JFK -> Penn Station -> Boston.... Have I left enough time

Yeah the taxi will be shite. don't do that.
 
Thanks for this dude
You're welcome, safe travels!

By the way, I missed the Acela from Washington to NYC once and had bought a discounted ticket. The gentleman at the fare booth gave me several acceptable alternative options, I paid an extra $50 (or so) and just hopped on a later train. If you're travelling on that, don't worry - it's made for business people that have to change their plans all the time.
 
For all those who mentioned it before, Fung Wah must take a back seat to Megabus(yes like in Ukania) or Boltbus. both leave from near Penn and are cleaner, roomier and have wifi and plugs. $20 or so for standby.

EDIT The MTA trip planner is saying that you'll make in in less than an hour using the air train and the LIRR. I vote for that. It's gotta be better than the late-night trip I took from Jamaica to the Upper West Side using the J, A, Franklin Ave. Shuttle and 2 train a few months ago. That was frankly scary.
Who the fuck did you survive?
 
Meh. I have "German" written all over me according to an American and I was perfectly fine riding the subway all the way from the Bronx (zoo visit) to JFK. I had taken the express bus on the way to the zoo, but just couldn't be bothered with it on the way back.

I suppose it might have ended differently at night.
 
Meh. I have "German" written all over me according to an American and I was perfectly fine riding the subway all the way from the Bronx (zoo visit) to JFK. I had taken the express bus on the way to the zoo, but just couldn't be bothered with it on the way back.

I suppose it might have ended differently at night.

I was fine, but being a fairly imposing 6'3" and 220 lbs., I probably have a leg up. The subway is no place to play around, especially in the sketchier parts of Queens, Brooklyn and the The Bronx. I was lucky, but that trip will not be repeated.
 
I just want to add to the consensus that the Mass Transit options are definitely your best choice (You're still cutting it close: JFK customs on the Non-US Citizens queue is a bit slow from what I've seen):

By car (taxi) from JFK to central Manhattan at 5PMish is a pretty big gamble. Some days are good, some very, very bad and directly outside the airport is always backed up for a couple miles. A taxi could probably get you to Penn in time for the train with maybe a little bit of time to spare, and would cost around $44 for the trip.

The Airtrain to LIRR to Penn looks like the best option. You could also use the Subway (Airtrain to A to 1,2,3 to Penn), but it is definitely slower and more confusing than using the LIRR. Google has an estimate of around 45 minutes for the journey from JFK to Penn by the LIRR.
 
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With these Amtrak tickets we bought, I can't seem to find if these are advanced fare tickets ie, cheaper than buying on the day. Anyone confirm? We were thinking of cancelling the tickets and buying on the day as a means of mitigating the loss on the tickets if we were delayed on the flight.

But I paid for ticket insurance anyway for what it's worth and also I suppose that we are just replacing one risk with another which will be risking there being no seats left. We are going on Acela train @7 pm because it's faster and wasn't really too expensive.
 
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