Short list and long term strategy for my next boat?

[OrangeCrush]

Hello all,

I just sold my first boat, a 1978 Pearson 26, and I've started saving up for a bigger and more seaworthy cruising sailboat. I've read a lot of posts like this (and seen some people get torn to shreds), but I'm hoping to explain my criteria and budget and see if you can help me critique my list and overall approach. I'm still in the 'vow of poverty' stage of this process and it will be at least a year, probably two, before I'm ready to start looking at specific boats. But of course that hasn't stopped me from obsessing over my options.

What I'm going to use it for:
I'm a middle school teacher in NYC with two months off every summer that I use to go sailing. I've sailed my Pearson 26 up the coast of New England and into the Bay of Fundy four out of the last five years. I've been joined by up to four friends so space on the P26 was absurdly tight. We're used to close quarters but we definitely need more space and a much more seaworthy vessel. Maybe more than 4 people would join me in the future if we had the room. I plan on going back up to Maine on a regular basis and well beyond to places like Nova Scotia, the Gulf of St. Lawrence, Newfoundland, maybe even Labrador and Greenland someday. I could also see sailing south to the Caribbean, over to Bermuda, and pretty much any other place we can get to from New York and back in two and a half months. Apart from summers, in 14 years I can retire and I plan on living aboard and sailing around the world, probably as a small family or with a few friends but also for some stretches by myself. Even though it's far away, I'd like my next boat to be capable of serving this purpose as well. I want a boat that can safely take me pretty much anywhere, and I have a particular affinity for cold and remote locations. I know that every trip will involve its own preparations, and I'm well aware that being offshore ready depends more on me than on the type of boat I have. I will be diligent about all my planning, but I want the boat herself to have proven and unassailable bluewater credentials as well. In other words, if I'm ready for Cape Horn someday but I have doubts about my vessel it would be a big disappointment.

What I'm looking for in a boat:
-Around 35 to 40 feet in length.
-Heavy, definitely over 15,000lbs displacement and preferably closer to 20,000lbs
-Full keel w/ cutaway, or if not full then at least an extremely robust hull with encapsulated ballast and a well protected rudder/prop.
-Cutter rig strongly preferred, but a sloop could do if I rigged a solent stay for a place to put a storm jib. I don't really want a ketch but I'm not ruling it out completely.
-I'm willing to sacrifice speed for comfort and safety but something at least relatively fun to sail and not terribly slow would be a huge plus.
-Not fussy about cabin layout but I think decent motor access is crucial.
-I'm not afraid of maintenance but I'd prefer simplicity over complex systems in general

My budget:
I'm hoping to spend about 50k-60k on the initial purchase of the boat. At this price I'd like the boat to be more or less ready for coastal cruising, and it absolutely needs to be structurally sound, but it wouldn't have to be completely bluewater ready. I could take time and make more upgrades little by little. If I found that the best boats were still a little out of my reach at that price, I could wait another year and save more, and buy something closer to the 75k range, or just keep looking until I found a really good deal. I'm willing to be patient in order to get a boat that will keep my satisfied for decades, maybe for life.

Here is my list so far, with a thought or two about each one:
Tayana 37 (a little pricey but perhaps my favorite, especially one with a fiberglass deck)
Cabo Rico 38 (maybe hard to find in my price range in good enough shape)
Cape Dory 36 (fits my criteria perfectly but perhaps a little overpriced compared to the Alberg 37, others)
Kaiser Gale Force 34 (seems amazing but barely any out there to choose from)
Baba 35 (not sure if it's a good enough value for the size)
Southern Cross 35 or 38 (not a full keel but strong and good performance, although maybe the 38 is too expensive)
Cabot 36 (overall build quality concerns)
Valiant 40 (Possibly too expensive if in good shape w/ no blisters)
Pacific Seacraft 34 (great boat but a little small for the price)
PSC Crealock 37 (probably too pricey)
Rafiki 37 (harder to find on the East Coast)
Bristol 39/40 (lots to choose from but cutters are harder to find)
Alberg 37 (good value, maybe a little tight below decks and tender)
Morgan 382/383/384 (good price point but concerns about overall quality and keel/hull strength)

Hopefully you can see some thread of continuity in what I'm looking for and what I want to do with it. I'd be eager to hear if you think any good boats are missing from the list, if any boats should be moved to the top, or any that should be taken off completely. I'm also curious to see if you think my budget is realistic, especially given the context of a very patient search process.

