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Strengthening and Building Your Fleet


Bud Brown, March 4, 2022




Sailing Fun + Energy = Friendship and Growth


To be honest, I was a little stumped when I started writing this article. I am no expert on fleet building, so I was interested in discovering how others went about it... the necessary elements, what types of events were suggested and how fleet leaders prepared and organized.  Races, socials, and ‘exposure events’ (demo days and sailing lessons) are typical items on fleet calendars, but I wanted to know if there were other ideas and concepts that were less familiar or more effective. In addition, almost everyone recognizes that fun and friendship are two very important elements of fleet building, but how does one go about guaranteeing either of those elusive human experiences? In the movie, The Field of Dreams, a farmer’s faith is inspired by the philosophy… “If you build it, they will come” … which is probably a reliable building principle for sailboat fleets, especially since it is widely accepted fact that Sailors Have More Fun!  Beyond that familiar bumper-sticker though, a better grasp of the concept of 'fun' might be helpful. While I have always had fun sailing, racing or just socializing with folks, I have never even considered WHY I was having fun, what it was, its usefulness beyond the experience, or even how the sensation was created.

Youth Sailing
This Youthful Team Prepares for Some Close Action



According to Travis Tae Oh, Ph.D. in his article, What Is the Underlying Psychology of Having Fun?:

“‘Having fun’ is a sensation of liberating engagement. It is a temporary release from various internalized and externally imposed restrictions, such as work, parenting, schoolwork, etc. Throughout my research journey, the theme of ‘letting loose’, ‘being carefree’, and ‘getting away from it all’, was a recurring topic within really fun experiences.” 

Of course, ‘fun’ is individually defined, but the common theme includes an escape from responsibility and stress through a pleasant, welcome and engaging distraction.

Interestingly, there are very good reasons for ‘having fun’. According to Psychology Today, “Play is serious business… it is a banquet for the brain, a smorgasbord for the senses, providing nourishment for body and spirit.”  It may sound paradoxical, but the concepts of play and fun are vital to our health and well-being. 


Play has been shown to:

·       Relieve stress and depression symptoms by releasing endorphins that make you feel good.

·       Build connections with others through sharing fun and laughter.

·       Improve brain function through challenging activities that require thinking or problem-solving.

·       Promote creative thinking by stimulating your brain and imagination.

·       Increase your energy level and immune system, building resistance to illness.


It is sad, then, that as a society we seem to be starving ourselves of play and fun, even though it has been somewhat necessary in these times of sporadic pandemic. With COVID diminishing, however, the time is right to re-introduce these needed elements into our lives.


As people who are familiar with sailing, particularly in the versatile Ensign, we are in a remarkable position to develop, enhance and capitalize on the opportunities for fun in our lives through fleet building. Sailing provides an exciting, intriguing escape from the burdens of everyday life. Sharing the experience with others in new and refreshing ways can be an even more enjoyable and thoroughly rewarding experience. If your sailing calendar has fallen into a bit of a rut, then freshen it up! It is up to you to break the mold. Variety is the spice of life and new experiences are only limited by your imagination.


So, how have others built and strengthened their fleets? What kind of events have added fun, spice and variety to fleet calendars? A bit of research and reminiscing resulted in a list of concepts and ideas.



Learning to keep a sailboat in tune with the wind and the waves begins as a challenging mystery. With a little practice though, the wind and the waves become familiar rhythms as sailors learn to adjust sails and steer a smooth path. Sailing is a magical adventure, and as a shared experience, can create a setting where instant camaraderie and easy friendships are the general rule. This ‘Instant Friendships – Just Add Water’ atmosphere can make strengthening a fleet as simple as inviting others into the sport and planning some socials where friendships can form and relationships can flourish. The season calendar is vital for everyone’s planning, but it can also be an instrument of effective marketing and a tool for growing a culture of helping each other, building value and spending time together. After the calendar is set, good communication is important for reminders and last-minute details. Most importantly, if new sailors are introduced to a boat that fits their needs, and are welcomed into a family of friendly, supportive sailors, they will have fun… and having fun is the entire point of belonging to a fleet.


