The Benefits of Belonging to a Virtual Sailing Fleet



Fleet 5 Long Island Sound is a virtual club with the motto, “Sailors with a Passion for Cruising.” Founded in 1991, Fleet 5 LIS has a rich history, with its roots tied originally to Catalina Yachts. Over time it has expanded into a more inclusive cruising club, with members who own sailboats from most manufacturers along with a sprinkling of trawlers. 
Fleet 5 LIS offers sailors an opportunity to leave their dock and get out and cruise in an organized group atmosphere. It’s perfect for those who are looking to venture further than they would normally cruise on their own. Sailors with a Passion for Cruising can have various interests. Most dream of doing some coastal cruising – and the coastal cruising grounds of the Northeast are the greatest in the world – while others look to cruise long distances.


This mooring in Port Jefferson, NY is part of the new Fleet 5 mooring program. © Tom Lanzilli



Members cruise as a group for safety and for added enjoyment. Photo courtesy of a Fleet 5 member

Of course, Fleet 5 LIS also has members who look forward to the occasional race or are content with daysailing, and even those who have retired from boating and just want to be part of it all. This is all OK, and it’s what makes this fleet so exciting. Fleet 5 LIS is a growing group of friends, all of whom partake in their love of the water and visiting new and friendly ports of call.

This club is much more about the lifelong friendships that have developed and this goes way beyond a shared love for sailing. Members share in each other’s family joys like new grandchildren as well as their family grief. Each member thrives on the camaraderie of this uncontrollable interest they have in sailing and cruising. Think of all the times you’ve run into the challenge of fixing something on the boat or planning a new trip. How cool is it that you can reach out to someone who’s done it and then learn from their experience?

The fleet also plans and enjoys an annual summer cruise to places such as Nantucket, Provincetown, Edgartown and elsewhere on Martha’s Vineyard. These trips are carefully planned and are continually the best events on the Sound. The summer cruise is the fleet’s marquee event of the year, and six to seven months of planning goes into it. Cruises can cover more than 200 nautical miles, so we cruise as a group because there is safety in numbers. We check in as a group each morning to discuss the day’s plan, we review fog situations when appropriate and we understand what each of the captain’s plans is for the day. Sailing can have its trials, both boatwise and healthwise. Having friends around to help when a situation occurs is not only very helpful and comforting, but it can be lifesaving as well.


Members of Fleet 5 LIS on an annual summer cruise to Narragansett Bay. © Ken Berta

In addition to the annual summer cruise, the Fleet 5 LIS calendar is packed with events both on and off the water, including rendezvous, fleet meetings, various boat shows, and even a snowbird gathering in Florida. Sometimes we travel together to other parts of the world: Bermuda, Mexico and Greece, to name a few. We meet all year long and are a group that loves to get together and party where we can, of course always with safety in mind. You can feel this when you read our cruise write-ups or attend an event. It has always been that way. As our members say, “Attend a Fleet 5 cocktail party and you will instantly become a member.”

Today, Fleet 5 LIS offers members value in the form of a new mooring program that we intend to grow year by year. Docking is expensive, finding a municipal mooring is often challenging, and locating a good, un-crowded anchoring area is becoming difficult. Having a club mooring program is a tremendous asset, and will offer greater benefits as the program grows.

Fleet 5 LIS has a lot going for it. Feel free to check out our website at It is full of great information. You can be part of the fun by joining the fleet online at

A resident of Norwalk, CT, Tom Lanzilli is the current captain of Fleet 5 Long Island Sound. His sailing experience includes taking his Catalina 36 MKII Ithaka to Bermuda and back.

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