Captain Bill’s Whale Watch – Gloucester, MA

Whale Watch

At this point it should be abundantly clear that we are a couple of weirdos who thoroughly enjoy seeing animals in the wild. Now, we’re not about to run off and join PETA, but if you tell us there’s a bear or a moose nearby, you better believe we will go looking for it. After coming off back to back weekends of bear sightings in the Outer Banks and New Hampshire, we decided to switch over to aquatic mammals for a change and go on a whale watch.  There are plenty of options in Massachusetts, but we went with Captain Bill and Son’s out of Gloucester. The tour went from 9-1 and costs $50 per person ($25 with a Groupon).

whale watch gloucester

The 100 ft Miss Cape Ann sailed directly to Stellwagen Bank, which is the place to be if you’re a whale. The ocean current collides with the bank and propels plankton and small fish to the surface for the whales to devour. While we were out there, we followed two pairs of humpbacks and one fin whale (second largest mammal after the blue whale). We could see them partially breaking the surface of the water before periodically diving and resurfacing, and at one point they popped up directly below where we were standing. Even though we only saw five whales, they all stuck around for a long time so we were looking at whales practically the entire time we were out there. No complaints on our end.

*It is likely that the lower quantity of whales can be attributed to the fact that they heard that we are both members of “The Whalers“, a world renowned championship kickball team… Classic misunderstanding. 

whale watch gloucester

whale watch gloucester

gloucester - whale watch
Tarr and Wonson Paint Manufactory

Where to Eat: Latitude 43 – Gloucester has plenty of good places to eat but Latitude 43 was excellent. They have outdoor dining right on the water and a sushi bar inside.


    1. I realize the photo placement might be misleading. The building in the photo is actually just an old paint factory that used to make anti-barnacle paint for ship hulls.Latitude 43 was awesome though. The fish burrito was a life altering experience.

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