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Jul 28, 2011 11:04 AM

Weekend in Portland area

Trying to come up with a long weekend itinerary for 5-6 soon to be 50 yr old friends (just writing that makes me nauseous). It is proving very difficult to find something that we can all agree on so I want to put in a good pitch for Maine. We would be flying in from Toronto. We are open to renting a car but don't want to spend a lot of time driving since we only have a weekend. We all want great food, some want shopping, some sightseeing but we all want a special hotel so if we just want to hang out with a glass of wine (or micro brew, in my case) and talk we've got a nice spot for it. Is there a special inn in or near Portland? Would still want easy access to downtown for day trips. Your help would be greatly appreciated!

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  1. Well, you'll definitely want to check out the Inn on Peak's Island:
    It's only a 20 minute ferry ride, and the ferries operate pretty close to hourly. It's a very nice spot, and you'd have access to all the great food in Portland and an easy (and scenic!) trip back, no car required. Depends on when you're coming: I suspect they're pretty booked at this time of year. There are a couple of more-than-adequate hotels in the Old Port area, but none of them really has the "hanging out" quality I think you're looking for.

    14 Replies
    1. re: mainemal

      Wow, that looks pretty near perfect! I wonder why it didn't come up when I Googled Inn Portland Maine?

      "Don’t miss the cask conditioned ale brewed right on the premises." -perfect for me!

      Is the restaurant good?

      1. re: crawfish

        I'll let others weigh in, as I haven't eaten there in a couple of years. By most resort community standards, I'd say it was quite good...but this is Portland. Certainly it will be more than adequate for any meal that you didn't get across the bay; and there are a couple of small somewhat funky places on the island that people like as well. If you get a res, by all means set aside time for a circumambulation of the island out to the Atlantic side.

        1. re: mainemal

          Well, we all pitched our locales and Portland, Maine won BUT they are concerned that the ferry to our hotel will prove to be a downside so I am looking for a spot in town. Isn't there a hotel in an old school? Any other special hotels walking distance from the port?

          As for food, for a splurge dinner I want to try Street & Company. The menu just looks perfect for us. Then I know we'll need a casual lobster pig out (the "money shot" of the lobster dinner is what won the day for Portland). Looking at other threads I see J's Oyster Bar? The Porthole? Any other suggestions? We will not have a car.

          It's looking like Duckfat is a must go but I'll have to put a good spin on it. Should 50 year old women really be eating a lot of duck fat? :)

          I'm really excited to be showing this group of Toronto friends Maine and really excited to explore Portland. I have been coming to the mid coast area my whole life (Mom's from Rockland area) so this will be a wonderful meeting of two important parts of my life. Thanks for your help!

          1. re: crawfish

            The Regency fits all your requirements,1.5 blocks from Fore St. 3 from duck fat. Nice bar,many micro brew bars etc.Novare Res particularly good for brews ,could be frigid but being from Toronto I'm sure your tough!

            1. re: LeRique

              Yes, the Regency would be nice, it is right in the Old Port within easy walking distance to lots of shops and so many delicious restaurants. It is located in an old Armory so the rooms are unique, some don't have regular windows but have skylights instead. There is also a spa and a lovely bar where you can hang out with a glass of wine or beer and chat. Duckfat would be totally appropriate, the fries are delish and not everything there is made with duckfat!

            2. re: crawfish

              This 65-year old thinks regular helpings of duck fat is just perfect. And please think carefully about the Peaks Island possibility: the ferry is a great way to get back and forth, operates on a good schedule, etc., and unless it's the middle of winter or a hurricane, couldn't be more pleasant. Of course, you originally wrote in July and now it's January, so not sure when you're coming. The Regency's a nice hotel, but not an exciting destination for your special event.

              1. re: mainemal

                Originally I thought it would be this Spring but looks like it's going to be Fall.

                It seems that the group is envisioning spending the majority of time in Portland so they are wary of going back and forth on the ferry after late dinners and too much wine. I agree that the in town hotels are not very inspiring. I am seeing the group this Friday so I'll spell out the options.

