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My crazy boss sold everything, bought a boat, and is sailing for an entire year (sailingondine.com)
142 points by bdickason on Dec 11, 2010 | hide | past | web | favorite | 95 comments

I've lived on a boat in the Copenhagen harbour for the last four years.

I bought it in Holland, and knew absolutely nothing about boats when I started out. My thought was that the only regrets you have when you get old are all the things you didn't do. Besides I'm enough of a businessman that I'd be able to sell it without a loss if it didn't work out. So I gave it try.

Four years later I'm still here and wouldn't want to live any other way. The boat is paid for so my only expenses are $200 a month in harbour rent and roughly another $200 a month on repairs. Internet isn't a problem since 3G is everywhere now - I can surf hacker news while at anchor somewhere off the coast of Sweden.

The upsides are pretty obvious: A gret free lifestyle, beautiful views, ducks right outside your window and the ability to go anywhere you want (within limits...)

The downsides are that it's cold in the winter, you don't have a lot of space, and you need to become a bit of a handyman. I've bought powertools I didn't know existed five years ago.

But overall it can only be recommended. Oh, and drop me a line if you're ever in Copenhagen I'll take you for a trip through the harbour, it's beautiful just before the sun sets.

That's amazing! I have a client who runs an acting studio (also an actor himself) and he lives on his boat for most of the year, docked at harbour-front right in Downtown, Toronto.

He tells me the harbour rental is one of best kept secrets. He only pays $100/mnth (a 1bdr studio in the area would go for $2100/mth) and lives in a beautiful yacht, with a master room and guest space, just minutes away from the downtown core and all the essentials. It's the kind of free-spirited lifestyle i'd like to live in the near future.

My question is, how do you deal with icy water? don't you have to pull out the boat when ice starts to form? In Toronto you could pretty much skate out on the lake in winter.

If your boat is in good shape and you're in a harbour it's not a problem. If you're not protected from the open sea by a bulwark of some kind the ice might drift towards land powered by wind and put a lot of pressure on a boat or whatever else is in the way. This will only happen if you're moored somewhere you shouldn't be though.

Basically what happens is that your boat just gets stuck in the ice and moves with the ebb and flow of the water.

The only problem you have is that you can't go anywhere until the ice breaks up. Last winter I got stuck in the ice somewhere in the Copenhagen harbour a few miles from my homeport and ended up staying there for almost three months. Here's a picture: http://tinypic.com/view.php?pic=oa2m2b&s=7

Well, you have a steel boat. Leaving GRP boat to ice might not be as good an idea, although we had one here one winter and it still seems to sail fine.

That sounds amazing.

Side note as someone who grew up in Toronto and lived in the downtown core for several years: A studio would go for under $1200/mo. You can get a pretty swanky 1bdrm for under $1400/mo. Though I have no doubt one could also find an apartment for much more than $2100/mo, too.

I did a quick search for monthly boat fees to park them in the marina, looks like it's around $20.25/ft/mo [1]. Any idea which marina your friend uses?

[1] http://www.harbourfrontcentre.com/thewaterfront/marine/rates...

Sure, the harbor's cheap ($200/month) say but what about the Yacht itself? Probably costs more to rent than the apartment!!!! No?

I paid $40.000 for the boat and spent around $15.000 on repairs and upgrades. If you take a loan you're going to pay around $800 a month.

In my part of the world that's pretty cheap. Might be expensive elsewhere though.

What part of the world is this? How big is the boat, and where did you find it so cheap?

I see yachts selling for over $500k...

I am seriously considering this. Can you please point me to some links? I am in NYC. Maybe I can buy a yacht somewhere else and sail it to NYC?

Do you have an e-mail? I'll mail you some links.

How do you deal with passports, customs, borders etc? Can you just sail into the port of a new country or do you have to pass through some kind of registration or security each time?

I'm in the European Union where you're free to travel from one country to another as you like, so it isn't a problem. Theoretically I could be borded by a customs boat, but I've never had it happen and suspect it's quite rare. I'm not sure how it would work if I went to a country with stricter control of their borders.

You'd do well to keep your VHF radio open on channel 16 though(this is where boats communicate with each other when at sea). I've had customs call med up when passing the border from the Netherlands to Germany to hear who I was and where I was going. Once they got a satisfactory answer we never heard from them again.

