7 min read

Book Travel Better with Points and Miles: Phila to Maine and Boston

Book Travel Better with Points and Miles: Phila to Maine and Boston, AI-generated image of Boston and Maine
What an artificial intelligence thinks of for the prompt, "travel to Maine and Boston." Let me know in the comments whether you agree! 

After sharing our 2022 trip to Africa last year, I received an avalanche of amazed feedback. Today I'll share my planning and booking process so you can plan your own travel better. Cash is considered, but for this trip, I mostly used points and miles. The example below is for a flight from Philadelphia to Maine to stay with friends, a night in Boston, and then a train to get back to Philadelphia. Let's jump in.

What we booked for this trip:
1. Phila to Bangor Flight -- 22,000 American miles + $5.60. The cash price would have been $330
2. Boston Downtown Hotel -- 1 Free night certificate (max 50k points). The cash price would have been $389
3. Boston to Phila Train (Business class) -- 3,500 Amtrak points. The cash price would have been $98

If you can believe it, all this travel only costs $5.60 in federal taxes/fees for booking the American Airlines flight from Philadelphia to Bangor. The flight and hotel are also more flexible than booking with cash because the cancelation policies are refundable up until a few days before the travel. Canceling the Amtrak trip is also possible but would result in only getting back 90% of the points used to book.

Flight to Maine

Flights to Maine were the most challenging part of planning this trip. When looking at flights, I always start with Google Flights because it is the fastest search by a country mile. The search results show exceptionally quickly and are where I write down cash prices as a starting point.

In Google Flights, filter down to non-stop flights. I started with Philadelphia to Bangor here and discovered something important - American is the only airline that flies directly to Bangor. I made a note of this route and price and kept searching, this time to Portland, Maine. Again, American was the only carrier that flew non-stop from Philadelphia. I noted the route and price.

Google flights showing three American airlines flights from Philadelphia to Boston for cash prices from $335 to $415
Note: Google Flights does not include Southwest route pricing, but it does show the routes.

Because our Maine destination is centrally located, flying into any of Bangor, Portland, or even the smaller Augusta airport would all work for us. Augusta would actually be ideal, so I checked that too. Because Google Flights can consider nearby airports, it found a flight from Philadelphia to Boston for only $29!

Google flights showing frontier airlines from Philadelphia to Boston for $29, showing that a carry on bag is not included

I then searched for any flights from Boston to the three Maine airports and found a $123 flight to Augusta. That was promising, but this itinerary would be through separate airlines and adding the inconvenience of a stop in Boston. The total for this option was $152.

Popular fallout video game meme with meme text "hold up" and extra text "no carry on?"

But wait - see that little slash through the carry-on next to the price? Frontier, like Spirit, United, and a few other airlines, do not include a free carry-on bag as part of the base airfare. I checked what a bag would cost and got sticker shock at the $75 cost for a carry-on, more than twice the cost of the flight! So the real total for this option came to $227, which is much less attractive.

To be comprehensive in my Google Flights search, I check nearby airports. In this case, it didn't yield a good option, but who knows? Newark EWR and Baltimore BWI have Amtrak stations directly at the airports, so I never rule out taking a train to one of them and then a non-stop flight to my destination.

Finally switching to points and miles, I fired up the www.point.me search for my airport pairs. It's also possible to do this directly through airline websites, although that is more time-consuming when searching multiple airlines. The American flight direct to Bangor was 22,000 points. I also found two cheap United non-stops from Newark EWR to Maine for 6,000 points (Portland) and 15,000 points (Bangor). Unfortunately, the departure times of those flights left a bit to be desired, but they were worth writing down as an option to consider later.

Flight Process Summary

1. Start with Google Flights to understand which airlines fly non-stop to where.
2. For your preferred airport pairings, write down both the cash and points and miles costs for both non-stop (and potentially) 1-stop. For my trip, this was Philadephia to any of the three Maine airports: Bangor, Portland, or Augusta.
3. For the secondary airports, only write down the route if the cost is surprisingly attractive and non-stop to consider as an option later. For my trip, this was Trenton, Wilmington, Newark (EWR), and Baltimore (BWI) to any of the three Maine airports.
4. If needed, check for low-cost carrier fees, so they don't bite you in the ass when you travel.
5. Decide on paying cash vs. paying points and miles. Since the cash price of the American flight was $330, paying 22,000 miles is pretty good. That's a miles valuation of 1.5 cents per mile. My simple rule for all points and miles is that they should be at least 1 cent per point/mile. For this flight, a decent use of points would be 33,000 miles or less.

