What Is The Great Loop? (And How To Sail It For Free)

What Is The Great Loop? | Life of Sailing

Last Updated by

Capt Chris German

June 15, 2022

If you are just getting into sailing like so many of our readers at lifeofsailing.com, you may have never heard of “The Great Loop.”

But if you spend any time with cruisers, the term is bound to come up at some point. It is to the cruising world, (power and sail alike) what Sturgis and Route 66 rolled into one would be for the motorcycle world.

It’s the highwater mark for the liveaboard boaters of all stripes and if you have done it, you can say with pride that you sailed “The Great Loop.”

Moreover, The Great Loop is more than just a badge of honor for those who have had the fortune to do it. It is also a piece of Americana that runs through the hometown of more than 75% of Americans and is by and large the aorta of the American Shipping economy.


Table of contents

What Is The Great Loop?

The Great Loop is a hodgepodge of canals and rivers, lakes and oceans, gulfs, and sounds, all sewing one giant connected 6,000 plus mile channel around the Eastern half of the US and Canada.

Inception of The Great Loop

The Great Loop had a very inauspicious inception. There were no golden spikes driven into the ground to commemorate it’s creation and no brass bands playing “Stars and Stripes Forever.”

It was really a youthful notion that envisioned its existence in the first place. It was conceived by a small town American boy by the name of Ken Ransom, who in 1897 wanted to set sail on the Ocean in a sailboat he would build himself in Michigan.

But since then, it has blossomed into an entire subculture that centers around an American public works project that has been evolving since the first days of the Nation.

The first pieces were envisioned by the founding fathers themselves before the ink on the Constitution was even set. They sought a way to secure shipping interests by creating a series of canals which would allow ships to travel between the North and South and establish an alternative route to fuel the newly minted US Economy and interconnect the several states and territories of the newly established nation.

Washington himself created many of the surveys that would be used to set out the inaugural public works projects. And thousands of slaves, immigrants and natives would give their lives in the efforts to create such a vast network that over time would save Millions of dollars in shipping and fund the American experiment to this day.

The Original “Looper”

But it was Ransom, the original “Looper '' as they are known, who surmised that if he left that very dock on which he stood in Michigan, could sail the Atlantic Ocean, the ICW, the Mississippi River and the Gulf of Mexico and returned to that very spot, having made an entire loop in a sailboat.  

Kern Ranom
Photo sourced from BoatUs. Please visit for a more complete story of his voyage. Kern Ranom towed his vessel up the Erie Canal as seen here

What he could not possibly know, nor foresee at that time, would be the millions of vessels who would follow in his footsteps for the next 120 years and how this loop would become the holy grail of voyages for mariners from around the world.

The Great Loop Docu-series

It is with this eye to history and this enthusiasm for the holy grail of voyages, that The Charted Life aims to create a docu-series where they will select five teams of sailors to learn to sail, obtain a vessel and then set out to have their own adventures, sailing around The Great Loop.

The Great Loop | Life of Sailing

They will film every aspect of this voyage and share their adventures with an audience of viewers who no doubt share in the ambitions of Ransom himself, to complete a Great Loop of the Eastern Seaboard.

This project will require new techniques in storytelling and videography and will use the latest advancements in wireless and web-based programming to share the adventures of the five teams as they make their way around the Loop.

Each team will garner support for their vessel by creating a team of followers on social media who will support them through various patronage platforms and through in kind donations delivered by the online marketplace.

At the completion of all five voyages, The Charted Life will compile the footage obtained via on board cameras and microphones, as well as video footage they shoot from a chase boat on the water and a bus on land, as they follow these boats around the Loop.

With the compiled footage they will create a feature length documentary series that is broken into four seasons as inspired by Antonio Vivaldi, Winter Spring Summer and Fall.

A fifth pre-season will be included showing the selection process and sail training as well as the construction of the vessels in Tampa Bay, Florida at the Catalina Sailboat Shop and Factory where they will train, depart and finish the voyage one year from the start.

This voyage will not just be challenging from a technical perspective but also from a human and spiritual perspective.

When Ransom and his crew made the voyage, they suffered freezing temperatures, starvation and deadly situations on a regular basis.

The teams of voyagers will be made as safe as possible, but the fact that these people will live aboard a sailboat for one year will present a set of its own inherent challenges and risks.

They will be forced to endure long tiresome hours at the helm of a sailboat in some very challenging waters.

They will give up many of the creature comforts afforded to land-based dwellers.

Services like electricity on demand, limitless clean water and climate control are some of the few things these sailors will be forced to live without that will be certain to cause some hardship for these sailors.

What's more, the environmental wear they will encounter is certain to spill over into their interpersonal relationships and become a challenge in itself when teamwork and togetherness is paramount for success in a voyage like this.

The success of each team will be watched and supported by social media and so therefore, the daily interactions and personalities of these sailors will be of utmost interest to the viewers.

The team that best harnesses the support of their followers and translates that support into speed, comfort and safety will be awarded certain perks provided by their patrons as well as a cash prize at the close of the voyage and will be given the title to their vessel so that they may continue their voyage funded by their followers around the world.

The first time The Charted Life tried to plan this voyage and this project with one boat, they had great success.

They offered a 42’ endeavour for the purposes of the project and received 21 entries with over 200,000 views.

But it was this overwhelming success that convinced them to reexamine this effort and instead of selecting one team, expand the fleet to five boats and select five teams of sailors for this project with a fleet of newly constructed vessels.

By offering a brand new boat to the sailors, they can wire the boat for video and sound and can focus the story on the people and the places and history, instead of focusing on the restoration of the boat.

The viewers and social media will be key in the development of this project with the teams relying heavily on the support of their friends, family and followers just a Ransom himself did more than 120 years ago.

And it is in fact the power of social media that will begin this project as the entries will rely on their social media savvy to help them win a place on one of the five selected teams.

How Can You Enter?

Each entrant will create a one minute video answering the question, “why do you want to sail the Great Loop?” and submit it to The Charted Life.

They will then add that video to their Youtube Channel and share that video on our social media feed and website.

The top fifty videos submitted in terms of views calculated by Youtube will be submitted to the producers and of those fifty entries, twenty individuals will be selected to join one of the five teams of sailors.

Entries may elect to submit four separate one min videos as entries for each member of an affiliated group of entries and link to each other as a team.

Alternatively, individuals may elect to submit an individual video, unaffiliated with any other entrant.

Views will be calculated by dividing the total number of views of affiliated videos divided by the number of affiliates. (IE four videos are received as affiliated, all four view counts will be added together and divided by four).

By using social media to decide the top 50, they hope to involve their enthusiastic followers of this project to assist in its creation.

As this project will require a massive collaborative effort of sailors, web gurus and creative talent, they ask that anyone wishing to join in on this project send us a video resume explaining their interest in this project and how they might wish to assist.

Questions about the planning, production or rules of this project may also be sent here.

What Is The Great Loop? (And How To Sail It For Free)
Capt Chris German

Capt Chris German

Capt Chris German is a life long sailor and licensed captain who has taught thousands to sail over the last 20 years. In 2007, he founded a US Sailing-based community sailing school in Bridgeport, CT for inner city youth and families. When Hurricane Sandy forced him to abandon those efforts, he moved to North Carolina where he set out to share this love for broadcasting and sailing with a growing web-based television audience through The Charted Life Television Network.

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