One day in Boston...
 

My husband and I are planning a driving trip from Boston to Bar Harbour, Maine. This will be our last trip for a bit before our first child is born.

My plan is to go over Memorial Day weekend. We will fly into Boston - spend a full day in Boston (Friday) and begin our drive to Bar Harbour. What are some places not to miss in Boston? Should we stop in Portsmouth?

Any help would be appreciated!

We could give you a list of "places not to miss in Boston" that wold take you a week. Help us to help you be selective: Are you interested in historic sites, shopping, art galleries, architecture? Will you be far enough along so that an itinerary with a lot of walking might be problematic?

Do you plan to head out on Friday evening or Saturday morning? Of course, a lot of other people are going to be heading north at those times, too.

In Boston I would recommend the following - depending on your interests

Art - Museum of Fine Arts and Isabella Stewart Gardner museums

Sports - tour of Fenway Park

History - Freedom Trail or JFK Library

Strolling, shopping - Newbury St and Charles St.

Not sure of how long your entire trip is - if just the long weekend to get to Bar Harbor and back then you won't have time to stop in Portsmouth. If your trip is longer then I recommend the stop. I love Portsmouth - unique shops, restaurants etc.

Do not cut your time in Boston short to go to Portsmouth - while it is nice Boston is better.

In AM, select an interest - an art museum (Stewart Gardner), sports (tour Fenway), touristy and fun (Duck Tour). Have lunch someplace.

In afternoon, do the Freedom Trail - start around Boston Common and walk to Faneuil Hall area. Stop at whatever places of interest along the way intrigue you.

Evening - head from Faneuil Hall/Quincy Market area to North End and pick an Italian restaurant from menus posted in windows.

That is what I would suggest for a fast 12 hour tour of Boston - have a great time. Do not know what stage of your pregnancy, but the Freedom Trail has some areas that are cobblestones or uneven pavement, so be careful. Along Freedom Trail there are various coffee shops, ice cream places where you can sit and rest. The part of Freedom Trail I mentioned is mostly flat, except at beginning where you skirt part of Beacon Hill - not talking mountains, just some uphill walking.

I will be towards the end of my seventh month. I am pretty active, so walking shouldn't be too bad - plus I am from Florida so I am used to the heat!

I love historic sites, lighthouses, shoppping, etc. I am not too big into musuems or aquariams. I wanted to go to Fenway park for a game, but the sox are away that weekend. A tour of Fenway Park might be a good idea!

Congratulations on your baby. It sounds like a great trip. I would also go directly from Boston to Bar Harbor (Bass Harbor) and bypass Portsmouth. Boston has so much history and architecture. Faneuil Hall, Quincy Market, the Freedom Trail will be interesting. Bar Harbor/Acadia National Park will offer an outdoor experience with a variety of hiking options and opportunities to see the dramatic tide changes. Have a nice pre-baby vacation.
Enjoy your little one.

Hi jrm612--

If museums aren't your thing, you like history and shopping, and you're OK with walking, one approach might be:

1. walk the length of Newbury Street, starting at Massachusetts Avenue. There are plenty of shops and small galleries there, though food options are not very good except for the ice cream place Emack and Bolio's. Cross Arlington Street into the Public Garden, which should be in full bloom in May. Then cross Charles Street into the Boston Common.

2. follow the Freedom Trail (starts at the far end of the Common near the Park Street subway stop). Stop into the attractions along the way, which include several churches, historic buildings, the State Capitol building, old cemeteries, and Old Ironsides. The North End (the Italian part of town) is along this route, and is a great place for food provided you choose wisely -- excellent choices include Neptune Oyster (seafood), Pizzeria Regina (pizza, the original on Thacher Street only), Prezza or Mamma Maria (Italian, expensive, open for dinner only), Taranta (Italian/Peruvian fusion, expensive, dinner only), Pagliuca's or Daily Catch or Antico Forno (Italian, moderate, open for lunch or dinner), Modern Pastries or Maria's Pastry or Mike's Pastries (for cannolis and other Italian bakery goodies), and Gelateria (Italian gelato) -- but note that there are plenty of mediocre and just plain bad spots in the North End as well. Quincy Market/Faneuil Hall (which the Freedom Trail goes through just before the North End) may tempt you food-wise but tends to be middling to weak, though Durgin Park is the best place to try old fashioned Yankee style cooking (open lunch and dinner).

Tours of Fenway Park run from 9 AM to 3 PM, and you might want to do that before all the rest above if you want to include it.

Just for the record, the Aquarium, Museum of Fine Arts, and Gardner Museum are excellent in the unlikely event you want to take in something of this nature.

With this short a time frame, I'd also skip Portsmouth.

The traffic north on Friday is going to be horrendous. I would consider driving north first thing and doing a Boston sightseeing trip on your last day. I would consider Boston to Bar Harbor to be an all day trip. Spending the night in Boston and getting an early start Sat morning would be an idea. You will probably need to stretch your legs if you've had a long flight. Because of the length of drive, figure out where you'll be at lunch time. It would be great to have lunch in Camden ME and walk around a bit. It's small but the harbor is lovely.
But on Fridays the street vendors set up in Haymarket Sq. It is fun to buy fruit for your trip, maybe some cheese, etc. The North End is across the street. We enjoyed a culinary tour of the North End. Kind of pricey but nice food samples. You won't have time to shop. But if you get an afternoon tour you could have an early dinner.
Perhaps Portsmouth would be a good stop on your way back but there are lots of choices for meal stops.

I think dfnh might be right about the traffic. I'm unclear on your schedule, were you thinking of spending the day Friday in Boston, then leaving for Bar Harbor Friday late, like 5PM? because that is going to be horrible. Also, you'll want to start looking for hotels now, because Memorial day weekend is during graduation season, or student move-out season, and can be pretty awful.

If you're options include spending a non-weekend day in Boston at the end of the trip, I think that might work out better for you.

Make a reservation in advance:

http://www.bostonducktours.com/

It's the best way to get an overview of the city, and the tour is always fun.

I missed the timing of your trip. Do not drive north of Boston on the Friday afternoon/evening of Memorial Day weekend. Stay overnight in Boston, leave early in AM or skip Boston - or if absolutely essential that you leave, delay departure until after 8 or 9 PM and have husband drive.

If you try to make that drive on Friday evening of Memorial Day, you will hate Boston and surrounding areas forever - that is a guarantee. And if you are 7 months pregnant, there is a very good chance you will be stuck in hopeless traffic in dire need of a bathroom, which will not improvie the situation.

In Boston area, we have such a short summer season that the times between Memorial and Labor Days are precious to us - the only thing worse than driving north on that weekend would be trying to drive to Cape Cod.