Here is my shorthand note (I use Google Keep) that I made when searching for flights.

Shorthand note for flight planning from Philadelphia to Boston, considering both cash tickets and points and miles
AA = American airlines, NS = non-stop, and OW = one-way

Boston Hotel

Hotels were easy for this trip because I had five free night certificates at any Marriott property and only needed to stay a single night. I (of course) got those free nights from a limited-time sign-up bonus from the Chase Marriott Bonvoy Boundless credit card. The catch for the certificates is that they can only be used up to a value of 50,000 points per night, and downtown Boston is pricey.

Marriott hotels website seach, with points and miles "use points/certificates" checked

I found four hotel options, and in talking with my partner, whittled it down to two and then booked the one we liked the most. For fun, I will watch another Marriott Boston hotel that was just above 50k points per night. Why? Because the points cost of Marriott hotels change daily now, just like flights do. This is called "dynamic award pricing." Marriott points and certificates can be canceled and re-used without penalty if it is more than 72 hours before your stay. So potentially, we can upgrade to a slightly better hotel for free. For both cash and points, hotels are usually much cheaper two weeks before your trip and the cheapest the week of travel.

Returning from Boston

Boston is the last stop on Amtrak's Northeast corridor, and those who know me know I'm a sucker for riding the rails. Going from one downtown to another downtown is much less of a headache than airports located farther from city centers. When considering flying back from Boston to Philadelphia using Google Flights, it was about $150 non-stop, which isn't cost-competitive with Amtrak as long as you book far in advance.

A 90-minute flight versus an almost 6-hour train ride is a big difference. It's not for everyone. But I enjoy train travel - watching the world go by, riding through major cities, all with proper internet and power outlets in my seat. Oh, and I have a Scrooge McDuck-sized trove of Amtrak points from a credit card's signup bonus from *checks notes* 2018. The points remained after I closed the card in 2019.

There were many trains, and I found a 5:40 pm train with good availability. Amtrak cash prices have moved back to the pre-pandemic levels of being quite expensive unless you book far in advance. My search was more than a month in advance. The cash price for the train was $33 in coach and $98 in business.

Amtrak train booking screenshot showing cash pricing of $33 for coach and $98 for business class

Using Amtrak's quick toggle to switch the search from cash to points, I found that those same seats cost 4,400 for coach class and 3,500 for business class. Is Amtrak really charging fewer points for a business class seat than a coach seat? Yes. Remembering my rule from earlier, we want a minimum of 1 cent of the value of the cash ticket to use 1 point. Coach value here would be 0.75 cents per point, and business would be about 2.8 cents per point.

Amtrak train booking screenshot showing points and miles pricing of 4,400 for coach and 3,500 for business class
When booking with points on Amtrak, sometimes business class is cheaper than coach!

Booking Decision Time

So two things here: (1) The real decision was whether to buy a $33 coach ticket vs. a 3,500 points business class ticket. Coach vs. business class on Amtrak isn't as significant as on an airline. (2) Amtrak business class includes a reserved seat of your choosing, and you get complimentary non-alcoholic drinks from the cafe car. Since the travel time of 6 hours is pretty lengthy, I decided, what the hell, why not? I won't be chugging down a ton of complimentary coffee on this 6 pm train, but I promise to do my best to exhaust the stock of hot chocolate!

Here is my shorthand note that I compiled when searching Amtrak routes. These notes are in Google Keep, so I can refer to the drink list easily on my phone when I'm on the train. And yes, it may seem a little ridiculous, but I really wanted to know what complimentary drinks I can choose from in business class.

Shorthand note for train planning from Boston to Philadelphia, considering both cash tickets and points and miles

Cash vs. Points and Miles: Trip Booking Wrap Up

Those are my methods for planning travel with flights, hotels, and trains. Basically, write stuff down. Searching and taking shorthand notes gives purpose to your time spent searching. Seeing every option in one place helps a lot when deciding what to book. Once you get to booking, you will have the confidence knowing you're booking all the best options for you. Happy travels!