The wife and I will be celebrating our 1st anniversary in New England this October.

We are thinking of flying into Boston, hanging out there for the day and night, and the next day taking the Amtrak to Portland, Me where our home base will be for the trip.

Any recommendations for Portland?

Tentatively Oct 9-13th.

Thanks gang

Hi. I changed the title of your post and made it it's own thread. Enjoy and have fun!

Whoops, thanks Carol!

Lots of things close down after labor day. Our anniversary is in October and we have acces to a house in York Beach so we have been many times over our 25 years. Even though some restaurants close there are so many other sights to see. Ogunquit and Kennebeck are cool towns. Portland is a good base. The best thing we have done there is you can ride the mail boat every afternoon. It is about a 3 hour round trip and it goes to 11 islands. The views are great. You can bring refreshments on board. We did wine and cheese. I can't remember the price but it was cheap. Everyone I have told this to has really enjoyed as well.

Hi,

We will be in Portland as a cruise stop. Do you have any recommendations for must see in Portland? Also would love to find a place that serves great lobster rolls.

Thanks, Sue

TravelHat,

The mail boat thing sounds awesome and I think she'd really like that. Is this it? http://www.cascobaylines.com/maine-boat-tours/scenic-harbor-cruises/mailboat/

We're going for our anniversary and here's the timeline:

Fly into Boston Tuesday evening 10/07 or as early as we can Wed 10/08. Spend Wednesday & Thursday in Boston and then in the late afternoon Thursday take the train to Portland (if we don't rent a car). Then have all day Friday and Saturday in Portland, fly back home Sunday.

Right now we don't even have any lodging reserved. Any recommendations for either city on lodging?

Yes that is it. We took the 2:45 and caught the sunset on the way back. It is really a ferry of sorts. They off loaded a car on one island. It is a great way to see Casco Bay. There is a wine and beer store across the street.
In Boston I would look at hotels around the Copley/theater district. Close to common and easy to get around on the Green line.
We always stay in York Beach in Maine at family property so don't know much about lodging in the Portland area. I would recommend renting a car. Maine coast is beautiful and just driving around exploring is what I like to do. Portland is a great town with a good food scene but I don't know if it the kind of town to stay put in.

Don't know a must do in Portland. My theory is always been the worst lobster roll in Maine is probably better than one anywhere else.

For the Casco Bay ferry, a car isn't necessary right? When we get off the boat at each island, are they small enough to check out on foot?

Thinking of the Copley House for Boston home base: http://www.copleyhouse.com/

and the Inn at St. John for Portland home base:
http://innatstjohn.com/

Thinking about a rental car, but probably won't know for sure until a month or so out.

The Copley House is exactly where you want to be and it looks like a good place.
IMO theInn atSt John is too far away from the city center. Portland is hilly and the walk from town to the Inn is not desirable. You will either have to cab or have a car. I would definitely stay Downtown near the docks.

You don't get off the boat. It makes a loop around the bay and drops the mail, passengers and maybe a car off. It stays there for ten minutes then it is off to the next one. I think it is eleven stops. You just cruise and watch the boats, lighthouses, and boats go by. Then cruise in to the sunset. Bring a jacket as it gets cool late afternoon.

TravelHat,

What do you think of the Portland Regency Inn?
http://www.theregency.com/

Try j's Oyster in Portland. Great local bar

I'm not sure how firm your dates are, but the Fryeburg Fair is Sept 28-Oct 5. The Fair is one of the largest in New England and may be the largest in Maine. It's a very unique take if you've never been to a country fair. Fryeburg is 45-60 minutes west of Portland.

Yeah, due to our schedules our dates are set in stone so we will just miss the Fair.

It looks like Fore Play Sports Pub is a Cleveland Browns Backers bar...anyone been here? I need a place to watch the Browns/Steelers on 10/12!!!

We are renting a car as well, a little Chevy Spark or comparable haha.

