2 Months of Sailing the Caribbean [Plus Video]

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In two months, I lived and/or sailed on five boats in three countries, sailing the Caribbean. With a mild ocean-phobia and pre-disposition towards seasickness, this is something I couldn’t have imagined doing a mere six months ago.

But I’m ultimately so happy for that one fateful daysail I did on a friend’s boat in Grenada, because it opened up a whole new world to me of travel in an often financially sustainable (and even profitable) way.

Here is a sampling of my sailing experience to date:

Here's what it's like to sail the Caribbean for 2 months, not a night on land! #sailing #Caribbean #travel #boattravel #sailboat #TheProfessionalHobo #Grenada #StMartin #BVI

This post was originally published in 2012. It has since been updated for accuracy of links and content. 


A day-sail lured me into the nautical world and tantalized me with the idea that I could live and volunteer on boats throughout the Caribbean.

sailing in Grenada

St Martin

I lived on a boat that was anchored, commuting to shore by dinghy, and sharing in the provisional expenses with the other two people on-board.  (See also: Getting my Feet Wet in St Martin)

My nautical home in St Martin

St Martin (Take 2)

I met a friend who took me on a day sail up the west coast of St Martin, snorkelling and swimming in the crystal-clear waters (after recovering from an ugly bout of seasickness).

day sailing in St Martin

British Virgin Islands

I met yet another friend in St Martin (the Caribbean sailing community is a small one and it’s easy to meet people) who was sailing over to the BVIs to host a couple of visiting friends for a charter experience. I joined the boat and sailed the 12 hours from St Martin (an experience that earned me my “sea legs” after another agonizing bout of seasickness – which thankfully never returned).

For the next week, I cooked delicious meals for the four of us while we island-hopped around the BVIs, snorkelling, swimming, and making landfall on idyllic deserted sand islands and exploring tiny artsy communities on larger islands. And I even earned some extra cash for this experience!

British Virgin Islands

St Martin (Take 3)

After the BVI charter finished, I hopped on a ridiculously cheap flight back to St Martin to rejoin the boat I was on before for a week. Then, I moved to yet another boat (again, somebody I met through my increasingly large circle of friends in the sailing community) to sail up and down the windier east coast of St Martin to enjoy more fun in the sun, including kite boarding, surfing, and paragliding.

Orient Beach, on the east coast of St Martin

St Martin (Take 4)

Lastly, I crashed for a few nights on (yes, another) friend’s tiny boat near the airport before flying out to Florida to spend my first night on terra firma after two months.

St Martin

How Much Does This Lifestyle Cost?

sailing lifestyle

As you know, one of the ways my full-time travel is made financially sustainable is by not paying for accommodation. (In 2011, I spent a grand total of $173 on accommodation – read more about my 2011 full-time travel expenses here).

And I’m happy to report that sailing is a very financially sustainable – and even profitable – lifestyle. Most of the boats I stayed and sailed on were similar to hospitality exchanges or couchsurfing, where you are expected to take care of your own expenses/share in the common expenses, and as a guest in somebody else’s home (er, rather – boat), you respect it as if it were your own and put in a helping hand wherever you can. (See also: How to Get Free Accommodation Around the World). 

Then, there’s the whole world of chartering – on anything from small sailboats to large mega-yachts – where crew members are needed as anything from deck-hands to cooks, hostesses, and even engineers or technical hands. Some positions are formal forms of rigorous employment, while others are more casual. In all cases, it’s a great way to make some extra cash. This is exactly what I did in the BVIs. (See also: 7 Surefire Ways to Make Money While Traveling – including on boats). 

mega yachts

For your viewing pleasure, here’s a montage of some of my Caribbean Sailing experiences in the last couple of months:

Can’t see the video? Click here to view it on YouTube.

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21 thoughts on “2 Months of Sailing the Caribbean [Plus Video]”

  1. Incredible Nora, good for you for facing your ocean fears with that first sail in Grenada! It opened up all these experiences for you. I look forward to reading more about how you traveled for free from boat to boat, as it’s something I will do in the future too 🙂

  2. Great pictures and tips, thanks for this. I have a question about whether earning income in foreign countries could put one in serious touble.
    When I volunteered in Peru 2 yrs ago, the embassy administrator said that even though i didn’t need a visa to visit the country, i had to make sure my work was strictly voluntary and not paid or i’d be in trouble with the local authorities.
    Earning income and the practicalities of paying taxes while abroad is one of the things I’d like to know more about, so any thoughts on the subject would be helpful (i suppose the bureocracy and procedures probably depend on one’s nationality, no?! 😉

    Take care

  3. What an amazing life. Tell me Nora–in the last few years, how many things haveyou done you thought you would never do?

