Day 494 – THE CARIBBEAN (DOMINICAN REPUBLIC): Well and truely on the road (sea?) again

Home. At least seven months and 10,000 miles of land and ocean stand between me and home.

I’ve been thinking about that more and more this last week. God knows I’ve had the time to think about it. 4 hour-long night watches on a small yacht in a big ocean ensure that. What will I do when I get home? A real job?

I’ve also been thinking a lot about Japan. I become more and more convniced that Japan is where I would like to be living. Dunno why…

Not feeling too flash off the coast of Puerto Rico

But for now, the immediate challenge that stands in my way between here and home is about five days more of sailing, before the challenge of 6,000 miles of skateboarding begins. I am crew aboard the delivery of Irish Jester II, a 38 foot French-made Kinnex sailing catamaran, from the US Virgin Islands to Alabama, USA. I will be getting off the boat in Key West at the southern-most tip of the state of Florida, USA. I will skate north through the Florida Keys, dodging aligators all the way up to Tampa, my first point of call in the US. In Tampa, I look forward to meeting up with Rick Smith, a good friend from my days as an Outdoor Educator in Switzerland. I also look forward to new cramic skateboarding bearings that have been kindly supplied by Bones Bearings.

The original plan was to try to get on a yacht from the British Virgin Islands to Nassau, in the Bahamas, so that I could go to the US Embassy there and apply for an extended US tourist visa. On a standard visa waiver, I can only be in the US for a maximum of 90 days. It will take more than that to skate across the US.

However, right now is not the season for yachts going north from the Virgin Islands to the US. So basically I had to take whatever came up. So the deal at the moment is that I have a 3 month stamp in my passport for the US. At some stage in my journey across the US, I will need to leave the US, and re-enter at some stage. This will most probably be somewhere like El Paso, in Texas. Pop over to Mexico for a couple of days and then re-enter for another stamp to finish the US leg off. At least I think that this is how it will all work. I’ll worry about the logistics of all that when the time comes.

Ocean World Marina, near Puerto Plato, Domincan Republic

Right now I am typing this on Captain Debbie’s laptop, aboard the Irish Jester II, in Ocean World Marina near Puerto Plata in the Dominican Republic. Yes, the marina where I lost my visa card about a month ago. I imagine that my next update will be from Florida. Until then, along with Captain Debbie and crew Connie, we will be fighting the strong northern Atlantic swell all the way to Key West. Send some flat-water-vibes my way!

14degrees Journey Update Video

Click for a short video update

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10 thoughts on “Day 494 – THE CARIBBEAN (DOMINICAN REPUBLIC): Well and truely on the road (sea?) again

  • Aunty Les

    Do you realise how much you sound like your Dad? It's rather uncanny looking at you talking and kind of hearing your Dad's voice!

    You've got plenty of time to clarify what you do next when your journey ends. I'll be praying for Godly insight.

  • Nana

    I think you have stayed in the Caribbean too long. You are beginning to look like a West Indian!!! You look so brown on the video.

    Distance lends enchantment to the view, so we are told. Now you have been away from Japan, it is beginning to look better as a place to live. What about all the outdoor things you like doing. I thought you missed those things while you were there – always having to do them on your own.

    I am so pleased you are at last on your way to the States and you can begin the next leg of your journey. Not so wild and woolly as the "Stans" of Eur-Asia, but no doubt there will be much of interest on the way.

    Keep safe.

  • Chris J

    Ok Rob, I am officially sending you as many "flat-water vibes" as I can muster. I hope they manage to reach you on the other side of the globe.

    More than that however, I am looking forward to the US portion of your journey and sincerely hope that you will continue to meet up with wonderful, helpful people.

    Flat-water-vibes away!

  • Joel


    I leave you for 3 months and next thing I know your on a yacht in the Caribbean. Amazing….

    Enjoy the US. It 's a great place, but you will find that out soon enough. Tres is in Arkansas if you are going that way…

  • Mum

    A bit of sea-sickness this trip? Hope it doesn't spoil things for you. By the way, I don't think you sound like your father at all. Must be all in the 'hearing'!

  • Daniel

    Hey Rob, I've arrived in Australia these days. Quite rainy over here but better climate than the smoggy late autumn Beijing.

    Checking for my ongoing visa requirements and found out that I probably can't get into the USA with the Waiver program as I want to cycle in from Canada. If you are not on a regular flight or ship the program doesn't apply – at least that's my latest information.

    Anyway, good luck (meaning don't lose your visa card again 🙂 and happy skating,

    Daniel from Sydney

  • Sunny/Chrissy


    So exciting you're going to be in the US soon! Even though you will be a good 10 states away…it still is wonderful to have you here. And the way you say "US" true Kiwi style right there mate! Thinking of you always Weka xx

    ps- Give Chimp a HUGE hug for me and ask him to give you one right back : )