Quick weekend away - mother son trip

Anonymous
Looking for any recommendations for a surprise mother/son trip for boy headed to college.

Direct flights from DC. Looking for a city, culture, plays, good food, walking around, etc. Domestic or international. Would need to leave on a Thurs night or Friday and return Monday morning -- so going very far wouldn't work well.

We've been to NYC a lot, so not NYC.
Anonymous
Charleston
Chicago
Boston
Montreal
St. Augustine
Anonymous
Boston
Anonymous
Portland Maine
Anonymous
Anonymous wrote:Portland Maine


I was going to suggest this too! The food is amazing and the downtown is very walkable. You can also take the ferry (~20 minutes) over to Peaks Island for a few hours. It's a different world over there.
Anonymous
Chicago!!
Anonymous
Nantucket or Martha's Vineyard
Anonymous
Anonymous wrote:Chicago!!


+1
Anonymous
Chicago, Portland, Montreal are all great choices. You will not be disappointed.
Anonymous
This is from the OP: Looking for a city, culture, plays, good food, walking around, etc.

This is one response: Nantucket or Martha's Vineyard

In law school, professors would caution us before exams not to "fight the hypothetical". I never got what that meant. Until now.
Anonymous
Chicago sounds perfect if it’s not too hot. Portland too far to travel for a long weekend.
Anonymous
Chicago for sure.
Anonymous
Anonymous wrote:Chicago sounds perfect if it’s not too hot. Portland too far to travel for a long weekend.


People said Maine, not Oregon. There are non stop flights.

But I’d choose Chicago too.
Anonymous
I did a quick NYC trip with my DD before she left for college and it was great. Hope you and your DS have as much fun!

Chicago and Portland are cities I know pretty well. They'd both be great; here are a few ideas for what to do in each:

Chicago --
walk or bike along Lake Michigan trail
architectural boat tour
pizza
Art Institute
Museum of Contemporary Art
Second City
music -- check out Old Town School of Music for folk or House of Blues
pick out one or two neighborhoods and just walk around them -- Hyde Park, Logan Square, Fulton or Pilsen are all good options, but there are many others
Cubs or White Sox game

Portland --
walk or bike along the Eastern Promenade
ferry to Peaks Island
Seadogs game
lobster rolls
roof of Canopy hotel (yes, really)
Bird Tacos
walk around the Old Port
music -- State Theatre
Anonymous
What about Providence/Newport, RI?

When I do weekend trips, I like to fly into smaller airports and Providence fits the bill.
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