Over my four years at Swarthmore, I rode Amtrak quite a few times. Through that experience, I picked up a couple of tips to make booking and riding cheaper and more pleasant.
First, if you are a student, use the student discount! This is a well-kept secret. You save at least fifteen percent, but it can sometimes be much more.
Second, you should book early (duh!). Unfortunately, Amtrak isn’t like regional rail: Amtrak prices rise – and rise hard – on the popular routes (especially on the Northeast corridor). Don’t try to buy a ticket on the train if you can at all avoid it.
Third, if you are booking early, use the “flex” fare for more flexibility when cancelling. The nice thing about Amtrak is that it has very flexible cancellation policies, especially if you pay a couple of dollars extra. You can get a full refund, instead of 75% back with the base fare. However, do the expected value calculation! If you’re considering a trip, book tickets early just in case and cancel as necessary.
Fourth, if transferring trains, consider splitting up your segments into separate reservations. Amtrak’s algorithm often chooses pricier connections if part of your trip is on the Northeast Corridor. If your second train leaves after the suggested connection, you’re still a “guaranteed” connection in Amtrak’s eyes. I’ve done this before, though this is probably still a small risk. But you can also be more cautious because Amtrak’s tolerances are often smaller than their trains’ propensity to be late.
Fifth, consider splitting a single segment into multiple tickets. It is worth checking. It is sometimes cheaper to book tickets from A to B and B to C than A to C even if they are all on the same train. For example, booking tickets from Philadelphia to Trenton and then Trenton to New York City can be cheaper than Philadelphia to New York. You can even stay in the same seat and everything.
Sixth, on the Northeast Corridor, consider using commuter rail instead. The strongest example of this is Philly to Trenton on SEPTA and Trenton to New York City using NJ Transit. The SEPTA connection is always $10 (or free for students with your KeyCard!), and the Trenton to New York City train is $20, even if you buy the tickets the same day. Even if you can’t make it all of the way (e.g. Philadelphia to Boston), you might consider breaking up into segments to get you most of the way there. The Philly to Trenton SEPTA is not great speedwise, so it can be worth booking Philly to Trenton on Amtrak and then Trenton to New York City on NJ Transit. You can also take the bus; that works too!
Seventh, book very late (what?). If you are going to take a commuter rail train (see above), it can be worth checking the Amtrak prices for the same connection. They can be surprisingly reasonable on the day of. The price also sometimes drops significantly in the last 5 minutes, so it can be worth “playing chicken” with the pricing algorithm.
Eighth, if you are flexible on what dates you use, consider using https://railforless.us/. It is a flexible date pricing tool that allows you to compare the prices between different days more easily.
Ninth, when booking trains, give yourself a buffer to when you need to arrive. Amtrak trains often run late, so it can be helpful to include a buffer for a SEPTA connection, or whatever event you are trying to go to.
Tenth, if you are curious about whether your train is going to be on time, see railrat.net. It has the same information as the Amtrak website or app, but this page is much easier to use. It also tells you how late the train is currently running, and whether Amtrak expects the train to make up the time.
Safe traveling!