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Sail to the Fabulous Isles of Scilly

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Embark Disembark Vessel DurationVoyage No
Sun 20-08-2023, 12:00Charlestown, Cornwall Fri 25-08-2023, 12:00Charlestown, Cornwall Anny of Charlestown 5 NightsAY200823

Set sail for the Isles of Scilly on Anny of Charlestown from her home base of Charlestown. Pass the famous headlands of the Dodman and Lizard before crossing Mounts Bay and on to the Scilly Isles. Enjoy exploring some of the fascinating and unique island before returning to Charlestown on the mainland. Possibility of overnight sailing and watch keeping.

  • Voyage
  • Vessel


  • Explore the Isles of Scilly
  • Famous Headlands to round – Dodman and the Lizard
  • Good dolphin and basking shark sighting opportunities
  • Possible overnight sailing

Anny of Charlestown

Sailing Areas Cornwall
Vessel type / Rig Topsail Schooner
Guest Berths 7
Beam 1602ft
Draft 9ft
Deck Length 63ft
Overall Length 89ft
Year Built 1930
More about the Vessel

Voyage Description


Adventurous beginners and sailors who love the mix of a coastal passage to find your sea legs, and then a short offshore passage beyond Lands End where you are truly out in the Atlantic Ocean. In the Scillies your landing stage is usually a beach, so if you like wild anchorages without marine type facilities then these wildlife and nature voyages are for you.  For those who have not been to the Isles of Scilly expect scenery not too different from the Seychelles, glistening blue sea water, stunning deserted beaches and 360 degree panoramas from anchorages where there is no light pollution. Bird watchers, wildlife photographers, Robinson Crusoe types and sunset watchers will love this place.

Full Voyage Description

  • Unique group of granite islands
  • Sub tropical gardens, flower fields & heather moorland
  • Good for bird watching, dolphins and seals
  • Clear waters for snorkeling but bring a wetsuit!
  • Intricate navigation and traditional pilotage to learn
  • 100 mile passage
  • Dazzling white sand beaches
  • Possible overnight sailing
isles of scilly
Tresco Flats, the isles of scilly

Charlestown to the Isles of Scilly

Anny of Charlestown is a good choice for a voyage to the Scillies. She is big enough to be comfortable when sailing offshore. With a long waterline her cruising speed is better than smaller vessels. Once at anchor in a beautiful setting, whether it is the Cornwall mainland on route or the Scillies, you have wide decks and plenty of places to sit and absorb the panoramic views. Ashore you can stride out around an island, clamber around the the granite tors, bird watch or beach comb. In Spring there are puffins and shearwaters and in the late summer the seas are having their pups.

On a sailing voyage nothing is guaranteed and the sailing itinerary may not be always adhered too. Skippers will always aim for the best sailing and shore landings for the forecast including all or some of the highlights described below, but you have to go with mother nature and not fight her. The description below is based on what Classic Sailing think might be possible based on past trips and experience. The Scillies does not have a single port or anchorage that is sheltered for all wind directions so if the forecast indicates bad weather or high swell then the skipper may have to seek our alternative sailing grounds. the crew will always endeavour to provide a holiday adventure as close in spirit to a ‘Scilles’ voyage as they can.

Spot Marine Wildlife along the Way

Leaving Charlestown you pass two famous headlands, the Dodman and the Lizard and the lonely Wolf Rock Lighthouse. Look out for dolphins and basking sharks where the tides run the fastest. Good spots are off the Lizard, Epsom Shoal, Wolf Rock, Lands End and as you approach the Scillies

Depending on the weather, Anny of Charlestown may make a stop in South Cornwall on her way to the Scillies but if the winds are perfect she may sail there in one long hop. The thrill of spotting the Isles of Scilly when this fascinating archipelago first appears over the horizon never goes away, however many times you visit. Choosing and making your destination in the Scillies is greatly cherished because not only do you arrive in style under sail but you have been part of the journey, your effort and team work has made it possible. Worth a pint in the Turks Head in fact.

Turks Head pub on St Agnes
Most Sw pub in England – Turks Head on St Agnes

Exploring the Isles of Scilly 

By sailing west to the Isles of Scilly and anchoring in quiet bays, you will get to know this fabulous archipelago from a sailor’s point of view. You can sail among and round the rocks, from island to island, often using intricate pilotage. 

Look out for Atlantic grey seals in the Western rocks or in among the kelp beds. Take the opportunity to snorkel or swim in the clear water of Scilly’s many wonderful bays, or ramble round on foot to experience the local flora and fauna. 

