It seems like you're trying to cover too much area in too short a time to me... just unpacking/packing each day, checking-in/checking-out each day is wasting a lot of your precious time.

Anyway, for Boston, most of the hotels in Boston are in good location. I'd focus on: Back Bay, or Theatre District, or Quincy Market/Faneuil Hall area.

Do you think we should just do Boston and Maine?

I would just do Boston or just Maine with that short of a trip.

Since you've never been to Boston before, I think you can easily spend the whole time IN Boston. But if you really want to visit Maine, it can be done as a day trip; that way, you don't need to pack/unpack and check-in/check-out.

The southern coast of Maine is about 90-min drive. If you're not dead set on Maine, the North Shore of Boston (Rockport area) is quite nice.

Alternatively, spend your entire time in Maine and save Boston for a future trip.

Congratulations on your upcoming anniversary!

Thanks for the advice. I think I am going to rethink the trip and repost later. Thanks again!

I second the day trip to Maine. As someone from New England, I would say that your money and time would be best spent in and around Boston for atleast a couple days. There are endless things to see in Boston. It's a great little city.

Depending on the type of beach you want, Rockport has some of the most beautiful and (almost) desolate rocky beaches I've ever seen. There is something so romantic about them. Kennebunkport and south is fabulous for beachin' it. kennebunkport has amazing beaches as far as sand and soaking up the sun. The food on the coast of Maine will not disapoint!

I would stay in Boston and day trip to Rockport/Gloucester.

It's not a lot of time and it's a special occasion trip. Think about how you want the bulk of your time spent; how much time do you want to spend in the car exploring the beauty and quaintness this area has to offer versus staying fairly put in Boston seeing/doing all the city has to offer, with a possible day trip.

I am not a big fan of Kennebunkport myself, although if you have never been to Maine you will be bound to like it. I much prefer Camden (further north). Depending on what you desire for a place to stay for your anniversary can help decide how you organize your trip. If you are fine with a lovely hotel in the city then there are plenty to choose from.I f you want some place that is more of an experience and unique, I recently spent a milestone anniversary in Camden/Lincolnville and we were so thrilled. http://www.innatoceansedge.com. It was very romantic, relaxing, and incredible food.

Maine can be stunning in September. Consider Stage Neck Inn for your anniversary night. Kennebunkport Inn or York Harbor Inn would be more affordable if you decide on a 3-night stay. A day trip to the NH mountains would be scenic and easy from any of these hotels. Drive through some of the lakes regions and countryside.