Never been there but it rates very good on Tripadvisor. Try to get a room on the fourth floor with a deck. Sounds good.

Confirmed home bases:

Boston 2 nights- http://www.copleyhouse.com/

Portland 2 nights- http://www.mercuryinn.com/

which location in Boston?



You may also want to check the groupons in Boston. The Park Plaza has been running groupons pretty consistently for the past year. This hotel is centrally located to the Theater District, the Boston Common, Back Bay, and sits on the edge of the South End. Even though that hotel isn't what it used to be, it is an option We've purchased deals there for as little as $89.

Park Plaza Groupon

The Copley House is located right near the Theater District, we already put the res in :-/ The address is 239 West Newton Street.

I took a look at the Groupon and right now, the latest you can book is August. We're touching down Thursday 10/9.

All sounds good, enjoy your trip.

I think the majority of one day will be spent on the Freedom Trail and the majority of the other will be spent on Harvard's campus.

Lots of bars, restaurants, shops sprinkled in I hope!

For a lobster roll or a lobster dinner in a truly spectacular location, head out to the Lobster Shack in Cape Elizabeth, only about 7 miles away.

Thanks Nemos, looks great!

Anyone know if there's any whale watching tours in Boston/Portland?

You can get a whale watching boat out of Boston. We got one in Barnstable on Cape Cod. Best whale watching ever. I'm sure the boats out of Boston go to the same area as from Barnstable.

Rfrimmel, do you think 10/9 10/10 or 10/11 is too late in the season for it?

I dont think so. We did it in late August and it was great.

Looking at this one - http://www.bostonharborcruises.com/whale-watch/

I'd make sure your tickets are refundable. We can get some pretty raw temperatures early in October. The last place you want to be in 35 degree weather is on the ocean.

Id recommend to buy them as you get closer to the date.

It can get cool, but 35 in early October???

early morning, yes. we have had days like that.

it was chilly when we went on our whale watching trip and that was in August.

Hey Brian 3000 I just stayed at a hotel called The Verb. I caught a 149.00 a night rate on a travel site called Secret Escapes. It was pretty cool and I think you would like it better than the place you found in Back Bay.

Good looking out TravelHat, but I get this when I search for Boston on my firm dates: "We don't have anything exactly matching your search. Are your dates set in stone? "

Try expedia or hotels.com

The Verb is outside of Kenmore Square behind Fenway park. Much less to do in that area than the Back Bay.

So you think I'm all set at the Copley House?

I liked the Verb for 149. I don' think I would stay there for over 175. There are good things to do in the Back Bay and in the Fenway. Either way you will probably be using the T and can get anywhere easily.

Has anyone been to Salem in October? Fun/worth it? It would probably just be a few hours on the drive from Boston to Portland. I've heard mixed things.

Yes. Salem is a blast in October. People watching at its best. From Boston, you can take the Commuter Rail (MBTA) to get there. Depending upon the train times, you could also use Uber to get back

sxmBoston, looks like we're making a stop, but we'll be leaving before it gets dark.

Here's what's shaping up:

10/9 get checked in and unpacked by about 3:30. Cab it to Harvard and hang out there for a bit and get some food and beers over there.

10/10 do the Freedom Trail and spend sometime down at the market, probably try the Union Oyster House, get back and dolled up and grab a drink at the Prudential Center, cab to a nice place for dinner.

10/11 do the 10am whale watch from the aquarium. get our rental, drive to Salem (this will be about 3:00/4:00) and check out the With House and the Witch Trials Memorial. Grab a sangwich at Red's. Head further north to Portland and check in/unpack before 9pm. Head somewhere casual for beers.

10/12 ??? until about 2:00. From 2:00-4:00 doing the fall foliage wine cruise, go out somewhere nice for dinner, maybe Grace?

10/13 can peruse Portland until about 3:30ish where we'll have to head back south and drop the car off and hang out at scenic Logan until our flight back home.

Need to fit in Cheers and Sam Adams in Boston, and doing more research for Portland stuff.