We run over to Block as well as Greenport from Westerly in our 255 on a regular basis. As mentioned earlier, the afternoon winds sometimes pick up and you will get some slop. Check the weather, water conditions, pick your day and go. You will be fine. Unless we find someone to tie up to on a mooring we usually go over to the dinghy beach area in the pond and throw out the hook. The water taxi can get you over to the docks. Once on land you can hit the Oar or grab a taxi into town. Have fun!