Classic & Traditional

Immerse yourself in a holiday of a lifetime with a classic sailing experience on one of our traditional vessels.

Bessie Ellen Sailing full Sails

Bessie Ellen

  • Rig: Gaff Rigged Ketch
  • Guest berths: 12

Built in 1904, Bessie Ellen is one of Britain’s last wooden coasting ketches sailing the coasts of Cornwall, Scotland, Denmark & Spain.

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Blue Clipper full sails Scotland

Blue Clipper

  • Rig: Gaff Schooner
  • Guest berths: 12

Blue Clipper was built in Sweden in 1991 and is perfect for those wanting an active sailing holiday from the Scotland, Spain and Portugal.

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Escape sailing

Escape

  • Rig: Gaff Yawl
  • Guest berths: 4

A 43ft gaff yawl built in 1937, true classic Escape slices through the water offering guests sailing in style while exploring the South Devon & Cornish coasts.

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Eye of the Wind Full Sail

Eye of the Wind

  • Rig: Brig
  • Guest berths: 16

Over 100 years old, Eye of the Wind is one of the last luxury tall ships of our time, sailing all over the world from Scandinavia to Scotland and the Caribbean.

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Florette Sailing Aeolian Islands

Florette

  • Rig: Brigantine
  • Guest berths: 28

An original Brigantine windjammer built in the famous Picchotti Shipyard in 1921, Florette is still sailing the Mediterranean today!

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Maybe-fullsail-blue-sky

Maybe

  • Rig: Gaff Ketch
  • Guest berths: 8

Gaff Ketch Maybe is a spacious classic with private twin cabins spending her summers sailing the coasts of Cornwall and Portugal.

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Noorderlicht-sailing-norway-full-sail

Noorderlicht

  • Rig: Schooner
  • Guest berths: 20

Built in 1910, Noorderlicht spends her summer exploring Svalbard & her winters watching whales and anchoring under the Northern Lights.

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Oosterschelde Cape Verde Sailing

Oosterschelde

  • Rig: Topsail Schooner
  • Guest berths: 24

From Antarctica to Cape Verde, Oosterschelde is the oldest and largest Dutch topsail schooner to still be sailing the worlds oceans to this day.

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Pilgrim at sea

Pilgrim of Brixham

  • Rig: Gaff Rigged Ketch
  • Guest berths: 10

With her iconic red sails, she is one of the last remaining traditional trawlers exploring the coasts of South Devon, Cornwall and the Channel Islands.

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Agnes full Sailing Cornwall

Agnes

  • Rig: Pilot Cutter
  • Guest berths: 6

A faithful recreation of the original Isles of Scilly pilot cutter, Agnes, she spends her days exploring the Cornish coast while offering guests exhilarating sailing!

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Pellew full sails Eigg small isles

Pellew

  • Rig: Pilot Cutter
  • Guest berths: 8

Pellew is the faithful recreation of Falmouth Pilot Cutter "Vincent" and is the fastest and largest Pilot Cutter to be sailing in Britain today.

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Aron of Svendborg Full Sailing Denmark

Aron

  • Rig: Schooner
  • Guest berths: 10

Traditional schooner Aron was built in 1906 and is still sailing in the Baltic Sea offering hands-on sailing in Denmark.

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Flying Dutchman under sail

Flying Dutchman

  • Rig: Schooner
  • Guest berths: 24

Built in 1903, the Flying Dutchman spends her summers sailing from Holland to Scotland with comfy twin cabins.

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Stella Oceana sails up

Stella Oceana

  • Rig: Gaff Ketch
  • Guest berths: 8

Custom charter boat Stella Oceana is perfect for relaxed Norwegian fjord cruising and Lofoten island exploration.

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Iris Sailing

Iris

  • Rig: Ketch
  • Guest berths: 10

Built in 1916, Iris was originally a herring drifter and has been transformed into a charter vessel.

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Katharina guests bowsprit

Katharina

  • Rig: Gaff Ketch
  • Guest berths: 14

Built in 1995, gaff ketch Katharina is an Indonesian pinisi boat transformed from commercial freighter to charter vessel.

