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Old 24-07-2019, 22:33   #1
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Planning ahead for sailing sabbatical(s)

My wife and I are having some serious thoughts of a longer term sailing lifestyle in our future. A Caribbean season at a minimum to start, but possibly 2-3 years, or even months at a time on-going for many years all over the world. We cannot do it now due to health issues with a parent, lack of funds to buy a boat (want to pay cash and not willing to sell our house and permanently move - yet...), and our dog is special needs. So we are looking for some advice to help prepare ourselves for the day that we can pull the trigger, maybe 4-6 years away. Time flies by, so we want to be ready!

I'm 38 and a software engineer, and wife is 35 in marketing and sales management. No kids. We have owned a 21' open bow Sea Ray I/O power boat for over 10 years, have scuba vacations 1-2x's per year all over the world, and just love the water in general. We live and work in Dallas, so we have to travel far to enjoy the ocean! We are on boats often during our trips, having done liveaboard diving a few times now. Last year we did our first BVI bareboat charter with 2 other couples, and I just got back from a nice 180nm sail from San Diego to Catalina over the 4th as Captain for about half the trip. I'd consider myself very mechanically inclined having fixed everything from cars to our boat to engines, and renovating our entire house ourselves certainly upped our experience!

I took Basic Keelboat last year and am signed up for ASA 103 and 104 this year. I'm going to continue taking further courses next year and my wife will do 101 at least next year too. I hope to join a yacht club locally to get to sail on lakes here and there, but not sure I want to sell our bow runner and buy a smaller sailboat here.

The plan for now is to bareboat charter at different places around the world at least once a year for 1-2 weeks with friends and family to gain more experience and figure out the pros/cons of different boats. We'll continue training and gaining experience while saving $ to purchase a boat eventually for these longer term plans, but who knows, we may decide bareboat chartering every year is the way to go instead, ha.

I've started reading books and as much as I can online, and we have both come to love "Gone with the Wynns" on YouTube. I just finished "A Sail of Two Idiots" which is amusing but also great to learn from their lessons. If all of these people can do it, then surely with continued training and bareboat charter experience over 5+years, we should be able to as well.

For any of you that have gone through this before, what else would you recommend we do to prepare ourselves or talk us out of this nonsense ?

Thank you!
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Old 24-07-2019, 23:55   #2
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Re: Planning ahead for sailing sabbatical(s)

Check Craigslist for a cheap dingy and trailer. Sail local lakes, tack lots, sail
on and off docks, sail all points and get comfortable in higher winds (this is relative to the size of the boat, but if you can be comfortable in a dingy in 20knt winds you’ll be off to a good start for less than 2k with virtually no maintenance or moorage. Dinghies are not as forgiving, faster (not just hull speed) and keeps
you sharp not mention a hell of a lot of fun. You can most likely sell it for what you paid when you’re done. If you’re adventurous you can even camp/cruise them.
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Old 25-07-2019, 05:24   #3
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Re: Planning ahead for sailing sabbatical(s)

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Check Craigslist for a cheap dingy and trailer. Sail local lakes, tack lots, sail
on and off docks, sail all points and get comfortable in higher winds (this is relative to the size of the boat, but if you can be comfortable in a dingy in 20knt winds you’ll be off to a good start for less than 2k with virtually no maintenance or moorage. Dinghies are not as forgiving, faster (not just hull speed) and keeps
you sharp not mention a hell of a lot of fun. You can most likely sell it for what you paid when you’re done. If you’re adventurous you can even camp/cruise them.
Great idea. I was thinking about the same with a Hobbie Cat, but a dinghy makes more sense. I keep forgetting that there are sailing dinghies.

Since I don't really have a place I could park one without paying a month fee to do so, I may reach out to a local yacht club to see if they have any and I could join for less than the monthly fee to park a dinghy. Then I could also potentially rent other sized sailboats through them too.
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Old 25-07-2019, 08:36   #4
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Re: Planning ahead for sailing sabbatical(s)

The only problem with clubs is a lot of them have serious restrictions (rightfully so) and you will be waiting in line to sail the same lake/area over and over. If you can find a 14-16’ dingy a lot of marinas has reasonable dry/trailer storage long and short term.
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Old 25-07-2019, 08:43   #5
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Re: Planning ahead for sailing sabbatical(s)

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The only problem with clubs is a lot of them have serious restrictions (rightfully so) and you will be waiting in line to sail the same lake/area over and over. If you can find a 14-16’ dingy a lot of marinas has reasonable dry/trailer storage long and short term.
Good point. I researched a few clubs on my way to work today and only found one that offers boat use, and it's around $600-700/yr for membership and ability to use their boats, plus they require 2 full days of marina work a year (so realistically $1k+ cost a year). Buying and reselling should be much lower.

