Gloucester’s inner harbor is much more protected from the elements than I expected. The price you pay though is that with it being a working harbor you can expect some wakes from time to time as the fishermen head in and out.

With Hurricane Henri on it’s way the wakes were well worth the price of admission. And honestly even without the weather the wakes weren’t too bad.

Springing for a mooring comes with some added benefits. Most significant is free use of the harbor’s launch which runs from 8am till 10pm. They will deliver you to several drop off spots as well as to any of the city businesses that have their own dock. One such spot is Cripple Cove Landing. This spot is special since it’s only 0.5 miles to a large supermarket (Stop & Shop) which makes it an excellent spot to provision up and you can use your own dinghy or take the launch. And there is another Supermarket not too far from the main dinghy dock (Shaws).

Multiple grocery stores, an abundance of marine supply stores, mechanics, and even a free pump out boat that will come right to your boat. Gloucester is certainly a spot to spend some time.

Gloucester is a cute little city with random events, solid restaurants, and with it being a working harbor this is an excellent place to pick up foul weather gear and to find marine experts. And me being me I found myself exploring the cafés. The Caffe Sicilia had great Italian pastries and I think we were the only people in there not speaking Italian. It felt like I’d walked into an episode of Inspector Montalbano and even recognized the cities they were talking about. We then found our way to the Lone Gull Coffee House and that was where I found myself returning to.

I was also impressed with the city having multiple bookstores. Although they were closed in the mornings when we were in town.