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Dartmouth Regatta Sail

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Embark Disembark Vessel DurationVoyage No
Thu 29-08-2024, 12:00Brixham, UK Sun 01-09-2024, 12:00Brixham, UK Pilgrim 3 NightsPM290824

Pilgrim’s Dartmouth Regatta Sail is one of the highlights of our season. As the second largest Regatta in the UK, the Dartmouth Royal Regatta features around 50 sailing races involving over 250 vessels. You’ll have the chance to see the racing from a unique perspective as well as participating in the Classic Craft Parade on the Saturday afternoon.

Pilgrim is a fully restored heritage sailing trawler, and a proud member of the UK National Historic Fleet.  She was built in Brixham in 1895 at Upham’s Yard, which was located right next to where she now berths.

  • Voyage
  • Vessel

Ideal Voyage for ..

This is the ideal short voyage for fun like minded sailors with or without experience. Pilgrim will provide you with the best seats in the house at the Royal Dartmouth Regatta.


  • 74ft length on deck historic sailing trawler
  • Friendly and helpful instruction
  • Freshly cooked food and accommodation all onboard.
  • Comfortable berths
  • Free seats at the Dartmouth Regatta
  • Participate in the Classic Craft Parade
  • Great food


Vessel type / Rig Gaff Ketch
Guest Berths 10
Beam 17.5ft
Draft 10.5ft
Deck Length 74ft
Overall Length 94ft
Tonnage 90 tons
Year Built 1895
More about the Vessel

Voyage Description


The Port of Dartmouth Royal Regatta always lives up to its reputation with superb on the water events and brilliant entertainment.

The focus of the Regatta has always been the sailing, rowing and swimming . This was the basis on which the first ever event was held in 1822! Since then a wide range of additional water and land based events have been added, making it a real highlight on the annual Regatta circuit.

This special short break covers the whole of the spectacular Dartmouth Regatta to include the famous regatta firework displays that are a real sight to behold – especially from the deck of a member of the National Historic Fleet!

During the sailing part of your days, we are very happy for you to get as involved in sailing Pilgrim as you would like to. There are plenty of opportunities to help the crew hoist the sails and even take the helm – or you may prefer to just sit back, relax and enjoy the view – it’s up to you!

Whatever you decide, enjoy the magnificent scenery as we leave Brixham, Torbay and set sail around Berry Head. This whole area is designated as an area of outstanding natural beauty. It is home to a sea bird colonies of guillemots, black legged kittiwakes, kestrels and gulls.  On our way to Dartmouth, we are often accompanied by dolphins or porpoises, so make sure you are up on deck with your camera to get some great shots of the amazing sea life.

Sailing past Berry Head, look for the lighthouse built in 1906 which has the distinction of being the smallest, highest and deepest lighthouse in the British Isles.  It is over 16 feet high and its white light can be seen for 14 nautical miles. Berry Head is also the site of a Napoleonic Fort built between 1794 and 1804.  Designed to protect Torbay from the French in the days when Torbay was a strategic naval anchorage.

Sailing on Pilgrim with Classic Sailing

Enjoy the seascape and dramatic coastal scenery with interesting rock formations creating rugged limestone cliffs, sandy bays, coasta­­­l coves and inlets.  We sail past St Marys Bay, a popular caravan holiday destination, the dramatic headland of Sharkham Point and then, hidden from view, the National Trust property of Coleton Fishacre, once the home of the Doyle Cart family.

A ‘Day Mark’ built in 1864 on the eastern side of the estuary helps us identity the River Dart.  We then pass the Mewstone rock just outside the mouth of the river.  This is often another spot to see the occasional harbour porpoise, common grey seal as well as cormorants, guillemots, gannets and sea gulls.

The rocky entrance to the r­­­­­­­iver is guarded on the west side of the estuary by a 15th Century castle, which also incorporates the church of St Petrox.

Kingswear, the harbour town directly opposite Dartmouth has its own historic castle. During the 2nd world war, the two fortifications were linked by chains at dusk to damage enemy ships attempting to attack Dartmouth.

Further up river The famous Britannia Royal Naval College sits above Dartmouth where officer training has taken place since 1863.

Other picturesque sailing areas that are within reach of Dartmouth include Slapton Bay and Salcombe Harbour or we can also sail up river to Dittisham and Conyton Fishacre the famous riverside residence of Agatha Christie.

During the voyage you will experience everything from illuminated vintage vessel parades to gig racing, many classes of yacht and dingy races, aircraft displays and fly pasts and of course the famous firework display on Saturday evening.