This is quite simple. Every time you sail into a new country you have to approach one of the ports of entry[1]. This has to be the first place you visit and there you can arrange all the formalities (customs, immigration, health, depends on a country). Afterwards you are usually free to visit any other harbour in a given country. Rinse and repeat for each country that you visit.


If I recall there was some mention of you possibly writing an how-to style eBook about your experience?

You're right - the memory of HN is excellent :-)

I've kind of shelved it for now since I'm pretty busy doing other things, but I hope that I'll have time to do it within the next year sometime. I don't think it's a great way of making money though, so it's not a top priority. More like a hobby project.

Would you happen to know a list of places where it's practical to rent out semi permanent harbour space, either just in the EU or (preferably) all around the world? I imagine in your planning of your current situation it's possible you compiled such a list?

Have always wanted to do this.

How do you use the bathroom? I heard that although boats have bathrooms, you cannot use them while in harbor because they essentially dump the waste in the water.

How do you shower?

Most bigger boats have a holding tank for grey water and a water tank for fresh water. When you shower you use the fresh water and dump it into the harbour, it's not that dirty just because you've showered. When you go to the toilet you use saltwater to flush and flush it into the greywater tank, which you can then empty either by having it sucked out (All European ports are required by law to have equipment for doing so, though many don't) or dump it into the ocean once you're more than 12 miles off the coast.

Simple :-)

but if you shower and dump it in the harbour aren't you basically dumping chemicals straight into it (shampoo, soap, conditioner)? Not that I think it's a big deal, I just thought rules were stricter.

Not a big deal? I actually was a bit scared when reading that. Sure, one person doesn't make the game, but a harbour is full of ships.

Sounds dreamy. I'd love to see some pics of your boat and / or the view.

What kind of boat do you own? I couldn't find it in your comment history. Given the choice would you still buy that particular boat today or would it be something else?

A dutch built steel canal boat. There's a link to a picture elsewhere in the thread. Covered in ice...

Overall I'm happy and would buy the same kind of boat again. The Dutch build excellent boats and have for centuries. The only thing that bothers me is that since it's a canal boat it has very low draft (0.8 meters) and almost no keel which is great if you're sailing in canals that aren't very deep, but makes for a pretty rocky ride once you hit some real waves.

I'd never buy a wooden boat, and I wouldn't recommend it to anyone that doesn't work professionally with wood.

Fun fact : for years Richard Branson lived on, and conducted business from, a canal boat moored in Maida Vale in the middle of London. I'm not sure if it ever moved or was permanently moored.

The downsides are that it's cold in the winter

Can you not sail south for winter to the Medditterranian? South of France or Italy would be a nice warm place to overwinter.

What about pirates and criminals at sea? (seriously.)

Well in Danish territorial waters I'm probably as close as you'll get to a pirate :-)

The poster is in the European area. Very few pirates in that part of the world.

I am doing something similar. I am selling everything I have (not much stuff though, I am frugal) and moving to SE asia (where I was born). This is the first time I will be there in a long time (15 years) so not sure what to expect.

I made the decision in 30 minutes. Bought the ticket, committed myself, sold most of my stuff, said good bye to most people I know. The plan is to visit 50 countries in the next 5 years. Leaving on Jan 3rd.

I am too content with my life. Sometimes you need a kick in the butt to get out of your comfort zone. The world is too big and not enough time.

Good stuff!

A similar thing happened to me recently. About a year or two ago I broke up with my girlfriend of eleven years and started to think what a waste everything had been during that time. We weren't married, no children etc and so when she left all ties were pretty much cut. Bam, there goes eleven years!

I went on holiday with a friend a few months later to cheer me up, and I met a new lady, and just last week I moved to Prague with her after spending some time travelling in the Middle East.

I gave up a decent job, sold all my possessions, left all my old friends behind and just went for it. I made up my mind on a wet rainy evening in Sheffield after watching another crap episode of regional news. I don't know what clicked that evening but it was sudden.

It's the best decision I have ever made. The alternative was to just sit around and carry on doing the same old stuff that I wasn't really excited about. Giving everything up is really tough, selling all your possessions is even harder but it's very cathartic.

