I go into Boston Hbr via the southern entrance, (Nantasket Roads); It's a very easy and safe entrance, and offers a nice view of Boston Light. Drop the hook on the north side of Peddocks Island in Portuguese Cove. Portugues Cove has a good mud bottom, Peddocks blocks the summer SW'r, and it's all well out of the traffic lanes. Row ashore, and have a campfire below the high water mark, and watch the sun set behind the Boston skyline. Enjoy the hiking trails. Peddocks is now part of the park system, and will be reopening this summer. If you'd like a slip, head over to Spectacle Island - also part of the park system. No water or electricity at these slips, but this highest of the Boston Harbor Islands offers amazing views of the city and airport. Spectacle is also full of great hiking trails, and cool little gazebo huts that serve well a lunch spots. Another nice spot to go ashore is George's Island, but the bottom is a little sketchy for anchoring. The old fort is also great for hiking and exploring.

Enjoy!
John