Skipper's Log

 Skipper's Log

Skipper, Herb Fredrick gives us a candid article about sailing.

In July of 1987, a friend invited me for a day of sailing with her and her friends. I loved it and felt at home. Since then I've organized and skippered on 49 bareboat charter sailing adventures, sailed with others, and attended two additional sailing classes.

As if I'd lived it in a prior life. One week later I attended a 3-day Bareboat Charter Certification course in Bayfield, Wisconsin with Sailboats, Inc., sailing instruction and sailboat charter company. I was hooked. During the next three months, I chartered a 35-foot sailboat four times and filled it each time with crews of friends, acquaintances, and I as their neophyte skipper.

Since then I've organized and skippered on 49 bareboat charter sailing adventures, sailed with others, and attended two additional sailing classes. Of those 49 adventures, seven were in the Caribbean and the rest within the United States. Nineteen were flotillas of two to six sailboats. Over 600 sailors have participated in these adventures. About one third to one half of them were new sailors. I did my best to teach them the basics with hands-on-training from the first hour on the water.

The most time-consuming parts of these outings have been investigating options, creating the trip format, and marketing. Initial choices to make were deciding on the sailing destination, the dates and length of the charter, which charter company to go with, the size and type of sailboats to charter, pricing of each crew member's share of the charter cost, and how to market the event.

Once everyone has paid their portion of the yacht charter costs the most time consuming and difficult task of the adventure is over. Then it becomes maintaining communication with crew members as needed, organizing things like provisioning teams, finding someone or four crew members to handle shared lodging when in the Caribbean for sailors that want to, and the gathering of crew info needed, especially for foreign events. This included the basics plus emergency contact, passport, passport exact name spelling, airline flying with that airline's toll-free, ticket, flights and times, lodging staying at and their phones, and more.

January 2-11 St. Martin TripFor Caribbean trips we usually had between one and three pre-trip pot luck dinner parties at sailors' homes to become acquainted and plan the details together. Some would volunteer and take on tasks like planning for provisioning that they would do on our sailing jump-off island.

catamaranThese parties were also great for bonding of the crew and to create enthusiasm and anticipation of good times ahead. Most of the sailors on these trips lived in and around Minneapolis/St. Paul, Minnesota where I lived so gathering in person worked out well. We sometimes organized and attended post-trip dinner parties, too, to share photos and share great memories, become better friends.

During organizing of my first Caribbean sailing adventure, I started out thinking big with three other skippers and myself on four yachts. Had my doubts, but went ahead anyway. We ended up with six skippers on six yachts and a total count of 40 new and experienced sailors and skippers!!! One of our skippers was the sailing instructor and USCG Licensed Captain who had trained me with Sailboats, Inc. back in 1987. He took the 52 footers.

The rest of our yachts were between 44 and 47 feet in length.

Catamaran sailing the last trip I organized and skippered on was for sailing the British Virgin Islands (BVI's) last January. Nine weeks before we boarded our yacht a long-time great friend of mine, James, who is from Australia, but lives in Calgary, Canada, called me asking me to skipper a sailboat for him and his friends. The most experienced of them had taken a 5-day introductory charter course so they needed an experienced skipper in order to be allowed to charter a sailboat. Out of the eight of us who eventually sailed together on that trip half of our crew had never touched a sailboat before.

Jame's friend Zoltan had been calling a charter company asking about sailboats, but with only five days on the water, no experience chartering sailboats, and no skippering experience he was getting the runaround. I called Sunsail, whom I'd chartered with before, and was able to get their 5% returning charter discount and a late-season 10% discount to help with the pricing of a 44-foot monohull.

James thought they had a crew of seven including me. Then two of his friends melted away when money was asked for. We were then five with a boat we'd priced for eight and only six weeks to find three more crew. YIKES!

Zoltan eventually invited a friend who joined us. The first of two Facebook “friends” that I approached was in New Zealand travelling but had a goal of living on a boat for a year. Within one week she'd paid for her share of the charter cost. She turned out to be a 54-year-old professional photographer who teaches it. She lives in Saskatoon, Saskatchewan, Canada. The last crew member to join us, about three weeks before we landed on St. Thomas, was my 35-year-old nephew Joe.