The saying Life's what happens when you're busy making other plans comes to mind. If you have something you want to do but aren't sure about whether the hassle is worth it - it probably is :)

I realized one day that my friends weren't good friends - they weren't bad friends, they just weren't an asset to me. I realized my job is just a job, I work in construction so it really didn't matter where I am I'll always be able to work. My dream of being a novelist is achievable anywhere, and from a logical perspective I make more money in North America than in the UK thanks to the exchange rates.

I took a chance and started visiting someone I'd met online, it went well so I gave up everything and moved to Canada. I'm now married, I have a good job with good bosses and good coworkers (in the year I've worked there, I haven't seen a single bit of drama).

What made me want to do all this? The Strange Life of Ivan Osokin by P.D. Ouspensky, basically the man made all his decisions wrong in life and is tortured by it at the end of his life as he relives his life unable to make a change for the better.

I realized I could either regret life, or not.

FYI, 5 years is not enough time to do 50 countries. It took me 10 years of traveling 6-9 months a year to break 50, and I'd say more than half of them are places I don't think I spent enough time in.

I'd recommend taking that half of the plan out, and just shorten it to "travel for 5 years or so". Chances are you'll find at least one country that traps you for an entire year. Probably best not to set yourself up to feel bad about it.

Thanks. I have a set of "life goals" and none of them are "rigid", think if it as a "baseline" goal so I know what I am aiming for. If things work out the way I planned, it nice; if I visit just 20 countries in 5 years its still 20 more countries that have not been to before. I am fine with it.

On the other hand, I've "done" seven countries in two weeks. (In Europe, of course.) It's easy to get into a travelling pace where one night is enough to feel like you've seen a city... unless it's a really big city like Rome or Paris in which case you need two.

I'm living in Europe and just have been to the USA for the first time. LA, SF, Vegas - 4 days each plus 6 days NYC (start and end point). I'm not sure you can do even the typical tourist stuff in one day where you don't have to think about where you go.

and it took me, well I'm not even sure, but probably 4-5 years of actual travel time to hit about 70 countries, and all up 12 years or more living abroad. I didn't see enough of _any_ of those countries. I agree it's not about hitting a number, but about enjoying the meandering, and allowing yourself to be trapped for a time in places that please.

I am since seven years in one country,China, and the rest of my life will not be enough to know it. I don't think you can say you know a country if you didn't speak to its citizen in their language, for example.

I keep reading stories of people who do things like this, on HN and I always wonder that how is it that people are able to afford something like this. Do you mind telling us (me?) how you're going to finance yourself for the next 5 years (I think you said you plan to work - freelance?), what you think you'd do once the 5 years are over (if you come back to the US/wherever, do you think you'd still have what it takes to be employed at a similar job again), how you plan to handle the potential loneliness (travelling alone for a long period of time can get lonesome, after a while) etc.?

BTW, having lived in Malaysia and visited some SE Asian countries, I highly recommend it (KL, Langkawi), Singapore and Thailand; but then again, these places were probably on your list already.

I can only speak for myself. I am not sure how others have done it. I have some savings and I am a frugal guy, Experience is more important to me than "stuff". By selling everything I have (except for the bare minimum) I won't be tied down to anything. My savings is enough to keep me going for at least 2 years. I hope to do some kind of work during this period - but only enough to help me with my expenses, not trying to be a millionaire. It most likely will be in the form of freelance work, but I am open to odd jobs working part time where ever I end up in.

One of the reasons I am doing this is my life is too easy and predictable. If I try to prepare too much on what "exactly" I will be doing on my travel or what I will do after 5 years; that defeats the whole purpose of doing this. I want to keep planning to the minimum and just flow with whatever happens. It might end up badly or it might be an awesome experience and I am mentally prepared for both and fine with both.

Loneliness is not a problem for me because I am an introvert and I actually enjoy quite alone time.

Yes I do plan to travel to singapore, thailand, malaysia. My plan is to start from asia and neighboring countries; as I get more used to travelling I will try other continents.

I don't have any plans to come back to USA, for now.

That sounds awesome, and best of luck to you. If you decide to blog your journey, please let us know. I (and I'm sure most people) would love to follow along.

Thanks! If I do blog, it will be here: http://iampavs.com/

That sounds absolutely fantastic! If one of the 50 countries is NL then be assured you have a place to camp out for a while here, I wish you much good luck on your travels.

