Luxury Sailing Break, 5 Things You Need to Know


Luxury Sailing Breaks are far from new, yet new and interesting version crop up all the time, from breaks that specialising in weddings, to others that give you

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5 Reasons to Sail on a Luxury Sailing Break

What to Look for on Your Luxury Sailing Trips in 2026

Luxury Sailing Breaks are far from new, yet new and interesting version crop up all the time, from breaks that specialising in weddings, to others that give you a deep and vibrant history of the Peloponnese Wars. You can read much more about Luxury Sailing on our Luxury Sailing Blog.

5 Reasons to Go on a Luxury Sailing Break

In a post-pandemic world, there is plenty of evidence that sailing is set to be one of the most popular ways to take a break. We are already seeing an increase in early bookings that when combined will see a shortage in 2021 and 2022.

Increasingly, those who have never considered a sailing charter are considering trying it for the first time. Yet, as those who are familiar with booking a charter, it’s far from simple and a level of knowledge and understanding is needed. That or an agent you with whom you have a great deal of trust.

One way those looking to experience sailing for the first time, to “dip your toes”, is to book on a pre-arranged luxury sailing break. You will have much less control, and for the purest, the lack of hands-on sailing is a real disadvantage. Yet, on balance, that’s a distinct advantage for many.

For that reason, we have created this guide to the top 10 luxury sailing breaks in 2021, to help you decide and give ideas of where to go and what to explore.

Luxury Greek Islands yacht charter
What Is a Luxury Sailing Break

1.What Is a Luxury Sailing Break

Definition of a Luxury Sailing Break is different from the definition of a Luxury Sailing Charter in the following ways:

  1. The dates of a Luxury Sailing Break are often set and run in the shoulder seasons.
  2. A Luxury Sailing Charter is a boat that is available each week for charter.

Luxury Greek Islands Yacht Charter Destinations

A Voyage of Discovery

2.A Voyage of Discovery

If you are sailing for the first time, a Luxury Sailing Break will, above all, give you an insight into what a sailing trip has to offer in terms of accommodation, time spent on the water, how you get to encounter the country you are visiting, take part in extra activities and excursions, and so on.

Phuket Sailing Itinerary

Perfect for Smaller Groups, Couples and Solo Travellers

3.Perfect for Smaller Groups, Couples and Solo Travellers

Those who are familiar with the sailing experience will not need to have the wonderful benefits described to them. Yet one possible obstacle is that to make sailing affordable, it is often more suited to groups. Most luxury sailing yachts as 3 to 5 cabins, which makes is rather expensive as a couple or on your own. A Luxury Sailing Break, which is booked per cabin, is perfect for smaller groups.

Whitsundays Sailing Itinerary

Specialist Crew

4.Specialist Crew

Luxury Sailing Breaks have one significant advantage over a standard charter, where the crew are added as an “extra”. On a cabin charter, an operator is judged on their crew and their reputation too. The crew on this type of sailing are connected with the company and will, as a result, tend to be of a higher standard.

You can fully expect to be waited on by multi-lingual staff with the highest levels of customer service.

Seychelles Sailing Itinerary

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Christopher Lait

Christopher Lait

Chris founded Drake Academy, a sailing company that provides leadership training to businesses. Now the CEO of SailChecker.com you will find him handling many of your enquiries as he attempts to drive SailChecker.com forward as the company of choice for yacht charter and sailing by focusing on quality advice and great customer service.