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Sailing Holiday: Devon, Cornwall and the Isles of Scilly

Sailing Holiday: Devon, Cornwall and the Isles of Scilly

Coastal Sailing

No previous experience required

Sailing along the coast of Devon and Cornwall is to experience English sailing at its very best. This is a sailing route of dramatic cliffs and rocky coastlines, visiting beautiful, historic towns, and anchoring in secluded coves and peaceful rivers, with endless footpaths, history and wildlife to enjoy. Further west we will also sail to and explore the Isles of Scilly, an archipelago of 140 micro islands just off the Cornish coast with  Caribbean-like blue waters and glorious beaches.  
Sailing location image

These are the available dates and routes. To book your place, please select the dates from the drop-down above the ‘Add to Cart’ button.


  • Start date / place: June 21 2021. Portland Marina, United Kingdom
  • End date / place: July 02 2021. Portland Marina, United Kingdom
  • Full price: £1,499
  • Deposit: £375


  • Start date / place: July 05 2021. Portland Marina, United Kingdom
  • End date / place: July 16 2021. Portland Marina, United Kingdom
  • Full price: £1,499
  • Deposit: £375


  • Start date / place: July 19 2021. Portland Marina, United Kingdom
  • End date / place: July 30 2021. Portland Marina, United Kingdom
  • Full price: £1,499
  • Deposit: £375


  • Start date / place: August 02 2021. Portland Marina, United Kingdom
  • End date / place: August 13 2021. Portland Marina, United Kingdom
  • Full price: £1,499
  • Deposit: £375


  • Start date / place: August 16 2021. Portland Marina, United Kingdom
  • End date / place: August 27 2021. Portland Marina, United Kingdom
  • Full price: £1,499
  • Deposit: £375


Please see ‘TRAVEL – GETTING TO & FROM YOUR TRIP’ tab for advice on start and end points.



This is non-refundable. On making payment, your berth is guaranteed. Full Covid money back guarantees apply allowing you to book with confidence.

Paying the balance
The balance of the invoice can be paid at any time. It must be received by Rubicon 3 90 days before the trip start date or your place will automatically be cancelled. We will remind you of the date nearer the time.

Cancellations and moving trips
Our expedition sailing yachts only have between 7 and 10 berths on them. When you book, you are committing to take one of these places. Due to these very limited numbers, we will often have turned away someone else who would have liked the berth. Unlike many other holidays, please understand this gives us little if any flexibility to make changes or to move trips. We will always endeavour to assist you (& the earlier you tell us the better), but unless we can find someone else to take your place, we usually cannot move your booking.

This is a sample itinerary only of our Devon, Cornwall and the Isles of Scilly sailing holiday. The exact itinerary is decided in association with you the crew in light of the wind and weather at the time.

Joining day

This is all about helping you get up to speed with the boat and to learn or refresh all the basic sailing skills. We allow loads of time and you will never be rushed or pressured. These holidays are all about learning and we know that people will be at all different levels. You will be given all the time and space you need to enjoy your learning or revision! Once we slip lines, we will be practising tacking, gybing, reefing, casualty overboard and all the other key skills we must have. We will likely stop in Weymouth on the first night and have some lovely fish and chips on the seafront.

Sail around Portland Bill to the fishing port of Brixham

Brixham Fishing Village

A gorgeous sail today as we head down the east shore of Portland and then round the infamous Portland Bill with its powerful today races. Once free of them, its around 40nm across Lyme Bay. By early evening, we’ll be making landfall again, with a whole range of destinations to choose from. One of our favourites in Brixham, a gorgeous little fishing harbour with brightly coloured chocolate box houses, an active fishing fleet, and some lovely traditional pubs.


Dartmouth Seafront

The next day, maybe it’s just the short sail to the glorious river Dart, and the famous naval town of Dartmouth. It’s really wonderful sailing up this river, with its high wooded sides and magnificent houses looking out over the water. Dartmouth is surely one of Devon’s prettiest tows, full of pastel-coloured 17th- and 18th-century buildings, most leaning at surprising angles, and a really picturesque harbour where we can doc for the night.


Salcombe Scenery

It’s fifteen miles or so from Dartmouth to Salcombe. This uber chic town is found at the mouth of the Kingsbridge estuary, and has a network of ancient, winding streets bordered by glistening water and sandy coves. Sheltered by the lovely hills that make up the South Devon Area of Outstanding Natural Beauty and renowned for its picture-postcard harbour, sun-soaked beaches and idyllic coastal views, Salcombe is one of our absolute favourites.

Anchoring in the River Yealm

River Yealm Harbour

Another 15-20nm sail today takes us to the River Yealm, just east of Plymouth. This is a bustling, sheltered anchorage, with a picture perfect backdrop. The Yealm is a perfectly natural harbour and sanctuary for protected wildlife. We’ll need to navigate the sand bar and shallow waters around the harbour entrance, before reaching deeper waters, and heading past the forested headlands of Misery Point and Warren Point until the unforgettable aspect of Newton Ferrers sweeps into full view.


Falmouth, Cornwall

A longer sail today, with around 40nm west south west to the iconic sailing town of Falmouth. Few seaside towns in Cornwall have such a lovely location as Falmouth, overlooking the Fal River as it flows into the English Channel. Surrounded by green hills and blue sea, Falmouth is a really gorgeous jumble of lanes, old pubs, slate roofs and trendy cafes and has Cornwall’s finest maritime museum.

