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Critique my itinerary - 3 days in Boston

Wife and I (late 20's/early 30's) will be coming to Boston in a couple weeks from NYC. Looking to do some fun and unique restaurants. Not really looking for anything too fancy b/c we can do plenty of that in NYC.

Please feel free to comment on the itinerary, as of now nothing set in stone:

Day 1 (Thurs): will be doing the Freedom Trail.

Lunch: Regina's Pizza - looking for something casual to stop by as we walk.
Dinner: The Gallows - looking for gastropub type place. nothing too fancy, with interesting food.

Day 2 (Fri): will be in Cambridge in morning/afternoon. not sure what doing later in day (open to suggestions). will be taking 7PM sunset cruise

Lunch: EVOO or Catalyst -- could not find many lunch options in Cambridge.
Pre-Dinner Drinks: Patio at Dillon's -- have a cocktail outside
Dinner: Vinoteca di Monica - want to do one North End Italian place

Day 3 (Sat): walking around Newbury Street. Red Sox vs Yankees game at night.

Lunch: I see ICOB gets a lot of good reviews, but it seems a bit pricey to me, not sure what the draw is. Also considering Sonsie for scene on Newbury St.
Pre-Game Drinks: Bleacher Bar - any other good options?
Dinner: eat at Fenway.

Day 4 (Sun): leaving in afternoon
Brunch: Winsor Dim Sum

Thanks!

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  1. Forgot to mention:

    We love seafood, especially fresh oysters and clams.

    We are not looking for any more asian other than our Dim Sum brunch, and also not big on steakhouses.

    We enjoy good beers and cocktails any time of day.....and are also very big coffee drinkers.

    1. ICOB doesn't do lunch.

      Sonsie is still there? That was a "scene" place 20 years ago. Not sure about today.

      The food at Fenway sucks so think about eating ahead of time or bringing it it. Highly recommend Dr. Pepper's sausage truck (yellow, second one in) and ask for the Inner Beauty and dust if you like spicy. There are a lot if options within close walking distance

      5 Replies
      1. re: C. Hamster

        ICOB has lunch menu on web site.

        I saw Sonsie mentioned on the Improper.com web site as "Boston's Best" People Watching.

        Thanks for the Fenway recommendation.

        1. re: foodchow

          ICOB does lunch on home game days. B and I pre-gamed there a few weeks back with my bro and SIL (NYers, but I don't hold that against them). We had a great time sitting at the bar with oysters, fish and chips, Maryland soft shell crab salads, clam chowder, corn chowder, lots of cold white wine and beer (and we had corner seats at the bar so we felt like we were seated at a table). We originally had a 2 pm reservation but when we showed up, the place was empty so we asked if we could give up our table for the bar. Definitely started to fill up closer to the game (4 pm start that day).

        2. re: C. Hamster

          Sonsie is fine for people watching and is a good place for coffee on Sunday morning when you can watch people walking by on Newbury Street. It is not a destination for great food.

          Thera are plenty of places that have 1 dollar oysters including monday nights at Rialto. ICOB has good shell fish; people are less happy with their fish.

          1. re: cambridgedoctpr

            To be fair this comment seems to be based on a thread from a poster who admittedly has only been there once? There are plenty of experiences to the contrary on this board. Have you been to ICOB yourself?

            1. re: Gabatta

              I have also had overcooked fish at ICOB fwiw. But it's worth going there for the drinks. +1 on Russell House. Craigie for drinks/brunch too.

        3. The Freedom Trail is just a really long red line that covers a good chunk of the city. That being said, Regina's is a good choice for pizza (though I might not send someone from NYC there).

          There are tons of lunch options in Cambridge. Not sure where you'll be, but EVOO and Catalyst implies Kendall area. I greatly prefer Catalyst to EVOO. Area Four, which is right next to Catalyst, is also quite good. Since you love beer, that area of Cambridge also has 3 good spots. You could start at Lord Hobo on Hampshire Street, then stop at Cambridge Brewing Company, then hit Meadhall as you're making your way back to Boston. Also, Voltage is right near EVOO, which I know folks enjoy for coffee (not my area of expertise).

          ICOB and Eastern Standard are the two best meals over by Fenway. Sonsie is definitely a scene (so is Stephanie's for that matter), but the food is not very good. I like Bleacher Bar. The location is the main draw, though. Other similar places in that area are Yard House, Boston Beer Works, Cask, and Game On. None of them are that different, at least in my opinion.

