Classic Sailing Fleet - Tall Ships and Traditional Boats - UK Mainland

By Sea

Sail to Scilly from the mainland as ‘hands on’ crew on our fleet of pilot cutters, luggers, and historic sailing ships. Once in the archipelago, enjoy different anchorages, explore ashore and island hop under sail.

Classic Sailing offer 6 or 7 day sailing holidays with a skipper as your guide. We provide freshly cooked meals and accommodation on board characterful wooden vessels for a fantastic Scillies adventure.

Parton Vrane, Portscatho, Cornwall, TR2 5ET
Contact business
Pilot Cutter Agnes

Additional Information

If you have a sense of adventure and a bit of romance in your heart then arriving in the Isles of Scilly on a good looking sailing ship, sets you apart.

You don’t need any sailing experience as our skippers and mates will train you to set sails, steer the ship and keep a good look out for wildlife and shipping.

These are sailing holidays where you live on board. Occasionally we eat ashore, but meals on board are a highlight and part of the price.

Once in the islands you are visiting as a sailor, so our days are dictated by weather and tides. You can help navigate the myriad of rocks and channels, island hop, beachcomb, wildlife watch, snorkel in crystal clear seas and chill out amongst the sea pinks. Watch the ocean sunset from wooden decks whilst supper is cooking, or enjoy an ‘off island’ after the day visitors have left.

It is a sociable holiday and ideal for solo travellers who relish the chance to explore the Scillies whilst doing something active.

Our 2016 Scillies Fleet include:

38ft pilot cutter ‘Eve of St Mawes’ – 6 day Isles of Scilly voyages starting and finishing in St Mawes, Cornwall.

46ft pilot cutter ‘Agnes’ - 6 day Isles of Scilly voyages starting and finishing in Falmouth, Cornwall

68ft three masted sailing lugger ‘Grayhound’ – 7 day Isles of Scilly voyages starting and finishing in Falmouth, Cornwall.

84ft West Country Tradiding Ketch 'Bessie Ellen' - 6 day Isles of Scilly voyage starting and finishing in Falmouth, Cornwall.

85ft two masted ketch ‘Irene’ - 6 day Isles of Scilly voyages starting and finishing in Penzance, Cornwall. A shorter passage on a larger tall ship that has two person cabins.

Other Classic Sailing vessels that often run Scillies voyages are Brixham Trawlers Leader and Provident and gaff cutter Eda Frandsen.

Classic Sailing has been successfully running sailing holidays to the Isles of Scilly since 1997. Most our voyages are scheduled for early and peak summer, but in the event of prolonged bad weather or dangerous swell, the skipper may have to seek out more sheltered sailing grounds, which maybe Cornwall or Brittany. Please ring us for advice if you have any mobility issues.

Island Hopping Voyages in the Scillies – all vessels, dates and prices

Opening Times

Trips to the Isles of Scilly offered from April - September. Please call our booking office on 01872 580022 (Monday - Friday) or reserve a place via our website. If the website shows availability, please fill in the online booking form for that voyage and vessel to reserve a place. Classic Sailing will confirm your reservation by email.

Facilities & Features

  • Historic sailing ships or authentic replicas
  • Suitable for experienced sailors or adventurous beginners
  • Participation in the sailing is part of this holiday
  • Child discounts available on Sailing Lugger Grayhound
  • 6 night prices for adults from £790 per person
  • Learn nautical skills from knots to navigation
  • Learn more about Cornish maritime history
  • Wildlife Safari with an Isles of Scilly naturalist included on all Eve of St Mawes voyages
  • All vessels are certified for charter by UK Maritime Coastguard Agency
  • 25 Scillies voyages to choose from, from April to September

Prices & Conditions

From £790.00 per person to £980.00 per person: price includes 6-7 days accommodation on board ship, travel to Scillies and back from either St Mawes, Falmouth or Penzance, all meals aboard, sailing instruction, ships professional crew, boat trips ashore and mooring costs. Child discounts on Grayhound

We have a range of vessel sizes and accommodation layouts that sleep from 6 to 12 persons with no supplements for solo travellers.