What would your ultimate sailing adventure be? We have inspiration for once-in-a-lifetime trips with our 12 dream sailing experiences

We’re all seeking experiences. Whether that’s taking on a sporting challenge, going on above-averagely-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.

A travel 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…

Photo: Studio Borlenghi/ACE

1 Watch racing megastars

This year is set to be one of the biggest for competitive sailing: Paris 2024, for which the Olympic sailing regatta will be held in Marseilles; a packed summer in Barcelona ahead of October’s America’s Cup; then in November the Vendée Globe sets off from Les Sables d’Olonne. With a bit of planning you could attend some of sailing’s biggest events from your own yacht.

Berths in Marina Marseille old harbour will be hard to come by, but close by is Les Îles archipelago, where Port du Frioul is just a ferry ride away. Along the coast Port de Bouc Plaisance and Port Sausset-les-Pins have train and bus links to Marseilles. Carry-le-Rouet is closer, though its marina is suitable for shallow draught yachts only.

When it comes to choosing America’s Cup accomodation, Barcelona’s Port Olimpic marina say they aren’t yet taking reservations, but have a list of those interested and plan to allocate spots closer to the Cup. Barcelona also has a handy coastal train that connects holiday towns such as Blanes, which has a marina, to the city.

In Les Sables d’Olonne, Port Olona, is unsurprisingly full: 40 IMOCAs need to squeeze in. But consider La Baule to the north and La Rochelle to the south. Both are a couple of hours away by train, but as the IMOCA fleet gathers weeks ahead of the start there will be plenty of opportunities to see these impressive machines up close.

Photo: fairtransport.eu

2 Deliver barrels of grog

For a truly unique sailing experience, crew on a traditional sailing ship delivering cargo. Passages with open berths vary from a three-day hop transporting goods like Scottish whisky or French wines, to month-long adventures visiting multiple trading ports across Europe, or a transatlantic to collect Caribbean rum and coffee.

Expect to join a diverse, salty crew for some communal living and a degree of physical work, particularly when it comes to loading and unloading the cargo, but also to enjoy the chance to experience slow living, sailing with a true purpose, and learning traditional skills handling tall ships.

Find out more at: fairtransport.eu; grayhoundventures.com

Photo: James Kenning/WCC

3 Sail across the famous Bay of 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.”

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Andy Schell, 59° North founder, says their Farr 65 Falken crossed Biscay in both March and September 2023. “Both offered pretty typical – read ‘heavy’ – conditions, though different. March had more heavy upwind conditions, with strong south-westerlies. September gave us a very good weather window and Falken had a heavy but mostly reaching and running passage, so it was much more comfortable.”

59° North always start their trips from the west – departing from Ireland or Plymouth. “I think the stereotypical ‘Biscay bashing’ happens most often to boats who are further inshore on the shallower continental shelf,” explains Schell. “You get this sort of worst-case scenario where cruisers who are new to offshore sailing want to go ‘offshore’ to get across Biscay, but don’t go far enough offshore to make it more manageable.”

Besides the confidence making the trip with an ocean-ready 60-footer can give, he says a westerly route offers several advantages: “easier wave action when or if the weather does pipe up; a lower risk of orcas further off the coast; and more time and sea room to heave-to when needed.”

The passage isn’t solely something to be endured, however, as crews leave an increasingly chilly Britain for some late season sun and warmth in southern Europe.

“The thought of sailing across Biscay terrified me and was far beyond what I felt capable of taking on,” says Anna Wenneker, from London, who crossed with Rubicon3. “I learned so much – be more worried about some things, and less worried about others – but I also just had a proper adventure. I usually charter a boat and have a lovely holiday, but I’ve been craving a proper sailing adventure and this was it.”

Find out more at: rubicon3adventure.com; 59-north.com

Photo: Kraken Travel

4 Sail to a rock concert on a cliff

Explore Norway’s Vega archipelago in a unique expedition available through Kraken Travel. The nine-day passage includes stops to climb the Seven Sisters mountains, sail a Nordlandsbåt fishing boat, and go on an eagle safari before the unforgettable finale – a coastal race to the truly unique Træna Music Festival.

Described as the world’s most beautiful festival, it sees live music performances atop windswept islands and even in caves and rock gorges.

