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Old 13-11-2022, 07:25   #1
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Daysail / overnight charter as retirement gig?

As a teacher rapidly closing in on 60, I find myself thinking more and more about retirement projects that might enable me to share my love of sailing without breaking the bank. Teaching ASA courses at a local school is one attractive possibility. Another is investing in an attractive older boat and running a small-scale, low-key daysail / overnight charter operation somewhere in the Great Lakes.

One model might be the kind of Airbnb "experience" for up to six passengers offered by Captain Andrew out of Newport Beach on what looks to be a refurbished 50' wooden schooner. An apparently similar vessel can be seen on YachtWorld for $65k.

I'm curious about how much annual chartering revenue might be required to break even with such an operation--or at least avoid losing one's shirt-- considering maintenance, dockage, insurance and winter storage costs. Any way this could be a viable hobby business proposition?
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Old 13-11-2022, 08:01   #2
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Re: Daysail / overnight charter as retirement gig?

A friend does this quite successfully, and a dock mate runs something similar with power cruisers (adding another each year) doing cruises during the day and B&B overnight. For the sailing version, income seems to be good and to sustain the venture. However, on a sailboat it seems essential to have another person on board, especially with larger boat, and my friend usually has another licensed crew on board.
The sailing operation I know of has used boats from 23 to 44 feet, and adapts adventures accordingly. I have crewed on a few of the trips, which include after-wedding outings, NYC harbor tours, etc. Occasional trips to islands in the winter.
Seems like you could come up with a rewarding plan.
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Old 14-11-2022, 07:04   #3
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Re: Daysail / overnight charter as retirement gig?

Thanks, Brioche.

Would anyone venture a guess on annual maintenance costs for a 60' 1960 wood-hulled schooner like this one sailing six months per year in fresh water?
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Old 14-11-2022, 08:06   #4
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Re: Daysail / overnight charter as retirement gig?

Just an opinion...

Seems like at best you'd end up with another full time job maintaining an old boat, running a business, trying to get insurance, and dealing with all the logistics of trips, weather, and hiring a mate, just to hope you'll break even.

I see the ASA teaching as a better option. We had some really interesting people teach our ASA classes and it was great. Plus they have flexibility in their schedule and can't end up losing money.

If I had enough hours for a captain license, I'd probably be doing the ASA route.
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Old 26-11-2022, 20:13   #5
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Re: Daysail / overnight charter as retirement gig?

The maintenance for a 30 foot Catalina is 7000 a year
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Old 26-11-2022, 20:15   #6
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Re: Daysail / overnight charter as retirement gig?

If you would like to become an ASA instructor, message me to help you. Lake St. Clair Sailing School in Michigan is in need for Sailing Instructors and Captains. www.lakestclairsailingschool.com
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Old 26-11-2022, 22:17   #7
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Re: Daysail / overnight charter as retirement gig?

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Originally Posted by leecea View Post
Just an opinion...

Seems like at best you'd end up with another full time job maintaining an old boat, running a business, trying to get insurance, and dealing with all the logistics of trips, weather, and hiring a mate, just to hope you'll break even.
Doesn't sound like a fun retirement to me either, but a great career change if your up for the hard work and long hours.
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Old 27-11-2022, 09:35   #8
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Re: Daysail / overnight charter as retirement gig?

Quote:
Originally Posted by dalepo View Post
Thanks, Brioche.

Would anyone venture a guess on annual maintenance costs for a 60' 1960 wood-hulled schooner like this one sailing six months per year in fresh water?
All boats are money pits, a wooden 60 footer especially so. Since you are taking paying customers the vessel must pass a Coast Guard inspection…not the pleasureboat courtesy inspection you may be familiar with. Watertight bulkheads, escape routes and hatches, life rafts, stability tests, etc. The list goes on and on.
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Old 27-11-2022, 09:45   #9
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Re: Daysail / overnight charter as retirement gig?

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Originally Posted by Orion Jim View Post
All boats are money pits, a wooden 60 footer especially so. Since you are taking paying customers the vessel must pass a Coast Guard inspection…not the pleasureboat courtesy inspection you may be familiar with. Watertight bulkheads, escape routes and hatches, life rafts, stability tests, etc. The list goes on and on.


It very much depends where you would be based but vessel compliance , certifications , insurance all add up to make it an easy way to loose money. .
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Old 27-11-2022, 20:13   #10
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Re: Daysail / overnight charter as retirement gig?

I always thought renting the boat would be the best way to go whatever the term for that is , Bareboat charter I’m thinking , For those that needed to prove their competency you could go along as deckhand and not be bothered by all the Coast Gaurd bs
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Old 27-11-2022, 20:41   #11
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Re: Daysail / overnight charter as retirement gig?

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I always thought renting the boat would be the best way to go whatever the term for that is , Bareboat charter I’m thinking , For those that needed to prove their competency you could go along as deckhand and not be bothered by all the Coast Gaurd bs
By Coast Guard definition a bareboat charter can not have the owner aboard.
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Old 27-11-2022, 21:26   #12
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Re: Daysail / overnight charter as retirement gig?

Yeah that doesn’t surprise me , well you’re only talking about one boat so Once you built up a clientele list you could just rent your boat to qualified people and not worry about it , I wouldn’t wanna be out cruising with people and having to entertain them not my cup of tea , I live on the Southwest Washington coast and know people who rent vacation homes they don’t need to advertise it’s the same people coming back over and over again , like I said it’s just one boat you have to keep busy , figure out a way around it , you could probably have your boat booked out a year or two in advance
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Old 28-11-2022, 04:30   #13
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Re: Daysail / overnight charter as retirement gig?

Since you are taking paying customers the vessel must pass a Coast Guard inspection

I know the requirements for CG inspection are tough to meet, so I'd been thinking of a smaller-scale operation. My understanding is that with a six-pack license, you can take up to six paying passengers out on an uninspected vessel, which hopefully would reduce the paperwork burden.
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Old 28-11-2022, 05:23   #14
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Re: Daysail / overnight charter as retirement gig?

Quote:
Originally Posted by dalepo View Post
Thanks, Brioche.

Would anyone venture a guess on annual maintenance costs for a 60' 1960 wood-hulled schooner like this one sailing six months per year in fresh water?


Her name should give you a very good idea of how much is going to cost you to maintain this wooden vessel and the transition from salt environment to fresh water, fresh water is more conductive to rot than salt water, specially when washing decks, then there is the swelling and leaking expected as you haul out, keeping up with any iron fixtures, and finally painting schedule every 2 to 3 years.

It will keep you fit
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Old 28-11-2022, 06:41   #15
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Re: Daysail / overnight charter as retirement gig?

Good luck getting insurance on a 62yr old wood boat. We've known a few people with old wood boats. If you do the maintenance yourself, it's a 2nd job. If you pay someone to do (assuming you can find someone who knows how), you could just buy a new fiberglass boat for less.

If there is money changing hands, you have to be properly licensed and insured. Your marina may charge extra for a commercial operation. Even if the CG doesn't require inspection, your insurance may up the ante over what they expect of a vessel in private use.

It is possible to run a charter business and make money but a lot of the costs are fixed regardless of how many trips you make per year, so you have to hit it hard to actually cover your costs. This isn't a couple sunset cruises per week during the peak 4 months on the Great Lakes and you will make money kind of situation.
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