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High on the plus side for this stop was the extreme helpfulness of the dock master in getting us tied up safely in a strong wind. My boat is a single screw, with a weak bow thrusdter and high windage but the dockmaster’s directions got us tied up quickly.
On the minus side I’d have to say that there’s not much in Cuttyhunk. The only “restaurants” (save for breakfast at the Fisherman’s Club) are shacks on the dock - two of which serve lobster dinners and a third serving tacos. The heads are barely adequate and have no showers. There is, however, an ice cream stand in one of the shacks.
WiFi was iffy - sometimes barely OK, sometimes nonexistent.
The island is fun to walk around on. The high point (literally) is the bunker on the hill. From here you have an unobstructed, 360 degree view of Buzzards Bay and the Vineyard Sound. That’s awesome! There is a market (which I cannot comment on because I didn’t visit it) and one souvenir shop.
If you want a place to just relax, be cut off from the world and maybe eat a lobster dinner, this is a good place to visit.