Housel Bay and Lizard Point

Housel Bay and Lizard Point

Around 20nm south west of Falmouth is the gorgeous Housel Bay, right next to Lizard Point. This sheltered anchorage is an absolute favourite with its sandy beach overlooked by soaring cliffs, and houses perched on the very edge looking out over the sea.

The Isles of Scilly

Isles of Scilly Sailing

It’s time to leave the mainland behind and sail the 40nm or so the wonderful Isles of Scilly. The archipelago is one of dramatic, rugged coastlines, with steep rock faces and deep inlets caused by the continuous pounding of the Atlantic Ocean. These stunning islands are famous for their white sandy beaches, archaeological sites, beautiful walking routes and a way of life seemingly from another time. The entire archipelago is an Area of Outstanding Natural Beauty and it’s easy to see why.

Although there are 140 islands in total, only five are inhabited: St. Mary’s, St. Martin’s, St. Agnes, Bryher and Tresco (with its world-famous Tresco Abbey Garden ).


Usually the first island we’ll see on the horizon with its famous red and white daymark erected in 1683 welcoming us to Scilly,  St Martins is just two miles long yet it has some of the finest beaches in the British Isles.


The Isles of Scilly’s largest island (population 1,800) and the gateway to the rest of the islands, St Mary’s main settlement is Hugh Town.


The smallest of the inhabited island on the Scillies, Bryher has some beautiful walks and scenery and just 80 people are lucky enough to call it home. Hell Bay Hotel or the Fraggle Rock Pub for a light refreshment is a must for everyone!


The second-largest of the islands, Tresco is a subtropical gem and home to the famous Abbey Garden, established in the 1830s by Augustus Smith. This horticultural paradise hosts a spectacular collection of more than 20,000 exotic plants from all corners of the world – many of which cannot be grown anywhere else in Britain.


The southernmost and smallest populated island of the Isles of Scilly is totally unspoilt and astonishingly peaceful. An island of extreme contrasts, with rocky outcrops on its exposed western side and serene beaches on the other side.

Along with these main islands, there are also a plethora of smaller uninhabited islands that we can explore.

Sail back to Portland

Our time is nearly up, but there is still one more exhilarating sail, and that is the 130nm sail back east to Portland. If we do this in one go, it will be a wonderful full 24 hour sail, watching the sun set behind us and carrying on under the stars, which is always special in the warmer summer months and will give memories of a lifetime. We’ll pass by Portland Bill and head up to the marina and the end of the trip


  • You should join the boat in Portland Marina, DT5 1DX, at 0900 hrs on the first day.
  • You will disembark the boat in Portland Marina, DT5 1DX, at 1200 hrs on the last day.


These adventure sailing holidays are open to everyone aged 18 years and over. If you are aged 70 or over, or have any concerns about your health, we ask that you get a doctor’s note before booking. This is just to make as certain as possible that you will be okay out on the water.


We provide the foul weather clothing, life-jackets and all other technical equipment you will need. You need to bring a sleeping bag and some waterproof boots.

See more information and the full kit list here


We believe that as many people as possible should be able to head out to sea and have a great adventure. However, it is essential for everyone’s safety that you are in a fit enough state to be on board. Ability to complete the five exercises below is a pre-requisite for joining as a crew member. They are not designed to be physically taxing and almost everyone should be able to complete them. Rather they are in place to check that you have the stability and basic physical condition to be on-board. If when you join the vessel the skipper believes you are not capable of completing these exercises, you will probably not be allowed to embark. If you have any doubts at all about your ability to complete these exercises safely, you must contact your doctor before attempting them.

Fitness to sail


Four weeks before your trip start date, you will be sent final joining instructions. At this time you will be asked to complete our medical declaration. At the time of booking, it is your responsibility to be sure that you will be able to pass all the criteria at the start date of your trip. If you cannot pass the criteria you will probably be refused permission to board.

See the Medical Declaration here


  • All crew must have adequate travel insurance in place for your sailing holiday.
  • We strongly recommend that you arrange insurance as soon as you book. This ideally will cover you for any mishaps, medical or otherwise, in the build-up to your holiday so that should you have to cancel, you can reclaim your fees.
  • Please note we will not refund your money or cancel your invoice due to medical issues that disqualify you from joining your trip.
  • For our latest guidance on travel insurance, please read here.


For a full explanation of what to expect with the various trip ratings please click here.


  • Foul weather clothing to keep you dry in any conditions.
  • Fladen immersion suits. These will keep you warm in even the coldest, windiest conditions.
  • Ocean-spec lifejackets. These are the best on the market.
  • All on-board food and snacks.
  • Daily sailing lessons and tuition from two highly experienced instructors.
  • RYA sailing qualifications where applicable.


  • Your travel to and from the start and end points.
  • Travel insurance (see our travel insurance page here)
  • Any alcohol – but feel free to bring your own or buy some along the route
  • Any meals you eat ashore


Everything’s included except for flights, travel insurance, a sleeping bag and some waterproof boots. There are no hidden extras.

  • These expeditions have small numbers of people on board. When you book, you are committing to being a part of the crew.
  • These are genuine adventure sailing holidays and you will be helping sail the boat, planning where we go, navigating, cooking and keeping the boat clean and tidy.
  • When you book, the deposit is non refundable. It is possible to cancel subsequently, however you may still be liable for the balance of the invoice, depending on how close you are to the start date when you cancel.
  • Please ensure you  have read and agreed to the T&Cs and read the Trip Notes before booking.

    Terms & Conditions