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How to throw yourself into the deep end while learning to Sail

A Woman in a blue hat, orange top and sunglasses sitting smiling on the deck of a white yacht at sea

Updated on March 27th, 2023

Learning to sail for me has been a journey of highs & lows. Here I share my stories from my many mishaps along the way.”


Onboard a number of yachts in Southampton (UK), Turks & Caicos Islands (TCI), Chicago & The Bahamas


For over 2 years now I’ve had ‘Learn to Sail’ as a goal on my Life List. Being on the water on a boat in the Kinabatangan River in Borneo was where I realised I had an opportunity to change tack in my life (pun intended) & how I am at peace on the water. Also, on my list are to discover the Caribbean & take part in a yacht race. The sensible choice would be complete a training course & then grow your hours & skills with friends locally, building up to racing or somewhere more exotic.

Me? I decided to throw myself in the deep end as usual & do an ocean crossing from Florida to the Bahamas!”

What did I do to prepare?

If you want to follow my (dubious) lead these are the steps you need to take in order to attempt an ocean crossing as a novice…

1. Make friends with someone who has a boat.
Views of a painted wooden sign pointing in numerous directions on the beach & a lodge on stilts by the shore Great Exuma, Bahamas, Caribbean

On my ‘way back’ from a month in Cuba in 2016, I decided to see more of this beautiful part of the world. I wanted to be able to get direct flights somewhere from Havana & that gave me limited choice. I eventually set my mind on spending a couple of weeks island hopping in the Bahamas. Island hopping involved numerous flights around the archipelago, often needing to stop for the odd night rather than pass straight through Nassau. The 2nd island on my itinerary was Great Exuma & I had a hotel booked in Georgetown.

Sting Ray, basks in the shallows, Bahamas

I arrived late & after checking in, I just wanted to enjoy a beer & catch up on my journal. It wasn’t long before I got chatting to a couple of guys who were touring the islands on their yacht. We got on well & I was fascinated & slightly in awe of the stories they shared about the adventures they’d had so far. It was amazing to hear about the tuna they’d caught earlier which had been half eaten by a shark as they hauled it in but still managed to make a delicious meal in the small camping stove on the boat.

I was hooked! I made a commitment to myself that if it was like that, I needed to get sailing in my life as a priority!

A billowing yacht sail on a sunny day in the Turks & Caicos Islands

They invited me out the next day to explore the smaller islands in their dinghy & I jumped at the chance (I hadn’t quite planned an alternative if I’m honest!). It turned out to be one of those occasions where travelling alone can open up opportunities you never expected, and one of the best days of my whole stay in the Bahamas.

We explored an abandoned resort (hit by the recent hurricane but furnished & by the looks of things never opened), went snorkelling in the Blue Hole (a cave full of fish), fed sting rays & drank cocktails….what’s not to love?”

Facebook (FB) is a brilliant way of keeping in touch with people you meet on your travels & we became FB friends & started messaging.

2. Go on a sailing holiday
Large spiky sea shell and a motorboat on a flat, deep green sea with a rainbow behind. Turks & Caicos Islands

Having kept in touch with my friend, Emanuele from the Bahamas, in June 2017 I went to spend 14 days on his yacht in the Turks & Caicos Islands (TCI), but it wasn’t all plain sailing (again, pardon the pun!).

We started the holiday with the boat ‘on the hard’ i.e. out of the water in a boatyard. This proved a challenge for me having to climb up a precarious step ladder to get on & off the boat each time. The worst was when I needed the bathroom in the middle of the night & on the way slipped flat on my back in a badly placed patch of wet clay. After gathering myself, I then had to make the precarious walk (waddle?) to the bathroom, covered in clay & mud. I proceeded to clean myself off fully clothed in the shower (which looked like a murder scene by the time I’d finished). I made my tentative way back to the boat & up the ladder & looked forward to getting the boat into the water & heading off the next day.

Unfortunately, the day we were due to leave early for a full day sailing, we lost the autopilot. We searched the boat high & low but to no avail & the only conclusion we could draw was that somebody must have gone into the boat & stolen it. It was not a good start.

There were only the 2 of us on board, with no relief from the steering without the autopilot & I was so inexperienced that even tying on the fenders & securing the boat at moorings was a complete struggle.”

I think it is fair to say that things were a little bit challenging between us but it was a huge relief when we found the autopilot 2 days later…exactly where it was supposed to be!

We spent days sailing the beautiful islands (much less stressful with the autopilot working its magic), and the nights drinking beer & rum. One day we even caught a fish off the back of the boat & my fantasy was complete! We struggled with it, I hid in the cabin to avoid its vicious teeth, we killed it by pouring rum in its mouth & cooked it up for dinner. It was delicious!… Or at least it was until we read about the hazards of eating barracuda & getting ciguatera fish poisoning (caused by a build-up of toxins through the food chain). Panic was mild when we read about symptoms like nausea, vomiting etc. then built up when we read about the potential end point of death! We eventually discovered that it wasn’t actually barracuda we had caught but instead a Sierra (Spanish Mackerel) which is totally harmless & delicious! Huge relief!

It was hot & humid in TCI in May, so I slept every night out in the cockpit under the stars.  It was an unforgettable experience.