          2 Replies
          1. re: mkfisher

            Thank you for those recommendations.

            With regard to Cambridge, we don't have any set plans, I thought wandering around the Harvard Square area would be a good idea. I will definitely look into some of those beer spots.

            1. re: foodchow

              For Harvard Sq, try First Printer and Russell House Tavern.

          2. Friday:
            For lunch in Cambridge, I swear by Russell House Tavern in Harvard Square. Be sure to sit inside, downstairs. On a totally different tack, Sofra is amazing, but it can be a bit tough if you don't have a car.

            I would *strongly* urge you to change your North End dinner to Neptune Oyster. It's not North End Italian, but honestly, I don't reckon there's anything about our North End Italian that you couldn't find at home. And if you're hardcore seafood fans, Neptune Oyster is arguably the best in the city. If you want a North End Italian experience, follow dinner with dessert at Modern Pastry or Maria's, and/or coffee and Amaretto at Caffe dello Sport or somewhere like that.

            Saturday:
            Saturday's sounding like the big weak spot to me. Newbury St.'s pretty enough, but it's been a long time since there's been much interesting there - the one-off shops disappeared over the years and now it's mostly chains. It's also just not big enough to spend an entire afternoon on, unless you expand it out to other nearby areas like Comm. Ave., Charles St./Beacon Hill, the Public Garden, etc.

            And I *really* wouldn't recommend Sonsie.

            My suggestion would be to have a lighter lunch somewhere like Parish Cafe (sandwiches designed by some of Boston's best chefs, and there is outdoor seating), then do a pre-game dinner at ICOB or Eastern Standard. (Note: you will need to book for either one, especially because it's a game night.) Food at Fenway isn't worth saving yourself for - go and get the good dinner ahead of time. Eastern Standard also has a great bar, and for mine is the best pre-game drinks experience near Fenway.

            6 Replies
            1. re: TimTamGirl

              This is helpful, thanks.

              Russell House Tavern looks like a good option, I think we will go there.

              Neptune looks great, but I was a bit worried about not having a reservations -- it seems like it can get pretty busy there.

              1. re: TimTamGirl

                There have been some hounds who have recommended Sonsie in the past. YMMV.

                1. re: Bob Dobalina

                  I'm one of those who has in the past and continues to recommend Sonsie when people ask for casual drinking spot / meal on Newbury. There just aren't that many options and to me Sonsie is one of the few choices. I agree that it's not the best food in Boston, but it's solid for a light meal. It also has great people watching, which is what people who walked around Newbury all day are typically looking for.

                  I also heavily endorse Parish Cafe and go there frequently when in that 'hood. Any other suggestions for Newbury, cause it seems like we hounds only recommend those two. Anyone been to Happy's yet? Where am I missing without venturing over to Kenmore for ICOB / ESK / Hawthorne?

                  1. re: Foodie_BBQ

                    foodchow, welcome in advance! In what area are you staying? so we can give you better advice.
                    This may be helpful:
                    Guide to Boston by Areas and Restaurants:
                    http://chowhound.chow.com/topics/781155

                    EVOO and Catalyst are in a part of Camb that really has no visitor-interest ; stay in Harv Sq for lunch (Casablanca is a 30 yr Harv Sq 'institution'; v. good food and fun interior.
                    Russell House Tavern has alot of + and - on CH and other sites.
                    OR have lunch in Boston and come to Harv Sq after lunch.

                    If Seafood is your love, you'd really be missing something to not eat at Neptune Oyster or ICOB. Try doing a search under their names and just LOOK at how many raves they get. Tons. ICOB prob gets more CH mention than any other Boston restnt. If I could put it in one word, i would: Lobster Roe Noodles w/ Oxtail; Biscuit; oysters. Neptune- you put your name in and walk around the No End til they phone your cell and say they're ready for you.(Easily more memorable than Vinoteca.

                    )

                    With your being from NYC, I would offer that prob our most unique dinner menu is to be found at Oleana in Cambridge; Turkish/Moroccan/Mediterr like you have not seen it before.James Beard award winning woman chef; menu is all farm to table (her husb's farm.). Had my Bday dinner there last wk and they are still the best game going. Beautiful patio too and if you show up at 5:30 when they open, you can usually snag a patio table. 10 minute cab from Harv Sq.

