Skipper’s Log

Herb Fredrick, an experienced skipper, shares his personal story about sailing and organising charter adventures around the world.

How My Sailing Journey Began

In July 1987, a friend invited me to spend a day sailing with her and several friends. From the moment we left the dock, I felt completely at home on the water.

One week later, I enrolled in a three-day Bareboat Charter Certification course in Bayfield, Wisconsin with Sailboats Inc. The course changed everything for me. I was hooked.

During the next three months I chartered a 35-foot sailboat four different times. Each trip included friends and acquaintances who joined as crew while I learned to skipper.

Since that first experience, I have organised and skippered 49 sailing adventures. Seven of those trips took place in the Caribbean, while the rest were within the United States.

More than 600 sailors have joined these adventures. Many of them had never sailed before.

Teaching New Sailors

Around one third to one half of the crew members on each trip were new sailors. From the first hour on the water, I tried to teach the basics through hands-on experience.

Watching people gain confidence while learning to sail has always been one of the most rewarding parts of these trips.

Planning a Sailing Adventure

Organising a sailing trip requires more effort than most people expect.

First, I research destinations and charter companies. Next, I choose travel dates and the length of the charter. I also decide on the type and size of yachts.

Pricing is another important step. Each crew member must know their share of the charter cost before committing to the trip.

Once everyone pays their portion, the most difficult part of the planning is complete. After that, communication with crew members becomes the main task.

Preparing the Crew

Crew organisation involves many small details. These include collecting passport information, arranging flights and confirming accommodation.

For Caribbean trips, we also organise shared lodging before boarding the yachts.

Before departure we usually hold a gathering so everyone can meet. These events help the crew bond and build excitement for the journey.

After many trips we also organised post-sailing dinners to share photos and memories.

My First Caribbean Adventure

When I organised my first Caribbean sailing adventure, I originally planned for four yachts and four skippers.

However, the trip quickly grew. We ended up with six yachts and six skippers. In total, forty sailors joined the adventure.

One of those skippers was the sailing instructor who trained me back in 1987.

The yachts ranged between 44 and 52 feet in length.

Sailing the British Virgin Islands

The most recent adventure I organised took place in the British Virgin Islands.

Nine weeks before departure, a close friend named James called me. He asked if I would skipper a yacht for him and his friends.

Their group needed an experienced skipper because most of them had limited sailing experience.

Originally the group planned for seven people. However, two crew members dropped out when payment was required. That left only five people for a yacht priced for eight.

With six weeks remaining, we needed to find three additional crew members quickly.

Finding the Final Crew

Eventually we filled the remaining places.

One crew member joined through a friend. Another responded after I contacted sailing connections online. The final crew member was my nephew Joe.

In the end our crew came from several different cities in the United States and Canada. Despite the distance between us, we quickly formed a strong team.

Planning Future Sailing Adventures

Planning Caribbean sailing trips usually begins at least a year in advance.

Early planning helps secure the best yachts and allows time to take advantage of booking discounts. Charter companies typically require a 30 percent deposit to reserve a yacht.

If the deposit is delayed, someone else may reserve the yacht first.

The St Martin Sailing Adventure

After returning from the BVI trip, I began planning a new sailing adventure starting in St Martin.

The route will travel clockwise through several islands including St Barts, Barbuda, Antigua, Nevis and St Kitts before returning to St Martin.

This voyage will cover around 320 nautical miles over nine days.

Building the Fleet

Initially I priced two yachts for the trip. These included a Beneteau 50.5 monohull and a Leopard 39 catamaran.

Within three weeks we secured three boats and attracted 25 sailors.

Early booking allowed us to lock in both a return-charter discount and an early-season discount.

Night Sailing Experience

Few sailors have the chance to experience night sailing early in their careers.

However, our flotilla includes several experienced skippers. Because of that experience, we feel confident sailing longer passages after dark.

During these passages we will stay within sight of each other and maintain regular radio communication.

Final Crew Opportunities

Three places remain available on the Leopard 39 catamaran that I will skipper.

Some crew members plan to sleep on the trampoline or in seating areas. This arrangement allows space for seven people in the main berths.

Final preparations now focus on communication and coordinating volunteer tasks before departure.

Contact

If you would like to learn more about sailing, chartering yachts or joining future adventures, feel free to contact me.

Email: herbsails@yahoo.com