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Retirement sailing -what worked for you?

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Created by EastCoastSail Two weeks ago, 5 Jan 2026
EastCoastSail
329 posts
5 Jan 2026 5:49PM
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I'm moving into retirement and want to do more international sailing, but I think I'm starting to make decisions without knowing all the options and therefore locking myself into an avenue of action. Can you explain what worked for you? For me to expand my horizons

Options I'm considering with my wife:
-Cruise with what I have, 33fter and head up to Indonesia/SW Pacific to explore it more
-sell my boat and buy an older 45ft'r, refit then , East circumnavigation via Cape of Good Hope and Panama.
-Find some new yacht timeshare in Med/Greece/Turkey. Work the Schengan VISA system for Ozzie Eu lifestyle
-Buy an EU boat, sail then dry store each year, maybe sail it home?
-Buy a boat in the EU/Americas then sail it home, sell on arrival in Australia /Fiji?
-Find some beneficial financing arrangement, buy a cat, sail for 5yrs then not make too much of a loss
-Just regularly charter in exotic locations.


My thoughts are:
- I'm not interested in doing more racing
-or doing the Red Sea, to cruise into the EU.
-I have always been disappointed with Australian charter boats, old tired sails and run down, are they the same around the world ?
-I like refitting and maintaining my own boats, it's as much fun as sailing
-I don't know if I enjoy sailing enough for a circumnavigation
-I prefer old monos or new multihulls (have owned cats, tris and monos)

lydia
1927 posts
6 Jan 2026 5:38AM
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So what regular medications are you on and what is the cost of the travel / repatriation insurance
ACE inhibitors , pre diabetic medication, prostrate?
Then reset the question
No seriously!

Just doing some research for a presentation and one question is the effect of empaglifozin (commonly prescribed pre diabetic medication) and severe side effects when dehydrated ( read seasick) that require immediate hospitalisation

same goes for ace inhibitors when dehydrated although side effect not as severe

Getting old sucks!

Ramona
NSW, 7730 posts
6 Jan 2026 8:57AM
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I would suggest keeping the yacht you have. Any serious offshore sailing should be done locally. One of our local sailors lives in Canberra but has a 50 foot yacht here. Recently he spent a few months in the UK. Bought a 25 footer and sailed around Scotland. Sold the boat and came home. He plans to do the same at another destination soon. The other alternative is to keep your yacht, travel the world sailing in the Masters in the class of your choice. The Finns Masters for example always have over 300 starters and plenty of Australians participate.

cammd
QLD, 4288 posts
6 Jan 2026 8:08AM
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Quit work last easter, rental income from house (small mortgage still) is enough to live off on anchor.

Happy with a 44ft mono, plenty of room for two, big enough to be comfortable and feel safe but still easily managable both sailing and cost wise.

Plans are going north again, then south next summer so sticking to east coast Aus for another year then we hope to go international. Not getting younger so now or never.

cammd
QLD, 4288 posts
6 Jan 2026 8:41AM
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These are my opinions on your list of options. Don't flame me there just my opinions

33ft is two small for two, I would want bigger.

Indo and SW pacific are on my plans

40 to 45 is the goldilocks size, imo, keep refit limited to just whats needed to go. I could spend 100k on my boat tomorrow filling my wish list but none of it is needed to go sailing now.

Time share in the Med?? Not sure about that, probably just charter first. The couple I sailed with on Huntress bought a boat in the med after losing huntress, they sailed it back to Hobart. I think they had a great adventure. It was a Aussie registered boat so no import or gst bill on arrival home.

I think if I could afford to buy and keep a multihill I would get a bigger mono. Maybe a boreal or garcia or something like that.

EastCoastSail
329 posts
6 Jan 2026 10:38AM
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On re-reading my post a bit later, it sounds like I'm an entitled prick with deep pockets. Not the case, I have finite funds but want to spend them wisely.

My Arends 33 is one of the larger 33's, which I find hard to fault, except it's a little slow and a feathering prop would do wonders.