Find out more at: kraken.travel

Photo: Truls Rosenkrantz/Kraken Travel

5 World’s most scenic beach clean

Kraken Travel also organises expeditions along the Helgeland coast, some of Norway’s most pristine waters – but with a twist. Run by SailNorge with Nordic Ocean Watch, the seven-night trip combines exploring stunning islands with a beach cleaning programme to help preserve the incredible ecosystem. Add archipelagos to navigate, the world’s only Arctic whisky distillery to sample, and Scandinavian saunas to enjoy, and it makes for a memorable cruise with a purpose.

“Over the past year, there has been an uptick in crew wanting to explore beyond their usual cruising grounds and get more out of their time on water,” observes Kraken Travel co-founder Mike Pickering.

“Using sailing to get closer to nature has become a common theme. There has been a real shift towards sailing holidays being more than just sailing.”

Photo: Nick Bubb

6 Cruise to a secret island

In an age where nearly the entire planet is mapped by satellite, the notion of stumbling on an undiscovered island seems destined to remain a fantasy. But there are still places in Europe where you’re likely to be the only yacht.

Despite lying midway between Madeira and Lanzarote, the Selvagem Islands are a small archipelago few cruisers have heard of. Nick Bubb, who cruised there with his family, was keen to visit the islands due to their biodiversity.

After picking up the sole mooring buoy in an anchorage to the south-west of Selvagem Grande, they met the island’s nature wardens (apply online in advance). “We had the most amazing few hours hiking among juvenile shearwaters and tracking the endemic Selvagem wall geckos. Our boys were also blown away to discover they were the only children to have landed on the islands all year.”

Photo: James Tomlinson/Waszp Class

7 Learn how to foil

No matter how many times you’ve seen it in photos, the experience of flying over water is breathtaking. Foiling is booming – not only for grand prix racers but probably at your local sailing club or beach, thanks to the popularity of wingfoiling and ever growing range of foiling dinghies.

If you fancy a go but – perhaps wisely – feel like warm water might make the learning experience more fun, many sailing beach club holidays now offer a foiling experience.

Mark Warner has foil-adapted RS Aeros, while Wildwind in Greece uses ILCA/Laser dinghies with ‘Glide Free’ foils, to let first time flyers try it out in a familiar boat.

“Foiling in a Laser is a great starting point for someone learning the ropes as it still relates to basic sailing skills meaning people with less experience can still have a go,” explains Ashley Deaton, Wildwind’s beach manager. “Being a sturdy boat, the Laser allows for you to make mistakes without the risk of hurting yourself.”

Minorca Sailing has a fleet of Skeeta and Nikki foiling dinghies. “The Skeetas are great for adults and older teenagers and come with two different size rigs depending on the conditions.

“The Nikki is ideal for children and younger teenagers – we’ve had children as young as eight years foiling. Wind conditions are also perfect to get up on the foil and sustain flight, but not so much that it becomes too much of a handful,” explains Minorca boss Ian Aldridge.

Alternatively, if you want to take on the Waszp, the one-design racing class, there’s nowhere better to learn than iconic Lake Garda. Sail Garda offers a 10-hour multi-day course for experienced dinghy sailors to get to grips with the foiling design (choose your own accommodation locally).

Find out more at: minorcasailing.co.uk; sailgarda.com; markwarner.co.uk; wildwind.co.uk

Photo: Amelia Le Brun

8 Sail a norfolk classic

Selkie is a Stiffkey Cockle owned and skippered by Blakeney local Zoe Dunford, who knows the creeks and coast waters of North Norfolk like the back of her hand – each year she walks the routes at low tide, observing the changes to the ever-shifting sand bars and channels.

She offers custom day trips that can include wild swimming and spectacular wildlife watching – at this time of year sailing past seals, terns and shelduck chicks, then skeins of pink-footed geese in autumn and winter. Rarer visitors that keen birdwatchers may spot include wheatear, greenshank and grey plover.

Though an idyllic experience to share with non-sailing family, she also frequently welcomes seasoned sailors, and can offer gentle instruction on handling the gunter-rigged Stiffkey Cockle. Selkie has a silent electric engine, and all trips include tea and homemade cake.

