How I Turned a Long Boston Layover Into an Adventure

Every traveler knows the purgatory of a layover. You’re not on your way, you have no designated adventures and if it lasts too long, it just feels like a waste of time. Kristin has provided excellent tips on how to take advantage of your layover (tips 7 through 10 are musts for me!), but what if you’re not stuck in the airport? If you still have a few hours before leaving, if your flight is canceled or if you have more than enough time to switch planes, those tips will just scratch the surface of that dead time zone.

This fall, I ended up in this scenario. I flew to Boston with a full weekend ahead of bridesmaid responsibilities, so I didn’t plan anything else. The wedding wrapped up Sunday evening, and I planned to sleep in and leave the hotel mid-Monday morning for an 11:35 a.m. flight. Plot twist: I was renting a car with two other bridesmaids, one of whom was flying out at 7:25 a.m. Turns out I was in for an early airport run!

After dropping off our early traveler, my friend Emily and I faced a choice: Would we spend almost six more hours at Boston Logan? Or would we squeeze in a tiny adventure with our gap in our schedule? Here’s how we spent our long layover in Boston.

Step 1: Embrace the Adventure

No surprise: We chose adventure! Also no surprise: We were not sunshine and roses before 6 a.m. out of our native time zones. After the drop-off, Emily and I maneuvered off the highway to the best-lit parking lot we could find at this early hour to decide our next steps. Though our brains were a little slow, we found a cute little diner on Yelp that would help us wake up.

Next time: I’d make plans the night before. If you plan better than we did, you can prevent sitting in a parking lot with only your phone as a guide.

Step 2: Expect Something to go Wrong

Or some things. Remember that cute little diner? We never found it—I don’t even remember what it was called. Google Maps was confused by Boston’s underground tunnels and wasn’t helpful with walking directions. We popped into a Pret a Manger we passed, but it was so early they only had beverages available. We had to give up looking for street parking and settle on a pricey garage.

Next time: I would be prepared to be spontaneous. Sometimes even Google Maps doesn’t work how you expect.

Step 3: Eat! Drink!

Don’t doubt the power of addressing the basic levels of Maslow’s Hierarchy of Needs — in fact, if you only do one thing on this list, pick this. After dealing with rush hour traffic and getting lost, Emily and I were, um, cranky. But when we sat down at Tatte on Summer Street, our morning and moods changed. Black and white tiles patterned the walls and floors, the menu boasted Middle Eastern flair and the atmosphere welcomed conversation. I scarfed down the Egg in a Hole, which was two eggs on a bagel. We perked up with caffeine (coffee for me, tea for Emily), and the sun was finally peeking over the skyscrapers. Morning commuters outside the window reminded us we were in the heart of one of America’s oldest cities, and we didn’t want to sit still.

Next time: When you’re out of your normal routine, it’s easy to forget to make time for a meal. Sustaining yourself on backpack snacks may be practical (and necessary when you’re cranky!), but it’s also one of the easiest ways to soak up local flavor.

Step 4: Look for the Best of What’s Nearby

Google and Yelp are your friends here. Emily and I filtered search results to find attractions that were already open and inexpensive. After scrolling through museums, landmarks, parks and more in Boston, we made our pick: Harvard University. I had never been, and it had been some time for Emily, so why not act like the Gilmore Girls and show up on campus with no tour guide?

We walked Harvard Yard, we found the statue of John Harvard, we found the first programmable computer in the U.S. on display in an academic building! And not sure if you’ve heard, but New England is gorgeous in autumn, and the campus was ripe for top-notch leaf peeping.

Next time: I would get to this part as soon as I can. Best to make that tiny adventure last as long as you can.

And there you go: Only four steps to make your awkward layover an adventure. You could be in one of the most exciting or beautiful places in the world, but you’d never know if you’re only watching for your departure time. Be open to adventure, be prepared to change the plan, get a snack and look around — your adventure is ready for you.

This is a guest post by Taylor Blake.  She is a contributing film critic for ZekeFilm, runs a movie review blog and co-hosts a biweekly Gilmore Girls-themed podcast. All photos courtesy of Taylor Blake.

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