We did something similar on the Okechobee Waterway. We had to get under a low railroad bridge at Port Myakka, so a crew from the local marina came out to us and strapped some water barrels on our side deck. They ran a line up the mast with the main halyard. The line was a measured length and had a weight on the end. Using a gas-powered pump on their launch, they filled the water barrels with water, the boat heeled, and the line swung out to the side. When the weight touched the water, they gave me the go-ahead, and I motored under the bridge.