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.

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.

Boating emergency – how to broadcast a MAYDAY emergency call

How to broadcast a MAYDAY emergency call   How to broadcast a MAYDAY emergency call if a vessel or person is in grave...

Feeling anxious at sea

  Some people feel anxious at sea. Will they be seasick? What if they get caught in a violent storm? Could the boat...

Top five windvane self steering installation questions

Top five windvane self steering installation questions answered by Sarah Curry of Hydrovane International Marine, courtesy of Viki Moore from Island Cruising NZ

Essential Knots: Reef knot

Essential Knots: Reef knot Use: Tying two ends of rope together, often used for tying up a bundle of loose sail around the boom. Step...

Fire safety advice at sea from the Marine & Coastguard Agency

Fire safety advice for boaters Top fire safety advice at sea: 1. Fit smoke alarms, carbon monoxide and gas detectors 2. Turn...

Sailing into fog – being prepared and staying safe

Most skippers will sensibly delay their departure, if fog is forecast. However, if fog begins to form when you are at sea it is important to be prepared, and know what precautions to take, to help make your vessel detectable or visible in fog and keep the crew safe.

Competent crew skills: arriving and leaving a berth

Skilled boat handling is needed when entering or leaving harbour. Crew tasks include preparing the mooring lines and fenders before docking and...

Boat ownership

Owning a boat is a big commitment that should bring no end of satisfaction for the owner as well as the owner's family and friends. In...

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...

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.

Capsize – understanding the risks

A skipper should know how their boat will cope with rough seas. By working within known limits and understanding the risks,...

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.

Hull inspection – the annual checks

With the boat ashore for the winter it is time to do a hull inspection - the annual checks. Are there any scratches and chips in the...

Safety at sea principles

Safety at sea is not as simple as just spending money adding shiny new emergency equipment such as liferafts, danbuoys, distress flares, EPIRBs and so on.

First Aid Afloat – jellyfish stings

  Wherever you are boating in the world I am sure you will be using a pilot guide to aid your navigation. Often in the...

Repairing chips and dings in gelcoat

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.

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.

The Round The Island Race 2023

This year’s Round the Island Race turned out to be a really thrilling and competitive event. 1100 boats entered the race, which took place on Saturday 1st July. The race started from the world famous Royal Yacht Squadron line in Cowes UK, with the largest and fastest boats starting first, leaving the rest of us to wait our turn.

Understanding tide tables and tidal curves

There are many factors that influence local tidal patterns and it’s essential for every sailor to have a good understanding of tide tables and tidal charts to ensure they can calculate the level of tide at any given time.

Marine diesel exhaust checks

You should inspect the exhaust system for corrosion damage regularly, especially around the injection bend. If you have noticed the engine exhaust smoking a lot during the sailing season this can also indicate a number of potential problems.

How diesel engines work

The basic principle of a diesel engine is less complex than that of a petrol engine. No spark plug or ignition system is needed, making the basic diesel engine a comparatively straightforward system that results in fewer faults and has lower maintenance costs than a petrol engine.

Understanding marine sealants & adhesives

Sealants, adhesives and adhesive sealantsThere is a bewildering variety of sealants, adhesives and even adhesive sealants available for...

Repairing a leaking hull-to-deck joint

If you suspect a hull-to-deck joint has failed, then being absolutely sure where the actual leak is occurring is of prime...

Keel design – options to consider when choosing a yacht

Keel design is constantly evolving and nowhere is this more apparent than in modern racing yachts such as the Imoca Open 60...