The white glittering sands are reminiscent of the Seychelles, the turquoise waters are crystal clear, but the water temperature is refreshingly British!  Exploring ashore is a key part of the holiday with tropical Tresco Abbey Gardens to visit, or you can wander lonely as a cloud over purple heathland or beach comb amongst the oystercatchers. The pilotage between the islands is complex and fascinating if you are interested in navigation. 

There is NO light pollution on the Scillies so star gazing at night is exceptional and words can hardly prepare you for the sunrises and the sunsets enhancing the peace and tranquility that these beautiful islands will offer you whilst sailing on a beautiful traditional boat. 

Great Bay St Martin, Isles of Scilly
Great Bay on St Martin, Isles of Scilly


Island Life Dependant on Boats

In the Scillies there are no marinas or places, so there is a lot of getting in and out of dinghies, and the anchorages are typically remote with limited or no facilities ashore.

gig racing twice a week on the Scillies
Photo Debbie Purser. Pilot gig racing twice a week on the Scillies



This voyage involves remote anchorages and the possibility of a bit of a roll in any swell, even in calm weather. Please note that  there is no guarantee that the ship will make it to the Scillies, as the passage there can get very rough in certain wind conditions. The skipper will always aim for maximum enjoyment for everyone on board, rather than pushing too hard to tick off certain destinations. Usually Anny does make it out to the Islands, but it can still be quite exciting on the passage even in fine weather! This voyage would be similar to a cross channel voyage in terms of offshore sailing. Between the islands there is some sheltered water sailing but it depends a bit on wind direction. The climate is often more sunny than the mainland and sub tropical plants grow well here.


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

Charlestown, Cornwall

This historic private harbour is the home port of Anny and Mascotte, but there are often several tall ships in the dock and you never quite know what you will find.

Charlestown Harbour is set on the rugged South Cornish Coast. The last open 18th Century Georgian harbour in the UK, Charlestown is proud to be a UNESCO world heritage site, with a unique history and geography. Charlestown is still a vibrant working port, with classic sailing vessels, beautiful beaches and great places to eat and drink.

Charlestown Harbour has also made a name for itself in the film and TV industries, featuring in Poldark, Taboo, Hornblower and many other productions.

A natural amphitheatre and great setting for your friends or relatives to come and wave goodbye from. Charlestown is tidal, so access both in and out is determined by high tide times. We will advise you nearer to departure of the exact joining times.

Kit List


  • Sailing Instruction 
  • Safety Equipment (Life jackets and harnesses) 
  • All meals to include refreshments throughout the day
  • Bed linen, duvet, pillows 
  • Waterproof jacket and trousers - but you are welcome to bring your own if you prefer

What is not included 

  • towels
  • Alcoholic beverages
  • Towels
  • wellie boots

What to Bring

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

Anny does have waterproof jacket and trousers you can borrow in a variety of sizes. if you have your own outdoor waterproof of any type you might want to bring your own so you know you can get a good fit.

 If you need any advice please ring us on 01872 580022

  • warm, windproof jacket for days when you don't want to wear a heavy waterproof jacket
  • 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 
  • Camera, binoculars, sketchbook, a relaxing read.
  • Passport for French Voyages, Reciprocal Free Health Care card in Europe.
  • Please bring a passport on French trips 
  • 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.

Anny 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.





We had the best time . Phil the Captain, Lucy and Coby were really great. We couldn’t fault our 4 days away and would gladly do it again.


The trip was about going too the Scillies, sadly we didn't manage to go due to the weather, however the crew quickly came up with plan B, this was agreed by all and we very quickly got over our dissapointment because the crew made such a great effort in Plan B, we enjoyed the great mix of sailing and trips ashore the crew looked after all our needs being helpfully to all during the trip. The crew of only three worked really hard ensuring we were happy and safe.


Beautiful ship, professional and very kind crew. Absolutely lovely experience!


Anny is an absolutely stunning boat, and the crew could not have done more to make our holiday magical and relaxing.


We had such a great weekend on Anny. She is a beautiful boat and the photos don't do her justice. She is well kitted out with a very comfortable galley area and the beds are all very comfy and cosy.


Beautiful clean boat. Great hospitality! Would totally recommend this lovely boat.


Vessel Gallery

Anny of Charlestown is a beautiful topsail schooner operating on the Coast of Cornwall for the first time, after years as a charter vessel in Europe and the Caribbean (as Fiddlers Green). She was built in Denmark in 1930 and her massive oak timbers create that homely and solid feel that only wooden sailing vessels can provide. We think she will turn many heads along the headlands, beaches and historic ports of Cornwall as well as further afield. A great mix of gaff sails and square sails on this pocket tall ship that only sleeps 8 guest crew.

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