The place we park our current boat is $80/mo for outside uncovered storage, and we get ramp access. Maybe I could get them to give me a deal on parking a smaller dinghy trailer next to it as well. Unfortunately we have a front drive at our house and HOA rules don't allow parking a trailer there. We could fit one in the garage, but have been trying to make an effort to get my wife's car in for a couple years ha.
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Old 25-07-2019, 10:09   #6
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Re: Planning ahead for sailing sabbatical(s)

One thing you might want to consider is getting into the ownership side of a bareboat charter arrangement. Supposedly you can have others pay your boat expenses for 5 years or so, while perhaps getting a small amount of cash flow, and you get to use it (or similar boat) on your charter vacations. When you are ready to "go" you take boat out of charter arrangement; of course you will still owe money as the loans are longer than 5 years so that monthly payments can be covered by charter revenue. I can imagine such an arrangement might be risky depending on who you go with. I have heard good things about CYOA in St. Thomas but know no one who has done it with Moorings, SunSail, or Dream.

I went a different route, I bought my boat on Lake Lewisville in Dallas area 10.5 years ago with the plan to move it to saltwater, which I did 4 years ago. Prior to the move, I bareboated in various places while sailing the crap out of my boat on the lake, upgrading it over time. Costly perhaps but I have never been without a boat since age 16 so boat expenses have always been part of my DNA.
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Old 25-07-2019, 10:21   #7
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Re: Planning ahead for sailing sabbatical(s)

Where are you located? You can buy a minimalist 30+/- foot sailboat for not much money. You do the maintenance and learn a lot.

Cheers, RickG
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Old 25-07-2019, 10:31   #8
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Re: Planning ahead for sailing sabbatical(s)

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One thing you might want to consider is getting into the ownership side of a bareboat charter arrangement. Supposedly you can have others pay your boat expenses for 5 years or so, while perhaps getting a small amount of cash flow, and you get to use it (or similar boat) on your charter vacations. When you are ready to "go" you take boat out of charter arrangement; of course you will still owe money as the loans are longer than 5 years so that monthly payments can be covered by charter revenue. I can imagine such an arrangement might be risky depending on who you go with. I have heard good things about CYOA in St. Thomas but know no one who has done it with Moorings, SunSail, or Dream.

I went a different route, I bought my boat on Lake Lewisville in Dallas area 10.5 years ago with the plan to move it to saltwater, which I did 4 years ago. Prior to the move, I bareboated in various places while sailing the crap out of my boat on the lake, upgrading it over time. Costly perhaps but I have never been without a boat since age 16 so boat expenses have always been part of my DNA.
Small world, our boat is at Lake Lewisville and that's where we've been going for over 10 years. That is a great idea to buy here, work on it, upgrade it, and practice on it, but I haven't seen many sailboats on the lake that we would consider buying and pay the hefty price to move down to the ocean.

Long term, I think we're considering a 40ish catamaran, but we've considered a 40-45' monohull as well if we're only on the boat for months at a time instead of a year +. I will admit that I've never sailed a cat before, but receiving certification to do so and bareboating one first is on the list.
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Old 25-07-2019, 10:48   #9
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Re: Planning ahead for sailing sabbatical(s)

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Originally Posted by RickG View Post
Where are you located? You can buy a minimalist 30+/- foot sailboat for not much money. You do the maintenance and learn a lot.

Cheers, RickG
We're in North Dallas, and go to Lake Lewisville about 10mins away.

