Our play ground extends beyond the English Channel. We venture south once the last gasp of summer in the UK passes in late September. Theres more sailing to to do.

  • The RORC Transatlantic 

  • The Raid Across the Biscay

  • Raid to Gibraltar

  • Raid to the Canaries

  • Canary Island Raid

  • Caribbean Raid



  • Good old fashioned mile builders


We can keep you sailing and smiling through the winter where the sun shines and shorts and tees are the norm.

RORC Transatlantic Race

The RORC have moved the start from November to January. Which is great news. Gives us time to play around in the Canaries. No rushing back from the Middle Sea Race and better weather for the sail across the Atlantic. Well in theory,

Probability it will now attract a bigger fleet but the challenge remains the same. It's actually a very safe passage. It's just the distance.  

It takes approximately 15-18 days and we race all the way across from Lanzarote to Grenada. 

Total time on the water approximately 17-20 days including training


Biscay Raid

The Biscay Raid is leg one of our epic adventure south chasing the sun.

It starts in Cowes and ends in La Coruna on the Costa del Morte in Northern Spain. We stop on route to avoid the worst of the weather and just to enjoy the local hospitality. Rosscof or Brest, Vivario where there treat yachtsman like rock stars and the beautiful port of A Coruna.

Head home or stay with us for the next leg to Gibraltar.



Join us from Cascaias as we head to Gibraltar & the Med. Depart in Gib or stay with us as we head either into the Med or further south to the Canaries.

We stop on route to stretch our legs and enjoy the sights of the Algarve and Southern Spain. Our route East or South is determined by our commitments to the Middle Sea Race. Ultimately you can stay with us all the way to Malta.


Gibraltar to the Canaries

Chasing the sun we leave Gibraltar for the Canary Islands. We will be heading for Lanzarote. The Canaries is full with ARC yachts. We will be participating in the RORC Transatlantic for our blast across the pond in January.

An easy sail sail south although the swell can build especially inshore along the North African coast.

Total time on the water approximately 7 days


Caribbean Raid

We arrive in the Caribbean in late January after completing the RORC Transatlantic. Thereafter we participate in the first of the Caribbean Regattas, Grenada Week.

We then set off on our Caribbean Raid. Grenada to Antigua through the stunning little islands of the Grenadines. You can fly in to Grenada with BA or Virgin and fly home on the same carrier home from Antigua.. We keep the number of guests down to 4 maximum and convert the yacht to cruising mode.


Anarchy Sailing is about fun first.

That said we love to race and we love to beat our rivals.

Each year we invest more into our yachts.

Sails, sail configuration to optimise performance against rating.

Smoother hull, new electronics and all kit replace when needed including halyards, sheets etc. 

We will always present the yacht in the best possible condition so there are no excuses on the water.

Ultimately we are a TEAM and regardless of your previous experience you will become a key member of the TEAM.

Remember      Life's a riot

Get In Touch

Hours of operation 

A bit random.

Small business.

Could be on the water?

Basically just give us a call  or email us 

contact us

67 York Street


Isle of Wight



+44(0)7870 403888