The Tipping Point – Is It Time for a New Boat?

A repower, new auto, more solar, lithium?, a water maker, more tankage.  Oh my!  Mine and Phillip’s heads were swimming.  It felt like we were on the spinny tea-cup ride at the Magic Kingdom.  But, we were committed.  Although we had not envisioned tackling such an extensive overhaul to Plaintiff’s Rest until it was time to really, really go, Covid taught us the “time to go” shouldn’t be some amorphous mirage on the horizon.  Now that we know the world can change in an instant, we knew we had to pursue our goal of full-time cruising with immediacy and far more tenacity.  “Now is the time,” became our motto.  And, with Plaintiff’s Rest already on the hard undergoing Hurricane Sally repairs, it seemed a prime time for us to finally get her cruise-the-world ready. 

This started a conversation that Phillip and I would have over and again—end over end, end at the beginning and start again at the end—over the course of two dizzying weeks.  Not only would this be a huge lifestyle change, i.e. switching from commuter cruisers who lived and worked aboard only part of the year to full-time liveaboards, full-time cruisers, the necessary overhaul to the boat, we knew, was also going to be a large financial investment.  And, we know all boats are depreciating assets.  Well, that’s putting it lightly, they are holes that we throw money into (because they throw adventure, pleasure, thrills, and mysteries right back).  Generally speaking, you’re always going to lose money on a boat.  Knowing that, and knowing we were about to throw a lot of money into our own hole, mine and Phillip’s motivation and reasoning became laser-focused on one goal: minimize our loss.  We also knew the decision had to be void of emotion.  While it pained us both to even think about parting with our 1985 Niagara 35, this was our future, our money, and the way in which we were about to spend the remainder of our most valuable commodity: our time.  We simply could not let a decision of this magnitude hinge on “aww … poor girl, we just can’t do that to her.”  If the wiser decision called for it, we were going to have to do that to her.

Phillip and I were approaching this as calculating professionals, focusing on the economic basics: minimizing our losses and maximizing our gains (the non-economic kind that is, all that a boat can offer, because the hole never really “fills”).  Once we considered everything in tandem, with hyper-focus on our losses and gains in trying to decide whether to invest in our Niagara or prepare to tack, it soon became undeniably clear …

It’s time to buy a new boat.

Here’s how we got there.


Unfortunately, no matter how capable, clean, simple (and how incredibly wonderful!) our Niagara is, she comes with an undeniable truth.  She’s 36-years old.  She has already depreciated significantly and will only continue to depreciate every day.  And, she will never sell for an amount equal to or greater than what we paid for her, no matter how many fancy systems we install.  And, while I’ll readily admit I am no economist, I would imagine, after the initial large knock in depreciation (the “minute you drive off the lot” dive), that it’s a graduated scale thereafter, depreciating more slowly in the early years and more rapidly each year after she’s hit her third decade.  Again, just a guess.  But, I’ll bet I’m not wrong.  Any boat that is only 5-10 years is going to hold its value better than our Niagara who will soon approach 40 years in age. 


This meant every dollar we put into her to “make her” the cruising boat we felt we needed to do the kind of full-time liveaboard cruising abroad we had decided to do now, Phillip and I would never get back.  That was simply a fact.  Whereas, if we put those dollars into a new, or slightly used, boat that already had all of those systems and upgrades, we would likely be able to re-sale a newer boat and recover a much larger percentage of the amount we purchased her for.  Hence, by buying a newer boat, we would undoubtedly minimize our loss if, for whatever reason, we had to sell her.  The reality of it pained us, but it could not be ignored or denied.  If we overhauled, all of that money would simply be embedded into Plaintiff’s Rest.  Six zeros forever fiber-glassed into her hull, come what may.  Would we enjoy the hell out of her with all of her new systems and the new places she would take us?  Absolutely.  But she would never be able to give us any portion of our overhaul money back.  So, under the minimizing our loss category it was Niagara 00, New Boat 01.  But, I mentioned “come what may.”  That was our next quandary: insurance.


Another sad truth that struck us in wrestling with this decision: a large financial sum dumped into Plaintiff’s Rest would not change her insurable hull value.  There would be no way to insure her for any amount that could guarantee we could recoup any portion of the cost of the overhaul if the worse happened.  The upgrade itself was not insurable.  This was a major concern.  Having just (barely) survived Hurricane Sally in September of 2020, Phillip and I (and every sailor in Pensacola) are all too aware of how possible it is for a hurricane to sneak up on you in the Gulf and devastate your community, and most of the boats in it.  If the worst happened, and another hurricane walloped us next year and, sadly, sunk our Niagara, our insurance company would only pay up to her hull value, which is a mere fraction of what it would cost to overhaul her. 

