Boston Drive to Southern Maine-July
 

DH and I (late 40s/early 50s) have a few days (about 5) for a getaway while our kids are away at camp. We had looked at flying into Portland from DC area, but are having trouble getting on a flight for the days that we need (BTW - I have some flying "issues" - I don't do small commuter planes....the small-ish jets - are ok, though)
Anyway...now I'm thinking it would be easier to fly into Boston (many flight choices) and sort of head up to Portland, maybe stopping in a different town each night, and then heading back to Boston.
Good idea or not? Any suggestions for towns with things to do/see/etc between Boston and Portland? We've been to Ogunquit once a few years ago. Also - is getting (driving) out of Boston a nightmare?
Thanks for any help or suggestions!

I think that sounds like a good plan; lots of option s for Maine. Driving north from Boston won't be a "nightmare," though from 3-6 PM on weekdays it will be slow. Boston rush-hour traffic is noticeably lighter in the summer.

Have u considered flying Air Tran from BWI into Portland? They are "regular" planes and usually have some good fares. Also SWA into Manchester, NH (also from BWI) is another option. Manchester is about 2 hours or so to Portland. I suggest this because I think Mid-Coast Maine area has so much to offer..Freeport if you're into shopping, Pemaquid, Damiscotta, Bath, Georgetown Cove, Wicassett, Boothbay Harbor where u can take a boat to Monehegan Island, Rockland, Rockport, Camden, Port Clyde. Really a very scenic area

We just booked a 5 night getaway from Norfolk into Manchester for $158 round trip....cheaper than flying into Boston and, with any luck, easier to drive in and out of. Planning on 3 nights Boothbay Harbor, 2 nights Ogunquit.

One caveat to the driving not being a nightmare - into Maine on a Friday night and back out on Sunday nights can be quite backed up.

I much prefer flying into Manchester when I go to Boston in October every year. Much easier to navigate!! Rental cars are right there; airport is smaller so not such a long distance to walk to/from gate to baggage; it's just a much more pleasant place to arrive IMO. Have a great time!

If you don't need to be in the Boston area, fly to Manchester, NH (MHT) and pick up your driving from there.

It's so much easier to get in and out of Manchester to go to Maine than to deal with Boston.

Try to include Portsmouth, NH as a stope along your travel route.

Thanks for all the suggestions! I realized that I was a bit vague when I said that we live in the DC area - we do, but it's really the exurbs of Northern VA. So, for us, BWI is close to a 2 hour drive....kind of a pain. I was hoping to go out of Dulles (first choice) or National (2nd choice). I wish we were closer to BWI, because they have such great (and cheap!)flights to so many places.
It looks like we'd be flying up on Sunday afternoon and returning on Friday afternoon. I wouldn't mind spending a night on one end of that in Boston (which would help avoid some of the weekend traffic issues).
And I love the idea of flying into Manchester, but there aren't non-stops from Dulles or National (except on United, but on smaller planes - not comfortable with that....I know it seems like I'm being so picky, but it's just my neuroses talking :-)
So, I guess my 2 options are:
Flying in to Boston and making it easy on us getting to the airport here
OR
Driving to BWI and having it easier once we arrive.
If we choose the Boston idea: can you suggest some coastal locations in Mass/NH heading north that are good places that we can do some touring, shopping and (most important!) eating good seafood (nothing fancy, just really good)?
Thanks again for all the suggestions and help with this!

In Mass, stop in the Cape Ann area, Salem, Marblehead, or Rockport. Salem has a nice museum (Peobody/Essex) and the National Park service does tours there. Rockport has cute shops, artists, B&Bs etc. both have ok dining.

After you leave Massachusetts and head up to Maine, stop for a day in Portsmouth, NH. Stroll around the Market Street area (boutique shops, eating places, and lots of historical scenery). If you are interested in local history, tour the Strawbery Banke Museum.

As said earlier, avoid road travel on Friday afternoons and going Sunday afternoons, there are exceptions depending on where you are. You may actually be going the opposite way from the traffic and then no problems.

Thanks! We've been to Salem, but Marblehead or Rockport sound great. We also have an elderly relative living in Peabody that we'd like to stop by to see for an afternoon, so that would work out great. And Portsmouth sounds good too. Thanks again for the suggestions...if anyone has more specifics for these towns (restaurants, hotels/B&Bs, etc), I'd love to hear them!
In fact, with the Peabody family stop, it may make sense for us to take the bus that goes from Logan to Peabody and arrange for a car rental there. Easier than trying to get out of Boston, I would think.

Renting a car in Peabody is usually a lot cheaper than renting one from Logan, so that might be enough to offset the cost of the Logan Express bus.

Note, however, that Enterprise and Hertz locations in Peabody are closed on Sunday and Avis is open only until 3 PM. You will find similar situations with other companies/nearby towns. So unless you have someone local who will chauffeur you around Sunday, you will need to get the car at Logan.

JetBlue IAD-BOS is $173 for M-F flight end of July (I am assuming those would be approximate days of week since it is a camp week). They fly 100 passenger regional jets - I also dislike mini-planes, but have flown on these and they feel big enough for me and the seat-back video/TV screens make it tolerable.

Rent car, head north on Route 1 from Logan (very easy) and get to Peabody to visit relative. (possibly taking Route 128/I95 depending on where in Peabody). Spend one night there or in Salem (close by). Then continue north on I95 to Portland - actually a very nice little city. You could base there and do daytrips to other parts of southern Maine or stay someplace else.

Drive back to Logan and dump car. Stay one night in Boston and do a whirlwind tour of the city - possibly taking the hop on/hop off trolley. Fly home, having had such a nice trip that you will not notice that the plane only has 100 seats.

Thanks, Cranachin and gail! Gail, your post about the JetBlue planes made me laugh. I don't have a problem with the 100 seat jets (well, I mean - I will fly on them :-) ) In fact, I flew JetBlue for the first time last month to Florida and I was very pleased with them. And the price is great...$79 each way!
SO, I think we will be flying in to Boston and figuring out the rest soon. We are thinking we might just stay in Boston Sunday afternoon and night and then head north on Monday.
Again, thanks for all the advice!