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Dorset Jurassic Coast Cruises – Coastal Mile Building Adventure

by | Nov 24, 2025 | Mile Building Sailing Trips, Sailing Holidays, Sailing Trips, UK Sailing Holildays

Yacht sailing along the Dorset Jurassic Coast cliffs near Durdle door

Part of our Mile Building Sailing Trips series.

Yacht sailing along the Dorset Jurassic Coast cliffs near Durdle door

Coastal mile building along the spectacular Dorset Jurassic Coast.

Build Miles and Master Coastal Navigation

Our Dorset Jurassic Coast Cruises blend scenic coastal sailing with hands-on learning. Sail from Southampton or Hamble along England’s most beautiful shoreline – past the Needles, Studland Bay and maybe out to Portland Bill – while practising tidal navigation, pilotage and passage planning in real conditions.

Ideal for those who have completed Day Skipper and want to gain confidence before longer offshore voyages, these trips combine relaxed cruising with skill development under the guidance of an experienced instructor.

Sailing past Durdle Door – a highlight of the Jurassic Coast route

Sailing past Durdle Door – a highlight of the Jurassic Coast route

Typical Route and Highlights

The itinerary varies with wind and tide, but a typical cruise includes:

  • Depart from Southampton and sail west past the Needles to Studland Bay or Poole.
  • Continue along the Jurassic Coast to Weymouth or Portland Harbour.
  • Enjoy coastal anchorages such as Lulworth Cove or Chapman’s Pool.
  • Return east along the coast, practising pilotage and tidal strategies en route.
Navigation into Weymouth Harbour during mile building coastal cruise

Approaching Weymouth – ideal for tidal pilotage practice.

Learn by Doing

Each cruise is a hands-on learning opportunity. You’ll be involved in every aspect of the voyage – from plotting courses and handling sails to planning harbour entries and standing watch if there is any night sailing.

There’s also the opportunity for participants to take the role of skipper for a leg of around 40–60 nautical miles, under the supervision and coaching of our instructor – excellent experience in general but also for anyone working toward Yachtmaster Offshore.

Student skippering yacht along Dorset Coast under instructor supervision

Take the helm for a coastal passage under professional guidance.

What You’ll Experience

  • Coastal passage planning and tidal strategy
  • Pilotage into busy harbours like Weymouth and Poole
  • Night sailing and watch rotations
  • Sail handling and reefing in variable conditions
  • Anchoring techniques in sheltered coves
Crew settling in to a night watch sailing along the Dorset Coast as the sun sets

Night sailing adds depth to your coastal experience.

Why Choose Our Dorset Cruises

  • Gain real tidal and coastal experience in a supportive environment
  • Perfect for building confidence after Day Skipper
  • Opportunity to skipper a coastal passage under supervision
  • Friendly crews and professional RYA instructors
  • Stunning scenery and memorable anchorages
Yacht anchored in Lulworth Cove on Dorset mile building cruise

Anchoring overnight in Lulworth Cove – a peaceful end to a day under sail.

What to Bring

  • RYA logbook and passport (if needed for identification)
  • Waterproof jacket and salopettes. We can provide FOC if needed
  • Warm layers and deck shoes with non-marking soles
  • Headtorch, sleeping bag, pillow.

Book Your Dorset Jurassic Coast Cruise

Join us for a Dorset Jurassic Coast Cruise and combine skill building with unforgettable scenery. Whether you’re collecting miles or building confidence, you’ll leave a more experienced sailor – and with memories of a truly beautiful coastline.

View more information on these Dorset sailing trips and see upcoming dates or email [email protected] to book your berth.

Enjoyed exploring the Dorset coast? Check out our other Mile Building adventures – short offshore Weekend Channel Hops, challenging 7-Day Channel Triangle Trips, northern Norway Expeditions and bluewater Atlantic Adventures. Learn more in our main guide to Mile Building Sailing Trips.

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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  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  All female boat for day skipper practical  - 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... read more

ALMC62
October 15, 2025

star rating  Excellent training course with Fergus!  - Excellent training course with Fergus! He made sure that across levels we were all learning and having fun! The extra context from his experience sailing was insightful and entertaining!

avatar thumb Jamie S
October 25, 2025

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