12 dream sailing trips

10 min read

ADVENTURE

WHAT WOULD YOUR ULTIMATE SAILING ADVENTURE BE? WE HAVE INSPIRATION FOR ONCE-IN-A-LIFETIME VOYAGES

James Kenning/WCC

Adventure can be found in a transatlantic crossing (left) like the ARC or a shorter passage across fickle Bay of Biscay (below)

We’re all seeking experiences. Whether that’s taking on a sporting challenge, going on aboveaveragely-adventurous holidays, or learning a new hobby or skill, we live in an era where ‘doing’ is more important than ‘having’. It’s evidenced by the rise in everything from ultra marathons to immersive art exhibits to Duolingo. Atravel trends report by Mastercard in 2023 found spending on experiences was up 65% over the previous four years, while spending on ‘things’ had risen just 12% .

What’s more, it makes us happy: officially. A 20-year study by Dr Thomas Gilovich, a psychology professor at Cornell University, USA, came to the conclusion that buying possessions might bring temporary happiness, but it fades quickly. By contrast, experiences shape us – and they stay with us forever.

But if you could do anything, what would be your ‘bucket list’ sailing experience? We find inspiration in 12 great sailing adventures - some on your own yacht, some a world away...

59° North Sailing

1 CONQUER BISCAY

The Bay of Biscay has a fearsome reputation, hence most skippers looking to sail their own boats will aim to cross in summer, when there is a better chance of settled weather between May and August.

But for sailors looking to gain experience of bigger conditions, a skippered south-bound Biscay crossing can be a memorable way to make this right-of-passage crossing, and a valuable learning opportunity.

59° North and Rubicon3 both offer Biscay crossings during the ‘off ’ season. This year 59° North will depart Plymouth in late September for Lagos, Portugal. Rubicon3 will be running a three-boat Biscay Masterclass, heading from Falmouth to Vigo, Spain, in October, with pre-departure workshops on heavy weather skills (last year included talks from ocean racers Mike Golding and Miranda Merron, and meteorologist Simon Rowell).

“Taking part in a training sail across the Bay of Biscay late in the season is a valuable opportunity for sailors to experience and learn how to handle heavy weather sailing. It’s something that many sailors seek, but few have the chance to practise in real-life conditions,” explains Rubicon3 founder Bruce Jacobs. “This experience is critical because it helps bridge the gap between theoretical knowledge and the actual skills needed if you ever encounter heavy weather.”

Andy Schell, 59° North founder, says their Farr 65 Falken crossed Biscay in both March and September 2023. “Both pretty typical – read ‘heavy’ – conditions, though different. March had more heavy upwind conditions, with strong southwester

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