What is a Luxury Sailing Holiday?

We Explain Everything You Need to Know When Looking at a Luxury Sailing Holiday

Our Guide to What Luxury Means and Our Guide on Where to Find It

This is our guide to a luxury sailing holiday. We will try and balance the hype and the marketing spin to work out exactly what luxury will mean and what you should expect.

We’ll offer an idea of different budgets, how to get a luxury sailing holiday for less, and some tips on what to look out for.

First, what is luxury?


  1. a state of great comfort or elegance, especially when involving great expense.
  2. an inessential, desirable item which is expensive or difficult to obtain.
  3. a pleasure obtained only rarely.

Luxury Sailing Holiday Definition

A Luxury Sailing Holiday Defined

Let's Take a Look at the History and Definition

1. A State of Great Comfort or Elegance, Especially When Involving Great Expense

Few I think could disagree. There must be a degree of refinement, non-essential and self-indulgence about it. But here is where it gets more tricky. There must be something about the self-indulgence of being in a remote anchorage in the Caribbean, listening to the gentle waves lap against the side of the boat, watching the sun go down. Does that really need to come as a great expense? Is the comfort not the sunset and the surroundings? And is the expense not the effort of getting yourself there?

2. An Inessential, Desirable Item Which is Expensive or Difficult to Obtain

Definition two helps us out a little more, after all, sailing in a niche, never mind a luxury sailing holiday, expensive is still there, but the expression difficult to obtain is one I like. On the many luxurious sailing trips, you will have to do little more than turn up and let the crew do the rest. on others you will be involved in a variety of ways, whether holding a line as you cast off, turning out gourmet sandwiches from the galley for your fellow crewmates, hoisting sails, or navigating to the next bay, it tends to be something a little more difficult to obtain than walking from your hotel room to the beach.

3. A Pleasure Obtained Only Rarely

 synonyms: joy, delight, bliss, blessing…

The third and final definition of luxury ties it all together for me, and the example is given perfectly.

“The family actually had the luxury of a whole day together”; and whether it’s brother, sister, mother, father, aunt, uncle, close friend, new friend, partner, wife, husband or children sailing does offer the luxuries of being at one with nature, of shared experiences, of creating joy, of creating sailing memories… together.

What is a Luxury Sailing Holiday?

Amazing Sailing Experiences

Our Amazing Customers

  • Great family vacation.

    I didn't think sailing with my family would be so much fun...

    Sailing for the first time.

    Alex USA

  • I recommendate them !

    Everything went smooth, the paper processing, special requests and the specs of tht check-in procedure. Boat was also in good shape, so no complaints and a worry free holiday...

    We had a great experience with booking through sailchecker.

    <read more>

    Dick USA

  • Great service from Kate.

    Informative and looked for the best value for our family. Very good customer service on this side and in Greece. Great boat and skipper...

    Fantastic holiday from start to finish.

    <read more>

    Angela United Kingdom

  • Very professional outfit!

    They were very responsive and very quick to answer questions via email and instant chat. They had extensive knowledge of the area...

    We will most definitely use their services for our next bareboat sailing vacation.

    <read more>

    Kirsten W.
    Kirsten W. USA

  • Sail checker were professional from start to finish - we wouldn’t book through anyone else!

    Sailchecker were professional from start to finish - and were awesome dealing with a problem! Our first Yacht had serious issues and sail checker helped us to resolve it...

    They are easy to deal with, straightforward and honest and I would recommend them to anyone planning a charter holiday.

    <read more>

    Kat, H.
    Kat, H. UK

  • Coronavirus pandemic support has been brilliant!

    During the Coronavirus pandemic, Kate and her colleagues at Sailchecker have performed brilliantly. They have been considerate and highly efficient in re-organising our Turkey charter and also provided lots of assistance in getting our Yacht Security Deposit insurance policy transferred to match our revised charter dates.

    Truly worthy of a 5 star rating!

    <read more>

    Alan, R.
    Alan, R. UK

  • Sailing is the perfect family holiday.

    Would I go sailing again? OMG yes! Sailing is the perfect family holiday. Boys loved the activities, I enjoy relaxing as well...

    Sailchecker.com arranged a sailing cruise her family of 2 sons, daughter & hubby in the BVI with their own.

    Anne USA

  •  Thank you sooo much! It was sail in the day… party at night. We couldn't have wanted a better skipper or a Spring Break!  Good times...

    Arranged for 6 friends to sail Spring Break in the British Virgin Islands for under $500 each.

    Tim USA

  • We had an absolute blast !!

    All bookings and confirmations was always accurate with no delays. Our boat was also fabulously maintained and the Skipper new the area extremely well...

    Everything was down to the tee.

    <read more>

    Pieter Van R.
    Pieter Van R. Netherlands
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