capecodda (Oct 6, 2009)

One other thought that some won't agree with. For the pure joy of sailing, of feeling the wind, the pressure on the rudder, the movement of the boat, there's nothing like dingy sailing. I'm an old man, but put me in a 420, or a star, or even a beach cat when it's 15 gusting 20. Feel that 420 climb up on a plane. Get out on the trapeze on a beach cat. 

One friend of mine who's adamant about this says that driving a cruising boat is like driving a truck. Well, I don't quite agree with that, but I do think a lot of cruising sailors are motoring a whole lot, and sailing a little bit.

Pick your poison. Or do what I do and suffer from MBD (Multiple Boat Disorder). No know cure.


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## outbound (Dec 3, 2012)

CC there's truth to what you say but don't you get your jollies in a 40-50'er surfing in the big stuff. All that mass. All that power. Just flying along in control. Or when a 40-50'er has a bone in her teeth going to windward. Going to windward perfectly balanced with just a finger on the wheel and green water creaming along the deck. Sparkles and rainbows raised in the air as the bow slices through.
Come on ain't that a close second to a night when the wife feels perky.


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## capecodda (Oct 6, 2009)

outbound said:


> CC there's truth to what you say but don't you get your jollies in a 40-50'er surfing in the big stuff. All that mass. All that power. Just flying along in control. Or when a 40-50'er has a bone in her teeth going to windward. Going to windward perfectly balanced with just a finger on the wheel and green water creaming along the deck. Sparkles and rainbows raised in the air as the bow slices through.
> Come on ain't that a close second to a night when the wife feels perky.


Yes, I agree. Or a big Asym set on a 52 footer, lots of attention required at the wheel to avoid a broach, just charging. Or short tacking a big boat up a narrow bay with a crew that can get that blade jib just right....or....

Multiple boat disorder. MBD.


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## Donna_F (Nov 7, 2005)

Don0190 said:


> ...
> 
> But it is kind of a useless discussion because it always seems to me that half the boats I see when out day sailing are sailing poorly no matter what size they are (pretty easy to tell by looking at the sails).
> ...


I think this is one of the downsides of being part of a forum...reading that there are people out there looking at my sails and judging how I sail. But it is hard not to because I do the same thing on the water. I don't have perfect sail trim 100% of the time. I consider each trip, whether it's around the buoy and back or out for a week, to be a learning experience. When I look at other boats it's mostly to see what the wind is doing where they are and possibly to see if maybe I should adjust my own sails, learning from the other boat in a way. But I like to think that in all cases I remember that I'm new to sailing and that I also have a lot to learn.


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## chuck5499 (Aug 31, 2003)

I can only tell you what worked for me. At age 55, in Dec 2000, took my first sailing lesson and the first time I was ever on a sailboat. The next spring took 2 more lessons and did a charter for 4 days on a 35'. Chartered a 40' the next year for 3 days and in 2003 bought a brand new 40' Jeanneau DS40. At the time lived in Miami so sailed the bay 3 weekends out of 4. 
At age 60 lost my job and did some consulting but sold my house and moved aboard and headed out single handed up the east coast of the USA to Hadley Harbor in 2008. My sig other joined me the next year and since then we have sailed the entire Caribbean from mexico to Colombia to Jamaica to Trinidad to Antigua and did a 2 person crossing of the Atlantic in 2013 and now just finished year 3 in the Med. 

Never sailed a small boat in my life and no desire to do so. 

Are we the best sailors out here? Not really but then again we got over 25,000nm+ under our keel and get to where we want to go and sometimes quite quickly.


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## popeye31 (Sep 18, 2015)

To the Op I skipped a few posts but my story goes. Decided I wanted to sail one day read a few things on line, rented a few books at the library, also rented a few videos for about a month. found a Mcgregor 25 around the corner from my house for $1200 brought it home cleaned it up fixed a few shives and took it out 2 weeks later. first time on a sailboat was a little stress full not knowing the order of doing things but got her sailing with in the first hour and have been hooked ever since. third time out it was a slow day at the Bonnable boat launch where I would launch her and I had a few friends coming out to see the boat so I had to show off and sailed it all the way to the launch no kicker all sails . the whole deal went flawlessly I was ecstatic. next I wanted to do the Wednesday night races. Crewed on a race boat called Juggernaut for one race just to get a feel of what was going to happen . The next week I was out racing, always cam in last but it would give me a sense of how I was doing as far as trimming the sails. I was getting closer and closer to the finish before the last guy in the race would pass me but I could see my progress. having a crew consisting of my 3 children ages 6,8,10 didn't help when they aren't interested. They just want to ride. I got her in the 8 knots range according to my gps one time figured I was doing good seeing most said it was a 9 knot boat. and it being only my first 2 months sailing with no prior training. I trailered it to lake Pontchartrain on and off for the next 2years till I sold it to put my oldest in sylvan. Its been 3 more years and Im looking at a hunter 30 want to do a few sails to Biloxi, Alabama, Florida and maybe work my way up the east coast. I figured most of the people that single handed the globe were in a 30 -40 footers so the little bit I want to do would be perfect. but it will only be my second sail boat so what do I know. Any way that's my story and Im sticking to it .


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## amwbox (Aug 22, 2015)

First boat I sailed on was my Grandfather's O'day 25. Sailed all over the Columbia River Gorge, at it held up well to the crazy winds and whitecaps. Crewed on a couple of Catalina 30s and a Hunter 33. 

Now I'm looking for my own first boat. Love to find a reasonable Pacific Seacraft 25, (or even a Flicka 20 if its a screaming deal  ). Nor'Sea 27 also really appeals to me. I like small pocket cruisers. Want to sail offshore in the region, and on up into Alaska. Need a fairly rugged boat around here.


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