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Anne and Jeff’s Big Adventure

Cruising America's Great Loop

Sixty-two hundred miles, an eleven month second honeymoon, countless new friendships and $500 worth of ice, for cold beer at the end of long boating days ---Priceless! Who knew the boating life would be so fulfilling? In retrospect we really didn't have a clue.


After reading an article in a boating magazine about the Great Loop, Jeff repeatedly told me he wanted to do "The Loop" when he retired. He joined the AGLCA (America Great Loop Cruising Association) and began receiving information from their website about trip itineraries, costs and types of boats people purchased and/or had for sale. I played along, thinking it was a nice dream, but one that really wouldn't come to fruition. We have a summer cottage on Hill Island, in the Thousand Islands. Making a commitment to live on a boat for a year would be taking a huge leap.

As retirement loomed closer Jeff kept researching boats. After reading two books, written by people who had completed the Great Loop, I came to the realization that if they could do it, so could we. In January 2015, our broker called our attention to a Mainship 390 Trawler that was for sale at Bonnie Castle, in Alexandria Bay. Nothing like doing business in your home waters with people you trust! The deal was sealed on June 10th and we were all in.

Everyone begins the Loop in a different location depending on the season in which they start. Typically you cruise the Thousand Islands, Trent Canal, Georgian Bay, Lake Huron and Lake Michigan segment in the summer. The best advice is to be in Chicago by the beginning of September, before making your way down the Illinois Waterway, Mississippi River, Ohio River, Tennessee River and Tombigbee Waterway during the fall.

There are many side trips to consider along the Tennessee and Cumberland Rivers including Nashville, Knoxville and Chattanooga. Most people we met wintered in various locations in Florida or the Bahamas. Spring finds "loopers" migrating up the Intercostal Waterway. Once up the Hudson River, you can choose to follow either the Erie Canal or Champlain Canal depending on the head clearance of your boat. Some people complete the trip (called crossing your wake) in a year; others may travel for a season or two, putting their boat in storage until they are ready to resume their trip.

We left our dock on Hill Island at 8:49am, on July 1, 2015. Were we ready? Not really, but as a friend told us at some point, you just need to leave. With Ian Corstine's book of the 1000 Islands on our boat (a gift so that we would remember our friends at home) we made our way towards Picton.

Within two days we arrived in Trenton, Ontario, ready to start the first of 45 locks in the Trent-Severn Canal. Right from the beginning we met other people who were doing the Loop. All had a white flag flying, with the AGLCA insignia and loop map. The trip was everything we had read about; how people would boat together and bond through similar trials and tribulations, meals, and of course docktails, at the end of a long, sometimes stressful day. Harbor hosts in Peterborough, Ontario, organized a docktail party for all the" loopers" who were staying at the marina. When we arrived, everyone was passing out business cards with pictures of their boat and contact information. Jeff immediately had cards ordered for us. I've lost count of all the cards we acquired throughout the year. We would travel with different people in various locations, reconnecting again several months later. Everyone has their own itinerary and times they "get off the boat."

People ask, " What was your favorite part of the trip?"

1) Georgian Bay is the Thousand Islands on steroids. This area is referred to as the 30,000 Islands but there are another 70,000 shoals under the water. It was a real test of our boating and navigational skills, but we made it without damaging our prop! We anchored out the majority of the time, here and in the North Channel, enjoying the remoteness and beauty of the area. It stayed light until after 10:00pm. Each sunset was more spectacular than the other. We bonded with a couple from Baton Rouge, LA, who said, "You know we didn't think we'd like boating with other people, but you Yankees are growing on us."

2) Cruising Lake Michigan was very enjoyable. If the weather or wave height was uncomfortable, you could duck into ports which were 20 miles apart. We had the best view of the Sleeping Bear National Sand Dunes, which were as high as 450 feet.

3) The eighteen hour overnight crossing of the Gulf of Mexico, from Dog Island to Tarpon Springs, with five other boats was incredible. It was an extremely calm, starlit nigh,t with shooting stars and meteor showers. Everyone conversed on their VHF radios, throughout the night, pointing out constellations and other highlights. Dolphins greeted us as the sun came up. It was truly a spiritual experience.

4) Arriving in NYC Harbor during the America’s Cup race and passing the Statue of Liberty.

5) Cruising up the Hudson River and Lake Champlain. The views along the Catskill, Adirondack and Green Mountains are amazing.

6) Meeting family and friends in Michigan, Chicago, St. Louis, New Orleans, Florida, South Carolina, New Jersey, New York and Vermont.

7) Discovering golf courses in eight states. Good thing we packed our clubs!

8) Last but not least - Making new friends and appreciating the helpfulness of fellow boaters. We no sooner docked our boat at Pickwick Landing in Tennessee, when a boater ran up to us saying, "I smell transients;  anyone need to borrow my car?" In Mississippi, JD insisted we take his car to play golf, so we could make our own memories. By the time we left the marina we were sharing recipes and he had made us a CD to remember him by. When we needed a new motor for our windlass, two other "loopers" spent two days with Jeff, bent over the anchor box until it was fixed. Mike had every tool imaginable on his boat.