                1. re: mainemal

                  What about this B&B?

                  Also need recs. for traditional casual lobster dinner.

                  I really appreciate all your responses!

                  1. re: crawfish

                    I don’t know the Percy much at all. It is located on a side street that my 50 something y.o. wife might find a little bit sketchy (novelty bar across the street next door to the adult novelty store) although IMO it is still as safe as anywhere in the city. You would be near/next to the Arts District with some very good restaurants, art galleries, music venues and some unique shopping. The place most visitors to Portland would want to be is in the Old Port, which would be about a 20-minute walk – for what it’s worth; the ferry from Peaks Island just happens to also be 20 minutes and drops you off in the Old Port. If B & B is your thing, the Danforth is a little closer to the Old Port and is very nice although my wife would also find its location to be on the fringe of a sketchy neighborhood as well (actually she thinks of most places as sketchy). Aside from the Regency, which is very nice, I like the Portland Harbor Hotel also in the heart of the Old Port. If the weather is nice, the courtyard is a great place for drinks sometimes accompanied by easy to listen (jazz) music. Several great restaurants and bars where those of us of a certain age would feel comfortable are literally within a 1-minute walk. I stayed once and the room we had was beautiful. Very pricey. There are several other hotels in/near the Old Port, which are all acceptable. They include the Hampton Inn, the Hilton Garden and the Holiday Inn. Oh yeah, Duckfat is a must for lunch. If you stay on the mainland, take the ferry to Peaks Island for your lobster lunch at the Inn (just steps from the dock). Great sightseeing, cheap boat ride and you really should get on the water if only for the short ride to Peaks. Enjoy!

                    1. re: bobbert

                      Very funny post, Bobbert, thank you. I could spin the "sketchy-ness" as a reminder of our youth when we drank under age at punk bars!
                      The Danforth looks really nice, they have some double rooms and I agree it's better to be close to the Old Port. Thank you!
                      So I'm thinking Street & Co. for Saturday night, Duckfat for lunch, Peak's Island for lobster on Sunday. We will fly in on Friday is there something casual within walking distance for Friday night?

                      1. re: crawfish

                        The menu on the Inn at Peak's Island website does not list lobster or much seafood at all. I want a shore dinner but indoors as we will be coming in the Fall. Steamers are essential. Ideas?

                        1. re: crawfish

                          The food at the Inn is fairly pubish. I'd call ahead about lobster - it's been on the menu usually as a "special". Believe it or not, Portland can be a tough place to find your basic Downeast lobster meal especially if it's cold outside and you want to eat in. The most basic is 3 sons where they'll send you out to a picnic bench and you'll eat your lobster on some newspaper. Then there's J's and Portland Lobster Co - both best if eating outside. If the whole turning 50 thing is bringing you down you can do Dimillo's floating restaurant/tourist trap. They cook a lobster as well as the next guy and, being only 50 years old, you'll feel downright young compared to the regular clientele.
                          Street and Co. is excellent but make sure everyone likes seafood.
                          As for Friday night, everything in Portland is pretty casual - I would not hesitate wearing jeans anywhere, maybe I'd wear shoes vs sneakers in the nicer places - and depending where you're staying there's probably several chow worthy places within a few blocks most with good bar options as well.

                          1. re: bobbert

                            I agree with Street and Co. This is fast becoming my favorite go to restaurant in Portland. Gilberts for lobster isn't bad, although, the chowder is served cool which is kind of a bummer.

                      2. re: bobbert

                        Over the past few years, we've stayed at 4 of the B&Bs in the West End - The Danforth, Morrill Mansion, Inn on Carleton, and West End. Since this is Chowhound, I'll focus first on the food -- Morrill and Inn on Carleton are the best. Both have excellent breakfasts. Danforth & West End (which have common ownership) were not nearly as good; food was ok but nothing special. We would return to Morrill on Inn and Carleton; unlikely to return to the other 2 unless we couldn't get in anywhere else. Not that they were bad, but just not as good. (Note also that The Chadwick has the same ownership as the Inn on Carleton and I suspect also a good choice.)