And to address the question of buying a boat 'for now' versus buying THE boat, fourteen years doesn't seem so far away to me. I've had the Pearson for eight years now, and in retrospect it was pretty close to the perfect boat for me when I bought it. Even so, I probably 'outgrew' it after the first 2 or 3 years, but I had already invested enough money and time equipping it that I felt compelled to keep it longer and sail it more ambitiously than what probably made sense. And as you might guess I am not getting a return on the money I invested. I'd like to avoid this pattern on the next boat by thinking a little farther ahead.

It seems like many of the qualities I'll want in a boat for circumnavigation are the same that would serve me well around the North Atlantic. Without a lot of support around for pleasure boaters, a full keel would have a much better chance of surviving an encounter with some rocks or ice and allow me to make it back to the safety of a port. Plus I plan on doing some offshore passages between the coastal destinations. I think if I got a heavy and safe boat in solid shape, I could gradually improve my own offshore sailing skills while upgrading the boat gradually so that when the time finally came, both of us would be ready. I know that some of you will suggest I don't buy something so heavy and slow until I really need it so I wanted to explain my thinking on that.

In the end it will come down to the individual boats that are available when I'm ready to buy, which is why I think developing a good list is important. But I'm also curious to hear your thoughts on my overall approach. I'm torn between the idea of reaching for the absolute nicest type of boat I can afford, even if it were not cosmetically perfect or fully equipped (but again, definitely structurally sound). I will have the time to make improvements after I buy it. I'm thinking things like the Tayana 37 and the Cabo Rico 38 fall into this category, boats that might be just out of reach but maybe worth reaching a little farther for.

Alternatively, I could buy something a little farther from the top of my 'wish list' that was better equipped/upgraded and in better overall and cosmetic shape. Boats like the Morgan 38, Bristol 39/40 or Alberg 37 might serve for this approach. This second strategy seems more practical and could save me money/time in the long run, but I might be less likely to get something that I'm really in love with.

Any other advice would be greatly appreciated as to how to approach this process, what factors to focus on, and how to decide when it's still time to keep saving up versus time to just pull the trigger and buy something.

Thanks a lot!

[retomas]

Hi. I have noticed your (former) boat from time to time in Brooklyn. You are welcome to view my Pacific Seacraft 34, currently at Gateway Marina.

[l2ridehd]

A few I might add, Island Packet, Whitby, Vega and a Moody. Hallberg Rassy or Oyster if you find some extra $$$$.

[FamilyVan]

I'm a big fan of Albergs, my brother has a smaller one, I had a dock neighbour who lived aboard year round on a 30'.

They are tight below, but I don't think to tight for what you describe. There is no way around it, 37' is a big boat. People who own them and cruise them extensively seem to swear by their seaworthiness and quality. They are relatively fast as well. They are appropriate to a teachers budget as well.

The other plus, is you are likely to be boatless for less time as you will likely find one below your budget.

You might not want to go too big, you will miss how handy and easy your 26 was.

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[jangann]

This is a great list. It overlaps with many of the boats we considered when we were looking. I might add something like a Pearson 367 -- it's a bit lighter than these, but will be much more affordable. It's a cutter with a deeper keel than its sister the 365.

Just a thought.

If you have a lot of time, it's possible a great boat will fall into your hands as you wait. Good luck!

[Hud3]

You might want to take a look at an Island Packet 31 or 32. They have significantly more living space and storage than most boats in that length range. More like a typical 35 or 36 footer. Friends of mine sold their Pearson 36, bought an IP 31 and ended up with more usable space.

[lilbabypenguin]

I do agree with Hud about the amount of space inside an island packet. I was very surprised by even in a 27' it was nice and roomy! We ended up getting an 32' Downeaster which is serving us well so far and may also fit into your specifications. You could maybe find a 35'. Best of luck- it sounds like you are on the right track and have the time and patience to hold out for "the one" ☺️


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[OrangeCrush]

Thanks for the advice and the words of encouragement, everybody. My new boat fund is coming along better than expected and I'm optimistic about my chances of finding something great when the time comes.

Retomas, it's nice to hear that you noticed me around Brooklyn and I'd love to take you up on your offer. I'm away until mid September but if you PM me your email I'd be delighted to come down sometime in late September or October. I'd be happy to help out with some jobs while I'm giving her a look, be it varnishing it job trimming as the situation demands.

Jack


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