I recognise that this all sounds idyllic but spending this amount of time together on a 25’ yacht without a shower or toilet was very testing. I wanted to fall in love with sailing but for much of the time I found it stressful & hated it. But I’m nothing if not persistent…

3. Learn to sail…properly!
SueWhereWhyWhat, taking a competent crew course, sailing on The Solent off of the coast of the south of England, UK

In July I took a sailing course back home in the UK. Although I obviously wanted to go somewhere more exotic I was told by several people that to learn with the RYA is the best training in the world. The Solent is also a great place to learn as we encountered all weather (& sailing) conditions while we dodged ferries, other yachts (I was there just ahead of Cowes Week, so many teams were out practising), container ships in a busy shipping lane & even a US aircraft carrier disembarking.  You can read all about my experiences in my post Learning to Sail – Competent Crew.

For all the inspiration you need on Adult Learning Vacations, check out my blog post.

4. Buy a share in a racing yacht & commit to spending a season in the Caribbean!

Emanuele then came up with a plan. He had friends who wanted to sell their beautiful 33’ racing yacht – Red Hot & he had the idea of moving it to the Caribbean to take part in the racing programme over the winter season. The plan was to get a group of 8 people together, each paying a share for the opportunity to cruise on the yacht and deliver it between the islands in time to enter the planned regattas (STIR in US Virgin Islands in February & Antigua Race Week at the end of April). The Red Hot Caribe programme was launched.

So, bearing in mind I can’t sail, I’m not sure I even like doing it, & I’ve never taken part in a race… I was tempted! Two days later I had a conversation with my neighbours who were having their house renovated from January. “Was I planning to be away (as usual) & if so, could they stay in my house?” It felt like fate was nudging me in a very specific direction… so I said yes to both!”

5. Get the boat ready.
SueWhereWhyWhat in white protective clothing & goggles while sanding & maintaining, the yacht Red Hot in a shed

Red Hot had been sailed a few times in Lake Michigan in Chicago but had been out of the water for a long time. This meant that for the ocean crossing & the racing season ahead there were a lot of preparations which needed to be completed.

On a visit to Chicago on a couple of (thankfully warm) October days, I found myself donning a paper suit & mask and helping to sand her bottom…if that’s not commitment, I don’t know what is!”

The yacht Red Hot in a shed undergoing repairs

It was especially challenging when we’d been sanding all day, my arms were getting harder & harder to hold up, I was hot & filthy. Then we realised we’d locked ourselves out of the car & needed to be rescued before we could head home (which of course made us late for a dinner arrangement & was also the night when both lifts in the block of apartments broke down & we had to walk up 17 floors!)

6. Buy some kit.

So now I appear to be a sailor (?!) & my first outing was agreed. I was committed to starting the Red Hot Caribe programme & for this, she needed to be taken across the Gulf Stream from Florida to The Bahamas. For me, it meant I needed to take things seriously & invest in some good equipment. Knowing my inadequacies with both sailing & balance (I am a little clumsy), safety was first on the agenda.

I invested in some good safety equipment – namely a life vest, a tether (to connect me & the boat at all times) & a personal AIS device which is set off if I ever fall in the water & alerts the crew of my vessel to my exact location.

Next, although it’s the Caribbean I need good wet weather gear. I bought a jacket & trousers to protect from all-weather, and it’s red, so my outfit matches the boat! And finally, shoes, even though most of the Caribbean sailing will be barefoot, for the racing it’s important to have shoes. So, I may not be able to sail but I’ve spent a fortune & definitely now look the part…until I get on a boat, at least!

7. Go Sailing!
SueWhereWhyWhat & her friends, with the Yacht Red Hot, BVI, Caribean

So, for 6 months I’m planning to be in the Caribbean with people I don’t really know so I can tick things off my Life List (explore the Caribbean, learn to sail, take part in a yacht race, 60 countries by the time I’m 50). I started with Florida to Bahamas leg in November – day 1 across the ocean overnight. Watch this space to hear how I got on with this whole new adventure but you can view my video in my Video Diaries

What else?

I am still determined that I will learn to love sailing or at least be an actual competent & reliable crew member. If not I’m sure I’m going to love the Caribbean. Just wish me luck & I’ll keep you posted!

Interested to read more?

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How to throw yourself into the deep end while learning to Sail

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    1. Gemma,
      Thanks for getting in touch & I have spent some time on motor boats too through the years (particularly around the Solent in the UK for some gorgeous lunches on the Isle of Wight!). I realised a few years ago that I find peace on the water so any opportunity I have I like to make the most of.

      Please keep in touch & I hope you are enjoying the blog – more to come on my first regatta experience in the next few weeks so watch this space

      Sue x

  1. Sue
    Interesting reading, you are game for any adventure and experience. Well done to you .
    when I am out walking with Luna I have what is known as doggie bags, even if I had the right gearbox for sailing I would need a mass of doggie bags, not good on the sea.
    Continue to enjoy whatever you do
    X Alison
    Ps had a nice email from Tracey nothing from Sally. Thank you for the birthday greetings, it was the big 70 celebrations on hold until this weekend due to the weather we experienced.

    1. Alison,

      Great to hear from you although I’m not sure I enjoyed the images created by your comments on doggie bags! The good thing is I don’t appear to suffer from seasickness which is a huge bonus. I hope you enjoyed your 70th celebrations – you are amazing & certainly look well on it! I have been in touch with Tracey too but it looks like we have lost Sally which is a shame. Enjoy the walks & thanks again for getting in touch!

      Sue x

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