All good ideas, an early enforced medical retirement, but at this stage no issues that stop sailing or critical medications, I should have a long life ahead of me( I hope).

I keep hearing from others in anchorages about med timeshare deals that work, or buying in EU and working the Schengen zone, dry storing for six months.

Any first hand knowledge?

DanNotStan
NSW, 15 posts
6 Jan 2026 3:04PM
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If you want to see a window into your "sailing up the east coast" option, there's a YouTube channel "The new adventures of Doxie" (www.youtube.com/@Dawnraider) which documents his sail up to Queensland in the Arends 33. He took it at a very leisurely pace and it seems like a great way to do it.

So relaxing to watch and I envy anyone owning a boat and having the time for such opportunity.

EastCoastSail
329 posts
6 Jan 2026 2:18PM
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I've only seen the Dixie episode in Tin Can Bay when the storm goes through. That's pretty nasty when he fends off dragging yachts with his feet in 40+ kts. Lots of potential to go wrong there.

Planter
NSW, 162 posts
6 Jan 2026 6:57PM
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Select to expand quote
lydia said..
So what regular medications are you on and what is the cost of the travel / repatriation insurance
ACE inhibitors , pre diabetic medication, prostrate?
Then reset the question
No seriously!

Just doing some research for a presentation and one question is the effect of empaglifozin (commonly prescribed pre diabetic medication) and severe side effects when dehydrated ( read seasick) that require immediate hospitalisation

same goes for ace inhibitors when dehydrated although side effect not as severe

Getting old sucks!


Exactly - Be wary if overseas on meds,as jnsurance/repatriation for existing condition ? = Mega $ ,and do due diligence to ensure that they have effective evacuation plan,to get you Home !

Do not be left on the mountain,like the old mate in Katmandhu,where altitude sickness caused another heart attack - will not do it again !

garymalmgren
1352 posts
6 Jan 2026 8:27PM
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RE: Retirement sailing -what worked for you?

Well I haven't retired yet.
72 last year and from February I will be officially there.
But that won't stop me from giving advise.

You have a 33 foot boat that you own and know.
You are in Australia. one of the largest and most varied cruising grounds in the world.
You speak the language and don't have any visa hassles.
If anything goes wrong, it is not an international flight to go "home".
If the wife wants to step off for family or other business she can, easily.
If you want a friend to join you for any leg, they can easily. Well, not really if you are in the Kimberlys.
If you need work done, you can sus out the location , yard and staff easily.
You will not be dealing with yard managers in a foreign language. Quotes? What are the?
If you need any supplies , you are familiar with what is in the super.
You can be pretty well assured of the quality of the fuel.
There are plenty of remote (I mean really remote) places to go.
There are plenty of almost urban places to go. Brisbane River comes to mind.
There are lots of like minded sailors to link up with.

45 years ago, I bought a boat in Perth. Sailed up the west coast and headed out of Australia as fast as I could.
Yes I had my adventures . The east coast of Kalimantan being one of them.
However, I realize too late that I had missed the amazing sailing that Australia has to offer.

So my advise is , sail Australia in the boat that you have.
Sprint off to the Aegean or Caribbean for a charter and then whip back home.

gary

EastCoastSail
329 posts
7 Jan 2026 7:59AM
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Gary,
Really good advice, I've lived in every state and territory of Australia,bar Tassie. Still so many new horizons to explore. Currently anchored in Jervis Bay and remembering just how good the diving is.

I see your posts and have recently read a book about an American couple that cruised Japan. Japan looks like a fantastic cruising area. I came into Yokosuka Port once in a work boat, completely different from Australia. It looked challenging to navigate around all all the aquaculture along the coastlines I found amazing.

Chris 249
NSW, 3521 posts
7 Jan 2026 9:59PM
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If at normal retirement age and fitness I'd be dubious about a 45'er, because the forces on a boat that size are very large for an older couple. I've sailed big boats and it's all great until something goes wrong, but if a furler broke down in a gale (for instance) I'd want to be in a 33-38ish or smallish 38-42 footer. The most experienced cruisers I've sailed with were happy with a smallish 40 footer, and they would cast off from their NZ home to sail to Alaska for an easy holiday in much the same way as others go from Sydney to Pittwater.

