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The Contessa was my first boat. It was pictures of her, with the beautiful deep full keel and storied history that turned me from a browser into a shopper. She was the first boat I looked at and although I looked at cheaper boats, bigger boats and boats in better shape (some boats were all 3) I kept coming back to the Contessa.

She's since carried me through conditions I had no business being in and I've poured over every system and put hundreds of hours of sweat and thousands of dollars into maintenance and upgrades. In short, I love the boat.

But here I am looking at different boats online all the time. She's small even for a 26' and the with boat economics being what they are (high cost, low reward) some of the final maintenance hurdles are probably unjustifiable.


I'm scheduled to look at a J/28 this weekend. At the opposite end of the sailing spectrum, on paper at least, it's a lot more boat for the 2' of extra costs (identical actually, if anyone called me out for the protruding transom rudder, which they haven't).


So my question is how do you know when it's right to "move up". Who got the bigger boat they wanted and regretted it? Who worried about the decision but then never looked back?
 

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For us, the decision came when we decided that we wanted to extend our sailing range and cannot do it using our current boat. We decided on Next Boat, but until we're actually ready (lots of other things have to fall into place) we're more than happy with our current boat because it's just fine for where we're sailing now.

I'm a firm believer in buying a boat to meet your current needs, not what you think you'll be doing ten years from now. If we buy Next Boat now, it is a huge jump in expenses all the way around for a boat that will not be sailed in the conditions for which it was built.
 
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I'm with Donna.

My first boat was a Catalina 25 that I bought for a low price. It was the perfect boat for me to evaluate if I liked sailing and what kind of sailing that I liked. A $20k boat would have been the wrong tool for the job at that time.

My second boat is my Pearson 28-2. It provided a ton more interior storage, standing headroom, and comfort in big seas that the Catalina could not. It is a much better cruising boat for my wife and I. As long as we are coastal cruising and not racing the boat seriously it is the right boat for the job for us.

If I ever quit my job and do an around the world trip then my Pearson will be too small and I'll evaluate larger boats.

If I ever get serious about racing and want to campaign my own boat I'd also look for something a little larger and more sporty.

In the meantime I'm sticking with what I've got. For coastal cruising and a small family (2 adults, <=2 small kids) a good ~30' boat (like my Pearson 28-2) is a great choice. Expenses go up significantly for me if I get a slightly larger boat (like 33'), so that isn't something that is on my radar today.
 

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bell ringer
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Well my first boat was 39'. Within a year of the 2 of our older round bodies crawling into and out of the cramped aft berth we knew we wanted a larger boat. Now we have a 43' boat and can crawl over each other pretty easy in that berth, but wish we have a centerline berth. So..................we still want a bigger boat, but wouldn't get one unless we somehow have money fall from the sky.
 

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Hey,

I think you know you're ready when either your requirements change, or you have gained enough experience to know your current boat isn't 'the one' anymore, or you have found enough $ to make buying a newer / bigger boat not so painful.

I started with a cheap Catalina 22. Great boat to learn on. Fun for my wife and I. My kids were really young at the time (9, 5, 2) so didn't have much impact on sailing. After a year with the C22 I was hooked on sailing. We used to go camping as a family in an RV and I wanted to transition from land to a similar experience on the water. The C22 was too small for that. Once I felt comfortable sailing, docking, anchoring, etc. I moved up to a Newport 28.

The Newport had the right size, price, condition, and features. I happily sailed that boat for 3 years. We went away on many fun filled weekend trips. However, once we were in 'night mode' where everyone was in a bunk, the boat got REAL small. Like there was no where to put all the gear you need. Like it was real hard to move from the vberth to the cockpit without tripping on gear lying around.

I had recently changed jobs, and made some extra money. I was very comfortable sailing the 28 and thought that a bigger boat, something in the 34-36' range would be better. It would be faster, more spacious, able to handle bigger weather, carry more gear, etc. So I moved up to an O'day 35. We did a number of week long trips in the O'day, and it was everything I hoped it would be. No regrets buying it at all.

After sailing the O'day from 2006 to 2013 I decided to change tacks a little. My kids were now older (19, 16, 12) and my oldest didn't go away with us anymore. My wife never really liked spending nights on the boat. I had been doing some racing, and wanted a boat that was significantly faster than the O'day. My two younger kids had some done some casual double handed racing with me, and we wanted to do more. I also had a bunch more $ to spend. Long story short, I bought a C&C 110 (36') at the end of 2013.

I must say that I regretted it a little at the beginning of the season. The reasons were mostly because it was difficult to sell the O'day. I was very busy with work, coaching soccer, family obligations, etc, and didn't get the C&C ready until mid June. The C&C is also a very different boat than the O'day. I knew everything there was to know about the O'day, but I felt lost on the C&C. After sailing the C&C for a month, finally selling the O'day, and making a few changes on the C&C I can say that I am finally happy. We did the double handed serious in the summer and really enjoyed it. We also did two casual fully crewed raced and my wife really enjoyed those. That surprised me, and I think we'll do some more racing.

Long story short (too late?): If you have good reasons to change (good reasons for YOU) then you won't regret it. Do some serious thinking about the kinds of sailing you WILL do (as opposed to the kinds you HOPE to do), find a boat that is well suited for that, and you will be happy.

Barry
 

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1 - A Tanzer 22 - we loved it, did everything we could to make it the perfect boat. She was the one! We happiuly sailed her for five years. Then we spent ten days in a row on her and put her up for sale.

2 - A Tanzer 28 - we loved it, did everything we could to make it the perfect boat. Even put a brand new Yanmar 2GM20F engine in her. She was the one! Nine summers - 21 days vacation - down the coast of Maine. We had radar, AIS, we had everything. Then I retired and we spent six weeks on her and put her up for sale.

3 - (current boat) Irwin Citation 34. She is the one! Six summers - five or six weeks each summer down the coast of Maine. We have radar, AIS, a shower, hot and cold water, a solar panel, we have everything. But darn it is hard getting my 68 year old bones into that V-berth. Anyone want a fully loaded IC34????



:)

Rik and Linda
 

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bell ringer
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I think a big issue with moving up is what you are moving up from. If you have a 27' boat moving to a 33' seems HUGE. But if you already have a 40' moving to a 50' just doesn't seem unreasonable in your mind.
 

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Well, you are boat shopping, as you tend to do - and you happen across a boat that you cannot NOT buy. Things change. You jump off the cliff. Enjoying the ride...
 

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If it's constantly on your mind that you'd like a) more speed, b) more space, c) longer range, and find yourself browsing Yachtworld in an obsessing manner than I'd say you're probably ready, as long as the financial end makes sense to you.

As lovely a boat as the Contessa is, it's not difficult to make significant improvements in those areas listed above, though you may give up a bit of 'row away factor'. A friend of mine moved from a Contessa 26 to a mid 80s Ericson 32 and has not regretted it.

I think you'd be truly astounded by the overall improvement in perhaps everything but seriously heavy weather sailing by going to a J28 or something in that same vein.

If it's constantly on your mind and you find something you can afford, it's probably time. Do keep in mind though, that other than moorage the cost increases will not be linear.
 
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