I certainly like the idea of selling our bowrunner and getting a 30+/- sailboat here, but while we're working we are limited in time for the additional maintenance a sailboat requires, and slips are $5k+/yr. My wife and I both work a lot, so we want to get experience occasionally on something not requiring much maintenance for now, plus bareboat charters on vacation, but when we have the opportunity to job transition and take this sabbatical, I don't mind maintenance at all.
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Old 25-07-2019, 11:02   #10
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Re: Planning ahead for sailing sabbatical(s)

The romance of sailing often blinds people to the reality. Buy a small boat and try living on it, maintaining it and pretend you can’t escape anytime you want. Doing so while uncomfortably cold or hot and while seasick also helps cure the illusion. Only after doing that should you start planning.
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Old 25-07-2019, 11:16   #11
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Re: Planning ahead for sailing sabbatical(s)

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The romance of sailing often blinds people to the reality. Buy a small boat and try living on it, maintaining it and pretend you can’t escape anytime you want. Doing so while uncomfortably cold or hot and while seasick also helps cure the illusion. Only after doing that should you start planning.
Definitely agree. We are trying to look at all of this from that angle instead of being glassy eyed "everything is going to be great if we do this!". That's why I want to continue with certifications, bareboat charters, reading about other's stories, etc... before we dive in. And it certainly doesn't hurt to start saving $ now. If we decide later that it's not actually something we want to do, then we'll have plenty of funds saved for a "land" sabbatical collecting passport stamps the way we have been for 15 years .
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Old 25-07-2019, 12:03   #12
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Re: Planning ahead for sailing sabbatical(s)

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For any of you that have gone through this before, what else would you recommend we do to prepare ourselves or talk us out of this nonsense ?
First up, research cruising grounds. Take into consideration such things as availability of boats, ability to go there beforehand, difficulty of sailing grounds, the seasonal weather patterns (and what to do in the off season), any propensity for homesickness on your part, a realistic bailout option and resale.

After a lot of research we decided we just didn't want to commit to Europe (my first choice) or the Caribbean (my second choice) and for a number of the above reasons decided to stick close to home (the PNW). I haven't regretted that once.

Look at boats. Look at more boats. Decide what you want and then toss that and try again. I absolutely guarantee that you list of must haves will have some things you will find later are a waste and you will utterly regret not considering others. But that's the way it always works; all you can do is keep an open mind.

Try and evaluate the hidden costs and decide when you are going to pay them. We only had a year and I wanted to maximize my time cruising so we bought something "turnkey" and then paid to have the broker get the rest of the work done before we arrived. We could have done a bunch of it ourselves but between the time lost through learning curves and the cost of a slip, I am not sure it actually cost us that much extra. I certainly don't regret paying for the privilege of casting off 4 days after we arrived.

Have a start plan. But don't stick to it too vigourously. Knowing what your first week or two is going to be like and being able to research the sh$t out of it will take some stress off the initial period, but be sure to keep an eye on the bigger picture. Be aware that chartering is often sail-marina-sail-anchor-sail-marina...etc. Once you are on your own boat and comfortable it will more likely be sail-anchor-anchor-anchor-anchor-sail etc. We covered way less miles after we moved aboard and spent days at anchorages.

Speaking of which, charters often get you habituated to marinas and mooring balls. Work on your anchoring skills and confidence. Our last 1-month trip had exactly two visits to marinas: once to meet friends and once to sit out a storm. When we first cast off we probably spent 2 nights out 7 at a marina.

Depending on your final destination I wouldn't sweat the sailing skills (unless that's your thing). You will learn and it's a lot easier when you are relaxed, in your own boat and not feeling the pressure. I tried really hard to get on other people's boats with experienced skippers in harsh conditions and as luck had it all those trips were benign. So we learned to ride out big winds and bad conditions the hard way

And be prepared to fall in love. We fully intended to sell our boat after our year was up and just couldn't bring ourselves to do it. So now she's a part of a charter fleet and we get a month or two "free" sailing every year. So ya, an exit plan is good but flexibility is better.

Good luck!
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Old 25-07-2019, 12:12   #13
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Re: Planning ahead for sailing sabbatical(s)

We did the following to get up the learning curve.


ASA 101-106 Off shore Sailing School
Annapolis School of Seamanship Advanced diesel course
Annapolis School of Seamanship electronics course
Mahina Expeditions Ocean sailing course
Crewed in Pacific Tahiti to Cook Islands
Charter in BVI

Purchased a boat probably more complex than was probably advisable, but we are quick learners, and are still learning. But after three years of cruising for 6 months of the year we feel we know what we are doing.

Considering RYA Yachtmaster next fall

Try to do training for both of you, not just you.
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Old 26-07-2019, 05:36   #14
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Re: Planning ahead for sailing sabbatical(s)

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Originally Posted by Macblaze View Post
First up, research cruising grounds. Take into consideration such things as availability of boats, ability to go there beforehand, difficulty of sailing grounds, the seasonal weather patterns (and what to do in the off season), any propensity for homesickness on your part, a realistic bailout option and resale.

