Adventures Expeditions Private Charter
Classic Tallship Sailing Holidays
Our Ships
Variety of Classic Sailing Adventures For All Ages
Blue Clipper
On board TS Blue Clipper, enjoy a hands on classic sail training adventure and sail to areas of the world you had only dreamed of visiting. Become fully immersed into life on board a classic tall ship and learn all about sailing this beautiful classic schooner.
Maybe
On board TS Maybe, enjoy a hands-on sailing voyage around the UK, Ireland and Western Europe. With many youth sail training voyages throughout the year, tall ship adventure holidays and the opportunity to take part in the International Tall Ship Races and Regatta, there is something to suit everyone.
Leila
Welcome to our tall ship Leila, the oldest ship in our fleet dating back to 1892 and the most recent one to join the fleet. Restored to her traditional gaff cutter sail configuration, we offer sail training opportunities around the UK, Ireland and Europe.
About Maybe Sailing
Maybe Sailing operates three Tall Ships
offering a variety of sailing holidays for all ages
to experience and enjoy hands on classic sailing voyages.
Maybe Sailing also provides private charters, expedition charters and corporate events at sea and in port. Love sailing and need a holiday with adventure? Then please come and join us on one of our Tall Ships.
What Clients Say
Our Voyages
Drogheda Sail Training Voyage 2
Port of Drogheda - Port of Drogheda
June 8, 2026 - June 12, 2026
Sailing in the Hebrides £1440
Oban, Scotland - Oban, Scotland
June 9, 2026 - June 14, 2026
Cork Sail Training Bursary Voyage 18-30 year olds
Dun Laoghaire, Ireland - Dun Laoghaire, Ireland
June 15, 2026 - June 19, 2026
Outer Hebrides and St Kilda £2085
Oban, Scotland - Oban, Scotland
June 16, 2026 - June 24, 2026
Sail Training Bursary Voyage under 18
Dublin, Ireland - Dublin, Ireland
June 22, 2026 - June 26, 2026
From the Hebrides to the Faroes
Oban, Scotland - Torshavn, Faroe Islands
June 27, 2026 - July 8, 2026
Live Tracking
Follow Our Ships
Is someone you know currently on board Maybe or Blue Clipper? Click the links below to track Tall Ship Maybe and Tall Ship Blue Clipper live using our yellow brick tracking system. You can follow their voyage every step of the way and even send them a message on the blog!
Our Blog
Get News and Updates from Our Ships
Photo Gallery
TS Blue Clipper Photos
Photo Gallery
TS Maybe Photos
Videos
The Inner Workings of Blue Clipper
Videos
Sailing In The Windward Islands
General
Welcome to Our Winter Charters
General
Pelle Fagerlund
General
Exploring Bequia in Winter 2020