I will be honest with you. I absolutely hate cold weather. I know few people who invited me go to Nederlands and I have said I will think about it. I hate it when its 23F here in NY, last week someone told me it was ~-20F in NL.

Have to go there during summer, if I do. :)


Summer usually falls on a Tuesday in July here, plan accordingly.

My plan too, although I took a detour through Berlin and New York. Are you going to try to earn some kind of income while you're there or just travel on savings?

I do plan to work. Not sure what.

I made the decision in 30 minutes.

The only thing I can think of that would get most people to do that would be heartbreak. Did somebody leave you?

Haha no :)

Something clicked inside me. I have been wanting to do this for a long time but always had some kind of lame excuse not to do it.

I'm planning on doing something similar in a few years once I've saved up enough. Just curious - what is a good amount to have saved up to do something like this? Are you still planning on working while your traveling?

Yes I am planning to be working during my travels. I have a decent savings but I don't know what would be a good amount. I have options to fall back to if things doesn't work out though.

I just came from S.E Asia after 3 years. its pretty gritty there so you must watch out. Where will you be and what will you do exactly?

Will be in Dhaka, BD and not sure what I will do for work. I have savings to keep me going for couple of years. But I do plan to do odd jobs.

What country in SEA ? Malaysian here. Holler if ur nearby

Bangladesh. I do plan to go there. I will start from Asia and go to nearby countries first.


Bangladesh is South Asian, not Southeast Asian.

Looks like you are right. Tells you how much I know about the region.

Will you be living in Dhaka?

Go easy on the street food, at least at first. Get a water filter or, at the least, boil all your water. If you are fluent in Bangla, always speak it. And if you're not, then best of luck. Don't try and give away that you are from the West, everyone will try to take advantage of you. Know your crowd and where you are; it's still a very conservative country.

I can't speak too much about the quality of infrastructure there in recent years, but the last time I was there ~5 years ago it was abysmal. I don't imagine too much has changed, though I hear you can get somewhat decent internet depending on where you live.

Sounds like a lot of negatives. And, they are, at least to a spoiled American like me. However, there is a lot of beauty in the country as well. Check out Cox's Bazar, St Martin's Island, Patenga beach all in the south. Take a steamer out to Barisal for a day.

Yes I will be Dhaka. That will be my base location. I have family there so I should be ok and I do speak the local language, not fluently but good enough to hold a conversation.

If you're ever in Singapore, hit me up.

Thanks will do!

I've been living in a motorhome and travelling full-time since January, so I've been on the road for close to a year. I'd originally planned to do this for a year, maybe 18 months, but now that I'm a year into it, I don't see any reason to stop. I'm going to Mexico, and Central and South America next fall and plan to spend all the cold months way down south. When I've done all the driving on the American continent I want to do, I plan to buy a sailboat and keep travelling (buying or renting a van or motorhome when I get to various countries I want to spend some time in).

I highly recommend it. All of it, or any part of it.

Selling and giving away all my accumulated crap was liberating beyond what I could have ever imagined. Getting out of the rut of daily life in one place and going to see lots of new places breeds a zen-like state of peace over the minutiae of everyday life (I guess your comfort zone just expands to be really wide). Living smaller means you can focus on the things that really matter. Cost of living can be as high or low as you want it to; I'm currently parked in an RV park that is home to formerly homeless people who've been placed in RVs by a charity organization, as well as retired couples living in $250,000 rigs, and everything in between.

Living on a sailboat is pretty much the same idea, with a few additional logistical challenges, if you need to keep working (I've been running Virtualmin from the road, and I just had to solve the Internet and power problem; on a boat, the Internet problem is much more expensive to solve). It seems to attract the same sorts of people, and I've met a lot of RVers who have lived on boats in the past, or live on boats some of the time.

How are you planning on getting a motorhome across the Darien Gap?

A good question. It's pretty tough for 4 wheeled vehicles to get across the Darien gap between Panama and South America. Driving is absolutely not an option - the track has been done I think twice by motorcycles, but that's it. Plenty of guerrillas in the midst of the jungle along with those horrific jungle conditions. There simply is no easy answer, and plenty of horror stories about boats used to transport drugs using a vehicle as a bit of cover. I've taken a motorcycle across the gap - the normal way, which means flying the bike from Panama to Quito or Bogota.