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Ombak sailing

Ombak Putih

  • Rig: Gaff Ketch
  • Guest berths: 24

Built in 1995, gaff ketch Ombak Putih is an Indonesian pinisi boat transformed from commercial freighter to charter vessel.

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Grayhound full sail

Grayhound

  • Rig: Lugger
  • Guest berths: 12

Built in 2012, Grayhound is a traditional replica of the original 1776 customs Lugger sailing from Sweden, exploring fjords & canals.

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Traditional and Classic Sailing Immerse yourself in a holiday of a lifetime with a classic sailing experience on one of our traditional vessels. Here at VentureSail holidays, we offer a variety of classic and traditional sailing holidays with voyages all over the world. Our traditional fleet of historic boats are oozing in maritime history with many of them on the National Historic Ships Register. Each owner and skipper is dedicated to keeping these fascinating classic boats sailing for generations to come. They love nothing more than involving guests in the traditional sailing; showing them the ropes and passing on their invaluable knowledge. A sailing holiday on a classic boat is something you’ll never forget. From hoisting the sails by hand with fellow guests and crew, to feeling the sheer power of the wind in the sails as you take the helm – a traditional sailing holiday on a classic boat is truly an exhilarating experience. All of our classic boats love to keep things traditional while at sea, and for as much as possible, they prefer to be powered by the wind, showing the boat off as to how it would have originally been sailed. Classic boats, as well as their crew, come with a whole host of fascinating seafaring tales too. From the original working life of these traditional boats to how they have become the charter vessels they are today, the history is paramount to our maintaining our rich maritime heritage. The crew of classic boats also appreciate the need for good food and cosy quarters after a day of classic sailing, inhaling that fresh sea air. There is nothing better after a day at sea than settling down in the cosy saloon for a hearty home-cooked meal. Traditional boats are just as beautiful above decks as below decks. Traditional craftsmanship and carpentry is shown in every bit of the boat. From classic boats that are over 100 years old still maintaining their original oak planked hulls to modern replicas that have been built using the very same traditional methods.  
Sailing on a classic boat also makes many opportunities for sailing off the beaten track in locations that are rife in wildlife. The skippers of classic and traditional boats prefer, as much as possible, to harness the power of the wind in their sails and not use the engines. This makes spotting wildlife all the better as they are not disturbed by the sound of a noisy engine. Traditional sailing holidays on classic boats are easily and widely accessible for all our guests. From solo travellers to couples, groups or even private charters, you certainly don’t need any experience to climb aboard. Voyages across our classic sailing fleet range from short weekend breaks, week-long adventure and even month-long Atlantic crossings. Sailing a classic boat with friends and even strangers makes for an unforgettable holiday experience. The need to work together while sailing is always a momentous occasion – there is always one that starts a sea shanty chant to get everyone into the sail hoisting rhythm! Classic sailing in Scotland and the Hebrides is a popular choice for our traditional boats. The abundance of islands and vast stretches of diverse coastlines mean that the area is little saturated making for plenty of places off the beaten track to explore and discover. From the high basalt cliffs of Canna to the quiet seclusion of Loch Scavaig on Skye, nothing quite prepares you for the spellbinding beauty of exploring this part of the planet under sail. At the opposite end of the UK along the coasts of Devon and Cornwall, a host of our traditional and classic boats are proud to call this part of the country home. The beautiful coastline, quaint harbours, rivers, creeks and waterways give guests a wide range of places to explore under sail with the wind direction in this part of the country also making for perfect sailing conditions. Our classic boats still retain the need to satisfy their original scopes of travel and still love to venture to those further flung bucket list locations. From the Norwegian fjords to the Swedish skerries, to the Canary Islands and across the Atlantic to the colourful Caribbean; no two classic sailing holidays with VentureSail are ever the same. With so many beautiful classic ships to choose from with a host of wonderful locations to explore, you’ll be left coming back for more.