The Lovely Caribbean – Riley

The Lovely Caribbean

Written whilst listening to Before ‘the Fire – Gallon Drunk’. Listen to it. Its good.

When we left Europe it was getting cold. I do have fond memories of Greece in particular but the whole atlantic crossing was a bit of a seminal event for myself, Elayna, La Vagabonde and perhaps Jack also. So when we arrived and it was hot and the beaches were awesome I felt like I had accomplished something. I felt like a sailor. This could go some way as to explaining why I loved this place so much. Europe verses the Caribbean is multivalent enough to warrant its own individual post however for me you could break it down to History, which I love, versus fish, which I eat.

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I know that the coast of the Mediterranean has amazing history but often it is slightly inland and then you need a marina, which $$$, or a perfect anchorage and then your worried about your tender getting stolen. For example the temple of Knossos is just another half excavated ruins. For the amount of effort required to get there by Yacht, I prefer the romantic images that are bestirred in ones imagination whilst reading about it rather than the sub par tour and bovinesque meandering queues that are the reality when you arrive.

The average distance between the Caribbean islands is 40 nautical miles. This is a very small distance. One island is very different from the next and despite the reports I had read before I arrived, there are fish. This was important to us. There are many beautiful, crystal clear beaches found on each island throughout the entire chain of Leeward Islands down to the Windwards.

The ease of sailing in the whole Carribbean, especially in the BVI makes it a perfect destination for sailing. No I’m not getting payed to write this. Usually pulling up anchor, invariably a sandy bottom, and setting it in another completely different island within a day. Being so, so easy it is also a sailing mecca which means mooring balls and lots of other Yachts. Beautiful beaches filled with lively bars and restaurants yes, secluded anchorages no. You don’t feel like your completely “away from it all” in the BVI. But it is good fun for a short amount of time and definitely worth the visit.

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We have so far been to the BVI’s, Anguilla, St Maartin, Saba, St Eustatius, St Kitts and Nevis, Montserrat, Martinique, Antigua, St Barts, Guadeloupe, St Lucia, Cariacou and Grenada.

If I HAD to say to skip one it would be St Eustatius which ironically was the centre of commerce for quite a while in the region.  Two of my favourite beaches we visited along the way were White Bay on Jost Van Dyke (BVI) and the main port in Anguilla, Road Harbour.

A few places that stood out to me and brought us some great memories:

Elayna and I stopped in at Redonda which is just a small jagged rock island in between Nevis and Montserrat, with nothing you would call an anchorage. We were lucky enough that the wind and swell was in our favour, so we were able to drop the anchor on the leeward side of the island (which you can’t usually do) and hope conditions wouldn’t change. It didn’t, so we made the most of it and went spearing along the back of this rock for a couple of days with just the two of us and really pleasant conditions. The swell finally wrapped around the island and La Vagabonde started rocking around like anything, so that was our que to head off.


We also really enjoyed the island Saba (in picture below). Saba is excellent for diving and the mountain that you climb there is quite remarkable. One of the best climbs I’ve done. The best, better than Ben Nevis. The two main little villages are quaint, neat and picturesque and not westernised at all. The medical university students means there is cheap healthy food. Thumbing a ride from one village to the next is the norm and you wouldn’t want to walk it too often as the terrain is all mountain. There are mooring balls but the anchorage is very rolly and its still 2 miles to get a different mooring ball to go into town. From the main anchorage at Wells Bay, there are heaps of dive sites to snorkel or free-dive, however, scuba diving is only allowed through the dive centre.


