Boston on Three Dollars a Day

By Gary, aka John Doe

I remember watching Rachael Ray going across the country on her $40 a Day campaign. I also remember that it was possible, in theory, if you were OK with stiffing the wait staff on tips, as Rachael would usually leave somewhere in the area of a 2 percent tip to keep this $40 budget alive.

That’s all well and good, but what if you don’t have $40, and you have no option of spending the day inside or sleeping in? Well, my friends, have no fear, because I ‘m here to tell you how you can do Boston on a mere $3 a day.

Since I’m an early riser (and by that I mean, the shelter throws us out by 7:45 am), I like to start my day with a fresh cup of coffee. Now, please keep in mind that we do need to leave the shelter for this because the coffee there is…well, frankly, words escape me, but trust me, it is no way to start the day, so it’s off to McDonald’s we go.

The first stop always needs to be McDonald’s, because the Newman’s Own coffee is actually a very nice, strong cup of coffee, and you can get a large for $1. Some locations, such as the one I am typing this article in as we “speak,” even offer free refills for your dollar.

One of the things to keep in mind is that a simple cup of coffee is so much more than that. That $1 cup of coffee is also a warm, dry roof over your head. It’s a seat to rest on and gather yourself. It’s a bathroom, it’s wifi, it’s electric outlets to charge up your phone and/or computer. So that’s a lot of life’s basic accommodations for a single dollar.

Plus, there’s quite the social scene and entertainment at the local McDonald’s, especially if you choose the one closest to a homeless population.

Here I sit, with Pops across the table from me working on his next novel that, sadly, nobody will probably ever read. We have a friend who has an interesting “I was really wasted one night in …” story for just about any town in the USA.

Here we also get to mingle with the ladies of the women’s shelter. And by “mingle” I mostly mean “avoid eye contact out of fear of being cut.” Listen, there are some very nice ladies there — but there are more than a few that are louder, meaner, tougher, and straight-out more violent than the hardest guys in most prisons. These women don’t play around!

Nor do they possess an internal filter, so really, just best to avoid altogether. But hey, if you don’t mind spending a portion of the day in the emergency room or filing police reports, by all means, feel free to get into the mix. It’s still free, so it’s included in the spirit of this article.

Next stop: time to take in some local flavor. Now, there’s lots you can do around town. You can do a little window-shopping around the Downtown Crossing area, and if you go on certain days, you can catch a car show, a local band, or an outdoor art exhibit. You can easily kill a good hour or two there, and then head right up the block to Boston Common. The Common is a great place to catch an impromptu rally, parade, or entertaining gathering of some sort. If not, you always have the option of finding a nice shady spot and enjoying a little quiet time. Personally, I carry a backpack with a sheet, a small transistor radio and a book, so I’m ready for such an opportunity at any given time or place.

If it’s a particularly nice day, we can move this party right to the beach by jumping the Blue Line right at State Street and heading over to Revere Beach.

Another key spot for the day is the Boston Public Library. Just on a visual level, the library at Copley Square is fantastic. It’s a huge old majestic building with marble stairs and balconies. There’s a courtyard with a fantastic fountain and a very relaxing vibe. If you don’t have a computer, this is the place to get in all your Internet time using the public computers. If you do have your own laptop then you are free to find any quiet spot on the grounds, plug in to one of the many electric outlets, and tap into the wifi.

Once again, the library is another place to enjoy the security of shelter and a clean bathroom.

Another great option here is to take in a movie. Simply find the audio/visual area of your local library and grab yourself a DVD, pop it in the computer, and you’re now relaxing and enjoying a good movie. If you don’t have headphones, fear not, just go to the desk and they will give you a pair to use.

At this point, we’re already well into the day and we’ve only spent a dollar. Since we have $2 left in this experiment, it’s time to once again treat ourselves. Personally, I like to grab a couple of sandwiches from the shelter and throw them in my bag so I have them for later in the day, as well an extra one or two to give to someone else on the street who might be hungry.

So I’m going to take my $2 and go for more coffee to get that little midday pick-me-up.

This time we’re going to go for a more refined experience and head to Starbucks, where I’ll grab a Grande Bold for just under $2.

Once again we now have a relaxing environment with all the accommodations needed (bathroom, wifi, electricity).

However, if you prefer to go for food over coffee with your last $2, you can always grab a cheap slice of pizza somewhere, or you can hit Wendy’s and grab a couple of 99-cent Double Stacks.

Now, keep in mind, I’ve been out the door early and up since dawn. At this point, I’m ready to head back to the shelter, take my shoes off, and lie back for a bit. If you want to continue on, there is always more to do later in the day, such as free outdoor movies behind the Boston Harbor Hotel, free concerts at the Esplanade, and plenty more.

So don’t feel that you have to stay indoors if you don’t have a lot of money. Just get out the door, embrace the day, and go have fun. There’s always something better to do than just sit around watching life go by. Don’t be like me, and wait until you hit rock bottom to realize that there’s a whole world out there.

Gary,aka John Doe, blogs at





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