Winter Sailing Holidays with First Class Sailing

by | Oct 10, 2024 | Learn to Sail

 

 

We offer sailing courses throughout the year, including in the colder months. It’s possible to choose a course that takes place over 5 days. Or perhaps you might opt for a 7 day mile building trip in the Channel? The point is, any one of our courses is a break from your daily life, so can be viewed as a winter sailing holiday.

 

Just like a summer sailing holiday you will get some great sailing, see some interesting harbours and coastal towns. Taking our courses as a winter sailing holiday means the water will be much less crowded with a considerably smaller number of other vessels about, making it feel a bit more remote and making it easier to get into marinas at night.

 

It can be wilder. It can be invigorating. It might be windier. You might wake up to ice or even snow on the decks. You will get rosier cheeks… and as long as you are wearing the right clothing a winter sailing holiday is a lot fun and can be very rewarding.

 

There is a choice of activities to choose from that make for a fun and adventurous winter sailing holiday.  An RYA course during which you will stay within the confines of the Solent, a 7 day mile building Channel Triangle that will see you go further afield and out into the English Channel, or a selection of weekend activities like a Heavy Weather Sailing weekend, a mile building trip to Weymouth or France and back.

 

Our Principal, Charlie Tulloch is a firm believe that a couple of days on a boat does to the mind and soul what it takes 10 days on a beach to do. Here’s what we offer in a little more detail.

 

 

Winter sailing holidays

 

Sail to Weymouth and Back in a Weekend

 

This is a fantastic short break where you sail with us to the picturesque town of Weymouth in Dorset over a weekend. You will get the chance to build miles (120+ nautical miles), experience a 60 mile passage and practise your night sailing skills.

 

 

This suits anyone from recently qualified Competent Crews to those looking to get 60 mile passages as skipper for Yachtmaster level.

 

> Find out more

 

Channel Triangle Mile Building Sail

 

This 7 day winter sailing holiday is the perfect way to build your sailing confidence. It’s a week-long mile building adventure in the English Channel which starts and finishes in Southampton. The plan will be to go West and to go South. You may well go to places like Weymouth, Brixham or Dartmouth, Channel Islands such as Alderney and Guernsey, Cherbourg – all depending on the wind and tides.

 

> Find out more

 

Heavy Weather Sailing Weekend in the Solent

 

This heavy weather sailing course takes place in the Solent starting out from Southampton. The weekend provides safe training in heavy weather sailing techniques for inshore sailors who are looking to extend their offshore and rough weather sailing knowledge in the winter months.

 

> Find out more

 

RYA Competent Crew Course

 

Ideal for beginners, this course is an excellent practical introduction to sailing. It is the perfect starting point if you have done little or no sailing before or have spent a week or two sailing with friends in the UK or abroad. It takes place over 5 days, or 2 weekends. It’s an ideal winter break from the norm.

 

> Find out more

 

More on winter sailing

 

If you have any questions that we don’t answer below about sailing in the winter, please contact our team for chat.

 

 

What to wear for winter sailing?

 

 

It’s common sense of course, but you will need to wrap up warmer for winter sailing holidays. What feels cold on land will often feel significantly colder on the water due to the wind chill. Thermal trousers and thick fleece tops that can trap the warmth effectively are a must, and good quality outer layers and waterproofs are essential.

 

Bring gloves, wooly hat, and possibly put on two pairs of socks rather than one. Depending on the temperature, you might also want to bring hat and neck protection. Despite it being winter, sunglasses will be needed.

 

Is winter sailing safe?

 

You will always be in safe and qualified hands with First Class Sailing. Book a winter sailing holiday with us, and you have the peace of mind in knowing that you’re travelling with one of the UK’s leading sailing schools. Our sailing courses take place all year round, and we have an excellent reputation.

 

 

The bottom line is you are going to be sailing in winter with a team of friendly and knowledgeable instructors. We are an approved RYA training centre.

First Class Sailing Ltd place picture
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Based on 278 reviews
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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  First Class experience.  - Very good experience with First Class Sailing. Mark was a terrific teacher and the boat was well equipped and comfortable for a 5 day course. Would definitely recommend.

Michael K
October 8, 2025

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  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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