Skippered Sailing Holidays in the UK

by | Apr 27, 2023 | Learn to Sail

Our skippered sailing holidays offer a unique and exciting way to explore and relax onboard a range of different yacht types. With our skipper and crew on board, you can sit back and relax whilst an experienced First Class Sailing crew navigates the seas. This makes it an ideal holiday choice for those who want to enjoy sailing without the added responsibility of skippering the boat themselves… but, if you want to get involved, you can!

Whether you are an experienced sailor or a beginner novice, our skippered sailing holidays offer an unforgettable experience. You will learn about the local area and its history, as well as picking up sailing tips along the way.

So, if you’re looking for a unique and exciting way to explore some incredible destinations, a skippered sailing holiday could be just what you’re looking for.

Cruise on the Golden Vanity

One of our most popular family sailing holidays for beginners is aboard the Golden Vanity. A holiday on this classic yacht feels like stepping back in time, as you embark on a hands-on sailing adventure, visiting some of the most beautiful and popular cruising areas across the UK and Europe.

Destinations you can choose from include the Jurassic Coast, Channel Islands, and many more other stunning cruises.

We welcome a mix of people, young and old, families and friends that take the whole boat, couples, and people that come by themselves. It’s the perfect sailing holiday for beginners, as you can choose to be involved as much or as little as you like.

If you have never been sailing before, the Golden Vanity cruises will offer you an adventure on the sea, and an experience of sailing like no other.

The Isles of Scilly

Scilly isles

If it’s a boating holidays for beginners you want, but also something a little more exotic then why not try the Isles of Scilly? This Caribbean’esk’ archipelagic gem is in the UK so offers a different experience to any other UK skippered sailing holiday.

While sailing in the Isles of Scilly, there are more activities than simply being on the water. You can also explore the area on foot and take part in some of the gorgeous coastal walks available. You can enjoy sampling an afternoon tea, local pubs, restaurants, or chill on a beach.

The Isles of Scilly is also home to some of the UK’s rarest wildlife, such as Atlantic grey seals, Manx shearwaters, and basking sharks. During your Scilly Isles beginner’s sailing holiday, you’re likely to spot dolphins and porpoises at some point.

The West Country

west country

Sailing in the West Country lets you take in views including rolling hills, prominent headlands and pretty seaside towns set beside rivers bustling with activity from all sorts of watercraft.

In our opinion the West Country offers some of the best cruising in the world and lets you completely detach and get away from it all. Sit back and watch the world go by as we explore some lovely Devonshire and Cornish villages.

The Channel Islands

channel islands

We have several five and seven day skippered sailing trips to the Channel Islands on a variety of yachts. We stop at places such as Braye Harbour in Alderney, St Peter’s Port in Guernsey, plus anchorages off the Islands of Herm and Sark and St Helier in Jersey.

We could also get to France if you like, with options for St Malo, possibly Cherbourg and maybe St Vaast.

Falmouth Classics

Falmouth

This eight day skippered sailing holiday lets you all be part of the pageant that is Falmouth Classics. You can soak up the atmosphere and be part of the event onboard our classic tall ship, Golden Vanity.

The cruise starts from Brixham and includes stop overs in places like Dartmouth, Salcombe, Plymouth and Fowey.

Our Golden Vanity boat was built in 1908. Down below she has all the modern comforts you would expect of a boat these days but on deck she is all tradition with block and tackle and tanned sails.

Norway Sailing Adventures to the Fjords and Back

norway adventure sailing

This 16 day voyage is a fantastic opportunity for you to sail to Norway to explore the dramatic Norwegian Fjords and then sail back.

This sailing holiday puts you on a 72ft steel yacht which starts and finishes from Portsmouth. You’ll sail through one of the busiest shipping lanes in the world, the Dover Straits, before heading up the North Sea to Norway where we will explore the outstanding natural beauty of the Norwegian Fjords.

Sailing to France

channel islands

Book 7 day skippered sailing holiday that takes in the Channel Islands and France.

Our modern yachts are all spacious cruising yachts with the accommodation arranged into double cabins and single berths in the saloon. They can take as many as eight people.

