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Tips on Buying a Sailboat

Matt and Davina, generously donated to ‘cruising coffee’ and they had some questions about buying a boat.  We edited out the specific info on the boat they’re interested in until they make a decision.  With their permission, here’s what they had to say..

I sent you guys a five spot on cruising for coffee because Matt and I are at a spot where we need some concrete info from someone who has “been there/ done that”. We are so appreciative of all the words of wisdom and the inspiration thus far.

First, we’re looking at an older seventies era sailboat  that a couple has been living aboard for several years now and they are asking in the high seventy thousand range in the Florida Keys.

IF money was no option would you give consideration to buying this boat?  We are really attracted to the boat.   The space and layout speak to us.   She’s fully equipped, dingy and all.   The owners seem to feel that knowing what we want to spend we should have no problem coming to an agreeable price.

Thanks for the donation.

First, there are some boats that just speak to you.  When we were looking for a mono hull, the CSY just jumped out at us.  That being said, if I knew then what I knew now we could have saved some cash and heartache.

Second, it’s dangerous to fall in love with the dream of a boat.  No matter what I say, there’s a VERY good chance the first boat you’ll buy will be a compromise of fantasy and reality.  Hopefully the reality will cover the shortcomings when the dream wears thin.  That’s OK, it’s the same for everyone so you’re in good company.  A boat is a massive compromise of needs and wants.  Many you won’t even understand until you’ve been living on a boat for awhile.

There are TWO things I can promise if you like boats:

  1. You’re first boat will not be you’re last boat.
  2. You will ALWAYS lose money selling a boat.

Keep in mind the boat market is in the toilet.  My CSY should’ have sold for high 30’s and it sold for 29.5k.  Our Gemini they were asking $69,000 originally and it ‘should’ have sold for mid to high 50’s (because of cosmetic condition) and it sold for $38,500.  That’s a big hit.  So the price that is advertised is merely a starting point.  I regret with both the CSY and the Gemini that I didn’t start my offer lower (in hindsight).

When buying your first boat,  especially with little on the water time, our tendency was to go beefier.  Thicker fiberglass layup and older construction means a slower boat- but speed really doesn’t matter if you’re living on the boat.  Our feeling was that we wanted a boat that would take a grounding while we were still learning.  We never did run aground hard enough or on reef that it would have mattered, but peace of mind speaks a lot to a new sailor.

We we’re lucky.  We ended up loving our CSY.  We didn’t go far or fast, but it was a very comfortable boat and served us well.

I am curious as to your advice on surveys (I’ve looked on line). Some seem reasonable and then some prices are off the chart, especially for the rigging survey. You know our situation. The money we shell out is pretty much coming out of our retirement. I have spoken with a couple in Maine who said their “catamaran” surveyor (supposed to be respected) really missed the boat on their survey and they’ve run into all sorts of issues. Who do you trust? Would you put out a post on Sail Net or something to ask for suggestions? We want to be thorough but don’t want to overspend.

The best you can do with surveyors is find one who has surveyed the specific model of boat you’re considering.  You can even ask for references of the owners.   Search for a users group and see if there is a surveyor that can be suggested.  I wouldn’t skip a surveyor.  You probably could skip the rigging survey.  A visual inspection should be fine for the kind of sailing you are looking to do.  The full rigging survey is usually for folks setting off for some blue water sailing.  I think for the Gemini we were looking about around $400-500 for the survey.  You really want the surveyor to focus on the hull.  You can do a lot of research beforehand and have a checklist of things you want them to address.  I would follow the surveyor around when he working to see where everything is located.

You typically do a haul out as well to check the hull.  That costs anywhere from $250-$400 depending on the lift and the length of the boat.  It’s usually quoted by the foot of boat length.

What about documentation procedures? How, where, costs involved?

You might want to use a documentation service.  It’ll cost about $500 or less to research the title, change the name if you want, and register it with the USCG.  They changed the procedures and it’s a lot more complicated than it used to be when we bought our CSY.  We had to use a documentation service for the Gemini because the boat was in Mexico.  Especially for the money your looking at, it’s good insurance that the title will be clean.  You can register the boat in the state it’s located (often required) and you can also document the boat with the USCG.  The USCG keeps a title history for boats that have been registered.  Florida is a big pain in the butt registering boats and a lot more expensive than Georgia.  Transferring ownership from Florida to Georgia would be easy.  The other way around is a lot more complicated- but doable.

In all the process goes like this:
1. Offer-Counter offer- contract.
2. deposit (10% is typical)
3. inspection period; time to arrange the following
4. survey ($500 ish),  sea trial (sail and motor the boat), haul out ($300-400 ish)
5. based on the survey you can request deficiencies to be fixed or a comparable price reduction.
6. final contract based on survey (you can actually re negotiate the price based on the survey)
7. close and transfer of funds.

You can pay a broker a nominal amount to organize the process and documents if not offered for sale by one.  It could cost a couple hundred or up to 5% of the sales price of the boat- reach an agreement first.

The close typically requires a USCG bill of sale and USCG documented title (owner signs back) and a transfer document if the boat is registered in the state.

The documentation service will handle all the paperwork is you use one.  That will cost about $500 but they check the title for liens against the boat.

How long would it take to sail a boat along the Florida coast from Key West to let’s say Jacksonville?