Her surviving would be our only protection and that’s simply not guaranteed.  Particularly where her extensive repairs, and the time they would require, would likely leave her, yet again, in Pensacola—well within the hurricane box—for hurricane season next year.  Our plan, if we did keep her, was to haul out at the first sign of a storm and keep her hauled the entire hurricane season 2021, but that’s still no guarantee she’d survive inside the box.  What was worse, at the time (December of 2021) our insurance on the Niagara was set to cancel in April with no other insurers writing policies at the time, due to the massive hurricane damage on the coast.  So, there was a chance we would not be able to insure her at all, even for just a fraction of the money we were about to put into her.  If we did overhaul our boat and she suffered some devastating damage in the coming years, our loss would be total.  With a new(er) boat, however, we could easily insure not only the boat but all of her bells and whistles, too, and, at the very least, recoup our purchase price if something were to happen to her.  Considering the insurance, over and above the inability to recoup any of our overhaul dollars in a resale, put the Niagara at another disadvantage: Niagara 00; New Boat 02.


This realization got Phillip and I seriously thinking about going an entirely different direction.  Should we get a … we banished the thought the minute it struck our minds.  But maybe it’s time to … Scandalous!  After enough toying around with it—a back and forth, end over end conversation that unraveled and rewired us—and considering the gravity of the cost, the repercussions, and the life we wanted to live going forward, we finally started to allow ourselves to at least entertain the thought of … (don’t say it … okay say it!) … getting a new boat.  The minute this little door unlocked in our minds it instantly flooded our brains.  It was a Pandora’s Box of wonders, fears, and emotions.  A new boat?  More systems?  More water?  Hot water?  We could have hot water?  Copious amounts of it?  Fuel, too?  A generator?  AC, could it be?  Don’t say it!  Say it.  But, Jesus, the complexity of those systems?!  I’ll be honest, lithium kind of blows my mind.  I don’t understand its voodoo magic.  I also don’t know how to pickle a water maker.  I’ve never worked on a hot water heater.  I don’t want more thru-hulls.  And, a boat with all of those extra systems will undoubtedly have to be bigger.  Phillip and I were fully aware that in adding all of the things we were talking about adding to our Niagara, it would cramp what little extra stow space we felt blessed to have.  But, we didn’t really want anything too much bigger, or heavier, as our Niagara had proven over the years to be just the right size for Phillip and I to single-hand as needed and easily jointly maneuver her or (when needed) man-handle her, even, if the occasion called for it. 


Honestly, toying with the idea of a newer, bigger, more complicated, more costly boat wasn’t an instant “Yes!” for us, as we have always (always!) stuck to our mantra to K.I.S.S: Keep It Simple Sailor.  Phillip and I adore the simplicity of Plaintiff’s Rest and relish in the fact that we know her.  Every nut, every bolt.  We know how to troubleshoot and repair every system.  There is a lot of value in reaching that status, and we would simply be giving all of that up in switching to a new boat.  Sure, much of our knowledge base—the mechanics of the diesel engine, the physics of plumbing and pressure, how pumps work, how to change the impeller, how to wire gizmos up, running batteries in parallel versus series, all things that function marginally the same on all boats—would translate, but not all of it.  Purchasing a newer boat, with all the bells and whistles, would require a considerable amount of new time devoted to research and learning all of the new, far more complex systems as well as maintaining, troubleshooting, and repairing them.  However, if we wanted to work aboard, which would be a heck of lot easier in a comfortable, spacious, quiet, climate-controlled interior cabin, Phillip and I had to take that lifestyle with all of the fancy systems it would require.  As with just about everything when it comes to boats, it was a tradeoff.  For that reason, this consideration—going from simple to complex—was a bit tougher than the first and resulted in only a slight win for New Boat: Niagara 00.4; New Boat 02.6.

Quality (of Life Aboard)

With New Boat in the lead, however, I think this final factor became our real tipping point.  Our goal was to maximize our quality of life aboard by finding a boat that would not only allow us to minimize our loss (if the world flipped itself on its head again, or our health or financial circumstances changed) either through insurance or resale but one that would also let us live and work comfortably aboard full-time, that would carry us safely and quickly everywhere but was also fun to day-sail (think, not an 8-foot draft tank), that was practical but exceptionally well-built, beautiful but as simple as comfort would allow.  Simply put, we wanted to find a premiere ocean cruiser.  This sent us skittering down approximately 43.29 different paths (two more tickets for the tea cups please), considering boat after boat, slightly used, newly built, ones on back-order, others that were turn-key.  We looked at Tartans, Hylases, Hallberg Rassies, for a brief crazy minute, the twin-keeled Sirius 40 deck saloon, even the aluminum-hulled Ovni 40.  We were all over the place!  But, we let our quest to maximize what we wanted to get out of the boat guide us in asking the important questions.  What systems and design features were truly the most important to the life we wanted to live aboard?


