I meant to post this last week, soon after the Bar Lola post... to keep them semi-contiguous... but got distracted. Even if it's a little late, I still want to comment on the viability of taking the train up to Portland for the day... including a nice dinner... and back to Boston to sleep in our own beds.
Here's the weekend schedule of Amtrak's Downeaster. In truth, the "day trip" works the best in the reverse... Portland-Boston-Portland... which I guess it perfectly reasonable, if personally inconvenient. The last train down to Boston from Portland is at 8pm... a bit tight for a leisurely dinner (as we discovered)... but if you take a 5:30pm reservation instead of the 6pm one we took, I think you'd be fine, even doing multi-course. You might have to setup to have the host/hostess call you a cab while you settle up the bill, but I'm pretty sure it would work. The city is just not that big, nor traffic that bad, for you to really need that much time to make the train.
The other issue is, what to do for lunch? You've got two train choices for a 5:30pm dinner reservation... the 8:50am train, which gets you to Portland at 11:15am, or the 11:10am train that gets you in at 1:35pm. Neither is really ideal in my view. I guess the 8:50am train means you can have a reasonable sized lunch and still be hungry by 5:30pm... but getting up that early to make a train doesn't seem like a whole lot of fun... though you can sleep on the train, so maybe that makes up for it. Instead, you could have a really big breakfast, take the 11:10am train, and then just snack a bit until dinner. We did neither... having a light breakfast, taking the 11:10 and then having a light lunch at around 2... which, I guess, was very European of us?
All of the above is doable/reasonable... the main problem with taking the train up for a day trip is the cost. A ticket is $24 per person, each way (though you can, right now at least, get a round trip for $39 with 3 day advance purchase).... so about $100 for the two of us to get up there... which is what I paid for a night at the Eastland Hotel when we missed the train. Originally, the idea of doing a day trip was to avoid having to pay for a hotel room for the night... and the train seemed superior to driving since it meant no late night 2+ hour drive after a full day, nor any skipping wine or cocktails with dinner... Anna could sleep and I could read, and the ride is comfy. However, if the train is going to cost as much as a hotel room, it a lot harder to justify the day trip financially. I mean, if you get a room and drive, you have a lot more time to hang out (and spend more money obviously) and don't have the firm time constraints of a train schedule... making it more relaxing and convenient. The major negative of driving (not considering carbon emissions) is traffic, but traffic isn't really that bad from Boston to Portland... certainly a lot of people head up to Maine for weekends in the summer, but traffic is seldom a disaster in my experience. Note that the AAA trip cost calculator says it would cost us less than $20 in gas for the round trip (in Anna's MINI Cooper).
The bus is a cheaper option (but not as much as you might think), and unfortunately, the times are even worse for dinner... with the last bus leaving Portland at 7:30pm.
So not a great review, I guess... at least if you have a car. The train wins on a Green standard, regardless, but not by a significant margin on price. Thus it's certainly tempting to skip the whole hassle and just drive up and get a room for the night instead. On the other hand, if you don't have a car... and some spare cash... it's not a bad way to get out of the city for a day. I think I'd like to give it another shot, now that we've done it once... but I think our rail corridor could really use some improvements in speed, and a commitment of public funds to make the trip more affordable.