Chesapeake Bay boaters make the leap from small boats to a vessel that took them on a 13-month circumnavigation around the eastern half of the United States: America's Great Loop.
Embarking on a great adventure
After Covid changed their retirement plans to travel by plane, Jim and Leslie Wilkins discovered on Facebook the 6000-mile Great Loop, a waterway circumnavigation of the eastern half of the United States and part of Canada. The Annapolis boaters were stunned to learn that such a trip was possible and declared, “We should do it!” And they did, embarking on a 13-month great adventure at 10:30 a.m. on May 18, 2023.
Both Jim and Leslie grew up boating. He with his grandfather on the waters off Long Island and she with her family’s small powerboat on the Severn River. As a couple they have been boating together for decades, beginning in college when Jim would take his 14-footer out of Cove of Cork, run up the Severn River, pick up Leslie, and head back down the river to Annapolis.
The couple wanted to raise their five children in a boating environment, so during the last 10 years of their 29-year Navy career the family purchased a 20-foot bowrider, and over the course of the past 30 years have owned three runabouts at a time, including a 22-foot Regal Bowrider, a 16-foot Boston Whaler center console, and a 13-foot Boston Whaler classic runabout.
For their Great Loop adventure, the pair knew that they would need a substantially larger boat than any they had previously owned. In 2021, one day after retirement, they flew to Forida and closed on a 2004 Meridian 459. They got underway the next day with only limited big boat experience and lots of excitement and trepidation. Over the next three weeks they brought it 1300 miles to their home slip on the Severn River.
Making the leap to a cruising boat
Jim: When we started looking for our Loop boat, I knew that I wanted twin diesel engines and a flybridge. My grandfather’s boat had a flybridge, and I wanted the view that it offers and to experience the joy of being in the sunshine that I remembered from my childhood. We’d never owned a boat anywhere near the size of the Meridian, and it was quite a learning curve.
Leslie: Our five sons often referred to our home as the Jolly Roger, a sort-of pirate house, so since the new boat would be our second home, we named it Jolly Roger Too. It has a huge salon, large walk-around queen beds both fore and aft, bow and stern thrusters, and a swim-platform-mounted dinghy davit that makes launch and recovery of the dinghy simple and fast. I love the sliding glass doors in our aft stateroom.
Slipping the lines
Jim: Prepping for the trip and taking in the last line on the first day was one of the hardest parts. There’s always one more thing to do before you leave, so six months in advance we picked an exact date and time that we would leave.
We exited the Bay via the C&D Canal to Cape May, slipped offshore to New York City and around Long Island Sound to Montauk, and back to NYC. We headed up the Hudson through Lake Champlain (we didn’t do the Erie Canal) to the Chambly Canal and the Richelieu Riverway to the St. Lawrence Seaway (SLW). We then turned downstream for a two-day voyage to Quebec City, and against the SLW to Montreal and up the Ottawa River to Ottawa.
Summertime and new friends
Jim: Form Ottawa we traveled along the Rideaux Canal system to Thousand Islands in New York and ventured back up to Canada to the Trent-Severn Canal System and on to Georgian Bay and the North Channel. Georgian Bay, with Lake Huron to the south and the North Channel on the western side is one of the best boating areas on the Loop. We were intentionally there in June, July, and August to enjoy the warm weather and fresh, clear water. We found areas that we didn’t even know existed.
Leslie: One of the things that surprised us about doing the Loop is the friends we have made. In Canada we had lots of fun together swimming, hiking… even playing bumper boats with our dinghies! We have stayed in close contact with our new friends and have even vacationed with them afloat and ashore.
At a Looper rendezvous in Norfolk prior to departure, we met Aubrey and Terri Smoot—and their dog Yudee—from the Chesapeake Bay (See The Great Loop: A Real Retirement Adventure). We met them again in New York and buddy boated for a while and bumped into them several other times. They are just one of the dozens of couples that we met and have maintained friendships with. Back in the Chesapeake, Aubrey and Terri hosted us and Jolly Roger Too overnight at their home in Kilmarnock, VA.
Jim: Heading south on Lake Michigan, we bounced down the many wonderful port cities on Michigan’s west coast until we got to Chicago. There we took the Illinois River to the Upper Mississippi and to the Ohio River and the Kentucky Lake region to meet up with the Tennessee River. We traveled east on the Tennessee River to Chattanooga for a few days and turned around and followed the Tennessee River back to where it becomes the Tenn-Tom (the canal system connecting the Tennessee River and the Tom Bigbee waterways).