EastCoastSail
329 posts
8 Jan 2026 4:07AM
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I guess my problem with staying in Australia is for years I was an engineer of a hydrographic survey ship. For years I have been part of surveying going past remote islands in PNG, Indo, Solomon Is, Tonga, Vanuatu, etc. Transiting past what was typically old steel yachts tucked into bays. Living the life.

Once the lifestyle is glimpsed it's hard to forget.

cammd
QLD, 4288 posts
8 Jan 2026 7:01AM
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Select to expand quote
Chris 249 said..
If at normal retirement age and fitness I'd be dubious about a 45'er, because the forces on a boat that size are very large for an older couple. I've sailed big boats and it's all great until something goes wrong, but if a furler broke down in a gale (for instance) I'd want to be in a 33-38ish or smallish 38-42 footer. The most experienced cruisers I've sailed with were happy with a smallish 40 footer, and they would cast off from their NZ home to sail to Alaska for an easy holiday in much the same way as others go from Sydney to Pittwater.






Yeah, just get a boat set up with a cutter rig and enjoy the extra space, comfort and speed you have everyday.

You want to be able to make easy miles without having to push the boat, that breaks things. Comfort at anchor is a must, you spend most of your time at anchor and you need something that is capable of carrying a load without destroying its sailing capabilities.

Edit: replace all the "you" above with "I" they are criteria that were important to me.

JonE
VIC, 549 posts
8 Jan 2026 8:04AM
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Have you sailed in the Med? It's great. If the answer's no, and you're still on the clock, maybe go and do a flotilla charter in Greece and or Croatia for a week or two each.

I've done a couple of flot charters and it's a great way to sample a few ports/anchorages in a short space of for relatively low outlay, the security of someone else to come on board and fix issues if required. The "lead boat" crew, who are paid employees of the company, i.e. Sunsail often have a ton of local knowledge.

There's usually a few hours downtime in the mornings that you could spend checking out brokerages, talking to other boat owners etc.

cammd
QLD, 4288 posts
8 Jan 2026 7:25AM
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Select to expand quote
EastCoastSail said..
I guess my problem with staying in Australia is for years I was an engineer of a hydrographic survey ship. For years I have been part of surveying going past remote islands in PNG, Indo, Solomon Is, Tonga, Vanuatu, etc. Transiting past what was typically old steel yachts tucked into bays. Living the life.

Once the lifestyle is glimpsed it's hard to forget.


Just do it

To quote Colin from Parley Revival "years from now you will regret what you didn't do"

lydia
1927 posts
8 Jan 2026 8:48AM
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Select to expand quote
EastCoastSail said..
I guess my problem with staying in Australia is for years I was an engineer of a hydrographic survey ship. For years I have been part of surveying going past remote islands in PNG, Indo, Solomon Is, Tonga, Vanuatu, etc. Transiting past what was typically old steel yachts tucked into bays. Living the life.

Once the lifestyle is glimpsed it's hard to forget.


If that is where you want to go particulaly PNG and Indo don't rule out a displacement powerboat, even single screw.
Plenty of space, shallow draft, cheap to maintain, you don't live down in the cave. And good shade and ventilation in the tropics.
EN 590 is easy to get and if it has a Leehman it can run on JetA1 as well.
One new sail now days buys a lot of diesel.

EastCoastSail
329 posts
8 Jan 2026 10:09AM
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Just looking at all options.
Your right about the cost of a 'sailors eco powerboat' , they can be economical. But the best thing about sailing is when the engine get turned off.

I will not take my wife to either PNG or the Solomon Islands. Two of the most beautiful countries in the world ( I have done a lap of New Britain by bicycle, been to PNG five times, two times as a soldier to Bougainville ). There is an underlying level of violence there, I have seen it turn from paradise to grave fears for your safety in an instant. Unfortunately both places seem to be deteriorating as time goes by.

