Select Page

Jester Challenge – A modern experiment in old-fashioned self-reliance, self sufficiency, and personal responsibility.

 

The Jester Challenge was created for skippers of small boats who want to test their skill and self-reliance, is a uniquely successful experiment in single-handed ocean sailing. This site tells you everything you need to know about it: its history, philosophy, guidelines and future events, along with the views and experiences of skippers who have taken part over the years.

There is a Challenge every single year and new skippers are always welcome. If you like the idea of developing your offshore seamanship in a relaxed and supportive environment, visit the Jester Challenge website. 

This is the eighth of a 10-part post where solo sailor Bernie Branfield shares his first hand account of his single-handed, 2022 Jester Challenge, from Plymouth, UK to the Azores, in his 26′ Invicta Mk2, Louisa. You can read more about Bernie at the end of the post.

Angra do Heroismo

I reached Terceira after 25 days at sea and was so grateful to be on shore. The trip over had been a challenge! I was aiming for Praia do Vitoria but due to the wind direction in the final 24 hours ended up in Angra. 

Angra do Heroismo is the capital of Terceira and, as I was to find out, had been the capital of Portugal twice in its history. For a capital city, it is the size of a medium sized town in the UK and was a great combination of old and new. The marina is situated at the bottom of one of the main streets in the city so access to all areas is a 2 minute walk. There are churches, shops, museums and walks around the area within 10 minutes of the marina. I fell in love with the area almost immediately. Having travelled all over the world I often have a feeling that it might be interesting to live in some of the places I visit but usually discount this thought when the practicalities become obvious. This was different, I could see a life in Angra, albeit I’d need to speak Portuguese. 

First night ashore I treated myself to a steak. 

It took almost a week before I could sleep properly after the trip over. I regularly woke up poised for action just because the wind had changed or the rigging made a noise.

I visited the Jesuit College that became the Captain General’s palace and had a guided tour, just me. It was excellent and was the best way to find out more of the history of the island. The palace is beautiful and very well maintained. There are some items of very high quality furniture and the decoration and ceilings were of a very high standard. 

I also visited the main museum, this was not a guided tour but gave glimpses into several eras of Terceira’s past. The first and second world wars featured as did Jesuit and Royal influence. Adjoining the museum is a church which was quite large and incredibly well decorated.

I also walked around quite a bit and enjoyed the peninsula which forms a natural harbour for the city. Angra suffered a sever earthquake about 40 years ago, every building with a bright orange roof was badly damaged. The geography is determined by volcanic action and the peninsula is an extinct volcano. 

While I was in Angra marina I met a great couple from Ireland on their fabulous catamaran. They were on their way to Portugal for the winter and had been in the Caribbean prior to the Azores.

I didn’t go in but at the centre of the city is a cathedral which is lit up at night. All of the pavements in the centre area are made from black or white volcanic rock and set out in geometric patterns. Some shops have their signs set out in the stonework. 

Angra deserves another visit, they were getting ready for a large festival just as I was leaving to go to Velas on São Jorge. I had been there 10 days, recovered from my trip over from the UK and was looking forward to seeing another island.

The best thing about Angra was the people, without exception they were friendly, helpful, patient and fun. A local politician and friend of the Jester Challenge came over to Angra to take me out for a drink and a local cake, a German singlehanded sailor, Hans on Snowball, help me sort out the rigging, Alex from Sailtours was all round fun and local shop keepers helped me find what I wanted. Just for the people alone I’d come back.

About Bernie Branfield

I have been sailing since I was 7, I started in Mirror dinghies at the local gravel pit and made my way up to VLCCs for a large oil company as Third Mate. After a break for family life I bought a MacWester Rowan 22’, Chantilly, which I sailed to Holland, Belgium, France and Ireland as well as around the UK East Coast. I still have Chantilly. For a short time I owned an Achilles 24, Mischief, that I had hoped to sail to the Azores but abandoned this plan after an eventful trip back from Ireland. My current boat is an Invicta 26’ Mk2, Louisa, which I bought just before the Covid lockdown. Due to timing, work commitments and various other factors I decided to enter the 2022 Jester Challenge to Newport Rhode Island. When I am not sailing my own boat I try and crew on a yacht delivery each year to build up experience. I have around 30,000 sea miles in yachts and various qualifications including YM Offshore under my belt. Louisa was built in the early 1970s and suits my singlehanded sailing needs to a tee, she is moored at Hoo Ness Yacht Club on the River Medway in Kent.

An explanation of the IALA maritime buoyage systems – IALA A and IALA B

What are the differences between the two IALA buoyage systems, IALA Region A and IALA Region B, and where are they used?   As recently as the 1970s...

Jester Challenge 2022 – Sailing single handed from Plymouth UK to the Azores: Part 3 – Preparations

Jester Challenge – A modern experiment in old-fashioned self-reliance, self sufficiency, and personal responsibility. This is the third of a 10-part post where solo sailor, Bernie Branfield, shares his first hand account of his single-handed, 2022 Jester Challenge, from Plymouth, UK to the Azores, in his 26′ Invicta Mk2, Louisa.