Our crew was spread out over five cities and two countries. We were from Chicago, Illinois; Boulder, Colorado; Green Bay, Wisconsin; Calgary, Canada; and Saskatoon, Canada.

We filled the boat, but it took many hours of effort reaching out and playing a numbers game of asking our friends, acquaintances, family, and co-workers. In this case, I also spent many hours asking individual Facebook “Friends”, posting invitations on Facebook sailing group pages, and sending emails far and wide.

stmartinBased on past experience I've usually begun investigating and creating a Caribbean sailing adventure at least a year in advance. Others doing the same often do, too. So the sooner one can pay the 30% downpayment charter companies to want to hold onto individual yachts and early season discounts, the better. I've counted on chartering the largest bareboat sailboats available only to find that someone else reserved them before I was able to.

In mid-January, on returning home from sailing in the BVI's I began work on a St. Martin Sailing Adventure for 2016. I was checking on yachts to charter out of Guadeloupe, Martinique, St. Lucia, or Grenada in the Windward Islands. I'd sailed a two-sailboat flotilla from Guadeloupe down to Palm and Union Islands in the mid-Grenadines and back to Martinique during a two-week trip before.

After five months I decided on a return to St. Martin. However, I wanted it to be more adventurous so chose a January 2-11 float plan sailing clockwise from St. Martin to St. Barts, Barbuda, Antigua (at the furthest point from St. Martin), Nevis, St. Kitts, St. Barts, and back to St. Martin. This will be nine days covering 320 miles having the longest legs be 40, 50, and 70-mile open-ocean passages between islands.

Leopard 39 foot catamaran saloon priced two boats, a Beneteau 50.5 foot monohull and a Leopard 39-foot catamaran with crews of 10 each to keep the initial bite low to attract enough sailors to pay-in-full early enough to cover the required 30% down payment. I initiated marketing on July 1st, picked up two very experienced skippers and another Beneteau 50.5 foot monohull, and rapidly attracted a total of 25 crew and skippers plus myself to pay their per person charter costs in full within three weeks. Locked in all three boats and a 5% return charterer discount and 10% early season discount for all the boats.

By going with 10 crew per boat and locking in the boats and discounts with early and rapid signups we were able to save $320 per person over the cost of going with a crew total of eight per boat. We might not have been quick enough to reserve and hold the boats and gain the 10% early season discount.

The other two primary skippers and I have each sailed large charter sailboats with crews of 10 and enjoy the socializing with large crews. Too, we will be sailing 320 miles over only nine days to everyone will be able to participate at the helm and other sailing tasks numerous times.

We, three skippers, have also each done open-water, blue water passages while sailing through the night and plan to do it two to four times during our St. Martin trip. This will be enjoyable since January weather in the islands is mild with fairly constant winds and there will be no light pollution to spoil gazing at the stars and galaxy. Cruise ships travel between islands at night so passengers have most of the day to sightsee and enjoy ports-of-call. Our trip will feature this benefit as well.

sailing enjoymentFew new sailors or even fairly experienced sailors ever get the opportunity to do night sailing or overnight passage making experience. Since we have experienced skippers and others who have signed on already who have night sailed we feel confident about it. Too, we plan to sail within easy sight of each other on the longer passages at night and maintain hourly radio contact as a safety caution.

Only three spots remain open for the St. Martin adventure. They are on the Leopard 39 catamaran I'll be skippering. Three of us plan to sleep on the trampoline, in the saloon settee, or on a stern dining and seating area settee. That will leave room for seven to sleep in four double berths.

From here the rest of the organizing is mainly communications and coordination of volunteers to take on needed tasks before we depart on our yachts January 2nd as a flotilla from Oyster Bay, St. Martin.

If you have any questions about how to go about initially becoming involved in sailing, how to charter sailboats and what is required of you, or our upcoming St.Martin Sailing Adventure please contact me by email at “This email address is being protected from spambots. You need JavaScript enabled to view it.


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