Taster Sailing Holidays

Our taster sailing holidays are perfect for those looking to try something new or those looking for a short break under sail. From overnight sailings to long weekends, our taster voyages are suitable for all experiences and ages.

Easter Sailing on Bessie Ellen

Discover life aboard a traditional tall ship as you explore the sheltered coastline of Cornwall from Fowey.
  • Date: 6 April 2023
  • Vessel: Bessie Ellen
  • Duration: 5 days
  • Where: Fowey, Cornwall

Cornish Coastal Sailing Adventure

Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
  • Date: 7 April 2023
  • Vessel: Pellew
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Easter Weekend Sailing in the Hebrides

Explore the magic of the Hebrides on the West coast of Scotland with modern yacht Stravaigin.
  • Date: 7 April 2023
  • Vessel: Stravaigin
  • Duration: 4 days
  • Where: Oban, Scotland

Easter Sailing Weekend in Devon

Enjoy a real taste of traditional sailing exploring the coast of South Devon on the magnificent heritage vessel Pilgrim of Brixham.
  • Date: 7 April 2023
  • Vessel: Pilgrim of Brixham
  • Duration: 4 days
  • Where: Brixham, Devon

Easter Sailing with Lugger Grayhound

Discover the Cornish coast this Easter with a taster sailing holiday adventure onboard lugger Grayhound.
  • Date: 7 April 2023
  • Vessel: Grayhound
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Taster Sailing Weekend in Cornwall

Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
  • Date: 14 April 2023
  • Vessel: Pellew
  • Duration: 3 days
  • Where: Falmouth, Cornwall

Coastal Sailing in South Devon

Explore the wonderful coast of Devon with a sailing weekend on a classic boat. Perfect for those wanting to get to grips with life under sail.
  • Date: 14 April 2023
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Weekend Sailing in Cornwall

Discover life aboard a traditional tall ship as you explore the sheltered coastline of Cornwall from Fowey.
  • Date: 14 April 2023
  • Vessel: Bessie Ellen
  • Duration: 3 days
  • Where: Fowey, Cornwall

Overnight Tall Ship Sailing in Devon

Enjoy a real taste of traditional sailing with a two-day voyage in Devon on the magnificent Pilgrim of Brixham.
  • Date: 22 April 2023
  • Vessel: Pilgrim of Brixham
  • Duration: 2 days
  • Where: Brixham, Devon

Coastal Sailing in South Devon

Explore the wonderful coast of Devon with a sailing weekend on a classic boat. Perfect for those wanting to get to grips with life under sail.
  • Date: 28 April 2023
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Heritage Sailing on the South Devon Coast

Enjoy a real taste of traditional sailing exploring the coast of South Devon on the magnificent heritage vessel Pilgrim of Brixham.
  • Date: 28 April 2023
  • Vessel: Pilgrim of Brixham
  • Duration: 4 days
  • Where: Brixham, Devon

Overnight Tall Ship Sailing in Devon

Enjoy a real taste of traditional sailing with a two-day voyage in Devon on the magnificent Pilgrim of Brixham.
  • Date: 6 May 2023
  • Vessel: Pilgrim of Brixham
  • Duration: 2 days
  • Where: Brixham, Devon

Taster Sailing through the Kiel Canal

Join Eye of the Wind for a tall ship taster sailing adventure from Hamburg to Kiel passing through the Kiel Canal.
  • Date: 8 May 2023
  • Vessel: Eye of the Wind
  • Duration: 5 days
  • Where: Hamburg, Germany

Taster Sailing in South Devon

Enjoy three days sailing the coasts of South Devon on classic trawler Pilgrim of Brixham.
  • Date: 12 May 2023
  • Vessel: Pilgrim of Brixham
  • Duration: 3 days
  • Where: Brixham, Devon

Taster Sailing in the Hebrides

Explore the magic of the Hebrides on the West coast of Scotland with modern yacht Stravaigin.
  • Date: 16 May 2023
  • Vessel: Stravaigin
  • Duration: 4 days
  • Where: Oban, Scotland

Brixham Heritage Regatta Sailing

Climb aboard this stunning classic yacht for a weekend discovering the Brixham Heritage Regatta. Sail to this beautiful port from Dartmouth, marvel at traditional vessels and race them.
  • Date: 27 May 2023
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Coastal Sailing Break in South Devon

Explore the wonderful coast of Devon with a sailing weekend on a classic boat. Perfect for those wanting to get to grips with life under sail.
  • Date: 2 June 2023
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Sailing the Baltic Sea & Exploring Denmark

Explore the Kiel fjord and the South Funen Archipelago of Denmark with historic windjammer Eye of the Wind
  • Date: 3 June 2023
  • Vessel: Eye of the Wind
  • Duration: 8 days
  • Where: Germany/Denmark

Sailing the Baltic Sea & Exploring Denmark

Explore the Kiel fjord and the South Funen Archipelago of Denmark with historic windjammer Eye of the Wind
  • Date: 10 June 2023
  • Vessel: Eye of the Wind
  • Duration: 8 days
  • Where: Germany/Denmark

Tall Ship Taster Sailing in Scotland

Discover the West coast of Scotland with a tall ship taster sailing adventure exploring the Isle of Mull.
  • Date: 13 June 2023
  • Vessel: Blue Clipper
  • Duration: 4 days
  • Where: Oban, Scotland

Falmouth Classics & Sea Shanty Festival

Sail and race with Escape as she takes part in the iconic Falmouth Classics Regatta and Sea Shanty Festival.
  • Date: 16 June 2023
  • Vessel: Escape
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Sailing the Baltic Sea & Exploring Denmark

