33 Minute Layover

Would you be booking one ticket or are you looking to book those legs separately. If it's one ticket you should be fine but I would not do that on my own with different tickets.

Your chances of missing the connection are fairly high given that any delay will put you in a bad spot. You will probably make it, but your chances of not making it are much higher than if you had an hour. To be honest, your inexperience flying probably increases the odds.

I’d probably try it but it depends on how badly I needed to be in Boston on time and what my other options were.

Also, Cuse will have good advice so I’d listen to him not me.

That's a tight connection. It's not necessarily unworkable but if the first flight is delayed thats your problem.

National is pretty easy to get around otherwise.

This summer I had a 40 min layover at DCA heading to VT. Luckily I only had to go over a few gates but had plenty of time. On the way back I had an hour layover but ended up getting to the gate with 5 mins to spare because we circled the Chesapeake Bay for a while.

as the others said there will be plenty of options to Boston from DC if you get delayed. If it’s the cheapest flight then book it

DCA connection will require no terminal change if you're flying on the same airline.

Something that hasn't come up so far... We don't know if you're changing airlines (from AA to DL, etc.) If you are, you will not make it. You're just flying to Boston, so it'll probably be fine, eventually, but I'd also suggest considering ATL as the source to give yourself more options. I picked rando dates in April, and there are ten direct flights in one day from ATL to BOS.

You won't have to go far if you are flying AA. I would do it.