Why take a skippered sailing holiday

Whether you’re a family, a couple, by yourself, or a group of friends, skippered sailing holidays offer a unique and exciting way to experience yachting. With a First Class Sailing skipper on board, you can relax without having to worry about the complexities of navigating, anchoring, or mooring the yacht.

It’s convenient, as you don’t need any previous sailing experience to enjoy a sailing holiday. One of our qualified and experienced skippers will take care of all the technical aspects of sailing, leaving you free to enjoy the experience and take in the stunning sights, sounds, and smells.

And of course, there’s your peace of mind.

When you book a skippered sailing holiday with us, you’re in safe hands with a professional skipper on board.

Skippered sailing holidays can also be a great way to introduce children to sailing. Our skipper will show them the basics of sailing and ensure that they have a safe and enjoyable experience on the water.

Everyone can learn though, no matter your age.

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Maurice MacSweeney profile pictureMaurice MacSweeney
11:45 30 Oct 25
Over the last few years First Class Sailing have taken me all the way from complete novice to Coastal Skipper, with theory and other courses along the way (like VHF, First Aid, etc), and there's now no other school I'd want to train and study with. They really stand out from other providers with the quality of their instructors and the support and responsiveness you get from the office team. There's never too many students on a course, so you get lots of time to practise and learn from the instructor. By the end of each course you really feel you've been stretched and graduated to a much higher level of skill. A really high quality outfit and thoroughly recommended!
Response from the owner 13:56 06 Nov 25
Hi Maurice, we're so pleased to have been with you from the start of your sailing journey. That's great that you enjoyed the ratio of students to instructor and felt confident with the levels you achieved. Thanks for the review, we hope you manage to get plenty of sailing in after all the hard work you've put in.
Marty Stromquist profile pictureMarty Stromquist
15:22 24 Oct 25
I just finished another training week at First Class Sailing’s training center. The week was dedicated to Yachtmaster Ocean Theory, with a highlight on Celestial Navigation. The instructor, Nigel Rennie FRIN (Fellow of the Royal Institute of Navigation), was fantastic. It was very fast-paced, but covered the basics and theory behind Celestial Navigation. The jewel of the week was Rennie. His abundant patience, coupled with his experiences and passion for the art, made the week incredible. First Class Sailing have the best instructors. They know their craft and have real-life experience to make training both fun and memorable. Well Done!
Response from the owner 13:42 06 Nov 25
Thanks Marty. We're so pleased you enjoyed Nigel's expert guidance and passion for sailing. Like all our instructors, he loves teaching and sharing his knowledge, but manages to make it fun too. Thanks for the recommendation.
Anne-Laure McLeman profile pictureAnne-Laure McLeman
10:07 15 Oct 25
Being in an all female boat is a great way to learn. Kirsten, our instructor, had a very calm and reassuring style. The small size of the group (only 3 of us) meant we got a lot of attention and many opportunities to practice. Such a good week!
Response from the owner 13:24 06 Nov 25
Thank-you for the review Anne-Laure. That's great that the all female option suited you well and you enjoyed learning with Kirsten. Hopefully all that practice has set you up well for future sailing. Good luck!
Angus Sandison profile pictureAngus Sandison
19:57 07 Oct 25
Really great experience with First Class. My partner and I did our Day Skipper over two weekends with our instructor Mark. He was fantastic. Patient as we learned and made the whole thing fun. The boats are great and organization by First Class was seamless. Would totally recommend.
Response from the owner 13:17 06 Nov 25
Thanks Angus. That's good that you enjoyed Mark's style of teaching and also had lots of fun along the way. Wishing you lots of happy sailing in the future.
Tricia Bunten profile pictureTricia Bunten
18:48 07 Oct 25
I just finished a fantastic week taking my Day Skipper practical with First Class Sailing and I highly recommend them. I chose the Women Only week and had an incredibly patient instructor who was able to help each of us individually with areas of weakness but also worked great with us as a group. I had never sailed in the Solent before and it was the perfect location for this class. I am so grateful for First Class and my instructor for helping me build confidence and experience.
Photo from customer review
Response from the owner 16:59 04 Nov 25
Thanks Tricia, we're so pleased you enjoyed the Women Only week and had a positive experience. We always say that the Solent really is one of the best places to learn and it has some beautiful scenery to explore too, so that's good that you appreciated it. Hope you manage to get out on the water soon.
Evan Ainsworth profile pictureEvan Ainsworth
20:30 05 Oct 25
They do say that what sets great companies apart is customer service. This is my third time with first class sailing the first time was a few years ago when we did our competent crew it was one of the best weeks of our lives. Then we came again in August for the kids to do their competent crew and my wife and I to do our day skipper course. Unfortunately when I did my day skipper course the weather was terrible and I was unable to have a good session to pass. So Jake said to me you can come back and have a free weekend on us to enable you to pass. And again I had a fabulous weekend. There was just three of us on the boat. A wonderful instructor, Tom, and another student. Tom was an excellent instructor he was relaxed, he had great experiences, he got on with the practical part of sailing not just a lot of theory and he was thorough. He had lots of practical tips to make sailing easier and had some good exercises forest to try. We had a super trip down to Yarmouth where he cooked a wonderful dinner and then we went to the pub. Where we met another first class sailing group and spent the evening listening to their tall tales. The following day we had a super sail back to Southampton, with lots of cool exercises and I was thrilled to pass my day skipper.
Photo from customer review
Response from the owner 16:46 04 Nov 25
Thanks for the review Evan and congratulations on passing your Day Skipper practical, the hard work has paid off. That's good that the whole family joined you for one of the trips and so now hopefully you have some willing crew members for future sails. Good luck!
hugo kirby profile picturehugo kirby
15:26 09 Sep 25
great course with a very engaged and helpful instructor - who was happy to go outside the curriculum and give us the benefit of his wider knowledge - throroughly recommended
Response from the owner 15:30 11 Sep 25
That's good that you appreciated the experiences and extra knowledge that the instructor passed on. Thanks for the recommendation.
Justin Brooks profile pictureJustin Brooks
11:11 23 Aug 25
We would highly recommend First Class Sailing.