Antifouling for leisure boats – Part 3

Antifouling is one of the least pleasant boat maintenance jobs to do, but it has to be done. The very worst job of all is removing the old antifouling as this can get seriously messy and is very hard work.

How to use tides and currents to your advantage

If you are contemplating a cruise through tidal waters and strong currents, then planning your trip carefully in advance is essential to enable you to take advantage of favourable tides rather than constantly fighting against them.

Jester Challenge 2022 – Sailing single handed from Plymouth UK to the Azores: Part 6 – Communications

Jester Challenge – A modern experiment in old-fashioned self-reliance, self sufficiency, and personal responsibility. This is the sixth of a 10-part post where solo sailor, Bernie Branfield, shares his first-hand account of his single-handed, 2022 Jester Challenge, from Plymouth, UK to the Azores, in his 26′ Invicta Mk2, Louisa.

Sailboat rig checks – Part 2

In part two of Sail boat rig checks we run through some useful rig maintenance tips and then finish with a brief look at what a professional rig check involves.

Essential Knots: Round turn and two half hitches

Essential Knots: Round turn and two half hitches Use: Tying a rope to a pole or a ring. Step 1. Pass the end around the object. Step 2....

Estimating your position at sea

Navigators use a combination of techniques to estimate their position at sea. The primary method used today is GPS (Global Positioning System), a network of 24 satellites that became fully operational in the 1990s and was originally restricted for use by the United States military.

Passage Planning Advice & Safety for skippers

Passage planning helps you to: • Decide where to go • Calculate how long it will take to get there • Avoid bad weather •...

Jester Challenge 2022 – Sailing single handed from Plymouth UK to the Azores: Part 9 – Around the Azores

Jester Challenge – A modern experiment in old-fashioned self-reliance, self sufficiency, and personal responsibility. This is the ninth of a 10-part post where solo sailor, Bernie Branfield, shares his first-hand account of his single-handed, 2022 Jester Challenge, from Plymouth, UK to the Azores, in his 26′ Invicta Mk2, Louisa.

Peer to Peer yacht charter – How can you monetize your boat?

There is a growing trend in peer to peer yacht charter. How does it work? People already rent rooms, cars and bikes from one...

A five day sailing cruise of the Solent, UK

Welcome to our virtual Solent sailing cruise – a five day sail in the south of England from Bosham Quay in Chichester...

Liferafts

Liferafts should be stowed where they are ready for immediate launching. All crew should know the location of the liferaft and know how to launch, inflate and board it. They should also know what equipment it contains.

You Need To Understand The IRPCS ColRegs To Pass Your Yachtmaster, Master of Yachts and Coxswain Certificate of Competence

IRPCS ColRegs Rules of the Road at Sea and Yachtmaster Learning, understanding and remembering the International Regulations...

Wooden Hulls – Part 1

Traditional wooden boats have a plank on frame construction, a centuries old boat building method that is still in use today. Variations of the traditional method include carvel, clinker and strip planking, which all relate to the way the planking is attached to the frame.

Essential Boat Safety Briefing

Skippers Responsibilities Skippers are obliged to give a safety briefing to the crew even if they are a regular crew. At...

ColRegs when sailing single handed

  Don’t neglect the Colregs when sailing single handed Sailing single-handed represents several challenges for skippers, not least how to...

The give-way hierarchy – sail boats and power boats

Who gives way to who at sea? Even seasoned sailors sometimes get this wrong and in a crowded harbour this can easily lead to a collision or at best considerable embarrassment for a boat that mistakenly thinks it has right of way over another.

Preparing for sailboat cruising

Preparing for a sailing trip entails a lot of planning. In this blog, we take a look at some of the many safety aspects that a skipper needs to consider before heading off on a cruise.

Gybing a sailing boat

Gybing is the sailing manoeuvre used to change a boat's direction through a following wind. As with the tacking manoeuvre,...

Boat maintenance below decks

While most interior maintenance work can be done when a boat is afloat, some jobs such as servicing the seacocks have to be done ashore. It makes sense to do any major interior repairs and improvements with the boat hauled out in the boatyard.

Man Overboard Drill

How to respond to crew overboard under sail • Keep the MOB in sight • Tack into the heave-to position, do not adjust the...

Cleaning & polishing gelcoat topsides

The gelcoat topsides of a GRP boat can be pampered and restored to their former glory relatively easily when it is ashore. Gelcoat is only a very thin outer layer of the hull, often less than 1mm thick, so you should avoid cleaning it with highly abrasive cleaners, or an-ything that could potentially damage its surface.

Boat Handling – anchoring

Anchoring your yacht or motorboat Anchoring is one of the most important boat handling skills. If you can set an anchor...

Stress cracks on GRP boats

It is quite common to find cracks in the gelcoat when inspecting the deck and superstructure of a GRP boat. It is important to differentiate between a gelcoat crack and a scratch.