Taster Sailing Holidays

Looking to try something new or searching for a short break under sail? Our taster sailing voyages are designed to suit all levels of experience and ages, from overnight sailings to long weekends on the water. Whether you’re a seasoned sailor or a first-time adventurer, experience life under sail and discover the beauty of life at sea.

We have found 46 voyages with berths available.

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

Coastal 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: 23 September 2023
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Taster Sailing in South Devon

Enjoy a three day sailing experience on the coasts of South Devon with classic boat 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 an overnight 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 Devon

Enjoy a real taste of traditional sailing exploring the coast of South Devon on the magnificent heritage vessel Pilgrim of Brixham.
  • Date: 29 March 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 4 days
  • Where: Brixham, Devon

Overnight Tall Ship Taster Sailing in Devon

Enjoy a real taste of traditional sailing with an overnight voyage in Devon on the magnificent Pilgrim of Brixham.
  • Date: 6 April 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 2 days
  • Where: Brixham, Devon

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 South Devon

Enjoy a three day sailing experience on the coasts of South Devon with classic boat Pilgrim of Brixham.
  • Date: 19 April 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 3 days
  • Where: Brixham, Devon

South Devon Sailing Experience

The perfect voyage for beginners looking for a new experience on the water, exploring the South Devon coast with classic yacht Escape.
  • Date: 20 April 2024
  • Vessel: Escape
  • Duration: 2 days
  • Where: Dartmouth, Devon

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

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: 3 May 2024
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Traditional Taster Sailing in Cornwall

Join traditional pilot cutter Pellew as she takes guests on an exhilarating taster sailing adventure around the coast of Cornwall.
  • Date: 3 May 2024
  • Vessel: Pellew
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Tallship Taster Sailing Holiday in Denmark

Join traditional schooner Aron for a taster sailing experience in Denmark as you explore the South Funen archipelago from Svendborg.
  • Date: 5 May 2024
  • Vessel: Aron of Svendborg
  • Duration: 4 days
  • Where: Funen, Denmark

Sailing Taster Weekend in Mull

Sail the Hebrides with Zuza, exploring hidden anchorages and amazing landscapes on foot - the perfect time of year for wildlife watching!

  • Date: 10 May 2024
  • Vessel: Zuza
  • Duration: 4 days
  • Where: Oban, Scotland

Traditional Taster Sailing in Cornwall

Join traditional pilot cutter Pellew as she takes guests on an exhilarating taster sailing adventure around the coast of Cornwall.
  • Date: 10 May 2024
  • Vessel: Pellew
  • Duration: 3 days
  • Where: Falmouth, Cornwall

South Devon Sailing Experience

The perfect voyage for beginners looking for a new experience on the water, exploring the South Devon coast with classic yacht Escape.
  • Date: 11 May 2024
  • Vessel: Escape
  • Duration: 2 days
  • Where: Dartmouth, Devon

Overnight Tall Ship Taster Sailing in Devon

Enjoy a real taste of traditional sailing with an overnight voyage in Devon on the magnificent Pilgrim of Brixham.
  • Date: 11 May 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 2 days
  • Where: Brixham, Devon

Tallship Taster Sailing Holiday in Denmark

Join traditional schooner Aron for a taster sailing experience in Denmark as you explore the South Funen archipelago from Svendborg.
  • Date: 14 May 2024
  • Vessel: Aron of Svendborg
  • Duration: 4 days
  • Where: Funen, Denmark

Taster Sailing in Scotland

Join adventure yacht Steady for a taster sailing holiday in the inner Hebrides, Scotland.
  • Date: 17 May 2024
  • Vessel: Steady
  • Duration: 4 days
  • Where: Oban, Scotland

Brixham Heritage Regatta Sailing Weekend

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: 25 May 2024
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Sailing Taster around Mull, Scotland

Sail the Hebrides with Zuza, exploring hidden anchorages and amazing landscapes on foot - the perfect time of year for wildlife watching!