Insightful leadership can provide most of the necessary ingredients, but no ‘science’ or ‘formula’ can guarantee fleet growth. The ‘Growth Magic’ lies in the fleet members, whose excitement, involvement, efforts and contributions directly impact a season’s success. So, the season calendar should be a plan that excites the entire fleet. A multi-faceted calendar provides for the variety of interests and needs within a fleet. In addition to races, socials, parties, cookouts and other events, there are also a few marketing opportunities that could enhance a calendar’s effectiveness. Every fleet’s seasonal calendar might incorporate some of the following:


·       ‘Take A Friend Sailing’ Days. Also known as ‘Demo Days’, these are days when newbies are taken for a sail to introduce them to the boat and the class. Rolled out by any number of invitation techniques (club newsletter, bulletin board sign-up, telephone calls, email, etc.), this can be made into a high-visibility event where numerous boats show up to accommodate the curious or the inexperienced. Following up ashore with an informal, icebox and hors d'oeuvres social is a great way for everyone to get to know each other. Though not really an immediate fleet growing opportunity, this is an effective way to plant seeds, find new friends, pick up a crew and demonstrate to all onlookers that your fleet cares about growth and is open and inviting to others.


·       Adult Sailing Lessons.  This has proven to be a really effective, long-range method of adding boats and members to your fleet. In general, teaching newbies how to sail is not about teaching them how to race. It is about:

  • Showing them that sailing is a beautiful blend of nature, sport, skill and camaraderie. 
  • Creating an enjoyable experience, with patience and expert handling of a sailboat. 
  • Addressing their questions and curiosities in an uncomplicated way, without force-feeding them more than they can handle.
  • The exhilaration of some occasional spray but not the apprehension of whitewater on the leeward rail. 
  • Books and programs have been written on this subject if you need some help getting started.


·       Visible Fleet Gatherings. The gatherings can be of many types, but the key marketing concept of visibility is important. If the fleet is going to meet somewhere, it’s an advantage to find a time and place where outsiders can witness the camaraderie. More than one pirate has ‘jumped ship’ for better swag and reward. The gatherings might include:

  • Consistent Post-Race Chalk Talks, where the teams from all the boats gather at a pre-designated place and time to share a brewski and discuss the events of the day.
  • Regular Fleet Cookouts are a great way to get together at the club, just as another opportunity for friendship and sharing.
  • Clinics, Seminars and Demonstrations are an underestimated opportunity to build value in fleet membership. The topic could be any interesting subject from maritime art, knots and splices, the racing rules, sail trim techniques… anything to draw a crowd. Invite other fleets. Invite other sailors. Get it on the club calendar and bulletin board.


·       Off-season Events, Parties and Socials. Usually held when sailing is limited (late autumn, winter, early spring), these events are on the calendar just keep the ball rolling and friendships alive. Ideas for this category that have been seen on fleet calendars are:

  • End of Season Banquet and Awards
  • Midwinter Social
  • Spring Ski Trip


·       Days for Helping Others. The first thing that comes to mind is reaching out to help newbies get up to speed, but it doesn’t end there.

  • One-on-One, Expert-Newbie Time - Sailboat racing is fun, but winning sailboat races is even more fun. It’s a steep climb to the winners’ circle, so winners need to take an active role in lifting up the back of the fleet. Newbies need to see progress, or they may become frustrated and bail. The best fleets are the ones where ideas are freely shared, winners are generous with advice and with coaching support. 
  • Grab-Bag Racing – When the serious season is over, use a four or five race series to mix up crew members. Skippers remain with their boats, but the other positions are filled by drawing names from a hat, with the idea to completely remove sailors from their normal skippers. The rewards are sharing of techniques and putting together people who might never get to sail together otherwise.
  • Fleet Work Days – The idea for a fleet work day is have everyone gather to address the repairs or maintenance needed on boats in the fleet. Incorporating an ‘equipment swap’ would be a great way to upgrade older equipment. The expertise, the helping hands, the sharing of ideas is a great way to build value, renew and strengthen friendships, and might be especially helpful in bringing fleet members who have been absent for a while back into the fold.
  • Wounded Warrior - There are numerous programs for sharing the sport of sailing with surviving veterans, the visually impaired, and the physically handicapped or other people with special challenges. The rewards are great for everyone involved.