There are always different laws as you sail from one island to the next and checking in and out can get annoying, but thats sailing I suppose. In the Mediterranean, we found this process to be a lot more difficult and expensive. Sometimes checking in or out of a country in the Med has taken us half the day. Finding customs or police buildings scattered in a town or city can sometimes be very annoying and near impossible. There has been many times Elayna and I have been walking around and around in circles for half the day, in a country where no one speaks english to help point you in the right direction. And it doesn’t help when sometimes the only ‘directions’ we had received was along the lines of: “a small blue shack on top of a little cafe near a tall tree with a red door with stripes, you can’t miss it”. In the Caribbean it has just been easy. Plus, everyone is really relaxed which also helps the whole process run smoothly. A guy in Dominica stamped our passports wearing thongs and socks. In the Caribbean I have found myself sometimes jumping up and marching around the boat looking for jobs to do, or mentally planning our next rout, and then I would stop and go lay down, maybe grab a rum.

Wind acceleration. For goodness sake be careful when heading out from behind the coverage of an island. The 20 knot trade winds feel like they have disappeared and then all of a sudden there is a wall of wind. Either down a valley alongside a mountain on the island or (remembering it is a prevailing Easterly trade wind) around the Northern or Southern edges of the island you will experience this phenomenon. In some places we have actually had wind coming from the exact opposite direction of the trade winds for a small while due to mountains, valleys and we think maybe magic.

Elayna and I whilst heading south from Dominica decided that we would do an overnight sail and tow the tender but take the motor off. We experienced 0 knots of wind for 10 minutes then up to 7 as I turned the engine off and about 5 minutes after that it blew from 7 to 35 in about 15 seconds. You will find your boat rounding up and if your as silly as I am your tender flips over and your rope snaps so you have to go looking for the frigging thing in the middle of the night. Sails were dropped and furled in respectively, engines switched on, curses hurled at the heavens and a search mounted.
We actually handled this one really well, Elayna in particular snaffling the tender with a boat hook which is actually a fish gaff tied to a broomstick. So she did well not to pop the poor tender “Cunningham II” who has been through quite a lot really. Don’t forget its still blowing 35 knots now whilst we have gaffed the tender which has now suctioned into the water probably due to the initial submersion after being flipped before the rope snapped. After wrestling with it for a couple of minutes it “pops” free of the sea and is then easily turned over and fastened pretty much in the middle of the cockpit.
Lesson learned.

The hurricane season is now over, and as of two weeks ago we flew back to Grenada to prepare La Vagabonde for her relaunch. She is now officially floating on the water again, which we are very excited about. From here, we have a few stops on the way to Panama where we plan to go through the Panama Canal in Feb and into the Pacific! Along the way we hope to visit Trinidad, Venezuela, the ABC islands, San Blas islands, and Columbia. There might be a few we have to miss out on, but there is so much to see in the Caribbean and it is a place that we will go to again on our second spin around the globe! Fingers crossed.


Comments 25

  1. Thanks guys for your motivation posts and setting up a nice sailing goals for future.

    Please share your experience and impressions of the places you’ve visited.

  2. Small typo. It’s Colombia not Columbia.

    I just discovered you two and I’m excited to track your adventure. Best of luck and happy sailing.

  3. Someone asked me a while back what sailing in Hawaii was like and I told them it was fantastic once you learn the spots where the wind funnels through mountain passes. Nothing more fun than going from a nice leisurely sail to almost getting knocked down in seconds. Once you know the spots you are either further off the wind or closer to it depending on a variety of things but at least you aren’t caught completely off guard. Because it isn’t the same speed as the trades. The trades may be 10-15 but the funnel is 25-35 because of the velocity increase pushing the same volume of air through the gap. Anyway, look forward to the start of at seas videos, the prior ones have been great fun to watch. And it was fun to see Western Australia. Sydney was great but I’ve always wanted to see Perth and parts nearby.

  4. Thanks Riley for sharing your blog entry.
    Have to say that both my wife and I truly enjoy all your content; whether it is the youtube channel or Elayna’s album.

    Our paths will cross this coming January; we’ll be travelling (from Montreal) down to Saint-Vincent for a 10 day charter aboard a catamaran.

    Would be really cool to bump into you two, but sounds like you’ll be further West.

    Thanks once again for everything.

