I generally sail on Solings, Sonars, J24's and J27's in Boston harbor. But, I've also done some longer duration and overnight trips on bigger boats.
In 2022, I crewed on a 43' Beneteau for 14 days. Traveling from Rockland, Maine to Woods Hole, MA.. We explored the coast of Maine, New Hampshire, and the north coast of Massachusetts. Then traversed the Cape Cod Canal for the and explored Buzzards Bay and Vinyard Sound. We anchored in a different port on most nights. This trip covered about 350 nm.
In 2021, I crewed on a 43' Tartan, for 6 days and 5 nights. This trip took us from Bar Harbor, Maine to Newport, Rhode Island (~200 nm). Anchorage spots included Bar Harbor, Somes Sound, South West Harbor, North Haven and Newport, RI. This trip had one overnight sail where a watch schedule was followed. Had a great time and gained a tremendous amount of experience. I am looking forward to the next opportunity!