The short answer is- as long as you like:)

We sailed offshore and it took 5 days to get to jacksonville.  That’s with pretty favorable winds and sailing 24 hours a day.  On the other hand to motor the ICW from St. Simons to Jacksonville took us about the same time and it’s a lot shorter.

Considering this would be a shakedown sail, two weeks would be a decent schedule.  In a typical sailboat you can average about 40-50 nautical miles per day in a 10 hour day of sailing/motoring at 4-5 kn per hour.  The speed is not that important, because it’s time well spent.

DEPENDING ON THE DRAFT OF THE BOAT- you can cruise the inside of the keys.  We couldn’t with the CSY it was too deep at 5.5′  The tides are only about 2′ down there.  There’s a reef on the ocean side that separates the keys from the ocean that most people sail up and down.  You’d want to watch wind and tide to match or else it gets lumpy (a common theme for everything you do- wind and tide).  From Miami you can motor/sail the ICW to Jacksonville.  This will be a good experience working out some kinks in the boat.  You have the safety net of knowing you’re close to shore and can drop anchor anytime in case of emergency.  A good set of charts and a depth sounder and you’ll be fine.

The ICW is boring and aggravating in Florida because the big sportfish boats are rude and wake you or cut in front of you from Miami up to about Stewart.  It’s better to deal with them than deal with the inlets on your shakedown cruise.

IMPORTANT NOTE:  Your primary objective with your new boat- not scare the bejesus out of everyone aboard!  Seriously!  Even if you feel comfortable sailing offshore, take baby steps so everyone is comfortable and has pleasant memories of being on a sailboat.  Worse thing you can do is scare the life out of the kids and they HATE being on a boat.  Pick daily spots to drop anchor close to little island so the kids and swim and play- make it a fun experience.  Throw a trolling line behind the boat and try to catch some fish.

Key Biscayne is Glorious- stop in No Name Harbor.
Palm Beach is gorgeous by Peanut Island  (weekends are busy)
Daytona was fun
St. Augustine is worth a few days or more (we spent two weeks)
Jacksonville is confusing.  There’s a few places to anchor or get a slip just past Ponte Vedra outside of Jax that you can stop and get your bearings before navigating.

It would be worth it to get someone familiar with the waters to tag along for a few days when you start to ease your worries.  A third pair of eyes never hurts.

IN SUMMARY (and frank honesty):

Given that this is new territory for you guys.  Given that money is always tight.

I’d try to find a boat under 50k (closer to under 40k would be better).

My argument goes like this.

If you hate living on a boat, you’re retirement doesn’t take a huge hit (20-30k is a pretty big loss right now) when you sell the boat.  You don’t want a note on the boat, you’d prefer not to pay for full coverage insurance ($1200-$1500 per year and rising with a new survey needed every two years AND they don’t like OLD boats more than 10 years old) and it likely won’t cover hurricane damage anyways.  So the boat has to be cheap enough that a loss won’t break you.

If you love living on a boat, the more knowledge you have about how you live on a boat, the more you’ll say, “on my next boat I want this…” and then one day, the perfect boat will show up and you’ll want to sell your boat to get the ‘perfect boat’.  So you don’t want to take a bath on the sale of your first boat to get into another boat.

The next part.  The less money in the bank, the longer you’ll have to work.  If you REALLY like living on a boat, you’ll realize that less (like WAY LESS) is more (like MUCH MORE) and you might want to cut loose sooner than later.  An extra 20-30k in the bank making even 4-5% interest will go a long way.

Keeping that in mind, we budgeted $20-30k for out first boat and ended up spending $43k.  We fell in love with it and it drove our decision making even though others told us we could find as good a boat (even the same kind of boat) for less.

For this Gemini, we budgeted $30k and ended up spending $38.5k because it was what we wanted and a great price.  It cost me about two months of hard work to make the extra dough and ANY financial cushion we had in the bank, but we did it anyways.  Not exactly prudent financial practices, but hey, it’s just money.

Janis Joplin said,

Freedom is just another word for nothing left to lose..

With total assets of about $40k, we’re in a different position that you might be facing.  In my mind and with our previous experience, I am confident that if something tragic happened to the boat, the loss of the $40k wouldn’t be the end of the world- we just have to get a job and be like everyone else.  But the opportunity we have on the boat could be enormous!

If I had about a 100k-150k in retirement.  I’d shoot for a boat in the 30-40k range and cut overhead to figure out how to cruise more and work less.  Hey!, with no retirement to speak of, that’s what we’re doing anyways!

Email me more questions or if you disagree- let me know and we can discuss the reasoning.  I’m not omniscient, different strokes for different folks.

I hope the response was worth the donation.


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2 comments to Tips on Buying a Sailboat

  • i am into sailing and i am also a diy fiberglass sailing boat enthusiasts for 5 years now. i really love sailing.;`.

  • Chuck Reynolds


    Enjoyed reading your article. I’m looking to retire next year and my next passion is to buy a sailboat and sail the Atlantic coast. Currently living in Charleston SC and just starting my research for purchasing a sailboat. Your advice on budget and taking it slow is certainly well noted. Having sailed while living in California many overnight trips from Long Beach to Catalina. Not a long sail (26 miles) but enough to satisfy a need at the time. Looking now to sail East Coast and Carribean. Would love to hear what you feeling is the necessary equipment for a 37′ to 42′ boat for partial live aboard (2-4) months while crusing.