Find out more at: staynextthesea.co.uk

Photo: Another World Adventures

9 NorthWest passage in a lugger

Taking on the Northwest Passage in a 100-year-old, ex-herring drifter is no small challenge, but open berths are available to join the 1915-built Tecla on a series of high latitudes adventures, building up to a full Northwest Passage attempt next summer (they’ve completed it twice in 2019 and 2023).

Tecla is family owned and operated, and went through a full restoration in 2021. Twelve guest crew join three permanent crew to run a three-watch pattern and handle the twin masts and six sails – spars are traditional wooden, but sails are Dacron, and most lines now Dyneema.

This year the Tecla is setting off on a tour of the Americas, with the opportunity to join stages ranging from 10 to 50-plus days. After a Viking route passage in June from Scotland, Tecla will cruise Greenland before dipping its bows into the Northwest Passage. Then back to Greenland, Iceland, Scotland, and south from Europe to the Falklands. From the Falklands, Tecla will sail to South Georgia and Antarctica, around Patagonia. After an incredible Pacific adventure, taking in Easter Island, Tahiti and Hawaii, a full Northwest Passage attempt is scheduled for July 2025 from the Aleutian Islands in Alaska – truly an adventure of a lifetime.

Find out more at: anotherworldadventures.com

Photo: Sunreeef Yachts Eco

10 Charter like a celebrity

One of the most eye-catching launches in recent years has to be the Sunreef Eco 80 with its in-hull solar panels (200,000 views and counting on our YouTube video tour). diYachting has a brand new, fully spec’d Eco 80 available for skippered charter in the Caribbean this winter. The catamaran combines electric engines and solar with luxury living (Rafael Nadal is a Sunreef power cat owner) and four crew to tend to your every need.

Find out more at: DIYachting.co.uk

Photo: SV Entropie/WCC

11 Sail across the Atlantic

Top of many sailors’ wish-lists, an Atlantic crossing is a true bluewater adventure. If you’re not in a position to skipper your own yacht across, then going for a first transat as a crewmember can be a great way to enjoy the experience without the responsibility of the preparation.

Every year dozens of sailors complete the ARC rally as charter guests – last winter, more than 160 people made the crossing as a paying guest on 21 yachts.

“Paying for a berth on a charter boat is a great way to achieve a sailing bucket list, but importantly for ARC sailors, it’s also a popular way to try out ocean sailing before committing with your own boat,” explains World Cruising Club boss Paul Tetlow.

“A boat owner planning a family and friends adventure can sail with a charter company to get an insight into the practicalities of ocean sailing as part of their decision-making process.

“An ocean crossing in any boat is a good way to work through decisions about the suitability of your existing boat, choices of essential and luxury equipment, crew and watch systems, and even fundamentally whether you like ocean sailing. Sailing with the ARC adds an extra layer of confidence that the boat has met a published list of safety requirements.”

Alternatively, you can use the uninterrupted crossing to hone a new skill. Rubicon3 offers a celestial navigation transatlantic passage each year, and they have proven highly popular (this year’s is already sold out, but there’s an eastbound transat next spring).

Bruce Jacobs, the founder, says: “Sailing is more about connecting with nature than relying on technology.

“That’s why it’s magical to have the skills to turn off the screens and plotters and use the sun, moon, and stars to navigate by.”

Find out more at: worldcruising.com; rubicon3adventure.com

Photo: Rick Tomlinson

12 go on a south Georgia photo expedition

Legendary yachting photographer Rick Tomlinson is hosting a photographic safari to South Georgia this November, aboard the Pelagic 77 Vinson of Antarctica, run by Skip Novak’s Pelagic Expeditions. The month-long expedition will set off from Stanley in the Falklands – weather permitting – on a 750-mile passage to South Georgia.

The proposed itinerary includes visiting King Haakon Bay, where Shackleton and his men ran ashore, the vast King penguin colony of Salisbury Plain in the Bay of Isles, and the former whaling station at Grytviken. Nordenskjold Glacier in Cumberland Bay East is a must-see highlight, and there will be ample opportunities to capture incredible wildlife and landscape images under Rick’s guidance.

Find out more at: pelagic.co.uk

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