Explore the Kiel fjord and the South Funen Archipelago of Denmark with historic windjammer Eye of the Wind
  • Date: 19 June 2023
  • Vessel: Eye of the Wind
  • Duration: 5 days
  • Where: Germany/Denmark

Coastal Sailing in South Devon

Explore the wonderful coast of Devon with a sailing weekend on a classic boat. Perfect for those wanting to get to grips with life under sail.
  • Date: 7 July 2023
  • Vessel: Escape
  • Duration: 4 days
  • Where: Dartmouth, Devon

Weekend Sailing in South Devon

Explore the wonderful coast of Devon with a sailing weekend on a classic boat. Perfect for those wanting to get to grips with life under sail.
  • Date: 14 July 2023
  • Vessel: Escape
  • Duration: 4 days
  • Where: Dartmouth, Devon

Sailing Weekend in South Devon

Explore the wonderful coast of Devon with a sailing weekend on a classic boat. Perfect for those wanting to get to grips with life under sail.
  • Date: 28 July 2023
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Taster Sailing in South Devon

Enjoy three days sailing the coasts of South Devon on classic trawler Pilgrim of Brixham.
  • Date: 15 August 2023
  • Vessel: Pilgrim of Brixham
  • Duration: 3 days
  • Where: Brixham, Devon

Taster Sailing in South Devon

Enjoy three days sailing the coasts of South Devon on classic trawler Pilgrim of Brixham.
  • Date: 19 August 2023
  • Vessel: Pilgrim of Brixham
  • Duration: 3 days
  • Where: Brixham, Devon

Sailing Dartmouth Regatta

Climb aboard this traditional Brixham Trawler as she sails around Berry Head for the Dartmouth Regatta.
  • Date: 24 August 2023
  • Vessel: Pilgrim of Brixham
  • Duration: 4 days
  • Where: Brixham, Devon

Summer Sailing in South Devon

Explore the wonderful coast of Devon with a sailing weekend on a classic boat. Perfect for those wanting to get to grips with life under sail.
  • Date: 25 August 2023
  • Vessel: Escape
  • Duration: 4 days
  • Where: Dartmouth, Devon

Sailing the Cornish coast

Sail with traditional wooden boat Pilgrim of Brixham to explore the Cornish coast under sail.
  • Date: 31 August 2023
  • Vessel: Pilgrim of Brixham
  • Duration: 4 days
  • Where: Brixham, Devon

Cornish Coastal Sailing Adventure

Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
  • Date: 7 September 2023
  • Vessel: Pellew
  • Duration: 6 days
  • Where: Falmouth, Cornwall

Taster Sailing in Cornwall

Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
  • Date: 15 September 2023
  • Vessel: Pellew
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Tall Ship Taster Sailing in Portugal

Sail with tall ship Maybe from Portimao and explore the Algarve region of Portugal for a tall ship taster sailing experience.
  • Date: 15 September 2023
  • Vessel: Maybe
  • Duration: 5 days
  • Where: Portugal

Taster Sailing in Cornwall

Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
  • Date: 21 September 2023
  • Vessel: Pellew
  • Duration: 5 days
  • Where: Falmouth, Cornwall

Tall Ship Taster Sailing in Portugal

Sail with tall ship Maybe from Portimao and explore the Algarve region of Portugal for a tall ship taster sailing experience.
  • Date: 22 September 2023
  • Vessel: Maybe
  • Duration: 5 days
  • Where: Portugal

Taster Sailing in Cornwall

Discover and explore the Cornish Coast with exhilarating sailing by day and hidden anchorages by night onboard Pilot Cutter Pellew.
  • Date: 29 September 2023
  • Vessel: Pellew
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Taster Sailing in South Devon

Enjoy three days sailing the coasts of South Devon on classic trawler Pilgrim of Brixham.
  • Date: 29 September 2023
  • Vessel: Pilgrim of Brixham
  • Duration: 3 days
  • Where: Brixham, Devon

Tall Ship Taster Sailing in Portugal

Sail with tall ship Maybe from Portimao and explore the Algarve region of Portugal for a tall ship taster sailing experience.
  • Date: 29 September 2023
  • Vessel: Maybe
  • Duration: 5 days
  • Where: Portugal

Overnight Tall Ship Sailing in Devon

Enjoy a real taste of traditional sailing with a two-day voyage in Devon on the magnificent Pilgrim of Brixham.
  • Date: 14 October 2023
  • Vessel: Pilgrim of Brixham
  • Duration: 2 days
  • Where: Brixham, Devon

Easter Sailing Weekend in the Hebrides

Explore the magic of the Hebrides on the West coast of Scotland with modern yacht Stravaigin.
  • Date: 29 March 2024
  • Vessel: Stravaigin
  • Duration: 4 days
  • Where: Oban, Scotland

Weekend Sailing in the Hebrides

Explore the magic of the Hebrides on the West coast of Scotland with modern yacht Stravaigin.
  • Date: 5 April 2024
  • Vessel: Stravaigin
  • Duration: 4 days
  • Where: Oban, Scotland

Weekend Sailing in the Hebrides

Explore the magic of the Hebrides on the West coast of Scotland with modern yacht Stravaigin.
  • Date: 12 April 2024
  • Vessel: Stravaigin
  • Duration: 4 days
  • Where: Oban, Scotland

Taster Sailing in the Hebrides

Explore the magic of the Hebrides on the West coast of Scotland with modern yacht Stravaigin.
  • Date: 29 April 2024
  • Vessel: Stravaigin
  • Duration: 4 days
  • Where: Oban, Scotland

Taster Sailing Weekend in the Hebrides

Explore the magic of the Hebrides on the West coast of Scotland with modern yacht Stravaigin.
  • Date: 27 September 2024
  • Vessel: Stravaigin
  • Duration: 4 days
  • Where: Oban, Scotland