I've heard of flying or boating a bike around, but never anything as big as an RV. I imagine any option is going to be really expensive, though I suppose anything is possible.

Boat would be the only option for a rig as big as mine, and "really expensive" is a relative term. The cost of living full-time in a motorhome is highly variable and often has a very different shape than living a more stable life. When I'm doing very long trips, I probably spend more on gas in a month than most people spend on rent and food (I spent about $2000/month on gas during my Alaska trip, totalling about $5k for the whole journey). Spending $1000-$2000 for a ferry or ship to take my motorhome across wouldn't be what I would consider a show-stopping expense, and it's my understanding that that's the ballpark for this particular trip. It's just another thing to budget for. Moving, in a traditional fashion, to South America would probably cost even more, so from that perspective it's a bargain.


It's my understanding it is reasonably easy and cheap (compared to shipping to Europe or similar; $500-$2000 is the range I've heard of people paying), but I haven't actually done the research on the subject yet. I have the additional logistical problem of getting my dog safely through (and she's too old for me to be willing to inflict flying on her, even a short distance), but I'm guessing we can catch a boat, as well.

This is something that I dream about doing.

Unfortunately, buying a boat is expensive, and I have no knowledge of sailing.

So I've found something that is the same concept, but might work even better: bicycle touring. A world class touring bike (a Surly Long Haul Trucker) can be had for $1200. Much cheaper than a sailboat. A good tent can be had for ~$300.

I've made a deal with myself that I have 2011 to either get back into school, get an interesting, fulfilling job, or have founded a site that is producing enough money for me to work on it fulltime. If I don't accomplish this, I'm selling everything, loading the dog into a trailer, and riding across the country.

"Much cheaper than a sailboat."

You'd be surprised. Where I'm currently at (Montreal) there's a lot of 40-year old ~21 foot sailboats going for $3-4k. Me and a buddy planned to buy something this summer, but he spent his share of the money on travel. I was too lazy to learn to sail and don't like carpentry and other crap that goes into maintaining a boat, so I decided not to get a boat by myself.

Even when you factor in repairs, harbor fees and the possibility of having to write the boat off after 1-2 years because it's spending all its time in the water (most of the boats we looked at were dry docked for most of their existence), it's still cheaper than rent.

About touring bikes, it really doesn't matter what you tour on. I've known people who've toured on Wal-Mart bikes (not a good idea), 70s 5-speed bikes, track bikes (also not a good idea), double-stack welded tallbikes, etc. There was even a guy riding a BMX backwards across the USA for charity.

I have a bunch of friends that swear by the LHT, but I like to tour on late 80s-early 90s rigid-fork steel mountain bikes (all the rigid-fork mountain bikes made today are suspension-corrected, which makes them useless for just about anything). On mountain bikes the rear rack sits lower and handling gets smoother as the rear is loaded, which isn't always the case with road-type frames. This means you can go with rear panniers only, which is great because front panniers really mess up handling. As a plus 26" wheels and tires can be found almost anywhere, and are usually stronger than 700s.

If it's the cost of a boat that concerns you, take a look at this Instructable series, wherein the author details how he got a free yacht and set about repairing and improving it:


I spent a couple months living on a sailboat off the coast of Colombia and Panama last winter. I was crewing for somebody, but it was easy to see that it wouldn't take a lot of investment to get up and running on your own.

Worth knowing, from a developer perspective, is that Colombia has really good 3G coverage. Unlimited mobile internet access will run you on the order of $20/month, and it's available pretty much everywhere. Including anywhere you're likely to set up shop on your boat.

The San Blas off the coast of Panama are where you really want to be, but unfortunately the internet access isn't so great. You can get online in a lot of unlikely places (there are islands with literally nothing except coconut trees and a solar-powered cell mast), but it will cost you.

Head to Cartagena and ask around at Club Nautico. Chances are you'll find somebody who knows somebody who has a boat to sell.

Good to know about Colombian 3G coverage. I'm actually going to Medellin soon. Will probably stay for a while. If any hackers are in that area would be great to connect.

I had a friend who, tried to, do something similar. Unfortunately he knew almost nothing about boats and bought a boat that ended up costing him almost as much as he paid for it in repairs, sank once, and that he eventually sold for a tiny fraction of what he paid for it a couple of years later having only been able to spent a few hours at sea.

