Sailing the Great Loop: Lifetime Adventure

boat tied up at the docks
The Mon Amour, the Great Loop boat owned and used by the Pierces, sits in the marina in downtown Sarasota, Florida. (Photo by Jeff Orenstein)

Want to visit Chicago, the whole Florida coast, New York City, Montreal, Toronto, Cleveland and Detroit on one trip? Howbout doing it by boat?

This month, while we are on the road researching more stories, we’re reporting on one of the most fascinating trips we have ever encountered: sailing the Great Loop.

Full disclosure: Even though we live on the Gulf of Mexico, we don’t own a boat so we are not planning to take this trip ourselves. However, we are amazed at those adventurers who do. And just a little bit jealous.

Here is the story: We were walking along the path at the downtown Sarasota, Florida, marina and struck up a conversation with Dwight and Christine Pierce, a friendly couple sitting at the stern of their docked 38-foot Morgan 381 sailboat. As we talked, we learned that the couple had just sailed their boat from Lake Michigan, more than 1,700 miles away.

Christine and Dwight Pierce
Christine and Dwight Pierce, co-captains of S/V Mon Amour, at O’Leary’s Tiki Bar on Sarasota Bay (Courtesy of Dwight Pierce)

More extraordinarily, these “Loopers” (as those who do the Great Loop are called) were far from done. They were only in Sarasota for a while, living on their boat and visiting relatives, and planned on sailing from the Gulf of Mexico port to Key West and then up the Atlantic Coast to New York and the Hudson River and the Erie Canal, into the Great Lakes and back to Lake Michigan — more than 5,000 miles. Wow!

As Dwight Pierce explained to us, “There are hundreds of boats doing this journey each year. We keep in contact with those that are nearby and often meet up with them along the way and share stories, advice and maybe even a glass of wine. Everybody has been super nice and willing to help others.”

He said, “Most people use powerboats, but we are doing it in a 38-foot sailboat. It’s what we already owned and are used to. We had to have the mast removed in Chicago to get under the bridges and it shipped to Mobile (Alabama), where we reattached it for the remainder of our trip.”

Asked what he’s learned so far, he said, “Don’t be in a hurry. Spend some time in ports because each is a little different and worth exploring. Also, being friendly and outgoing pays off. The friends you meet are the best part of
the trip.”

Most people spend between 140 and 160 actual sailing days on the trip (not including extended shore stays). Some take 10 months for the whole tour.

If You Only Have One or Two Days in a Port:

Must-sees for a short stay are:

  • Local points of interest within walking or public transportation distance from your docking space
  • Local hop-on-hop-off bus tours give a good overview of the area if available.
  • Getting stores for reprovisioning

If You Have Several Days in a Port:

  • Visit museums and other locally unique features of a region.
  • Have an occasional stay in a nice hotel to enjoy the amenities, budget permitting.
  • The facilities of local marinas, budget permitting, often include pools, grills, showers, laundry, etc.

Ginny O’s Tips for Dressing the Simply Smart Travel Way:

Follow the Boy Scout motto: Be prepared. Layers will get you through a lot. This is not a fashion trip, but you may want to visit some classy places after being on the water for so long.

This Destination at a Glance:

Over 50 Advantage: It’s the bucket trip of a lifetime if you can put up with cramped quarters and enjoy the water.

Mobility Level: Moderate to high. You have to be able to get on and off the boat at docks and handle it expertly at sea, in canals and so forth. Being a good swimmer helps, too.

Simply Smart Travel Tip: If you are going to do the Great Loop, be prepared. Make sure you have the right boat (less than 5-foot draft), are experienced seafarers and have the right equipment. This is not a casual trip for beginners.

When to Go: If you are coming from the Great Lakes, fall is a good time to boat southward and spend the winter in the Gulf of Mexico. Winter up north is not a good time to be on the water.

Where to Stay: Most Loopers stay on their boats, but some enjoy a few days ashore at luxury resorts and the like.

Special Travel Interests: Boating. And sunsets!

Jewish Great Loop Participation

Practicing Judaism while traversing the Great Loop is different in some ways than practicing it in a given location because, as a Looper you will traverse about 18 states and potentially visit hundreds of ports.

The places you pass through and may choose to visit will range from big cities with a variety of Jewish places of worship and institutions to tiny towns with little or no Jewish presence.

Fortunately, you can bring most of the religious practices and traditions you want and enjoy onboard. You may not always have a convenient synagogue or fellow Jews close by at all times, but your boat is your home and how Jewish you want to keep it is the same matter of personal choice as it is at your land home. If you want to keep kosher, there is no reason not to. You can pack kosher food for the first leg of your trip, and good advance planning will allow you to buy kosher provisions at various places along your chosen route.

The same goes for worship services. If you want to attend Sabbath services ashore, you could plan your itinerary so you dock your boat on Friday within walking distance of a synagogue or you could hold your own prayer service onboard.

If Jewish fellowship is important to you, you can arrange to travel with other Loopers who are Jewish and keep close to them as you proceed around the loop. It is not likely that you will randomly find a large number of Jews in each port, but it is not impossible either.

Jeffrey and Virginia Orenstein are travel writers from Sarasota, Florida.


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