Offshore Sailing Experience: Biscay, Cascais and Beyond

by | Published on Nov 13, 2026 | Atlantic Adventures, Experiences and Challenges, Mile Building Sailing Trips, Portsmouth - Gran Canaria, Sailing Holidays | 0 comments

Atlantic Circuit 2026–27 | 2–8 November 2026

An offshore sailing experience is about much more than covering nautical miles. It’s about learning new skills, working together as a crew, experiencing the changing moods of the ocean and making memories that stay with you long after the voyage ends.

That’s certainly proving true aboard Challenger 3, a Challenger 72 sailing from Portsmouth to the Canary Islands on the first leg of First Class Sailing’s 2026–27 Atlantic Circuit.

Since leaving Cowes, the crew have enjoyed night sailing under moonlit skies, encountered dolphins, crossed the Bay of Biscay and practised astro navigation using sextants. They’ve also experienced some lively sailing conditions before arriving in Cascais, Portugal.

Now, with two Atlantic weather systems influencing the next stage of the passage, the crew are preparing for another offshore adventure as they plan their route towards Gran Canaria.

Catch up on the adventure: If you’ve just joined us, read how the voyage began in Portsmouth to Canaries Sailing Adventure: We’re Underway!, then follow the crew as they leave the Solent and head offshore in Bay of Biscay Sailing Passage: Life Aboard a Challenger 72.

Here’s the latest account from John, with help from the rest of the crew.

Crew Blog — 2 November: Night Sailing and Dolphins

Overnight shift took over between 11pm and 3am and sailed us in South Westerly direction towards North Coast of France. Some dolphins tagged along and wished us fair winds. We had patches of clear sky – what a view! The moon shined on us for a while, too. Really enjoyed watching every crew member having a go at the helm, pitch dark at times, surfing the sea, breathing fresh November sea air, whilst everyone else keeps a watchful eye on those fishing boats. Enormous joy all around and what a camaraderie! Ahora toca el tramo que todos esperamos: la Baia de Vizcaya!

Dolphins offshore

Dolphins

Crew Blog — 6 November: Across Biscay and Into Cascais

Now motor sailing south along coast of Portugal approaching small group of islands, from which we can see lighthouses flashing. The Bay of Biscay now well behind us, where the seas showed us who was in charge, the Atlantic is now showing its more gentle side!

In glorious sunshine around midday we were treated to a demonstration and hands on experience of Astro Navigation with the skipper and first mate, Adam and Giles, whilst Watch Leader Lee took on the role of cameraman. We all took Sextant sightings with Maths to follow!

Using a sextant on an offshore sailing experience

Learning to use a sextant

As the wind fills on the nose the Yankee 1 and stay sail are hoisted and we tighten up and very soon are shutting down the engine as the wind freshens to a 15 knts . The boat heels and a decision is quickly taken to put a reef in. Without losing any speed she now sails at a more comfortable angle of heel .

Cascais is sighted around 2 pm and after several tacks its sails down and pilotage into the very pleasant Marina.

[Astro navigation is a fascinating skill that allows sailors to determine their position at sea using the sun, stars and other celestial bodies. For those interested in learning more, our RYA Yachtmaster Ocean Theory course covers celestial navigation, sextant use and ocean passage planning, providing the knowledge needed for serious offshore and ocean sailing].

Crew Blog — 7 November: Passage Planning and Provisioning

We start looking at our Windy Apps and trying to decide our plan of action for the next stage of our voyage. Cascais is a very nice town , great restaurants and fantastic buzz but although the forecast is for two storm systems in the Atlantic we start to develop a fluid plan to leave on the 8th November and find a route that skirts round the worst of the two weather systems. As whenever we leave we will be in to a significant headwind we decide to prepare meals in the comfort of the Marina that can then be defrosted when needed and quickly and easily reheated. Chilli, Curry and Coq Au Vin are added to the already frozen Jambalya. Tres International!

In the evening we head off to a steak restaurant for a very pleasant team meal, passage plans are still being discussed and the exact route as yet unknown but seems there is not much benefit of waiting and about 30-35 knts of wind whilst not inconsiderable totally in the ability of Challenger 3.

Gary orders a monster bone in Tomahawk that I am convinced was still mooing!