This was our short, shifting list: 

  • Exceptional build quality with well thought-out design throughout
  • Designed and equipped for crossing oceans
  • Comfortable and intuitive design features for real world use
  • Flexible sail plan that just the two of us would feel comfortable handling
  • Proven design 
  • A draft under seven feet
  • A mast height less than 65 feet
  • Ideally no more than 40 feet in length
  • Self-sufficiency built into the design (i.e., adequate diesel and water tanks)
  • Alternative energy sources and impressive battery bank (ideally solar and lithium batteries)
  • Space to potentially install a water maker or generator
  • Comfortable and moderate cockpit (not too big but not too small) with the ability to brace and lay down while offshore and lounge and live-in when on anchor
  • Minimal freeboard 
  • We liked the deck saloon or at least a close feel to it that offered an easy transition, and a connection, from cockpit to saloon
  • Just one helm with the ability to walk around it comfortably getting in/out of the water
  • Great visibility of the waterline 360-degrees
  • Once I saw newer boats have “workshops” that became an Annie must
  • A performance sailor
  • An interior layout that we liked
  • Exceptional space for stowage
  • In other words, a Unicorn!

All of these things offered a completely different—not easier—but a more opportunistic, comfortable, safer cruising lifestyle.  She would be more costly, sure, bigger to handle and dock, sure, more maintenance, sure, but …

Can you feel it?  You’re starting to tip!  Stay tuned next time.  Now that we have shared our thought process on whether to overhaul our 1985 Niagara 35 versus buying a new or slightly used boat, we’re excited to share our boat hunt with you.  Boy was it dizzying!  If you were shopping for a new or slightly used boat right now, tell us, what boats would you consider to be at the top of your list?

Any guesses as to what boat we decided to go with are welcome!

First photo together at the helm of our Niagara and our … new boat (I’m not telling … yet!) taken eight years apart almost to the day! Life is short, fast, but exceptionally wild and good!

25 thoughts on “The Tipping Point – Is It Time for a New Boat?

  • A Southerly 38 ticks many of the boxes you listed. The Shards (Distant Shores) and “Sailing Ruby Rose” have cruised in their Southerlys for years. The only thing that doesn’t meet your requirements is a single helm station but the company may be able to build one with a single helm. Just a thought.

    • Ahhh fine choice. We are definitely familiar (not personally familiar) but aware of those boats and their amazing quality. That would likely top high on our list as well. The double helm would be a turn-off for us, but know this is all in theory (which it has to be when you’re merely shopping). Appreciate the input. We’re excited to share what we chose soon!

  • Annie and Phillip: Welcome to Phase 2. Every boat teaches you something… errr… many things. Then its time it over as you have learned what you needed to learn. You’ve cleared that hurdle. Plaintiff’s Rest will always be special to you.

    Recently we sold our beloved Averisera. Fourteen wonderful years and I will miss her every day. I am anticipating a new boat. Will keep you posted.

    I raced a Frers-designed Swan 36 from SF to Tahiti and will say she really ticked all the boxes. Four guys for 21 days, provisioned for 30 and a watermaker. Kept things tidy below the whole way. Good storage.

    Have fun!


    • Thanks. We’re glad to be here. We definitely felt like we had outgrown our beloved Niagara. She did teach us an astonishing amount and those lessons await for whoever decides to sail her into her next chapter. We are excited to share this news. A Swan would definitely work for us, those are tried and true boats. I’ll bet you were impressed. It’s hard to think about not owning our Niagara anymore. I’m sure I would miss her daily. I can absolutely relate to that. Appreciate you commenting Norm, and following along. Phase 2, here we come!

      • Hello, again:
        Averisera is an Aphrodite 101, designed by Paul Elvstrom, “the Great Dane.” Through her, he taught us a lot of sailing and a lot about mannerly design. We also learned that headroom at 4.5 ft was not working any more. We are now 71 and just don’t contort the way we did 14 years ago! So we are looking at headroom sufficient designs with the knowledge of what a great design means to us. Slim pickings!

        A feature of being a sailboat captain is that I sail a lot of different boats. (Kiss a lot of frogs, comes to mind, too.) Nothing matched the Averisera experience. In large part because I never spent 14 years with any of them. I thank Averisera as you will thank the Niagara.

