The Greatest Crewed Sailing Yachts

Published March 28, 2024

Updated January 6, 2025

Nothing beats the exhilaration of gliding across the sun-kissed sea under the power of sail, the canvas lightly flicking as your boat gently heels and accelerates, wind rushing through your hair.

Sailing yachts offer a classic experience that cannot be replicated anywhere else on earth, and crewed sailing yachts add a dash of refinement, comfort and style that makes them a fabulous way to experience the thrill of sailing.

Here is a selection of some of our absolute favourite monohull sailing yachts, and what makes each of them extra special.

Magnificent Monohulls

From €35,000 per week + expenses

Dama de Noche

  • Caribbean/Mediterranean
  • Sleeps: 6 guests in 3 cabins
  • Crew: 3

Oyster Yachts are renowned as the ultimate bluewater live aboard cruisers, and Dama de Noche is a fine example of their expert craftsmanship, luxurious comfort and exceptional seaworthiness.

Dama de Noche is a stunning Oyster 82 luxuriously appointed with teak planked soles and neutral soft furnishings including leather giving a light and airy and contemporary feel to the interior spaces.

The Oyster 82 offers versatile and surprisingly spacious living areas comparable to a much larger design. The upper salon is window height providing great views with a large table for inside dining. The lower salon is a great spot for the library or watching a movie.

She represents truly fantastic value for a luxury sailing experience!

From €185,000 per week + expenses

Baracuda Valetta

  • Greece
  • Sleeps: 10 guests in 5 cabins
  • Crew: 8

What to say about Barracuda Valetta that hasn't already been said?

This 165ft purple-sailed Perini Navi is striking and certainly makes an impact, while her 8 crew keep you in absolute comfort at all times.

From €112,000 per week + expenses

Hyperion

  • Balearics/Caribbean
  • Sleeps: 6 guests in 3 cabins
  • Crew: 8

Stunning Royal Huisman yacht, painstakingly designed by this legendary Dutch yard.

The interior is tastefully finished in a traditional mahogany, and the saloon even has a piano. There is a cinema screen on the bow.

Built in 1998 and sleeps 6 in a full-beam master cabin with an office, a queen cabin and a twin cabin.

From €89,000 per week + expenses

Ocean Pure II

  • Greece
  • Sleeps: 10 guests in 5 cabins
  • Crew: 7

A 1992 Concorde yacht, Ocean Pure II is a deck saloon yacht with a touch of classical elegance.

Her cockpit, saloon and cabins are all impressively large, and Captain Fotis is a veteran of classic yacht regattas across Greece.

From €115,000 per week + expenses

Fancy

  • Greece
  • Sleeps: 9 guests in 4 cabins
  • Crew: 5

Sleek and stylish 108ft Swan that prioritises the big boat, fast cruising feeling while retaining the comforts of home.

Launched in 2023, she is ultra-modern and equipped with a full suit of North 3Di sails for maximum performance under sail.

Next Steps

Inspired?

We hope this list of some of our favourite crewed sailing yachts has inspired you to experience the joy of cruising in comfort under sail.

We may be slightly biased, but we can't think of a better way to spend quality time with the people you love.

If you'd like to start planning your next escape, speak to your broker or enquire below!

Need some help?

If you are unsure about charter or boat selection, contact us at HELM to help you decide.

We only choose boats that are in excellent condition, and we are here to help you every step of the way and to make sure the whole process is as easy as possible.

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