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35th anniversary meal for parents

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My parents are celebrating their 35th wedding anniversary next month and I'm thinking of taking them out for a special meal. They're a pretty staid couple with, hm, not-so-adventurous palates, so I'm mostly looking for a place with excellent atmosphere/ambiance (must be a QUIET restaurant) and service. Outside of NYC is okay. Looking to spend maybe $300-350 on a meal for four? (It's likely only two of us would be having alcohol, so probably no bottles of wine.) They like traditional "red-sauce Italian" restaurants, seafood and traditional American food. (Basically, every time my mom considers a well-known upscale restaurant like the River Cafe, she looks at the menu and isn't sure anything sounds appealing -- so no Per Se or Eleven Madison Park for us.) Will probably present them with options so I'm looking to start a list.

Alternatively, we'd take them out to brunch with our 15-month-old -- but it's sort of hard to reconcile "nice brunch place" with "acceptable with 15-month-old," so suggestions there would be great as well!

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    1. Blue HIll, Telepan. Oceana is probably good, but personally I find it very cold. Craftbar has a very good, basic brunch.

      1. Scalini Fedeli would come in at the high end of your budget, but it is Italian and the atmosphere definitely fits what you describe.

        Union Square Cafe can be an option. Works well with the bf's parents, who are in the same category of non-adventurous eaters, but while it's not someplace you need to shout to hear each other, it's definitely not pindrop quiet.

        1. Take a look at Rossini's on E 38 St. It's an old school red sauce Italian place that's not too pricey.
          On Saturday they have live opera which is pretty good. Live piano on other nights.

          1. Annisa has fairly quiet and spacious dining area, which would be perfect for a "Dinner with the Parents" situation. I found Telepan a little too crowded and noisy for my liking, but it should be better if you go at a non-peak time. Maybe consider Tocqueville, Marea or Ai Fiori, or Picholine as well?

            Re: brunch, it seems like you'll want a place that isn't too busy during typical brunch times. Maybe somewhere like North Square (in Greenwich Village)?