Get Ready For Your Sailing Challenge!

Join us for a bucket list sailing adventure.  Start your trip off with training and familiarisation on our round the world racer.  With individual bunks and storage space allocated it won't take long to settle in.  Once watches are allocated and the voyage starts you can expect to be as involved as you are comfortable with.  Take part in watches, helming, navigation, trimming and, of course, keeping everyone fed in the galley! There are jobs for everyone and we welcome all abilities and experience.

We take care of all the planning so you just need to turn up, get ready and go!  With our challenge voyages normally involving a number of overnight sails you can expect to be challenged and be rewarded.  Night sailing holds some of the most rewarding views on the ocean.  Of course, making landfall after achieving hundreds or even thousands of miles at sea is, in itself, a great achievement.

Our challenge voyages often allow up to two crew to undertake their RYA Ocean qualifying passage.  If you want to know more about the requirements for the qualifying passage follow the link below to the RYA website.  *Note Ocean Sailing Scotland are not responsible for the content of external websites.


Our Challenge Itinerary!


A north atlantic rainbow!

A north atlantic rainbow!

The Round Rockall Challenge 2020

4 - 13 May 2020

Join us on our ocean racing yacht as we embark on a unique adventure to the UK’s most westerly point of land, made famous in marine weather forecasts, Rockall. Heading out from Kip marina on Scotland’s famous Clyde Estuary you can expect to spend some time exploring and getting settled into life on our Clipper 60 along Scotland’s stunning coast, including the famous Mull of Kintyre.

With skipper carefully watching the weather for a good window to head out the 200Nm to Rockall the North Atlantic will beckon. Returning through the Outer Hebrides there may even be time to visit St. Kilda and some of Scotland’s famous Islands. Arriving back into the west coast town of Oban you can enjoy one of the UK’s finest rail journeys back to Glasgow before heading home.


The idyllic and atmospheric village bay, hirta, st. kilda

The idyllic and atmospheric village bay, hirta, st. kilda

The St. Kilda Challenge 2020 

6 - 17 June 2020

Kip, Rathlin Island, St. Kilda, Lochmaddy, Dublin

Join us from our home base at Kip on the Clyde Estuary in 2020, Scotland’s year of coasts and waters as we participate in the Bi-Annual St. Kilda passage race.  Heading out from our home base your trip will begin with safety briefs and ocean training. Next our focus will turn to race training, tactics and preparation for the St. Kilda race.

After a few days of training, cruising and familiarisation it will be time to join the rest of the race fleet at Rathlin Island on the north coast of N. Ireland as we gather for the event start. With a constant watch on the weather to decide on the best race tactics it won’t be long before the start line is crossed.

As both line honours and overall winner in 2018 event we will be defending our crown in a race suited to the Clipper 60 offshore design. Upon reaching the finish line at the stunning archipelago of St. Kilda we will hopefully have some time ashore before heading to the outer Hebrides and Lochmaddy on North Uist for a programme of onshore festivities and prizegiving.

Finally you can expect to enjoy some relaxing cruising as we head south to the bustling city of Dublin where the trip will finish.


A "rare" north atlantic sunset in flat calm eerie seas!

A "rare" north atlantic sunset in flat calm eerie seas!

The Icelandic Challenge 2020 

TBC August 2020

Join us as Taeping heads out into the North Atlantic heading for the stunning Iceland. With ocean training and some island hopping cruising to start off the trip you can be confident of heading offshore armed with the knowledge needed for your ocean passage. Booking for this trip will open on 2nd December 2019.

As you watch the land slip away behind you and after three to five days at sea it will not be long before the capital of Iceland, Rekjavik comes into view. With time scheduled in to explore some local Fjords, and perhaps a hot tub on the beach you won’t want to leave!

With night sails and a watch rotation in place we will be hoping for amazing skies and passing wildlife on our ocean passage.


Your idyllic icelandic fjord!

Your idyllic icelandic fjord!

The Arctic Circle Challenge 2020

TBC September 2020

Long hours of daylight, stunning Fjords and sailing in the Arctic circle, this trip is all about tick box sailing. Start off your adventure in Iceland’s capital, Reykjavik as we sail Iceland’s west coast and take in the stunning North West Fjords.

Sailing into the Arctic Circle your adventure will take you along Iceland’s North coast, exploring, learning and enjoying. Next it will time to head back out of the Arctic Circle and aim for the Faroe Islands and some night sailing on our ocean racing yacht.


COLOURFUL torshavn

COLOURFUL torshavn

Northern Islands Challenge 2020

TBC September 2020

Island hopping, a canal transit and Scotland’s west coast, this trip has it all. Even better this trip will see some night sailing as we take in some longer passages as we sail what we like to call the Torshavn triangle!

With the Faroes, Shetland, Orkney and the Caledonian canal to enjoy this is a packed trip taking in some of the most spectacular scenery North of the South! Join our ocean racing yacht for this amazing Island Hopping adventure.