Dining Together at Oak Island  Watching the Sunset
Galveston Bay's Ensign Fleet 2 Cruised to Oak Island's Cabin Rentals, Enjoyed Dinner and a Sunset Together, Then Raced Home the Following Day on the Prevailing, Downwind Breeze 



·       Fun Races and Cruises. These are events specifically designed to be fun without the seriousness of racing. Some fun ideas include:

  • Organize a Long Distance Race - One of the most memorable annual outings on Ensign Fleet 2’s calendar was the cruise as a fleet to Galveston from Houston Yacht Club, the overnight stay at a hotel on the water, the dinner together on Saturday night and the twenty six mile, downwind race back to HYC. The prevailing sea breeze almost never let us down and the Saturday evening spent together was usually accompanied by a seminar or program of some sort.
  • Fleet Rendezvous for an Overnight Cookout – Some fleets organize and enjoy cruising as a fleet to a local destination for a campfire/cookout/cabin rental sleepover. Breakfast the next morning and a fleet cruise home. Great memories, fabulous pictures and fun times!
  • Riddle-Solving Poker Run – Organize a Poker Run for your fleet, where envelopes are hidden at five to seven destinations, each with a playing card inside, one envelope for each boat. Riddle-solving or a Treasure Map reveals the destinations. Scoring is by a pre-announced system of best poker hand, finish position back at the dock, and any bonus-point items one might find floating in the water or skimming across the surface. Everyone is a winner at the follow-up cookout.


Fleet Cruising
Cruise Together as a Fleet to a Nearby Destination


·       The Racing Schedule. Almost every fleet has race days in their season calendar. Indeed, the schedule for some fleets consists primarily of race days, but clearly, racing is not the only way to build value, camaraderie, and friendship with fellow fleet members. 


So, the calendar determines, to a large extent, the outcome of your fleet’s season. Feeding the success of this single document is the positive anticipation and contribution of fleet members and the never-ending communication efforts of the leadership. Reminders, timely invitations, constant oversight of upcoming events and the review of delegated responsibilities prevent important details from ‘falling through the cracks.’ Luckily, there exists wonderful online tools to assist in the leadership efforts, like email, Sign-Up Genius and a plethora of Google Tools.


No fleet building and strengthening program would be complete without the presence of one or two attractive Ensigns; available for purchase, charter or loan. Fleet 63 on Barnegat Bay has a successful Charter-To-Own Program where interested sailors have the opportunity to charter a fleet owned boat. If they do so for three consecutive years, the boat becomes theirs. Charter fees recoup the costs of initial purchase and refurbishing, whereupon the fleet reinvests those fees into yet another ‘fleet building’ boat. Essential to this program are ‘fleet work days’, where shortcomings in the ‘fleet boats’ are addressed. Proper rigging, seaworthiness and appearance are important considerations to a potential buyer. There is a limit, of course, but after all, we’re growing a fleet here! Rig it right and make it strong!


Some fleets are fortunate to have a dutiful, dedicated, fleet builder… an individual who methodically keeps an extra boat around, fixes it up and has it available for purchase when the efforts of fleet building are successful.

The Ensign Class Association has its Boat and Equipment Placement Donation Program whose main goal is to move old, unused or derelict boats into active fleets and/or youth programs. The program is an ideal way to attract young sailors to the Ensign Class in partnership with the Youth Sponsorship Program.” The committee is chaired by Zeke Durica, with committee members Neil Lynch and Bob Conkey.


In review, a fleet’s season calendar is the primary document for strengthening and building a fleet. Input from fleet members is vital to gain consensus, define direction, build excitement and ensure success through support and contribution. For full effect, the calendar should be multi-faceted, presenting a variety of activities that are proven to assist in fleet building efforts… racing, cruising, teaching, helping, socializing, parties, off season outings and especially those one-off, ‘fun’ events, whose creation is limited only by imagination. Leaders need to be in constant review of the calendar, thinking through the communication needs and delivering them in a timely manner. When the program is successful, growing the fleet will be much easier if there is an attractive boat nearby, available for purchase, and there are model, fleet-level programs that are easily adapted. 