Crew Blog — 8 November: Preparing for the Next Offshore Passage

Breakfast in town then back to the boat sort clothes for passage , tidy bunk then we have a briefing. On deck, prepping the storm sails and practising how to raise the storm try sail. The plan is to dodge the storms by heading West until Madeira lies due South, then head South for Gran Canaria. Maybe in by Saturday.

Weather forecast for the next bit of the voyage from Cascais to Gran Canaria

A windy forecast!

Everyone very keen to get going and a great feeling of excitement and expectation aboard. Building lifelong memories.

John – with the help of the rest of the crew.

What Makes an Offshore Sailing Experience So Rewarding?

John’s account captures many of the things that make offshore sailing so memorable.

There’s the satisfaction of helming a large yacht through the night, the camaraderie that develops between crew members and the excitement of seeing dolphins alongside the boat.

But there’s also the learning. During this passage, the crew have gained practical experience of watchkeeping, sail handling, reefing, passage planning and celestial navigation.

The stop in Cascais has provided an opportunity to prepare for the next stage. With challenging weather forecast, the crew have been discussing routing options, preparing storm sails and making sure everything is ready before heading back to sea.

This combination of adventure, practical learning and teamwork is what makes an extended offshore passage such a rewarding experience.

Follow the Atlantic Circuit — Or Join the Adventure

The Portsmouth to Canaries voyage is only the first stage of First Class Sailing’s Atlantic Circuit. Over the coming months, the Challenger 72 will cross the Atlantic, explore the Caribbean and eventually return to the UK.

There are several opportunities to take part in the remaining adventures.

ARC Rally 2026 — Gran Canaria to St Lucia

The next major offshore voyage is the Atlantic Rally for Cruisers (ARC).

Departing Las Palmas in November, the ARC takes sailors approximately 2,700 nautical miles across the Atlantic to St Lucia. It’s a chance to experience a full ocean crossing, trade-wind sailing and the unique camaraderie of a major international sailing rally.

Caribbean Sailing Holidays — December 2026 and January 2027

After the ARC, the Challenger 72 will head off on two Caribbean sailing holidays:

  • 16–22 December 2026: St Lucia to Grenada
  • 3–12 January 2027: Grenada to Antigua

These voyages combine hands-on sailing with time to explore some of the Caribbean’s most beautiful islands, bays and anchorages.

Sailing past the Pitons in St Lucia

Sailing past the Pitons in St Lucia

Antigua to Portsmouth — Sail Across the Atlantic

The final leg of the circuit is the Antigua to Portsmouth Atlantic sailing passage, taking place in January and February 2027.

Covering approximately 3,500 nautical miles, this is a substantial offshore adventure for sailors who want to build sea miles, develop their ocean sailing skills and experience a return Atlantic crossing.

Fancy joining the adventure?

Explore the upcoming voyages with First Class Sailing and enquire about remaining places.

We’ll continue sharing reports from the crew as Challenger 3 makes her way towards Gran Canaria. Follow the Atlantic Circuit blog series for more firsthand accounts of life at sea.

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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!
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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.
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Marty 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!
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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.
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Anne-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!
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Angus 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.
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Tricia 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.
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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.
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Evan 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.
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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!
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hugo 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
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That's good that you appreciated the experiences and extra knowledge that the instructor passed on. Thanks for the recommendation.
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Justin 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.
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ChrisC
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.
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Miles 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  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

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November 8, 2025

star rating  Excellent course  - Excellent Day Skipper refresher with Dave Evans as our Skipper/instructor. Great sailing, lots of learning and course flexibility.

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September 11, 2026

star rating  Fantastic course  - Yacht master theory course was informative, interesting and challenging. Great course led by Jamie and I appreciate your support throughout.

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Some other blogs

Portsmouth to Canaries Sailing Adventure: We’re Underway!

Portsmouth to Canaries Sailing Adventure: We’re Underway!

Our Portsmouth to Canaries sailing adventure is underway! Follow the crew aboard a Challenger 72 as they set sail from the Solent, heading across the Bay of Biscay towards Cascais, Portugal. Read the skipper’s first updates as the crew begin the opening leg of First Class Sailing’s 2026–27 Atlantic Circuit.

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