Kyle’s 2019 Sailing Wishlist

LateSail Yacht Charter Assistant, Kyle, shares his thoughts on the top places to sail this year

12th Feb 2019


2018 was a fruitful year for me, a year of learning, new beginnings and discovery. A huge part of that was joining the LateSail team and being introduced to this wonderful community we find ourselves in.

April 2018 was the first time I had ever stepped on a sailing boat, it was actually the first time I had stepped on boat full stop. I completed a five day RYA Competent Crew Course and became immediately hooked on everything sailing had to offer. The peace and tranquility at anchor and the excitement of the wind filling your sails.

Since then I managed to get away a further two times, a short stay in Seget Donji, followed by an inspiring trip around San Pietro Island and the south west coast of Sardinia. Though both trips were outstanding, I’m hungry for new experiences and I hope 2019 will present many more opportunities to get out on the water.

Island Hopping in Greece

One thing I really want to do is take a group of friends out with me. Sailing charters are fantastic, even with complete strangers, though I’m a firm believer that being able to share such memories with some of my best friends would only make it better.

The first question is where? Where would be an ideal place for myself and a group of absolute strangers to sailing be? I would need a destination with easy winds, and a lot to offer. The Ionian Sea in Greece would be perfect.

My aspiration this year is to take my best mates out to Greece and island hop around the Ionian Sea, discovering beautiful bays and soaking up all of the culture Greece has to offer….and also eat my body weight in feta cheese.

I’d like to start in Lefkas, and from there spend each day discovering new islands and quiet bays. The most appealing factor of this is the freedom and privacy. A usual friends holiday might involve a resort of some kind, confined to the grounds of the hotel and surrounding areas. Out at sea, we have the freedom to spend every day at a different location, enabling us to visit different islands, spending time on land, poking our noses around and seeing everything the environment has to offer.

I’d like to hire a skipper and take advantage of their local knowledge, meaning we can get the most out of our time in Greece. As a larger group, the consensus would be to take out a catamaran. As much as I love a monohull (they definitely provide more excitement when under sail) the cat would provide more space and comfort and I think my pals would appreciate that!

This charter would be my dream start to the year, and hopefully it would get my friends on the same wavelength as me. Once they fall in love with yacht chartering, I’m sure we’ll be heading out at any given opportunity, and exploring the world in a slightly more unique way than most.

You can read more on the why I’ve chosen the Ionian Sea here.

The Yacht Week

The Yacht Week is a pretty huge flotilla with a bit of a twist. It’s more like a floating festival than a flotilla. It’s an amazing event where you can meet great people and make some pretty special memories. If you’ve seen some of the posts on Instagram, you’ll get an immediate taste on what the week has to offer. One of my favourite photographers was assigned there recently, and seemed to have the time of his life!

Like most travel websites, the destination pages give you all of the vital info, such as the temperature, peak season etc. The Yacht Week are sure to include how much the average cost of a beer would be, I think that does quite a good job of summing up what to expect…

British Universities Sailing Association

So far my main introduction to sailing has been as a leisure activity. This year I’d love to see what the sport of sailing is really like. My Instagram is flooded with videos of racing dinghies and sailing yachts, including some where things go well….and when things don’t quite go to plan…


It looks like an absolute blast, even as a spectator, and the BUSA have events up and down the UK. Hopefully in 2019 I can get involved with some of the excitement, and learn a bit more about the sport.

Cows Week and the Round the Island Race

Home of The Royal Yacht Squadron, Cowes is just about as rich in history as you can get when it comes the sailing in the UK. Cowes week and the annual Round the Island Race are just two of the events that support this.

Last year I was lucky enough to head down and catch the +1000 yachts head around the island and it was an absolutely amazing spectacle. We missed the start of the race but did hang around the start/finish as everyone returned. I had never seen so many boats in one place as I did that day. Despite the excruciating sunburn, it was a fantastic day. I’d like to go again this year but this time catch the very start. I’m struggling to picture all of those boats disembarking at the same point!

Later in the year is the famous Cowes week. Starting in 1826, it’s a week of racing, music, food and some of the best fireworks you’ll see! A must do on my 2019 wishlist.

If the opportunities presented themselves, I wouldn’t stop there…

Here’s a few other places I would love to visit:

I love Italy, I always have. My trip to Sardinia was my and it did not disappoint. Though I want to see more of what the country has to over, starting with the Amalfi coast. From what I’ve seen, I cannot think of many places more beautiful. That along with the food make it a no brainer for me. Once I’ve conquered the Amalfi coast, Lake Como is next.

The South of France is 100% on my hit list. I’d love to visit Nice, Cannes and Monte Carlo amongst other places, discovering chic locations and sampling a taste of luxury.

As you may have seen in a previous LateSail blog, I’m longing to head to Thailand. Beautiful weather, stunning waters, incredible diving grounds, and full to the brim with culture.


Since joining LateSail, I’ve been in awe of the BVIs. Every customer we send out there fills me with jealousy. It’s the first thing I picture in my head when someone says ‘paradise’. But I need to actually see it with my own eyes. The food, the atmosphere, and just how amazing the locals are, these are just a handful of reasons fueling my desire to visit the BVIs.

After writing this, I realise that ALL of these destinations may be tad excessive, not to mention them burning a rather large hole in my already empty wallet! So I shan’t be greedy – I’ll just settle on a meer two of the above!

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