Do not stay in Chelsea, it is not the safest area, lots of gang activity, among other things. I work there and in Boston (we have multiple locations) and would not recommend it. Public transportation is fine, just be prepared for homeless people in and around the stations and since pot is legal in MA, the subway system (known at the "T") can reek of it. If you are going to be out late, check the time of the last train you will need. Boston is not like NY, often the last train is at 12:30am. Public transportation, from Logan, in most cases, will require you to transfer. You would take a Silver Line bus to either the Blue Line T station or stay on the Silver Line into the city (it's free from Logan, there are fares going back to Logan) and transfer to another line at South Station. If you stay in the waterfront/Fort Point area, the T is not bad and I would use it depending on the time of day, but if you are going to stay in the Back Bay area, I would advise against it, especially if it's around rush hour. It's not an easy transfer if you are not familiar with the T and it's not the best when you have luggage (Silver Line to South Station for a Red Line train to Park Street, then get off at Park Street to transfer to a Green Line train - make sure you get on the correct line, there are 4). A lot of the time the elevators or escalators aren't working and you have to lug it all up or down stairs. And they stink of urine (elevators). Ride shares are a good way to get around, as well as walking. You can do a trolley tour, which is a get on and off narrated tour of the city. I sometime recommend staying on for a full trip, then decide where you want to get off and explore. You can then hop back on and go to the next location. The Freedom Trail is also interesting for history buffs. It's literally a red line painted on the sidewalk or a red brick line that you follow. It is about 2.5 miles and it takes you from Charlestown (the USS Constitution) to Beacon Hill and the Back Bay. It's a self guided tour, though there are tours you can join (paid). If you like Italian food, go to the North End (where the Old North Church and Paul Revere's house are located). Boston is a great city, it's not quite as safe as it used to be, but still worth visiting. Just be smart and if it looks like a questionable area, don't go there. Boston is expensive, we pay a ton in taxes, but there is no tax on clothing/shoes! Look forward to hearing how your trip goes! Oh, and pay attention to the weather forecast. It can be crazy! We've had April's where it is over 90 degrees and we've had April's where we've had enough snow to shovel. Not sure exactly when you are travelling, but be prepared!