So I guess my point is, if you're going to do something like that, make sure you buy a really good boat.

As a life long sailor, I've seen too many stories like this one. Luckily your friend didn't die in the process, but too many people who think it would be very romantic to get on a sailboat and go round the world don't realize what they are getting into and do.

Just yesterday two men sank off of Nantucket on their homebuilt sailboat and the Coast Guard had to rescue them by helicopter. Luckily they were still close enough to shore to be reached. I don't know what they were thinking, but one of their most egregiously bad moves was bringing 1 survival suit for 2 people. And that is just the most recent story I've seen (like I said, it was yesterday).

as a new sailor, traveling with kids. it would probably be much better to use a regular monohull sailboat instead of a catamaran.

would cost more, but

There are some great cats like Gunboats or Chris White's Atlantics, but they cost a lot. Can't really compare catamaran's comfort to monohull, since effectively you have 2.5-3 times the living space in a cat.

Hence the quip: a boat makes you happy two times.... when you buy it, and when you sell it.

Dave Barry had a great line years ago; something to the effect of "a boat will end up costing you twice as much as you planned to spend, and you'll end up enjoying it half as much as you thought you would".

That's why they say a boat is a hole in the water that you throw money into. It's a beautiful way to spend money though.

I'd say most of these criticisms of boat ownership are nullified when you're actually living on the boat, though. The average boat owner buys a boat, enjoys it every weekend for two months, then every second weekend for the next two months, then every month for the next year, and never gets as much use out of it as they thought they would.

If you're gonna live aboard, though... it's probably cheaper than a house.

I don't think I'd do it myself, though. I'm just not a boat person. If I ever buy a stupid money hole it'll be an aeroplane.

One of my favorite CV's is that of Physics Professor Lyman Page, who researches experimental cosmology at Princeton. (I worked in his lab for a couple of summers. He earned his world-renowned reputation for working on the WMAP satellite and the ACT experiment.) In between interning for the Bartol Research Foundation at the South Pole (1978-80) and getting his PhD (1983-89), he has this entry:

> Self employed February 1980 - September 1983

> Rebuilt a 37’ wooden ketch and sailed about the Caribbean and East Coast of the United States. To support myself and my boat, I worked as a painter, carpenter, rigger, and cabinet maker in various ports of call. In the nine months before graduate school, I was based in Boston.

Cruising is a great lifestyle and can be done for less than $2000 per month.

There are plenty of people doing it on less than $1000 or $1500 for a family of four on sailboats from 30 to 35 feet.

More HN readers should consider living on a sailboat full time - it's fiscal mobility, grid independence, great stories, social without commitments and great views all in one.

Downside: Don't underestimate the work on a sailboat and you need to address maintenance issues right away - so be prepared to spend $xxx or $xxxx at random points in time.

It is almost always better to pay more for a better boat upfront than get a cheaper boat and fix it up along the way.

Cosmetic stuff is fine, but on a 30' boat, if you are fixing structure or engines, it is going to get expensive quick. And if the laminate itself is wet, you are probably headed for a dumpster.

Get a good mechanical survey and a good structural survey on any boat over $10k.

I agree with your views on sailing, I've been crusing for a long time, and it honestly is one of the best things I do. Though I leave the computer, tv, at home. I find disconnecting completely for two weeks to be far better than taking my work life out on a boat for a year.

good advice. Most insurance policies will require a survey as well.

This is awesome - I have a 30' sailboat that I don't spend nearly enough time on. I would love to cut free for a while this like this guy! It sure would take a lot of courage.

Oh yes, and boats do require quite a bit of maintenance. I do most of mine myself and actually enjoy it usually, but it's not always on my schedule (although I try to be proactive, that helps).

One last thing: as a geek I really love fiddling with the boat systems. Having only two car-type batteries is not a lot, so I've been doing little things like replacing lights with LEDs (every boater should consider that IMHO for 1/8th draw and better longevity), changing how the charging system works, getting some solar going (in progress), etc. It's off the grid living!

Just don't get one of the mini windmills that a lot of cruisers are getting. They are so freaking loud they destroy your peace and quiet (and for those around you). Solar panels are far better.