Just when we thought we wouldn't meet anyone else doing the Loop we ended up rafting off Miss Jazz, at a lock wall on the Chambly Canal. They had a gold AGLCA flag as they had already crossed their wake once, and were very hospitable. During the next few days,we met up with them two more times, sharing dinner, stories and a bottle of port wine. We felt that we had started and ended our loop in the same way; sharing new experiences . Our trip was ending on a very good note.

We crossed our wake at 5:20 pm on May 25, 2016. Our friend drove from Kingston ensuring someone would be on our dock to take pictures and greet us. We were joined by family and friends shortly after. Our friends from Alabama stopped by in June, saying this area was their favorite so far. It will be our pleasure to share the beautiful Thousand Islands with others doing the Great Loop.

By Anne Timmons

Anne Timmons grew up in Nyack, Long Island, and Syracuse, NY. She, her husband Jeff, and sons Jake and Luke, had spent many years camping in the Islands. After buying a property on Wallace Island (Canadian Sector) in 1982, a move to Hill Island came in 1998. Currently residing in Florida.  Anne retired from a thirty-five-year career in New York's Office of People with Developmental Disabilities.  Retirement has given her the opportunity to take writing courses to write about the Thousand Islands, and if you like or dislike snakes… be sure to see her first TI Life article:  “An Unexpected Visitor.”

Posted in: Places, People, Sports
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Debbie Hechler
Comment by: Debbie Hechler
Left at: 10:15 PM Sunday, August 14, 2016
Great article Anne!! Felt the experience! Still wished we could have waved you on from the shores of the Hudson, or welcomed you home on the St Lawrence. Maybe on your next trip :) :)
Gisele Beaulieu
Comment by: Gisele Beaulieu
Left at: 8:26 AM Monday, August 15, 2016
I loved the article Anne. Thank you for sharing your amazing adventure and congratulations to you and Jeff for your achievement.
Comment by: Sue
Left at: 5:50 PM Monday, August 15, 2016
Loved the article & pictures! Can't wait to see more! What an experience of a lifetime!!
Robin trymbiski
Comment by: Robin trymbiski
Left at: 6:37 PM Monday, August 15, 2016
Totally enjoyed your article. Frank and I followed your posts along the journey but this really sums it up. Spectacular!
Jan Joyce
Comment by: Jan Joyce
Left at: 7:07 PM Monday, August 15, 2016
Anne this article is great, and I love the photos that go along with your story. Congrats to you both on achieving Jeff's dream of completing The Loop! Keep writing.
Mike Phelps
Comment by: Mike Phelps
Left at: 8:30 PM Monday, August 15, 2016
Wow....what an adventure. Jeff shared some stories on the golf course but this trip really came alive with your descriptions of the people you met and the spectacular pictures you shared. Magnificent.
Barbara Stone
Comment by: Barbara Stone
Left at: 10:25 AM Tuesday, August 16, 2016
Great article Anne! Really enjoyed reading it!
Comment by: JOHN PRIBIK
Left at: 10:07 PM Tuesday, August 16, 2016
Anne and Jeff thanks for sharing we felt apart of your adventure..loved the travel log
Yachting keeps the dreams alive It's all about the journey
Pat and John
Patrick V
Comment by: Patrick V
Left at: 8:28 AM Wednesday, August 17, 2016
Love the re-cap Anne! Learning some new boating terminology by reading your work. Once the slideshow is ready for download definitely send (if not too large). The Harvest Moon up for another "crossing of the wake"? Great seeing you guys out in Bald Head Island last April. You'll always have safe passage through the Carolina's if another Loop in the works.

Pat & Kyle Varian
Susie Smith
Comment by: Susie Smith
Left at: 12:38 PM Wednesday, August 17, 2016
Comment from Joe Burkle:

Great story, Anne! I had not heard the term "crossing your wake" before in reference to making a 'loop' like this. But it is fitting! How many miles was this loop??? Good grief. Brave souls! We had an article in the TI Living last year about our own motorhome travels around the US and sailing the 1000 Islands. And we thought we were adventurous! We're wrapping up our second full year of life on the road and are presently in Georgian Bay with our sailboat at Bayport Yachting Center. Like you, we absolutely love Georgian Bay ... it ranks right up there with the TI as our favorite two places in our travels! We have a small powerboat with us as well and have ben enjoying cruising the 30,000 Islands on no wind days. We went through the lock at Big Chute two days ago and rode the Big Chute Railway on the Trent-Severn Waterway... obviously you did the same thing. We lunched at Severn Lodges down on Gloucester Pool. Memorable moments! Keep up the writing Anne... We will be in the Thousand Islands all of September and would love to meet up. I will ask Susan Smith for your contact info and I hope we can cruise over to Hill Island to meet you and share some stories while we're in the TI next month.
Denise and Mark Gillespie
Comment by: Denise and Mark Gillespie
Left at: 9:44 PM Tuesday, August 23, 2016
Excellent article! We so enjoyed getting to know you during our several stops together on the Loop - especially nice was anchoring out and rafting up with you. Hopefully one day we will be able to visit your "waters" now that you have cruised our Florida waters.
Look us up when you come south again!