EastCoastSail
329 posts
8 Jan 2026 10:18AM
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Select to expand quote
JonE said..
Have you sailed in the Med? It's great. If the answer's no, and you're still on the clock, maybe go and do a flotilla charter in Greece and or Croatia for a week or two each.

I've done a couple of flot charters and it's a great way to sample a few ports/anchorages in a short space of for relatively low outlay, the security of someone else to come on board and fix issues if required. The "lead boat" crew, who are paid employees of the company, i.e. Sunsail often have a ton of local knowledge.

There's usually a few hours downtime in the mornings that you could spend checking out brokerages, talking to other boat owners etc.


I will look into it.

lydia
1927 posts
8 Jan 2026 10:58AM
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Select to expand quote
EastCoastSail said..
Just looking at all options.
Your right about the cost of a 'sailors eco powerboat' , they can be economical. But the best thing about sailing is when the engine get turned off.

I will not take my wife to either PNG or the Solomon Islands. Two of the most beautiful countries in the world ( I have done a lap of New Britain by bicycle, been to PNG five times, two times as a soldier to Bougainville ). There is an underlying level of violence there, I have seen it turn from paradise to grave fears for your safety in an instant. Unfortunately both places seem to be deteriorating as time goes by.


But sail boats do not do 200 miles a day upwind or in no air.
Just saying.

EastCoastSail
329 posts
8 Jan 2026 7:41PM
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Not being negative, the motorboat idea has merit. It's just not my thing.

Serenite
48 posts
12 Jan 2026 8:18AM
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I've been watching this thread with interest because I'm planning the 'sell here and buy a 45 footer in the Med' option. With a view to getting it back here eventually after the Med, Atlantic and Pacific crossings. I'm thinking that will take 4 or 5 years in total so I'll be late 60's at the end of it. Then we'll cruise the east coast of Oz until fitness and agility mean we can't any longer.

My two cents supports the go now philosophy. Lots of long-term cruisers give that advice, go as soon as you can. You're unlikely to need less drugs to keep you healthy in five years time. The Europeans have doctors and hospitals, you just need to buy the insurance to cover you, that's a necessary cost and I don't believe it will get cheaper if you wait either.

I'd agree it can be hard operating in a foreign language too but English is pretty widely spoken even in little towns and google translate helps.

My wife and I have done 8 charters in the Med over the last 5 years or so and it's very different to cruising here. My experience is in Greece and Italy and 200 miles is a very long way there. We've normally only covered that distance in a week and that's when you've only got 1 or 2 weeks to look around (1 night per anchorage). If we're there full time it will be a much slower pace. There are a lot more people so a lot more towns and harbours and the next anchorage will likely be 10 or 20 miles away maximum, could be just around the next headland or to the next island.

Obviously, the passages (Atlantic & Pacific) are more significant undertakings but there are rallies you can join for both of those. I joined a yacht club with a cruising division a few years ago and we're getting to know people who are willing to help as crew for those longer stretches. I'll be willing to help them when I've retired.

The EU boat market is just so much bigger than the Aussie, means more choice and also reduces price. I also like working on my boats so I'm thinking I have 2 seasons cruising in the Med to get her set up the way I like and be ready to head out into the Atlantic. Lifting out for the winter is pretty normal over there so we'll be back for Aussie summers and to see the kids etc.

We're going as soon as we can, we're not getting any younger.

EastCoastSail
329 posts
Wednesday , 14 Jan 2026 1:21PM
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Thank you for the responses and your input Serenite.

My family and I are now midway through a month of cruising the east coast. My wife's major concern before this was the lack of socialising on the water. So we have emphasised that aspect, and having a marina respite every 7-8 days. It's working out well with good friends made, wife and daughter enjoying it. We are discussing keeping current boat for now or if we actually need to go bigger? I am enjoying a smaller boat in unknown places and marinas. Currently at anchor in Rose Bay.

This is enjoyable, heard lots of other ideas from cruisers, consensus seems to be buy overseas in the cruising area you want and sail it. Maybe import on return or offload it before.



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"Retirement sailing -what worked for you?" started by EastCoastSail