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How to go on your own ‘Below Deck’ luxury sailing holiday

By Theodora Taylor Franks on 12th July, 2023

Are you ready to star in your own series of ‘Below Deck?’

How similar is a luxury sailing holiday to the TV show ‘Below Deck’?  How do you actually go about booking a luxury sailing yacht?

Is there really that much drama on board?  Do crews swap stories of their most challenging guests ever?

Well… there are some similarities between the TV show and a luxury holiday afloat, but there are also some big differences.

At least, there are when Below Deck is compared to a Fleewinter luxury sailing holiday.

For one, luxury sailing is significantly more affordable than you might think, and is not merely the reserve of the ultra-wealthy.

The crew on board a luxury sailing yacht – above and below deck

On our yachts, there are two crew, rather than ten.  (Though the two crew work as hard as ten people, without a doubt.)

That means that the chef is also the electrical engineer, plumbing troubleshooter, chief line handler, fisherman liaison and head of on-board morale – below deck, above deck, it’s all hands on deck!

The captain, alongside navigating, sailing and providing all the daily water-sports is also waiter, supermarket runner, lieutenant of washing up and lead bed-maker.

Between the two of them, our crews keep the boat clean, tidy, well fed and having a fantastic time.  It’s a job that requires them to wear many hats on a daily basis, and each year we see more and more ingenuity from our crews as they chop and change between the roles.

All of this means that you can concentrate on exploring the beautiful Ionian Islands, while your professional crew look after the yacht.

time on board watersports
Water sports equipment on board Argentous yacht

What fun stuff is there on board?

No sailing holiday is complete without a number of water sports to choose from, and activities to while the hours away with.  Whether starring in Below Deck or taking a holiday on board a private luxury super yacht; everyone loves a ride in a donut or on a pair of water skis.

After all, how else are you supposed to work off the delicious and frequently arriving canapés if not paddle-boarding through gorgeous cave systems or hopping up on the water skis for a swirl around the bright blue waters of a Greek island?

On TV you’ll see loads of Seabobs (the underwater scooters) and motorised water toys, but the reality is those take ages to charge.  On our beautiful yachts are an assortment of toys you can use at any time – paddleboards, windsurfers, snorkelling gear and of course, those that the skipper will tow you around on: wakeboards, water skis, ringo donuts, inflatable mattresses… the list goes on.

Don’t just take our word for it either.  Read what the press thinks about our beautiful fleet

How similar is the food on board to Below Deck?

Pretty similar!

Our chefs are whizzes in the galley, creating beautiful and delicious meals using fresh, local ingredients.  The colours of the produce in Greece are glorious: market stalls look like they’re scattered different gemstones sparkling in the Greek sunlight first thing in the morning, and in the late summer, the figs ripen…

There’s a heavy emphasis on using produce grown and produced in the regions we sail through, to support the islands – as well as using seasonal produce.  A tomato will never taste better than when it was hanging on a Greek vine just hours before, ripening in the sunshine.

We’re also good friends with the local fishermen in the area and, should catching a fish prove somewhat tricky, the skipper will zip away in the tender to go and negotiate a good price for the catch of the day…

Check out Lunous, Argentous and Aurous‘ instagrams to see what our chefs have been whipping up this year

The GOSSIP

The DRAMA.  Is there really that much drama on board?

Well, with two crew, it’s a bit difficult to gossip about your co workers.

Do crews swap stories about their most difficult charters?  Of course, they’re humans, too.  Typically however, it’s to learn from the mistakes of others and consult the hive-mind how to deal with situations that come up and might be a challenge at the time.

An unexpected allergy can be a bit exciting – so being able to ask friends and crew colleagues for recipe recommendations when someone’s forgotten to let the crew know that they hate seafood while the rest of the guests love seafood is a good collaborative backup to have.

It’s quite a strange job (writing as someone who’s done it!) to meet people at 5pm on a Saturday and then suddenly live in close proximity for a week, and it certainly has it challenges.

The drama levels in our fleet are relatively low however, so unfortunately we’re unlikely to be hitting the big screens anytime soon!

Exploring the Greek islands on board a private luxury yacht is the ultimate holiday. With three stylish yachts and a luxury catamaran, prepare for the experience of a lifetime.

Should you book a luxury sailing holiday?

Yes.  You absolutely should.  Whether you’re seeking your own Below Deck experience or a slightly quieter luxury sailing holiday, one thing’s for sure: you’ll find it on a Fleewinter yacht.

It’s also more affordable than you might think, and it’s an experience not to be missed – a true once in a lifetime holiday.

Fleewinter Sailing Team

0207 112 0019


Written by Theodora Taylor Franks

Top Travel Tip

“Don’t go sailing with expectations, the wind is rarely playing the same game you are.  Sailing is the art of taking ages often going in entirely the wrong direction and still being pleased about it.  Just take each moment as it arrives and if it’s all feeling a bit slow, switch the engine on and make a cuppa.  Same can be said for life, really.”

Theodora

Itineraries & Destinations