The once-in-a-lifetime experience of sailing the Great Loop

Aerial photo of a vintage wooden boat in coral sea.

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What van life? The Great Loop sails through the eastern U.S. and Canada

The Great American road trip has turned nautical. There’s an alternative to the van life that has inspired so many to take to the roads for months or years at a time: ventures by watercraft.

Imagine a year spent weaving through intercoastal waterways, traveling through marshlands, and along rivers under the shadow of skyscrapers. Those who manage it are part of a select few called Loopers. GetMyBoat explores the wonders of the Great Loop with first-person accounts and interviews of these Loopers.

Aspiring Loopers can start anywhere on the route, which heads up the eastern Atlantic coast to the Hudson River, then toward the Great Lakes before turning down the Mississippi River to New Orleans. Boaters cross the warm waters of the Gulf of Mexico and skirt along the coast of the Florida peninsula to complete the circuit. This incredible experience allows lingering glimpses into the nooks and crannies of American life by the water—not to mention plenty of time relaxing on docks and, perhaps, even connecting with fellow Loopers (and future lifelong friends) flying the distinctive Great Loop burgee.

The Great Loop consists mainly of protected inland waters where mariners are not far from shore. It’s an excellent trip for tenderfoot boaters and seasoned pros alike. Power boats with comfortable accommodations below deck are a popular choice for Loopers. Some choose to let the winds carry them but pack backup motors just in case. Other crafts include fishing boats and yachts; a few even dare to use kayaks to complete the Loop.

Whether you are a seasoned nautical professional or just bought your boat last year, “as long as you’re comfortable and competent handling your boat, this trip is for you,” Kim Russo, director of America’s Great Loop Cruisers’ Association, explained. For history buffs eager to explore the oldest cities in the U.S. or a foodie who might enjoy trying local delicacies like shrimp and grits in the South and poutine along Canada’s waters, you’ll find your niche along these waterways.

Some boaters try to complete the Loop in one year, tackling the whole journey in one go, but others take a longer, leisurely view. “Other Loopers tell us it took them the entire 6,000-mile loop to learn how to slow down—so now their second time around, they’re lingering and enjoying the places they enjoy,” Jan and David Irons wrote. They completed their Loop on the Optimystique in 2018.

Mike O’Malley from Illinois completed the Loop in segments in 2017. “I was working full time. I would take a week off work at a time and leave the boat wherever I ended up,” O’Malley said. This approach allowed him to invite friends and family to join him along the way, including his wife Sharon, for whom he named his boat My Sharona. “It was an adventure. It was seeing what was over the horizon on a daily basis. It was meeting local people in both small and large towns across the U.S.”

Loopers work counterclockwise around the route, following the warm spring breeze up the Atlantic, making their way through the Great Lakes in the summer to make it to the Gulf Coast by winter. In preparation for the year-long journey, many voyagers take smaller, month-long trips called “mini-loops” to sharpen their nautical skills. These mini voyages are great for boaters who aren’t ready for the longer journey.

Nagui Matta, a solo Looper from Michigan, explained how the trip challenged him, “I learned a lot on this loop. Everything from navigation, weather, tides, boat handling. Finally doing it solo, I learned a lot about myself, from dealing with challenges and adversity to being spontaneous and ready for whatever the day brings.”

Boaters miss out if they don’t stop to stretch their sea legs and enjoy the many side trips along the Great Loop. Take a tour of the historical museums and mansions along the Chesapeake Bay, witness the majesty of the Statue of Liberty in New York’s harbor, swim in the clear blue waters of Bruce Peninsula National Park, try a tasty bowl of gumbo in New Orleans, and appreciate the abundant wildlife in the Florida Everglades.

As beautiful as the scenery is, most boaters agree that the people along the way made the trip. Jerry and Peggy DeCelle from New York told Stacker some of their highlights were rafting with other Loopers, sharing stories, dinner, and learning new card games. “The places we enjoyed the most were definitely those where we spent time with our new friends. We were awed by the beauty and nature with dolphins, sharks, manta rays, sea turtles, starfish, manatees, and even a whale sighting.”

Last year, 230 boats completed the Great Loop, and Russo says they are on course to exceed that number this year. Remote work opportunities in the previous few years have drawn more people to the challenge of this once-in-a-lifetime voyage. Explorers can discover the freedoms of the open road on America’s waterways.

Story editing by Carren Jao. Copy editing by Kristen Wegrzyn.