As you depart Dartmouth and set sail once more for Brixham you can relax with some peaceful sailing before stepping ashore.

guests enjoying the Parade of Sail, Dartmouth Regatta 2023


On a sailing voyage we never use the word itinerary, as skippers will always be aiming for the best sailing and shore landings for the forecast and most idyllic or sheltered anchors and ports. They are as keen as you to include some of the highlights described below, but you have to go with Mother Nature, not fight her. The description above is based on what we think might be possible, based on past trips, or experience, but nothing is guaranteed on a sailing voyage.


Whether you are an experienced sailor or a complete beginner, the professional crew will train you to be guest crew from the moment you arrive, with the intention that everybody works together to sail the ship. The common thread to all Classic Sailing holidays is ‘Hands on’ participation on ships that use ropes, blocks and tackles and ‘people power’ to set sail.


We cater for a wide range of ages and physical abilities and how much you are expected to do varies a bit between vessels. See the vessel tab above which explains all about the ‘sailing style’ and what to expect in terms of hands on participation. There is a lot of information about day to day life, the ships facilities and accommodation on the vessel pages.


Every customer sailing with us will need to fill in basic medical questions on their booking application. If you are not sure if your current level of fitness and agility are up to a voyage, then please ring the Classic Sailing Office on 01326 53 1234 and we can chat through your concerns and possibly find options that might suit you better.

Start & End Port

Brixham, UK

Joining or leaving point.

Assemble towards the end of the Events Pontoon Red Point above. Zoom in to your ship!

For Pilgrim, your boat will be berthed on Brixham Town Pontoon, on the east side of Brixham Harbour, opposite The Prince William Pub. Your joining times can be found on your confirmation email.

The boats can be recognised as follows:

PILGRIM Black hull and bulwarks with yellow stripe

Brixham transport and parking details

Kit List

What to pack for a sailing holiday on Pilgrim


  • Sailing Instruction
  • Safety Equipment (Life jackets and harnesses)
  • All meals to include refreshments throughout the day
  • Bed linen, duvet, pillows

What is not included

  • Waterproof jacket and trousers
  • Alcoholic beverages
  • Towels
  • Travel Insurance (see below)

What to Bring

Please limit yourself to one soft bag or rucksack as there is limited storage space on board. No suitcases please!

Pilgrim does not provide waterproofs. So you need to bring waterproof jacket and trousers. These don't have to be sailing waterproofs. Any good outdoor waterproofs should keep you warm and dry. If you are sailing on a longer voyage or in early spring or autumn you will find the sailing or mountaineering salopette type waterproof trousers will keep you warmer than walking trousers with waist. If you need any advice please ring us on 01872 580022

Please Note: Pilgrim requires ‘Insurance for more than 12 miles offshore’ on all trips of more than 1 night. This is because on these longer trips they often need to go offshore to reach the destination. E.g. Start Point to the Helford may involve us tacking south of the Eddystone Light. Classic Sailing require all guests to take out adequate and appropriate insurance on all voyages longer than a daysail. If you're sailing on a multi day voyage with Pilgrim please ensure your insurance covers Pilgrims above requirements. If you need any advice please ring us on 01872 580022

Please pack:

  • Waterproof jacket and trousers
  • Hats for sun and cold weather.
  • At least two sets of warm clothes - layers e.g. tracksuit bottoms, shirts, fleece jacket, wool jumpers, thick socks, and neck scarf. It can get cold at sea even in mid summer.
  • Swim suit, towel, and suntan lotion.
  • Flat shoes with a good grip e.g. trainers or sailing deck shoes.
  • Sailing boots or wellies as the sea can come over deck if rough*.
  • (An alternative to boots in summer is to bring another pair of flat shoes with a good grip in case the first pair get wet).
  • All terrain type sandals are great for dinghy trips ashore – but you do need shoes which protect your toes for sailing.
  • Scillies trips – Walking boots are useful and can be these can be worn on Pilgrims deck too
  • A small rucksack is useful for going ashore – especially on sailing and walking and Scillies voyages.
  • Camera, binoculars, sketchbook, a relaxing read.
  • Passport for French Voyages, Reciprocal Free Health Care card in Europe.
  • Please bring a passport on French trips or any 6 day voyage like Scillies where France could be an alternative venue.
  • Any medication, spare spectacles. Seasick tablets - check with your Doctor, which brand if you suffer asthma or are on medication.
  • RYA Cruising Logbook or similar if you want to log your sailing experience e.g. sea miles, night hours
  • Musical instruments are always welcome.

