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People are doing and have done the loop on a 38, or a Mariner 37 which is the older version. There is a guy that moved his 37 to the Illinois river and is in Florida right now On his way around. The air draft is currently about 17 feet to the top of the anchor light and approximately 14’10” to the top of the arch. Not sure if that is the same for the mast.
The arch and mast are hinged and the lowest bridge on the loop is in the western Erie Canal at about 15 feet. You can go around that by going through Canada. Most people really enjoy the CAnadian portion of the loop. I think there is one or two bridges in downtown Chicago where you would drop the mast also. The absolute lowest bridge you have to clear is in the 19 foot range south of Chicago. The 4 foot water draft would not be an issue.
The AGLCA is the group to join to start learning more about the loop. I can get you in touch with Kim Russo (owner of the site) if you want to talk with her before joining. Once you are a member, you can search for the boat type and contact members who have done, are doing, or planning to in a 38e. Just let me know.
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