Most of all, make it fun. An active, friendly, fun-loving fleet garners attention and is attractive to others. Regular, highly visible, meaningful and enticing activities will make YOUR fleet the one where outsiders know they can find the fun, value and camaraderie worthy of their time and investment.

Don’t know where to start? Below is a list of activities and ideas collected from around the web from a variety of sources, sure to enhance your fleet’s growing experience:

·       Throw a party open to all sailors

·       Host a breakfast social

·       Host a fleet mid-winter party and ask everybody to bring something.

·       Organize a boat work party.

·       Make arrangements to host a regatta next summer.

·       Take a road trip to Midwinters

·       Organize several ‘Take A Friend Sailing’ days

·       Offer help to someone on the water.

·       Spend an entire weekend afternoon practicing.

·       Carry your gear through the clubhouse wearing a huge grin on your face.

·       Always have an article in the club newsletter.

·       Hang a half model in the clubhouse.

·       Put invitations to join your club or fleet in the personnel offices of the major employers in your community.

·       Put perpetual trophies in your clubhouse.

·       Do race committee duty.

·       Print a fleet bumper sticker.

·       Sit at the sign-up desk for a regatta.

·       Help in the kitchen for a regatta.

·       Get your fleet on TV.

·       Do committee duty for some other fleet to avail your fleet some reciprocity.

·       Bring a cooler of beer and soft drinks to the rigging area and give it all away.

·       Set up a boat at a boat show.

·       Report results to your local newspapers or websites.

·       Invent a cool name for your fleet.

·       Mentor beginners so that they have fun.

·       Challenge another fleet to a contest, any contest, sailing or not.

·       Set up a fleet ski trip.

·       Send a group photo and article to the ECA Newsletter Editor.

·       Maintain a “For Sale” list.

·       Clean and polish your boat in as public a manner as possible.

·       Leave an enticing invitation on your clubhouse bulletin board for others to “Go Ensign Sailing”.

·       Video the fleet for a day.

·       Create a fleet scrapbook and leave it in your clubhouse.

·       Conduct a rules seminar.

·       Publish a fleet newsletter.

·       Loan out your boat when you do committee duty.

·       Target the parents of the kids who sail in the fleet with endless sales pitches.

·       Invite parents for a sail to show them how incredible the Ensign is at being a family day sailor.

·       Post race scores in a conspicuous place.

·       Give out a lot of silly but useful trophies.

·       Sail backwards in front of the club.

·       If you usually win, start late and coach the others as you pass them.

·       Create a fleet webpage.

·       Invite sailors from other clubs to visit your club and welcome outsiders when they show up.

·       Call the new guy by name.

·       Give somebody a new line for his Ensign.

·       Get your crew to join the ECA so they will get the yearbook and three newsletters and be on our e-mailing list.

·       Invite juniors out to sail.

·       Set up an e-mail list and remind everybody to come out every week.

·       Invite others to join you whenever you go sail.

·       Express personal disappointment any time a sailor misses an event.

·       Tell everybody how much fun it is to go out and sail all over the place in an Ensign.

·       Run weekly local races at your club.

·       Assign someone to be the crew finding guru. Rotate the position every year.

·       Assign someone to manage post-race socializing and debriefings. That person is responsible for making sure they happen and making sure that veterans and rookies are interacting.

·       Designate at least two events during the year where the top teams split up and crew with the teams that are struggling.

·       Offer a seminar yearly on how to pack and unpack a boat for travel regattas.

·       Create a "young professionals" program that invites interns and new employees from local companies to crew (and later skipper). Most companies you reach out to will embrace this because they love having their staff interact socially outside of work.

·       Create a list of alternative activities to do if the weather is not good.

·       Designate certain dates every year for coaching. Make sure to cover tuning, boat speed techniques, and tactics.

·       Have the yearly regatta schedule locked in and on six months before January15th every year.

·       Assign someone that will commit to weekly emails about upcoming events and to sending out results.

·       Call fleet members who have been missing for a while. Tell them you miss them and listen when they tell you what’s going on in their life.


Racing in the Ensign Mid-Winter Championship
Fleet Racing in the Ensign Mid-Winter Championship on Lake Murray, South Carolina



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