<p>It’s not clear from your message whether you are visiting colleges in Manhattan too. If not, you might want to consider flying into Newark. If you do take the train, it stops at the Newark airport. You can go straight to Boston. </p>
<p>If you want to rent a car, you might consider taking MetroNorth (commuter rail from Grand Central) rather than Amtrak (from Penn Station) to a station like Stamford or New Haven and renting a car there. MetroNorth takes a little longer, but it’s definitely cheaper–round trip to New Haven is cheaper than one way on Amtrak. You won’t need to drive in NYC and if your plane is late, you won’t be worried about missing the train. (No reservations on MetroNorth, while most Amtrack trains are all -reserved these days.)</p>