Pilgrim does not always have wine bottles for sale on board so you are welcome to bring modest quantities of alcohol e.g. to drink with evening meals, but drinking whilst sailing is not allowed.



Thank you for your email, and for providing such an amazing experience. 

The ship is beautiful, the crew lovely and friendly. We even were blessed with beautiful weather 🙂

 I had a bit of a problem with my work shifts changing, so my friend and I were really appreciative that you were so accommodating and swapped the day of our trip. I called, and spoke to someone called Roger (I think), he was very helpful. (Correct, Roger is very helpful.)

Things to improve - the crew seemed to be a bit shy. It would be nice if they would talk a bit about the ship, its history (I’m sure it has some), about its parts, may be about surrounding area, about themselves. I’m sure they have one or two stories to tell.

I’m not suggesting they have to talk throughout whole trip, but once the sails are up, particularly with nice calm weather, may be just spend an hour or so to warm up the atmosphere amongst the team, show interest in their passengers. 

Overall the trip was very enjoyable and everyone was very pleasant, and I would definitely do it again. 

Thank you so much for providing this unforgettable experience. 

Kind regards

Irina June 2024

Our family of 4 loved it! Our 11 and 12 year old boys enjoyed being involved, and the crew were great in including them where possible. Seeing them off screens and soaking up nature at a much slower pace was priceless and something they’ll always remember. It was very windy so quite a different experience from our last voyage, and welcome all the same. Great to see The Pilgrim in full swing again. We will definitely be back! Thanks to all at Classic Sailing. 

Sophie May 2024

Had a brilliant trip-many thanks to the crew!

Anonymous happy customer - July 2023

A fabulous first experience on a beautiful old ship. Skipper and crew were amazing. As was the food! Great Boat, Great Team, Great company. I would love to make a return trip and would highly recommend Pilgrim to anyone out there who is thinking about it. Sign up now! But leave a space for me please 🙂


Had an awesome time. Crew was superb and professional. Pilgrim is in fabulous shape.


Lovely boat and great crew. No question was too daft. A highly enjoyable education.


This was my first voyage on a tall ship and I had no previous experience of sailing. The crew were wonderful – friendly, calm and patiently explained and gave me confidence to help with sailing the boat. They also helped to build a warm, friendly and fun atmosphere among all of us onboard. I cannot wait until I have the opportunity to sail on Pilgrim again.


Sailing on Pilgrim was amazing. I loved every moment, she is totally beautiful. Swimming ashore and snorkelling. Building a fire on the beach. I love the freedom and peace being on the water, it's so natural and relaxing. I had such a great time with a great bunch of people.


I can't wait for the next time- sailing on Pilgrim isn't just a holiday, it's an adventure full of new experiences, friendship, laughter and fun.


A super day assisted by lovely sun and cloud, sheer joy at being on the water.


Fantastic few days sailing on Pilgrim, the experience was well past my expectations and this was the result of the crew who all worked very hard in making this an unforgettable experience.

Eddie P - Pilgrim Guest Feedback Photo
Eddie P - Pilgrim Guest Feedback Photo

Wow, what can I say about my first trip on the beautiful Pilgrim with Classic Sailing? It was amazing! I am still smiling about the utterly brilliant weekend. I booked this trip as a bit of an escape from the day to day normal life on the land and it was well worth it. I returned home more relaxed, a little sunburnt, but wanting to just jump straight back on board! I t was great fun being allowed to be involved in raising the sails and learning a bit of history about the vessel. If you hare thinking about booking a voyage, be it a day trip, weekend or longer... do it! I could not recommend it more highly and as a single traveller I also felt at ease and safe while on the whole voyage.


Brilliant, fantastic, I could not have wished for better. The crew couldn't do enough for us and made the day even more special. If you want to do something a bit different for a big birthday and something that your guests will talk about for a long time then I would highly recommend Pilgrim.


Pilgrim is a fantastic heritage project that deserves everyones support. I have sailed on her twice now and on both occasions the party has had a most wonderful sailing experience. Get out there and appreciate her!


The trip was one of the best experiences of my life and something I will never forget. Food was wonderful... beds were comfy... crew were faultless and very knowledgeable about the boat and its history. You can tell they have a true passion for their jobs. I would certainly return again and will be recommending to all I know!


Vessel Gallery

Restored Brixham Sailing Trawler Pilgrim in action and images. Photos from Classic Sailing customers, ships crew and professional photographers. We hope it gives a flavour of her sailing, life on board, the people that come, her beautiful sailing grounds and what it is like to live below decks.

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