                    **Make reservations** at all these places. Change later if need to.

                    so, my suggested itinerary:

                    Day 1 (Thurs): will be doing the Freedom Trail.

                    Lunch: Regina's Pizza - looking for something casual to stop by as we walk.
                    Dinner: Neptune Oyster

                    Day 2 (Fri): stay in Boston for morning >walk around the South End.
                    Lunch:The Gallows or Aquitaine (modern French bistro) in the South End
                    Go to Harv Sq for walking the Sq , Harvard, and up historic Brattle St., and/or museums; followed by Camb dinner.
                    Dinner- Oleana (quick one + cruise or unhurried romantic dinner on the patio and skip the cruise)

                    Day 3 (Sat):
                    Lunch- Parish Cafe
                    walking around Public Garden, Newbury Street and Comm Ave (designed after the Champs Elysees).
                    Pre game Drinks- Sonsie or ICOB
                    Dinner- ICOBRed Sox vs Yankees game at night.

                    (Just fyi, we have always had very good food at Sonsie, and top notch service and exc drinks and wines by the glass. V. comfortable and handsome room too.But we don't sit in the people watching area(cafe tables by front that opens up to the sidewalk). If dinner, don't order pizza; order the full entrees; high quality American Regional; generous portions well priced, interesting starches and treatments.)

                    Day 4 (Sun): forget dim sum;you have better in NYC
                    Brunch in Camb at Craigie St. on Main (if you chose this consistently CH raved spot, you could have Boston's most innovative ice cream afterwards, as Toscanini's is next door.),or East Coast Grill or North by Northeast (but it is innovative Asian) or Neptune Oyster,No.End. or Myers +Chang, modern take on dim sum (near So.End)

                    Depart for NYC, wishing you had more time to spend in Boston!

                2. re: TimTamGirl

                  yes, Neptune. You can't make reservations, but if you show up when they open before noon, you'll get in. I am a light eater and the hot butter lobster roll was enough for 2 meals for me and a companion. it's not cheap but it's worth it and you can walk around the north end while waiting for them to call you on your cell.

                  1. re: TimTamGirl

                    I second this! I was streaming through the replies seeing whether anybody had mentioned Neptune Oyster. I highly recommend it. Classy, high-chair, (marble?) bar! I recommend fresh oysters from the local regions (East Coast). Also their lobster roll and steamed clams! ::drool::

                  2. I like your itinerary. Just a couple of thoughts:

                    --I don't think the cocktails at Dillon's are very good.

                    --You have to get food at Fenway, of course, don't be dissuaded! This recent thread is helpful, esp. the recs from Fly: http://chowhound.chow.com/topics/836830

                    --Re: Cambridge, I agree with others about Russell House Tavern. Non-food related, you may want to check out the MIT Museum; this week they're opening a new hologram exhibit (Central Square, on the red line; one stop from Harvard Square and Russell House Tavern): http://web.mit.edu/museum/about/pr/20...
                    --Another Cambridge option in Central Square is The Druid. Irish pub, good fries, burger, fish & chips.

                    7 Replies
                    1. re: Niblet

                      The Druid is in Inman Square, not Central Square. .

                      1. re: mkfisher

                        you can walk several blocks to Inman from the central sq. subway stop.

                        1. re: Madrid

                          That still doesn't make it in Central Sq.

                      2. re: Niblet

                        Here's a link to the "Best of Chowhound Boston" post I wrote, which is a recap of the thread Niblet links to: http://www.chow.com/digest/110850/a-c... There are lots of good things to eat (and drink) near Fenway!

                        1. re: Dave MP

                          You can bring food but not drinks into the park. I've brought everything from burgers, burritos, Chinese, pizza, falafel, and even Indian food that did raise eyebrows.

                          I still maintain that the food inside the park sucks and costs a fortune. Even though they have tried to upgrade everything the food still lags behind most of the other MLB parks I've been to (maybe 2/3 of them).

                          1. re: C. Hamster

                            You can bring in 16oz of sealed bottled water.

                        2. re: Niblet

                          I agree with the Dillon's comment. The cocktails and food are expensive, bleh and not worth it.. and the service sucks.