        Swans are nice and the support system is note worthy. Oyster is another good builder. Do you see the Sailing Florence channel? Nice boat and a lovely couple. Also, the collaboration between Chuck Paine and Morris yachts produced some USA-built gems.

        Well… off to work. Keep well.

  • Dang…
    That last bit sounded an awful lot like the musings of a future catamaran owner…

    • I knew someone was going to say that! We will never convert. Sorry, we’re monohullers through and through. Having made significant offshore passages on both, we simply do not prefer the sail performance of a catamaran over a monohull. As one very wise French woman in the Azores said, and we agree: “They do not dance with the ocean.” But, like I said, I was totally prepared for a catamaran guess! : )

      • As I load up to leave for a catamaran training course… I will not tell the client that I agree with “don’t dance with the ocean.” Still true!

  • I have never seen one in person, but I love so many things about the Sirius 35ds and 40ds. The new Island Packets with the Solent rig (IP 349 and IP 439) also look very nice and maybe a bit more attainable.

    • Same here. We had not seen the Siriuses (Siriusi … ?) in person but the concept of it, i.e., the feel of a catamaran “cockpit and saloon flow” on a monohull intrigued us. Although it did appear to have a good bit of freeboard the reviews seemed to claim she sailed like a dream. And maneuvered well, too. We were a little curious whether we would like the saloon being set up higher than the galley with less head space above. A lot to consider and we would definitely have to really set foot aboard and spend a good bit of time on her before we would know whether that design was right for us. Solent rigs also offer a lot of options and flexibility in the sail plan so we appreciate that too. Thanks for sharing your thoughts!

  • Thanks for another great post. You capture the essence of the boat change process we had also gone through during the last year. Kelly and I agree most of your preferences and began our process about one year ago. Our “excuse” to upgrade from our Pretorien 35 was mainly to have more room to put stuff, and make use of time during covid-induced limited ability to cruise to faraway places.

    Heartbreaking as it is, we too gave up that tribal knowledge, having learned (with blood sweat and tears) every nook and cranny of our Pretorien, and sailing her thousands of miles to and from warm and cold places. So after reaching the point you have, visiting 21 boats on our “short” list, we settled on a Pacific Seacraft 40. We said we didn’t want another “project” but settled on a needy boat with good bones, and just reached the point to move aboard last weekend. Milestone! Now we’re again re-investing (feeling like starting over) to fixing, overhaul or upgrade almost every system ourselves. Labor of love, but scary nonetheless.

    How have you evaluated the question of how much work you’re willing to take on vs initial cost? It’s a tricky curveball when you think you’ve found your next home meeting your budget. We initially made an offer on a Valiant 42 on the upper end of our budget. But when the survey found several potentially costly or questionable issues, and the owner refused to budge, we had no choice but to swallow the cost of survey and back out. We tried our patience and eventually made a better choice.

    Good luck on your search! Glad you’re staying mono hull 🙂

    • Ahhh, what a thoughtful comment here. We have recently learned that transitioning from a boat you know and love to a “new” (to you) boat can be an emotional roller coaster. While we went through it ourselves just recently based on a financial decision, we have also “rode the ride” with many friends here in Pensacola who went through the process out of necessity as they lost their boats to Hurricane Sally here in Pensacola in September, 2020, but nothing will stop them from wanting to be on the water, so they all started shopping and looking for new boats. In that sense, it felt like many of us were going through this process together, but all with different motives, goals, and desires.

      For Phillip and I, we definitely did not want a project boat. We wanted it (to the extent possible) turn-key ready for us to move aboard and begin living and cruising. We felt we had earned that badge (so to speak) when we rebuilt our mast stringers, re-rigged, and just about re-everythinged our boat back in 2016. While it was an invaluable process and a great learning experience, it’s not something we wanted (or had the luxury to) repeat upon purchase. Work for us, as lawyers, is quite busy right now, and we need a stable home to be able to do that work, even while we cruise. So that was one factor for us that turned our sights on boats that were ready to go.

      That said, if an owner was not willing to budget at all, we had a budget limit that we, too, were not willing to cross, so if we had to bite the bullet and walk away from an awesome boat, like you had to, we were prepared to do that. Try pushing Phillip in a direction he does not want to go. I dare you! Ha!