After a lot of research we decided we just didn't want to commit to Europe (my first choice) or the Caribbean (my second choice) and for a number of the above reasons decided to stick close to home (the PNW). I haven't regretted that once.

Look at boats. Look at more boats. Decide what you want and then toss that and try again. I absolutely guarantee that you list of must haves will have some things you will find later are a waste and you will utterly regret not considering others. But that's the way it always works; all you can do is keep an open mind.

Try and evaluate the hidden costs and decide when you are going to pay them. We only had a year and I wanted to maximize my time cruising so we bought something "turnkey" and then paid to have the broker get the rest of the work done before we arrived. We could have done a bunch of it ourselves but between the time lost through learning curves and the cost of a slip, I am not sure it actually cost us that much extra. I certainly don't regret paying for the privilege of casting off 4 days after we arrived.

Have a start plan. But don't stick to it too vigourously. Knowing what your first week or two is going to be like and being able to research the sh$t out of it will take some stress off the initial period, but be sure to keep an eye on the bigger picture. Be aware that chartering is often sail-marina-sail-anchor-sail-marina...etc. Once you are on your own boat and comfortable it will more likely be sail-anchor-anchor-anchor-anchor-sail etc. We covered way less miles after we moved aboard and spent days at anchorages.

Speaking of which, charters often get you habituated to marinas and mooring balls. Work on your anchoring skills and confidence. Our last 1-month trip had exactly two visits to marinas: once to meet friends and once to sit out a storm. When we first cast off we probably spent 2 nights out 7 at a marina.

Depending on your final destination I wouldn't sweat the sailing skills (unless that's your thing). You will learn and it's a lot easier when you are relaxed, in your own boat and not feeling the pressure. I tried really hard to get on other people's boats with experienced skippers in harsh conditions and as luck had it all those trips were benign. So we learned to ride out big winds and bad conditions the hard way

And be prepared to fall in love. We fully intended to sell our boat after our year was up and just couldn't bring ourselves to do it. So now she's a part of a charter fleet and we get a month or two "free" sailing every year. So ya, an exit plan is good but flexibility is better.

Good luck!
Great advice. Another reason we plan to bareboat many places before moving forward with this is to figure out where we'd like to spend more time (a lot more time). I think Europe for an extended period of time is out for us before we even do a charter there. We definitely want to charter in Greece, and are planning to do the French Riviera or Croatia next year, but wouldn't want to spend a season or year+ there (mostly due to cold water for diving and cost probably). Europe is great for land based travel though. The Caribbean is much more likely, as is the South Pacific.

I can probably search on the forum more, but do you have a list of things that you thought were "must haves" but ended up regretting them and wish you had others? That would be really helpful as we charter and pay closer attention to boats more.

Good point about "turnkey" since we are in Dallas (not near anywhere to buy a boat, unless somehow we manage to find one on a lake to move to the ocean as recommended above). At the same time, I am not into project boats but am willing to do some replacements and upgrades over a period of weeks most likely.

Also very good point about anchoring considerably more. We do it on the lake often with our 20' bow-runner, but obviously it's much different with a larger boat on the ocean. I'll try and concentrate on that in my training with instructors.

Thanks!
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Old 26-07-2019, 05:43   #15
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Re: Planning ahead for sailing sabbatical(s)

Quote:
Originally Posted by Hobiehobie View Post
We did the following to get up the learning curve.


ASA 101-106 Off shore Sailing School
Annapolis School of Seamanship Advanced diesel course
Annapolis School of Seamanship electronics course
Mahina Expeditions Ocean sailing course
Crewed in Pacific Tahiti to Cook Islands
Charter in BVI

Purchased a boat probably more complex than was probably advisable, but we are quick learners, and are still learning. But after three years of cruising for 6 months of the year we feel we know what we are doing.

Considering RYA Yachtmaster next fall

Try to do training for both of you, not just you.
How did you find the crewing opportunity from Tahiti to the Cook Islands? That sounds like a great time. I get a month off of work in 2021 and something like that might be a good idea to do, or just our own month long bareboat.

Thanks for the recommendation on RYA Yachtmaster, I'll look into that more.

Yes, I'm going to try and get my wife in for more training than 101. If she's committed to boating then I would hope she will!
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