Thanksgiving with family on the Gulf Coast
Leslie: We followed the Tom Bigbee south to Mobile, AL, and into the Gulf where we turned west to visit Ocean Springs, MS, for Thanksgiving with family members. After the holiday, we headed east to Carrabelle, FL, a staging point to wait for good enough weather to attempt the 170-mile crossing to Tarpon Springs, FL.
A dynamic Gulf crossing
Leslie: We left Carabelle with 14 boats for a nighttime crossing. Half were headed to Tarpon and half to Clearwater. Although we had waited for what looked to be a good weather window, by 1 a.m. the winds and waves had really kicked up, and the seas were pounding us. There was no moon, so it was completely black. It reminded us of riding on Space Mountain roller coaster in Disney World. You couldn’t see what was coming next!
Jim: Although we never felt in danger, it was tricky to navigate, especially with boats passing us on the reciprocal course. Eventually we arrived safely and without incident. The lesson learned was that weather forecasts are just best guesses, and to be ready for anything!
The Keys and Bahamas
Jim: Upon reaching Tarpon Springs, we travelled over a few weeks to Fort Myers, Marco Island, and into the Everglades to reach the Florida Keys. From Key Largo we launched for the Bahamas (Bimini, Chub, Exumas, Eleuthera, Abacos). In addition to the Canadian waters, some of our favorite parts of the Loop were the Florida Keys and the Bahamas (particularly the Exuma chain). We had lots of fun there before returning to Key Largo and following the ICW north and taking the Dismal Swamp route to the Chesapeake Bay.
Leslie: Once in the Chesapeake we bounced back and forth across the Southern Bay (Hampton, Jamestown, Onancock, Crisfield, Smith Island, Tangier Island, Kilmarnock, Solomons Island, Oxford, St. Michaels, Kent Island) and had a wonderful time. This was the first time we’d really explored this part of the Chesapeake. We stopped at lots of wonderful spots, buddy boating and meeting up with friends old and new, before coming home to Crownsville, MD, on the Severn River.
Renting our home
Leslie: While we were away, we rented our home through iTrip, which worked well for us and allowed us to use the house as a revenue source to cover our fuel and marina costs. Over the course of the year, we had 35 different renters! The short-term rental paradigm gave us the flexibility to return home twice, once due to the death of a dear friend and pastor of ours, and once for three weeks at Christmas.
Jim: Both times when we returned home, we left our boat slipped at a marina and didn’t experience any problems while we were away. The marina operators and other slipholders checked our lines and watched our boat. Some people worry about thieves, but our entire trip was without incident. Others we have talked to have had the same good experiences.
Anchorage or marina slip?
Leslie: Both are wonderful. We enjoyed anchoring alone, but also dearly loved anchoring with friends in a raft of two or three boats. Marinas provide a great opportunity to relax and get ashore and meet other Loopers as well. Anchoring is cheaper and more private; marinas allow for comfortable transportation for reprovisioning and going out for meals.
Crossing our wake
Jim and Leslie: When we returned home our family organized an informal party. Our neighbors, friends, and church members met us at our dock. Completing the Loop feels like a real accomplishment, something we looked forward to, but also something that we didn’t want to end. As a transition period we kept renting the house until mid-October and hung out on our boat to cover some boat maintenance expenses.
Advice for someone considering the Loop.
Jim and Leslie: Just go… don’t overthink it. Everyone along the Loop is ready to help… and we all needed help at one time or another. The entire Loop can seem daunting, but if you just take it one day at a time, it is quite do-able. This adventure is eminently achievable by any couple (or even solo) that enjoys travel and a bit of adventure. You will surprise yourself with what you can accomplish.
Future plans
Jim and Leslie: We could spend two or three more summers visiting Lake Champlain and Canada. We’d love to spend more time in the Bahamas, and we’ve talked about the “Down East Loop” around Nova Scotia and Maine. In a few years we may want a smaller boat that takes less maintenance but is still big enough to explore the Bay. Most importantly, we have 16 grandchildren from Italy to San Diego that we want to visit!
More Tips for Would-Be Loopers:
- Don’t spend four or five years picking a boat, but once you choose one get to know it well before you cast off.
- AIS is hugely helpful. With GPS and electronic charts, even a novice boater can comfortably and safely complete the Loop with practice using these tools.
- We like the Active Captain app to find anchorages and marinas.
- Amazon will deliver to just about any marina, so it’s not hard to reprovision by ordering a day or two in advance.
- Americas Great Loop Cruisers’ Association is absolutely superb. Attend a rendezvous to gain confidence and begin your friendships with other Loopers.
As Told to Beth Crabtree