  4. @Patricia – Yes, I plan to write more extensively (and practically) about traveling and living on boats….stay tuned!

    @Despina – I must look into the official rules about this, but from those I have talked to, working on boats seems to be a wonderful way of escaping requirements for working visas. Because boats tend to fall outside of many countries’ jurisdictions (especially when sailing from one country to another, as I’ve done), it also falls outside of regulatory requirements for working visas etc.
    Now, this is all based on what people have told me thus far, and I’m not sure I’ve talked to people with the official scoop on what’s truly legal etc. But from what I’ve gathered thus far, working on boats might be that giant loophole that we travelers are all looking for! 🙂

    PS – If any readers have any solid info about the legality of working/earning money on boats, please weigh in!

    @Scot & Andi – Thanks!

    @Elena – Good question! Really and truly – if you had told me 10 years ago (even 7 years ago) that I’d have done half the things I’ve now done, and would be traveling the world full-time in a financially sustainable way, I’d probably have laughed! But then again, I love doing new things and pushing my comfort zones beyond things I ever thought were personally possible. Let’s see what the next five years brings…. 🙂

  5. Great pictures Nora! And including videos to your posts is something I don’t think enough blogs utilize enough, especially travel blogs. Really makes the wanderlust that much stronger!

    I’m a recent university graduate and after a year of depressing work in London, I quit and I’m now launching my own business. I hope to cut my expenses and fund my venture by geoarbitrage after I caught the travelling bug last year in Asia. I dream nothing more than sailing around the Greek Islands while I run my business from my laptop!

    Your site is great, and I look forward to reading more about your experiences of travelling and living on boats.

  6. Oh Nora, these sailboat living posts of yours are killing me! It’s something I’ve been wanting to do for quite some time. n fact, I got my very first invitation to do so though a CS group I’m part of…I would have homeschooled some kids and teach them Spanish. Unfortunately, I couldn’t go because I was still in school + working to gain experience as a translator. I really can’t wait to hit my 2-year mark in order to get certified, so then I can just be a freelancer and do what you are doing!! Keep the inspiration coming 😉 loooving these posts!

  7. @Mustafa – “Geoarbitrage” – what a great word! I’m determined to use it casually in a sentence sometime today, and see what sort of reaction I get. 🙂

    Sounds like you’ve got a good plan. Keep at it!

    @Maria – Too bad that sailing opportunity didn’t work out! That’s okay though; there’s plenty more opportunities where that one came from! Glad you’re loving the sailing posts.

  8. There are so very many boats sailing in and around the BVI, that you’re bound to find several that suit your needs. I’m so happy that you easily got your sea legs and the bout of seasickness did not return. Great tips… thanks for blogging.

  9. @BVI Boat – Thanks for stopping by! Now that I’m off the seas, I really do miss it. There’s something so wonderful about sleeping on the water….and what a great lifestyle I tripped upon. Perfect for a professional hobo!

  10. Hey Nora! Just found your page and I’m incredibly jealous and plan to do something like your doing for a few years. Any who, I haven’t read all your pages, but you said you worked on sail boats…was that paid or unpaid and how did you like it? I’m planning on including that in my trip one day…

    • Hi Thomas,
      Although I managed to board a few catamarans when I was in the Caribbean, I never actually sailed on one. They look like fun though!

  11. Wow! What fun! i only got to travel for a few days on a boat near Venezuela once, and it was great fun, a totally different kind of lifestyle, but I couldn’t imagine doing it for three months. Thanks for sharing! My dad was planning on living on a sailboat, built one and sailed a little bit, but then decided on just doing it over weekends and days here and there, he turned out to be a land lubber and missed being on the land. It’s a special breed that lives on boats for extended periods of time he found. He makes sails for sailboats though, and enjoys that a lot!

    • Indeed – it takes a special breed to live on the water. Generally speaking I’m a land lubber as well. But I’d totally try the boat life again if the right opportunity came up!

  12. As a new subscriber, I am anxious to read about your most recent travel adventures, tips on being a solo female traveler and other recent comments from your subscribers! I’ve recently retired from New Jersey, currently living in Costa Rica. I cannot wait to explore some of Planet Earth!

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