It is likely that many of you have been on some sort of a group cruise. Maybe it was a day trip in your trusty center console to a beach or restaurant somewhere. Maybe it was a weekend trip. Maybe it was a longer cruise to somewhere or nowhere. 

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AYC New England cruise leaders Bill and John at a 2018 event.

The pleasures of taking your boat out and joining up with friends, old and new, are undeniable. Cruising with friends and family is often the unifying vision in the varied daydreams of boat owners and boat shoppers.

Some of you have perhaps helped organize such a cruise. If so, you likely found it was a lot of work. So, what does it take to make a cruise fun for all? 

In the world of real estate, they say the three most important things are “location, location, and location.” Adapting that to cruise planning, perhaps the six most important things are “planning, planning, and planning,” joined by “communication, communication, and communication.”

As you read this, some 45 Annapolis-based boats, power and sail, with more than 100 crew members, will be departing for a two-plus week cruise to New England. The planning and communicating for this cruise were organized and executed by three seasoned New England cruisers, all members of the Annapolis Yacht Club. 

John Patmore, Bill Museler, and Chuck Hurley between them have close to 100 round trips to the friendly waters of Long Island Sound and southern New England. Each has planned many a yacht club cruise, and each has experience planning a New England cruise for a group. 

The trio, along with some fellow cruisers, worked together to execute the AYC cruise to New England in 2018. They came together to plan a similar cruise for 2020. That planning began in the fall of 2019. As one cruise planner suggested, “It is a great way to get through the winter around here.”

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Left to right: Port Captain Bob Smith, New England cruisers Nick Malakis, Noreen Makakis, and Patty Baumiller share a beverage on a sunny afternoon in Martha's Vineyard in 2018.

You know what happened next. As the fall of 2019 turned into the spring of 2020, and after considerable work on venues, events, and a list of cruisers, they came face to face with the realities of Covid. In April of 2020, understanding where Covid was headed, they shelved an immense amount of planning, canceled the cruise, canceled planned events, negotiated on event deposits, and hunkered down like the rest of us. 

But Covid would not be the final victor. The 2020 cruise planners decided, fairly quickly, to keep venue deposits already in place as well as the planned destinations for a “do over” in 2021. They were ‘betting on the outcome” that vaccinations would advance, as they did, and venues would open. This involved a certain amount of blind optimism and a little amateur epidemiologist skill.

It Takes a Village

The reengineered cruise covers 1000 miles and includes stops in Newport (twice), Cuttyhunk, Martha’s Vineyard, and Nantucket. By the time the boats leave Annapolis, the planning and communicating will have run 20 months. 

It takes a village, or in this case, a committee, to make it all happen. As good as the trio of cruise leaders are, they needed and welcomed help.

Help came in the form of committee members who joined the planning team to essentially master one stop along the way. If the cruise leading trio were the “Admirals” of the fleet, the committee members became the “Captains” of the port of call. The Port Captains included Maria Museler, Bob Smith, and Sue Pitchford. Their job, complicated enough, was to contact the venue, arrange the events, consider docking logistics, and work with the Admirals to build the communications.  

Given the Covid-induced extended planning period for this cruise, the committee had, by year-end 2020, a complete list of stops and eight venues for group gatherings, lunches, happy hours, or dinners along the way. They began communicating the cruise, building interest as they reinstituted planning for 2021.  

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Brant Point Light in Nantucket. Photo by Charles Hurley

The eight venues had different descriptions, restrictions, methods to pay, and even dress codes. To make it all work, they devised a necessarily complicated registration form and put it out electronically to would-be cruisers on January 15. By the end of the day, the cruise and venues were booked and oversubscribed so there was a waitlist.

Given the payment complexity built into the eight events, the committee also needed a matrix for the event payment. AYC’s finance chief, Anne Connolly, effectively joined the committee to manage that complexity, overseeing the cruisers’ registration. As the Admirals report it, the cruise would not happen without Anne. 

Another important staff adjunct to the committee was the AYC communications team. Recall that it is all about planning and communicating. The Admirals and Captains relied heavily on the communications team to articulate and simplify the complexity. Without them, all the planning in the world could be for naught.    

Managing Moorings and Communications

Along with the events, there were moorings or marina slips to get in five locations. Committee member Bob Smith had already agreed to be the Port Captain for the Cuttyhunk stop. Fortunately, Bob also took on the larger marina and slip “matrix” challenge. 

Marina slips are harder to find in New England and more expensive than on the Bay. Moorings are more the norm. Either were going to be in high demand in the 2021 season, especially given the Covid-impacted 2020 season. This suggested the need to know the first day of the season that dockmasters and harbormasters at the intended destinations would accept a slip or mooring reservation. Naturally, those “opening dates” varied among the destinations.

Bob mapped them all out. He developed a list of dock and mooring options at all five stops and determined the first day that summer reservations would be taken. He then worked with the cruise leaders to communicate that information to all registered cruisers and urge them to make registration a priority.

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Catboat approaching Edgartown Yacht Club. Photo by Bill Museler 

The cruisers, armed with this information, set the dates on their calendars and maybe even a bedside alarm. They dialed in, or connected via Dockwa, within minutes of the opening bell to secure their slip or mooring. A few computer glitches later, most had a place for their boat during the five stops scheduled for the cruise.
So, by early in the execution of worldwide Covid vaccinations, this New England cruise was planned, venues booked, and slips and moorings reserved. As winter turned into spring, the planners and attendees waited and hoped the vaccination push would work and our world would open up a bit and begin a return to normal. It did!

In that hopeful window of time, next up on the committee members’ agenda was preparing the fleet for the trip and building their knowledge of the itinerary. The Admirals used Zoom and later in-person meetings to discuss boat preparation, safety at sea, navigation challenges, marina stops along the way up and back, and so much more.   

The crown jewel of the cruise communications is the New England Cruise brochure. It is the bible of logistics, a comprehensive listing of all the above, from navigation to dress code. At press time, it was still being edited, all 113 pages of it. Once polished, it will be electronically delivered to all cruisers.

Finally, slip/mooring reservations done, event registration completed, planning sessions attended, and boat loaded; most of the cruisers will be on the way by mid-July. Next stop, fun! 

By Mike Pitchford

Stay tuned for a travelogue of the first part of this group cruise in PropTalk's September issue.