Whether you call it offshore cruising, offshore sailing, blue water sailing or ocean voyaging, it all means the same thing. It entails taking a sailboat across sometimes vast stretches of water in order to reach some distant and tantalizing shore.

So what draws those we presume to be otherwise sane to abandon the comforting safety of life ashore for the solitude of days at sea? Well doubtless there are many answers to that question but a plausible one arose recently that might at least provide some sort of answer.

‘If it wasn’t for those darned headlands I would be back home taking care of the garden.’

The scene was a Mediterranean anchorage, the occasion a small gathering of sailing crews in the cockpit of a smartly turned out cruising sailboat whose skipper had just uttered those words.

He spoke for everyone, for the urge to explore lies at the heart of all who are drawn to cruising under sail. And drawn we are. The instinct to explore has driven man to the corners of the earth, populating this small planet we inhabit.

In this, the seas and oceans have played a prominent part. With over 70% of the Earth’s surface covered by water, it’s easy to understand why there has always been an urge to make use of them. History doesn’t record when man first ventured afloat, but there’s no doubt that the migratory possibilities were recognised very, very early.

And with good reasons. In the days before roads and railways travel by sea can be a lot less demanding than going overland. For example, back in the 19th century, the 2000 mile Old Oregon Trail, over which wagon trains conveyed migrants from Missouri to the Pacific coast of North America, took about four grueling months. Three hundred years earlier Christopher Columbus spent just five weeks crossing the Atlantic – a journey nearly a third longer. Today a modern cruising sailboat would expect to complete the same passage in less than half that time.

Yes, of course, if you must get somewhere quickly, there are much faster ways to travel but think of this…

  • Can you watch the dolphins play from an airliner at 40,000 feet?
  • Or park your car within wading distance of an uninhabited island?
  • Or enjoy the starlight undimmed by light pollution?

It’s all a matter of preference, of course, but this website is unashamedly for those who would choose to travel by sailboat. It's also a very personal website, the aim of which is to hear your views on the various topics discussed.

Welcome on board!

(Incidentally, the island to the left in the heading photo is Isla Vedra, off Ibiza in the Mediterranean. It was used as the image of Bali Hai in the film version of South Pacific.)

MEET THE CREW ... an introduction

Andrew and Chele Simpson at Shindig's launch 2001

Chele (pronounced Shelley – it's short for Michele) and I have been sailing together since 1978. We met in Texas where I had been designing and building boats. I had sailed there from England in 1974.

My own involvement with the sea started way back in 1953 when I joined the 'TS Mercury', a training ship moored on the Hamble River on England's south coast. She had once been HMS Gannet, a square-rigged sailing warship, now restored and open to the public in Chatham Dockyard.

Three absorbing though challenging years later, just a couple of weeks short of my seventeenth birthday, I signed on as an cadet in the Merchant Navy. The next few years saw me traveling the world on various merchant ships. This was geographical!y enthralling but had serious social downsides. Having risen to the dizzy rank of Third Officer, family problems obliged me to come ashore for a spell and, by the time these were sorted, I had abandoned any thoughts of returning to the shipboard life.

But I still missed the sea. After a few years based inland in the aluminium industry I moved to the coast and started designing and building boats – mainly fast multihulls – the largest being a 49ft (15m) trimaran. In 1970 I competed in the two-handed Round Britain and Ireland race in Three Fingered Jack a 26ft (8m) trimaran of my own design. She was by far the lightest boat in the fleet, yet she still left many much larger and stouter craft astern in our wake. We crossed the line 10th out of 20 finishers.

Although vowing never to do anything so reckless again, four years later saw me putting the finishing touches to another entry – a 35ft (10.7m) trimaran named Whisky Jack. It was never to be. With Britain suffering calamitous industrial unrest I saw no future for custom boat builders in the UK. The decision was a tough one but, in response to some commercial encouragement from contacts in the United States, I sold up and sailed to Galveston via Madeira and the West Indies in 1974.

Four years later at a yacht club to which we were both members, fortune smiled and I met Chele. We had something in common. We were both recently divorced. I had two children to raise; Chele had a 40ft (12.2m) sailboat named Vaquero. For both of us the way forward was clearly marked!

The precise way forward manifested itself in late 1978 when Vaquero quit the waters of Galveston Bay and headed east. Our first stop was the Florida Keys. Next we went down through the Bahamas and out into the Atlantic. Ahead we were anticipating a 500nm beat to windward, but luckily (for us at least) a tropical storm that had just passed through had disrupted the trade winds in our favour. So thus it was that we had a wonderful beam reach towards the Leeward Islands, first to St Kitts and eventually ending up in Anguilla. In all, the whole voyage totaled well over 2,000 nautical miles and took the best part of a month to complete.

After ten very agreeable months in Anguilla it became clear that the children's education needed some longer term planning. Chele had never been to Europe and saw no good reason why we should go back to Texas at that time. She suggested we return to the UK where we have been based on the south coast ever since.

I designed Shindig specifically as an offshore cruiser for a short-handed crew – meaning primarily for Chele and me plus the occasional one or two guests. She was built in our workshops in Poole, England. We launched in 2001 and departed the UK in 2003. Since then Shindig has been deep into the Mediterranean, spending 8 years there, sailing as far east as Greece. She is now in the Caribbean.

Sadly, after uncomplainingly battling various cancers for over a dozen years, Chele finally succumbed in November 2017. A truly great lady and a wonderful shipmate.

Shindig in Menorca 2005


Andrew is also a professional yachting journalist. His monthly column in Practical Boat Owner — then Britain's biggest selling boating magazine — is now in its twenty-fourth year.

This link will take you to Andrew's blogs




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