      Thanks for sharing your process. It’s definitely a very tough decision as boats, for those who truly want to live aboard and cruise, are such an integral part of our lives. We’ve seen Pacific Seacrafts sailing along with us often. Very nice boats. Solid design and construction. I hope you two are pleased with her. Fair winds to you both! We will reveal our boat choice soon! : )

  • A puzzle. Do we see a solid curved stern rail behind your smiling faces? That sort of suggests a double-ender, but that would violate your “easy to access the water” requirement…hmm. Give us a clue,

    • I love puzzles! When you say “double-ender” do you mean two helms? A clue … it’s definitely a monohull. Maybe that was clear from the photo. Not sure. A clue. Great request. They’re fairly rare boats. Less than 100 of our model have been built. Does that lead to any more specific guesses? : )

      • Double-ender also refers to having a “canoe stern” or basically that the rear of the boat is fairly round rather than flat. The thinking is that this helps handling in foul weather, and it’s common on older bluewater boats. Modern boats have (almost?) all moved away from that design because it doesn’t allow for the swim platforms that everyone likes and it makes entering and exiting the boat a bit more tricky.

        Anyway, if that photo at the top of the post is supposed to be a hint, along with your comment that fewer than 100 were built, maybe we’re looking at a Valiant 42?

      • Aha! I am familiar with a “canoe stern,” but I had not heard the term “double-ender,” so … always good to learn something new every day. Thank you for that. Yes, Pam Wall, has preached to me about the offshore benefits of a canoe stern (in that it doesn’t slap and pound on the water). I don’t like that most newer boats tend to focus on a huge, wide, flat transom with two helms. Many of them I think would be very uncomfortable offshore. Just a theory, but the design speaks volumes. Very good guess with the Valiant. It’s not correct, but I think you will find it is close. : )

      • Ha ha. I have to admit that made me laugh. Not a bad guess. Probably a little too big and sluggish for our desires, but you did give me a chuckle with that one!

      • Yes, as David mentions, I was referring to a canoe stern. That rail does look Valiant-ish. I am somewhat tuned into such things because I just recently bought a Valiant. But then, Valiant quit building boats in 2011, so you cannot get one that is very new (which sounded like the direction Annie and Phillip were headed). But certainly some that qualify as lightly-used. Ha. We shall wait for the reveal. BTW, the Lewmar folding wheel does free up a little space in an otherwise tight canoe-stern cockpit.

      • Sage advice Craig. We have seen many models with the folding wheel and I think it has great potential. We have also contemplated removing the wheel for an extended stay on the hook. Reveal to come soon! This has been fun to share!

  • Annie, that’s some difficult decisions you have to make I would like to think that you would try to find a modern design, not a revamped retro design from 30 or 40 years ago, (like project Atticus did) they might be lovely boats but just don’t have the advantages of a modern boat, Great accommodations , swim platforms for easy boarding and off wind performance , accommodation below. Machinery access etc.
    I hope you don’t get too wrapped up in there let’s feed all the lines to the cockpit and give up reliability and ease of use. The single helm may be tricky as so many boats are sticking twin helms in there.
    Since most of your time will probably be used sailing under an auto pilot that’s a lot of cotpit space to lose for the extra helm positions in 40’.
    Factory support should be a major factor in your decision especially with new boats as you hear so many stories are breaking. Can be very frustrating did you get everything working properly on a boat they just don’t make them like cars where everything works first time.
    Don’t get talked into going to big I had friends in their 90s with a Jeneneau 43 ( Pre-Beneteau).
    Wonderful boat huge accommodations for the large family. I was looking after it for a year when they returned to England for a bit and one day I measured it on deck, it was barely over 38 feet if you didn’t include the large swim platform or the pulpit. I suggest you do the same just so you know exactly what you’re buying there’s nothing that says a ‘40’ model is 40 feet on deck which is your true measure of a boat and it accommodation potential,
    Have fun I hope you will share some of the journey
    Cheers Warren

    • Ahhh, insightful as always. Thank you for putting these important thoughts to words here, Warren. I’m sure they will be invaluable to others who stumble across this blog in their own pursuit of a new boat to realize their cruising dreams. Exceptional point on the deck measurement versus the LOA as the true “length” of the boat. I think, when you discover what we selected, this will prove true in the opposite way in that ours may sound a little longer but when you consider just the length of the actual deck, it’s much closer to what would truly be the right length for us. That said, when docking and de-docking, she’s every bit the full length … grrrr. But, what are you going to do, either bump sometimes or never leave the dock, right?! We cannot wait to share this decision with everyone as it was a very tough (but worthy) one to make. Thanks for adding your thoughts here. Quality and design were key for us and I truly think we nailed it. And, two helms? No. Just no. I can’t get on board with it. ha! Hope you’re excited to see what we picked! We will share soon!

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