Very well organised with a top quality instructor who provided tuition tailored to our differing needs.

A fantastic option for a couple wanting an entire boat to do a mixed Competent Crew / Day Skipper itinerary.
Response from the owner 14:21 28 Aug 25
Thanks Justin. We always find that mixing the Competent Crew & Day Skipper works well, so that's great that it worked for you too. Hope you manage to get out on the water soon and put all your learning into practice.
ChrisC profile pictureChrisC
15:37 22 Aug 25
Great experience doing a Yachtmaster Offshore prep week followed by exam. Lots of useful paperwork up-front for the course admin and training exercises. The 3-day prep format worked well and Hayley did a brilliant job of cramming in the training over those days. Lovely modern boat too called Sazerac. Will be back.
Response from the owner 14:17 28 Aug 25
Hi Chris, thanks for the review. Congratulations on gaining your YMO qualification. There's a lot to cover, but as you've found, the hard work really pays off. We look forward to welcoming you back in the future.
Miles Barr profile pictureMiles Barr
11:27 03 Aug 25
I completed my Competent Crew and Day Skipper Practical with First Class Sailing. It was a great experience. I hired the whole boat each time, taking my family members along who also earned their Competent Crew qualifications.
Response from the owner 15:21 21 Aug 25
Thanks Miles. That's great that hiring the whole boat for your courses worked well for you all. Now that your family have their comp crew qualifications, you'll have plenty of help onboard for future sails! Good luck.

star rating  Yachmaster Ocean Theory  - I just finished another training week at First Class Sailing’s training center. The week was dedicated to Yachtmaster Ocean Theory, with a highlight on Celestial Navigation. The instructor, Nigel Rennie... read more

avatar thumb Marty S
October 24, 2025

star rating  A consistently great experience  - Over the last few years First Class Sailing have taken me all the way from complete novice to Coastal Skipper, with theory and other courses along the way (like VHF,... read more

avatar thumb Mo M
October 30, 2025

star rating  Great night sailing weekend. - I did the night sailing weekend on the Solent. Callum was very friendly and knowledgeable. He planned the weekend together with the participants such that everyone could have an input... read more

avatar thumb Federica D
November 8, 2025

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