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Buying a Boat: The Pre-Purchase Team

schooner woodwind, a large multi-mast sailboat, sailing across blue water with full sails out and people out on deck enjoying the sunset. three radio towers are in the background on land.

We searched for a live-aboard cruising sailboat for over two years, and often did not take it very seriously. When we found Loka, we were not serious, and it was pretty obvious. Honestly, we had planned to buy “the boat” the following spring or summer 2023 (not fall 2022).

Yet, we found ourselves in a position where we’d found “the boat”.?

We had no buyer’s broker, no mentors, no loan or insurance lined up. All we had was some cash, willingness to ask for help, and awareness we were ill-prepared. Once we realized this 2006 Caliber 47 LRC SE was “our boat,” we moved quickly to assembly our Pre-Purchase Team.

Pre-Purchase Team

Early in our education, we learned that a Pre-Purchase Team would be beneficial in completing the purchase of a 40-50′ sailboat. Turns out, buying a 50′ sailboat is a large, risky deal with many moving parts. Our team consisted of the following:

  • Mentor – someone who has no vested interested in anything other than our well being (no commissions, etc.). They have nothing to lose if we don’t buy a boat.
  • Buyer’s Broker – a realtor for boats…kind of. Someone who has our interest at stake in navigating evaluation, negotiation, and other aspects of the purchase process.
  • Boat Mortgage Broker/Contact – much like a home mortgage broker, someone who can guide us through the process of getting the appropriate loan structure & rate
  • Insurance Broker/Agent – someone to help us navigate the trickiness of getting insurance on this big ass sailboat without breaking the bank
  • Surveyor – someone to do a pre-purchase inspection who will inform the final negotiations of the purchase agreement acceptance
sailing totem logo is a totem of animals and faces that are shaped in a whale arching around with its fin in the air
Sailing Totem’s logo

Mentors (paid or otherwise)

The first thing we did was call up Jamie & Behan Gifford from Sailing Totem and get grounded in reality. We were super-excited that we’d found “the boat”!!! All those exclamation points represent the high emotions we were riding. Our dream might come true! That first conversation with Totem was a great reminder that we had a lot of work to buy this boat, AND there were many steps to get through AND this deal might not be right. ❄️Cold water on our emotional fire.?

Now we had space to work logically through the logistics of answering “is this the right boat”, “what work does she need”, and “are we even ready for this right now?” If you have friends who have done this, they may be willing to help you at no charge. We were still building our sailing support network, so we hired Totem.

Buyer’s Broker

We were looking at boats by contacting the listing broker. In hindsight, that demonstrated how NOT serious/prepared we were when we found Loka.

Even though we moved forward with the Caliber Seller’s Broker for that deal, we found a broker (via our mentors) to help us continue our search for alternatives (in case Loka didn’t close). By doing this, if the Caliber deal fell through, we continued our search in earnest, AND demonstrated that we’re serious and prepared to make this move.

Our broker investigated several options for us, and was able to save us some time in chasing down boats and discuss

ing how they might fall short of what we were looking for. We’ll get a buyer’s broker up front next time.

Boat Mortgage Broker/Contact 

If you plan to pay cash for your boat, you can skip this. Because we still had a paycheck coming in, we financed the deal (for a little while) to keep our cash in reserve for up-fit and life transition costs (e.g. selling a house). Given that we had just made contacts while at the fall Annapolis Boat Show, we connected with a great mortgage broker who could help us navigate financing the deal. Financing was the simplest part of our process given our income situation.

Insurance Broker/Agent 

Insurance can be the most challenging part of the process. Our goal was to find the agent who understood how to help newbie cruisers to make the leap from little-to-no boat into big boat territory. Not every agent, even the amazing ones, is a good fit for the first-time cruiser.

In our first attempt to work with a broker, we discovered the perils of oversharing. We didn’t have a solid plan for the boat once we took ownership, and sharing that with that broker made it very clear we were a high risk, even to the broker. After re-grouping with our mentors, we came up with a new game plan for the boat (even if we expect it to change), and revised our approach to bringing that plan to the next broker.

Once we got a solid plan and the right broker (again, via our mentors), the process smoothed right out. If you’re struggling with your broker, maybe it’s time to start over–revise your plan and find another broker. It’s all about finding the best people for YOUR Team.

on the left, a windlass motor is rusty and covered in grime. on the right, a chainplate has dirty and rusted bolts.
starboard windlass (non-functional) & the inner forestay chainplate have seen better days


Identifying a surveyor is the 2nd most challenging part of the process. Search through the largest marine surveyor accreditation/certification bodies, and you get too many results to get through them all. Not everyone who is accredited or certified is guaranteed to be a good fit for your team.

We determined the main criteria for finding a trustworthy surveyor who would accurately report the state of the boat:

  • must have experience on large monohull sailboats
  • must provide a thorough write-up

After talking to several surveyors to determine availability (narrow the list), we requested examples of the work. Examples further refined the options because not all surveyors provide sample surveys.

Our goal for this Team member was to find issues. We don’t want a clean survey (I mean…that would be cool if it was true, but no boat is perfect). The Caliber 47 is a big boat with complex systems, so someone with relevant experience with the systems qualified them.

Lessons Learned

We assembled our team in a somewhat harried manner. As chronic planners, that hurriedness was abnormal for us. Hindsight is always 20/20, and we take this learning experience into future transactions.

  1. When we get serious enough, start with Buyer’s Broker. That will be much earlier in the process. Even making contact with a Listing Broker without a Buyer’s Broker can make it awkward NOT to use the Listing Broker, which is an obligation we do not want to be stuck with.
  2. Talk to the insurance broker/agent way earlier in the process.
  3. Have a plan for the boat, and say as few words as possible (the bare minimum) to the insurance agent about the plan. We’ll cover this in another post.
  4. It’s okay to ask a surveyor to travel, and it may be worth piece of mind and the value of a high quality survey.
  5. Find mentors along the way (so maybe we don’t have to pay someone to help us at every turn)
  6. Build the sailing support network! The sailing community is very small, and building those relationships is important 


Bonus Team Member: Rigger

I realized after publishing this post that I forgot the value of a rigger. We struggled to find a good rigger who could give a quality rigging survey before accepting the purchase agreement. The requirements for a rigger are similar to the surveyor, especially because we wanted a rigging survey. We wasted $500 on a rigging survey that ended with potato quality photos and an email with very little detail, and an estimate of $20-30k to replace it all without specifics of how he arrived at that number. Because the standing rigging on Loka is original (2006), we assumed a full replacement in our re-fit calculations, so the survey wasn’t critical to our decision making. On the next boat purchase, we will have a rigger lined up as part of the team.


3 thoughts on “Buying a Boat: The Pre-Purchase Team”

  1. What great info Pinky!
    So much info here love how you’re sharing all the details ins & outs- this will be a fantastic resource for those wanting ti take the plunge!!

  2. Pingback: Sailing Couples: Roles & Responsibilities – SV Loka

  3. Pingback: We’ve Got Virtual Mail: How We Get Mail on a Boat – SV Loka

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