  • Date: 31 May 2024
  • Vessel: Zuza
  • Duration: 5 days
  • Where: Oban, Scotland

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: 31 May 2024
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Traditional Taster Sailing in Cornwall

Join traditional pilot cutter Pellew as she takes guests on an exhilarating taster sailing adventure around the coast of Cornwall.
  • Date: 7 June 2024
  • Vessel: Pellew
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Overnight Tall Ship Taster Sailing in Devon

Enjoy a real taste of traditional sailing with an overnight voyage in Devon on the magnificent Pilgrim of Brixham.
  • Date: 7 June 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 2 days
  • Where: Brixham, Devon

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: 14 June 2024
  • Vessel: Escape
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Tall Ship Taster Sailing in the Hebrides

Experience the West Coast of Scotland with a tall ship taster sailing holiday. Perfect for those adventurers looking for something new and unique!
  • Date: 20 June 2024
  • Vessel: Blue Clipper
  • Duration: 5 days
  • Where: Oban, Scotland

South Devon Sailing Experience

The perfect voyage for beginners looking for a new experience on the water, exploring the South Devon coast with classic yacht Escape.
  • Date: 29 June 2024
  • Vessel: Escape
  • Duration: 2 days
  • Where: Dartmouth, Devon

Taster Sailing in the Firth of Clyde

Discover the idyllic landscapes and sheltered waters of the Firth of Clyde on the West coast of Scotland with sailing yacht Steady.
  • Date: 5 July 2024
  • Vessel: Steady
  • Duration: 4 days
  • Where: Firth of Clyde, Scotland

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: 5 July 2024
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Sailing Taster 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: 12 July 2024
  • 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: 26 July 2024
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Overnight Tall Ship Taster Sailing in Devon

Enjoy a real taste of traditional sailing with an overnight voyage in Devon on the magnificent Pilgrim of Brixham.
  • Date: 27 July 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 2 days
  • Where: Brixham, Devon

Outer Hebrides and Mull, Scotland

Experience the West Coast of Scotland with a tall ship sailing holiday on board Blue Clipper. Perfect for those adventurers looking for a sustainable way to explore the Hebridean islands.
  • Date: 27 July 2024
  • Vessel: Blue Clipper
  • Duration: 7 days
  • Where: Mallaig / Oban,Scotland

Taster Sailing in South Devon

Enjoy a three day sailing experience on the coasts of South Devon with classic boat Pilgrim of Brixham.
  • Date: 2 August 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 3 days
  • Where: Brixham, Devon

Sailing Taster 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: 9 August 2024
  • Vessel: Escape
  • Duration: 4 days
  • Where: Dartmouth, Devon

Overnight Tall Ship Taster Sailing in Devon

Enjoy a real taste of traditional sailing with an overnight voyage in Devon on the magnificent Pilgrim of Brixham.
  • Date: 17 August 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 2 days
  • Where: Brixham, Devon

Sailing Dartmouth Regatta

Climb aboard this traditional Brixham Trawler as she sails around Berry Head for the Dartmouth Regatta.
  • Date: 22 August 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 4 days
  • Where: Brixham, Devon

Sailing Taster 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: 23 August 2024
  • Vessel: Escape
  • Duration: 4 days
  • Where: Dartmouth, Devon

Taster Sailing in South Devon

Enjoy a three day sailing experience on the coasts of South Devon with classic boat Pilgrim of Brixham.
  • Date: 29 August 2024
  • Vessel: Pilgrim of Brixham
  • Duration: 3 days
  • Where: Brixham, 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: 6 September 2024
  • Vessel: Escape
  • Duration: 3 days
  • Where: Dartmouth, Devon

Traditional Taster Sailing in Cornwall

Join traditional pilot cutter Pellew as she takes guests on an exhilarating taster sailing adventure around the coast of Cornwall.
  • Date: 13 September 2024
  • Vessel: Pellew
  • Duration: 4 days
  • Where: Falmouth, Cornwall

South Devon Sailing Experience

The perfect voyage for beginners looking for a new experience on the water, exploring the South Devon coast with classic yacht Escape.
  • Date: 14 September 2024
  • Vessel: Escape
  • Duration: 2 days
  • Where: Dartmouth, Devon

Traditional Taster Sailing in Cornwall

Join traditional pilot cutter Pellew as she takes guests on an exhilarating taster sailing adventure around the coast of Cornwall.
  • Date: 20 September 2024
  • Vessel: Pellew
  • Duration: 4 days
  • Where: Falmouth, Cornwall

Traditional Taster Sailing in Cornwall

Join traditional pilot cutter Pellew as she takes guests on an exhilarating taster sailing adventure around the coast of Cornwall.
  • Date: 27 September 2024
  • Vessel: Pellew
  • Duration: 4 days
  • Where: Falmouth, Cornwall

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
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