Fasten your seatbelt because we’re taking a couple of one way flights, cabs, a ferry, a train and a rental car in this whirlwind adventure. We highly encourage you to book one way flights to maximize on adventure in a specific region. People commonly travel across Europe via trains to maximize on a region. We think you should do the same here in the U.S.
Like most of our adventures it’s a romantic comedy. Was Planes, Trains and Automobiles a romantic comedy? Haven’t seen it? It’s a must see. John Candy + Steve Martin= Hysterical laughter. Not with the kids though but I digress. The idea for this trip out east starts with me planning to meet up with a friend. This former coworker turned friend has relocated to Australia from Florida, but her hometown is actually Queens, New York. She’s was coming state-side to see her family and this was my opportunity to visit her. Since her trip serendipitously coincided with with my father in law’s 70th birthday we were also going to see him in Connecticut.
Fortunately, for me, Cal loves adventure as much as I do so he was completely on-board for what became a game of hopscotch through the northeast. We road trip to Connecticut once a year so the original plan was to drive BUT I found one way flights for $39 on Southwest Airlines. Don’t look a gift horse in the mouth! This $39 one-way flight to NY had me feeling lucky. A little research revealed a one-way flight from Boston to Chicago was $43, I can make that work…adventure is out there, people!
Ok, ok, flights are booked but how are we getting from NY to CT then from CT to Boston? The original plan was to rent a car in NY then return it in Boston – that proved to be ridiculously expensive, as in over $1,000 expensive. For that I could have just driven my own car, am I right? Now we get to the planes, trains and automobiles part.
After much deliberation we decided on taking an Amtrak train from NY to CT. It amazing. That was the smoothest ride, with the kindest conductors – I can’t compliment Amtrak enough. It did leave late from the station but minor detail. The girls were so excited to be on the train, they sat next to each other like best friends while Cal and I enjoyed the peaceful quiet that comes when your kids are getting along.
We spent a couple of day in CT, then drove our rental car to Boston for a day of fun. We spent the day with some friends that live in Boston then drove ourselves to the airport and flew home.
We hopscotched through 3 East Coast towns in a week by creatively scheduling our transportation.
Our Complete East Coast Itinerary looked like this
One way Flight from Chicago to New York
18 hours in New York
An Amtrak train from New York to Connecticut
3 days in Connecticut
Rent a car to drive to Boston
12 hours in Boston
One Way Flight from Boston to Chicago
From this itinerary you may think that we do the most….but we really don’t. We had three major stops on this trip but we weren’t necessarily trying to see everything that each of these stops had to offer. We focus on what we consider having fun and laughing with our girls. Laughter is the essence of the comedy that is life.
Please share some of you best travel laughs with us by commenting below.