NY Boston trip

NYC

Never lived there, but I've been over a hundred times and have stayed at the Waldorf and downtown Conrad a dozen times each and a few other decent hotels (4 Seasons midtown, TT, Mandarin, etc.). I like being able to get a suite without paying $2k a night, but if cost not an issue, then you can look at the 5-star standards (Peninsula, St. Regis, Carlyle, Plaza, etc). I don't think I'd want to have midtown as my homebase these days, so I would go with the Conrad downtown (or alternatively the new 4 Seasons in the Financial District - gorgeous building designed by AM Stern).

With the downtown Conrad, all rooms are suites, you can quickly access two malls with decent shopping across the street, there's a good number of restaurants underneath and next door to fall back on, plus an attached theater, and it's steps to the riverfront walk - with that, it'll at least make a good homebase.

I don't want to write a book, so a couple bulleted recommendations based on what I would prioritize if I could go again soon:

• Restaurants:
  • I'll spare you the Michelin-star places, bc you can just use the guide for that
  • Polo Bar
  • Pick an Italian spot that looks good on Mulberry St. (it's nice not to plan every meal)
  • Joe's Pizza in Greenwich for a nyc slice
  • Shake Shack if you've never been to one
• To Do:
  • Take the Metro North or rent a car and visit Greenwich for a few hours - have lunch off Greenwich Ave., I like Elm St Oyster house or L'escale at the Delamar and kick tires at Miller Motorcars, never know what you'll see there
  • US Open if you're there when it's in town. I've been 10 times, don't care about tennis, but is one of my favorite events by far
  • Met Museum - world class, in league w british and louvre
  • The baseball stadiums are a real pita to get too, but if you're into baseball, need to at least do yankee stadium once
  • Frick Museum, JP Morgan Library - beautiful old-money homes that are museums now. Cooper Hewitt is the old Carnegie mansion that is a museum now, it's a little weak from a museum perspective, but I love old-NYC mansions. If you do too, try any of these three or even the Ralph Lauren store at 867 Madison Ave (men's flagship)
  • I would take cabs with current climate vs taking the subway for fun
  • Intrepid Sea/Air/Space Museum (on an old aircraft carrier, great views)
  • Hi Line Park

Boston

Lived here for a year and ran a couple Boston Marathons, but not as well-versed as with NYC

• Hotel
  • You have a few standards (Ritz, Mandarin, two 4 Seasons, etc.), but I would probably do The Newbury if the reviews check out (was the Taj when I lived there)
    • Good location and close to shopping and the parks. Probably can't go wrong with any, but from the ground level I would start there. If you don't want to be in a real dense area, the wild card would be the Charles Hotel across the river in Harvard Sq, but I think that's only 4 star/diamond
• Food
  • Legal Seafoods is a local standard, but I would probably pick the Harborside location. There's a nice del friscos next door too
  • All my other recommendations might be too far out of the way or off for a trip like this. I will say that while I think the North End is cool, I've never had a good meal in there
• To Do
  • Fenway for Red Sox whether you like baseball or not
  • Freedom Trail is cool, somewhat of a must, but I don't know that I'd do the whole thing, maybe just Bunker Hill and Paul Revere house. Fanueil Hall is cool, but it's such a zoo
  • Watch the rowers on the charles river, check out the boat houses
  • Walk the Harvard Campus and downtown Cambridge, if you're into npr, I think you can see the old sign from the Click and Clack car program
  • Boston Public Library is a beautiful building, same league as the one in NYC
  • Museum of Fine Arts if you have some bad weather or extra time to kill

 

Ask away, I love this topic for a handful of places, especially NYC

 

Boston is like a mini-NYC, in that lots to do in a compact space unlike NYC.
When dining in NYC I'm sure you heard of the new rule for indoor dining starting on August 16th you must show your proof of vaccine card in order to dine inside.
With that said, if you want to enjoy authentic regional Italian: La Masseria on 235 W.48th Street. Mulberry Street is lively if it's during San Gennaro Sept-16th to 26th. The restaurants there are really not a big deal, very touristy, if you are down in the area try Emilio Ballato 55 E. Houston St.
If you want true thin crust Neapolitan Pizza, Keste at Fulton street. The original joint was on Bleecker but closed in 2020.
As far as things to do: Museums, High-Line, Hudson Yards...Go to EATALY in the Financial district and eat your way through each different food station!

Boston I know fairly well as my son went to school there and lived there for another 4 years.
the North end is their little Italy, depending on who you ask, maybe a little better than Mulberry Street, but you can get solid Italian elsewhere.
Giulia in Cambridge is very good, Benedetto was better but they just lost their lease in the Charles Hotel.
Seafood is what you want though in Boston, Atlantic Fish Co is a fun place on Bolyston.
In the Loews Boston Hotel is also a fun place to graze it's called Precinct Kitchen & Bar
and just for fun, you need to go through Faneuil Hall....not 5 star, but you get a flavor of Boston