My girlfriends parents sold all their possessions and their house when she was 10 years old and bought a sailboat. They sailed for a year, starting at the Chesapeake Bay and ending up in the Bahamas, then reversing the route and eventually finishing in Newfoundland. This was a pinnacle experience for her whole family, but for a 10 year old it was absolutely transformative.

Nothing else could duplicate the quantity and quality of learning and growing she did during that year, and to this day she still uses her experiences as a touchstone. Can not recommend undertaking an adventure like this enough.

I have a very flexible employer who allows me to work from home. So last summer I decided to bike across the US and work while I went. After buying the bike and camping gear my only expenses were internet and food. There's nothing quite like pitching a tent off the side of the road after a long day of cycling and pulling out your laptop to get some work done. However, sometimes after putting in 70+ miles in a day there is not much motivation left to get any work done.

We sold everything bought a sailboat and have been up and down the east cost of the US and the Bahamas for 4 years now. My children are 11 years old.

That's a beautiful boat. Is he still your boss? Always interested in hearing how people continue to earn money while sailing.

It's gorgeous, I went with him on a small trip around the NYC harbor the night before he left.

And nope, we are no longer working together! He and I left our company around the same time. We were acquired but it wasn't the exit either of us wanted. So he decided to go sailing and I joined an awesome new startup :)

There is at least one HN'er living on a sailboat (hey there Max T.), it sounds like your boss is going to be having an interesting year. It's going to be even harder to stop doing that a year from now, that sort of freedom is quite addictive.

If anything it reads like he's still running a company, albeit a smaller one :)

To anyone who is thinking about doing this, I highly recommend it.

When I was younger, my family sold most of what we owned, rented out our house, and moved onto our sailboat. We sailed from Seattle to San Diego, then down the West Coast of Mexico, and up into the Sea of Cortez. We were only planning on being gone one year, but since it was such an amazing experience, we decided to extend our trip for a second year.

On the second year, we sailed from the Sea of Cortez farther down Mexico, then down to El Salvador, Nicaragua, Costa Rica, Panama, through the Panama Canal, over to Colombia, up to Honduras, Belize, Mexico again, then Florida. This second year was certainly more rushed since we visited so many countries, but we need to get back stateside for me to finish school and go to college.

Many people believe it is unsafe and expensive to do such an extended trip. But if you are friendly to the local people and accept their culture, they are often welcoming and friendly. Never once were we approached by pirates (although the Mexican navy did stop us 100+ miles off the coast before leaving Mexico to enter El Sal, boarded our boat with AK47s and searched for drugs. Obvi nothing was there and they left). In fact, many welcomed us because we helping to boost their economy, and would improve their image as a "tourist" town.

As for expenses, living on a boat is extremely cheap if you are mechanically inclined. Granted, the boat is a big investment, but other than that there aren't too many expenses. We used solar panels for electricity, a mini-desalinazation machine for drinking water, and often fished off the side, catching fresh tuna. The only expenses were diesel fuel and food (which is cheap in 3rd world countries!). Occasionally we docked, but that was also cheap (we stayed at a high-end resort in MX, including 3 pools and a personal zoo with tigers, and we paid $20/ day). Also, since our home was being rented, that provided some monthly income with no work.

The one danger, and it is very serious, is when people have a lack of offshore sailing and boat handling experience. When (not if) you encounter bad weather you've gotta know how to properly manage the boat, be it at anchor or in the middle of the ocean. I've seen boats slam into rocks during storms in port, and heard captain's calling for help because they're boat is sinking far from shore. However, with some training near shore and a few trips to sea with experienced sailors, most anyone can learn what is necessary to take on an extended sailing voyage.

Also, for all you who need a constant internet connection, rig up an amplified wireless router. We bought an industrial antenna, mounted it halfway up the mast, and rigged up a signal amplifier. In our home harbor, this lead to an increase from 3 wifi networks to over 35 wifi networks! Usually had about a dozen free networks from local businesses.

When we returned home to Seattle, we simply moved back into our original home, met up with old friends, and had some great tales to tell.

For a similar adventure, check out bumfuzzle.com and go back to the very beginning of their blog.

Your very sane boss knows what he loves, and decided to go get it.

Been there, done that.It was awesome. It wasn't a boat though.

He is smart; not crazy!!

he is not crazy , he is sane

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