    Travel safe:)

  5. Thanks for this.. It’s fun and helps me travel from a distance.
    Was in the BVI a couple of times and am brought back there by your writings. Was there on a luxury sailboat for a 10 days back in 2012. Realy a sailors mecca. Every island merits a visit. Wether for it’s hiking trails or it’s secluded beaches. Most places are quite and rarely crowded. Almost all the beaches we were at were all but deserted leaving them to ourselves. The bars and restaurants are fun and sooo relaxed? Had a great time there with my wife a friends. Oh by the way…the sailing in an 82 ft yacht ….well living the life of the rich and famous for 10 days was exciting. Once in a lifetime opertunity!

  6. Good stuff mate. You are the real deal. Reef early – you’d be surprised how much speed you don’t lose. The foresail is the power, the main is the balance, (over simplification, but it works more or less). When you can leave the helm unattended and maintain your course, you are well trimmed – then hand over to Otto so as not to strain the ol’ boy.

  7. Great blog entry, Riley! Enjoyed your perspective and observations. When will you be around Trinidad? I’ll be in Chagaramas there, Jan 13-27, working on Avalon. She’s my friend’s Beneteau 50. “Power Boats” is the yard and marina. We’d love to ply you both with rum and grub! Fair winds. BG

  8. I really enjoy your posts and videos. I find them very inspiring and because of them I am not planning my first sailing trip. Just wanted to say thank you and that I hope you guys have some great sailing this season!

  9. Riley

    I’ve been following your journey and YouTube channel and its really been fun. You’re so luckey to do what you do. Anyway, I live in Trinidad. If you do get down here I’d love to meet up with you guys.


  10. Riley, Thanks for the up-date. I was beginning to wonder if you 2 got lost in the Bush and couldn’t find your way back to civilization! Now, if you’ll let Elayna out of the Galley from time to time so she can post your exploits on Youtube, that would be great. Oh, and Elayna, Thanks for showing the maps of your travels. I’m sure it helps a lot of us visualize where you two are.
    Take care of that Beneteau and she’ll take care of you.
    Best of Luck, Fair Winds and Keep us smiling. We Love ya!

  11. Good to hear you’re in the water again. You are an inspiration to a lot a sailors wanabe that want and will do it one day. Myself a year ago was watching all I could on youtube on sailing at sea and knowing you has given me the streangh to prepare my own adventure… with my wife and 2 kids(2 and 3 years old). Knowing little of the sea, we are getting ready to leave fort lauderdale for the carabeens. I wish you fairwinds in your pacific crossing and look foward to your next movie. Again, thank you for your inspiration and when the time comes, I hope you’ll share this passion with your kids(you’ll never have to wonder what to do anymore that is 😉

    SV Abaco

  12. Loved the Gallon Drunk song! The video is interesting. Glad you guy’s are back on La Vaga safe and sound. I recently received my order of books and merchandise with T- shirts from the website my wife and I loved it all!

    I would love to hang out someday with you Riley over a pint in a deserted anchorage under the star’s to ponder the mysteries of the universe! Ahhh, someday is just around the corner. Fair winds you two, may love and light carry you to the Pacific!

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  13. Really been enjoying following your adventures since listening to The Sailing Podcast by David Anderson an Fellow Aussie. It is great to see a young couple out exploring this great big blue marble that we live on. See the ways other countries live and see that people are interesting to talk to.

    Continue on these great adventures the both of have a safe travels.

    /) set the sails and pull anchor for the next place……

  14. Really have enjoyed the videos of your sailing adventures. After listening to you on The Sailing Podcast by David Anderson a fellow Aussie. It is so great to travel this big blue marble we live on and following our dreams.


  16. Hey Riley! Great to know you’re back in the islands again! Good luck, and watch out for the island/land effect winds!

  17. Good day,

    What type(s) of action camera or GoPro have the two of you been using to document your trip? In October I plan on sailing from Ontario, Canada through New York and then down to the Caribbean sea. The GoPro world is a hazy one so any insight you have would be appreciated. xo


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