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The Helmand, Oleana, or Trattoria Toscana for dinner?

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My mother, sister, and I want to go out somewhere nice and interesting (but not too pricey) for dinner next week. My sister is a vegetarian, and we all enjoy healthy, interesting food. I know these three are pretty different, but any recommendations for which to choose? Also, what is the deal with outdoor dining at Oleana? Is it true that you can't get a reservation? Would our chances be good on a weekday night? Thanks!

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  1. Haven't been to the third, but as for the first two, it's a tough call. Helmand is cheaper, more exotic, casual, rough around the edges, but (imo) hits higher high notes. The atmosphere and service at Oleana are far superior, the patio is gorgeous, the food is a bit more agreeable to American palates, and it's more consistently well prepared. My mother liked both. Oleana is a more guaranteed success. But money aside, if I weren't aiming to please someone I would rather take my chances at Helmand, because I don't find the food at Oleana special.

    2 Replies
    1. re: aventinus

      I agree. I think Oleana is overrated, and you can't make a reservation for the patio. I'd imagine you'd have to get there at about 5:30 for an outdoor table since you have to make a reservation for an indoor table about a week in advance to get the time you want. It is popular! If you do go, though, don't miss the Ricotta Dumplings, the one great dish I've had there.

      I like the Helmand a lot, and for healthy, interesting vegetarian fare, you can't do much better. I prefer the atmosphere here; not as warm, and roomier. It's fun and authentic.

      I haven't been to Tosacana either.

      1. re: pollystyrene

        I was at Oleana last night and the ricotta dumplings was the only dish I didn't care too much for. The dumpling itself was good...great creamy texture. However, I didn't care for the sauce. It honestly tasted like canned tomato sauce. I was very pleased with everything else I sampled there (deviled eggs, hummus, the beef appetizer with smoky eggplant, and the baked alaska).

    2. When I think Trattoria Toscana for dinner, I do not think "vegetarian," "healthy," or "interesting." I suppose one could find some veg and healthy stuff on the menu but that is not why you go. TT is outstanding authentic Tuscan, which is why you go there. Definitely recommend if you are looking for that at some point. Was there Friday night and the food was great as usual.

      1 Reply
      1. re: adams_jo

        I would highly recommend Helmand. My experiences have been excellent.....service as well as the food. I am NOT a fan of Oleana.....had a bad experience there. I insisted on going there for my birthday againist the advice of several foodie friends and was extremely disappointed. The service bordered on rude and the food was just okay.
        I know that I am in the minority with this opinion as far as fellow Chowhounds go. I have never been to Trattoria Toscana so I can't comment on that.

      2. Though all three are good, I think you're sister will have a hard time finding vegetarian (other than apps and pasta) at Toscana. Oleana is definitely overrated. Service is unspectacular and the food is nothing to write home about. Helmand, on the other hand, well, let's just say that I moved to NYC last year and I still make the pilgrimage. There's something about the way they're able to create a whole experience. Love it!

        2 Replies
        1. re: MoxieMax

          Weird how things change. When I first moved to Cambridge a few years ago, I think Oleana was the board's consensus favorite restaurant in Cambridge. I went and was disappointed. This year I've gone again and thought it was a nice dinner. Now I think the criticism is a bit too harsh. The prices aren't so high that I feel a visceral urge to pick the restaurant apart. After a couple of drinks and some very affordable mezze appetizers, the lovely atmosphere should sink in, and it will be a good dining experience.

          1. re: aventinus

            I think there are plenty of Oleana fans still on the board, myself included. I just don't chirp up with dissent every time someone from the "it's overrated" camp speaks up. I mostly remember it being controversial here.

        2. You can't make reservations for the patio at Oleana, but as long as you get there by 6:30 Tues - Thurs, you'll probably have no issue getting a table outside. Lots of vegetarian options.

          Ate at TT last week - still great; still great value. There are no secondi on the menu that are vegetarian though (unless your sister eats fish), so she'd be stuck with the appetizers and primi for her choices (there are a few pasta dishes that are veggie - not sure of your view of health vs pasta).

          1 Reply
          1. re: gini

            One note about Oleana: Talk to your waitperson if it has to be vegetarian. I remember the buttered hummus being wrapped in bacon, though there was no hint of such a thing on the menu.

          2. Thank you for the replies! I made a reservation for the Helmand tonight and I am very excited. Any recommendations? (I have read that the pumpkin dish, the leek dumplings, and the lamb are very good - anything else?)

            1 Reply
            1. re: fbf242

              I loved the charbroiled chicken. Very juicy inside, delicious marinade.