Tailwind Air isn’t an average commuter airline. There are definitely similarities to Seattle’s Kenmore Air, in that both fly seaplanes and do charters through some of the world’s busiest airspace, but Tailwind Air positions itself as a boutique service for the time-pressed Northeastern traveler.
This is their math: it takes at least four hours to cover the 200 road miles between Manhattan and Boston by rail or car, depending on traffic or service delays. By air, it’s consistently less than 90 minutes. And far more comfortable and glamorous.
Our flight was on Friday, March 5, 2022, which marked the airline’s annual resumption of service on the route – the flight doesn’t operate in the winter months.
The flight from Manhattan to Boston took 70 minutes thanks to a helpful tailwind, although we paid for that by having to fight the corresponding headwind on the way back, so that leg took 90 minutes. Considering it’s taken me 90 minutes to drive the length of Manhattan in Friday afternoon traffic, this flight is a wonderful option.
I made up a binder to plan our trip and this was on the cover… it is how I roll!
The movie Planes, Trains, and Automobiles is one of my favorite classics. It never gets old watching how a simple trip falls apart into complete chaos. It might have been a bit odd for me to be excited taking a trip using those exact forms for transportation (in the same order, none-the-less), but I was optimistic that our trip would turn out much better. Brittany (my lovely wife) and I were planning to take a plane from Seattle (SEA) to New York (via EWR); a train from New York (NYP) to Jacksonville, FL (JAX); and then a nice little drive down the Florida coast to Vero Beach, FL.
Brittany had never been to New York City and we wanted to visit my dad in Vero Beach. You probably can tell that I love flying, but I was at a place in my life where the idea of flying back and forth across the country twice in a few 737s was not appealing, so I started to get creative.
The outside of an Amtrak car with Viewliner Roomettes – Photo: Amtrak
I realized that for about the same cost to fly from New York down to Florida, we could purchase a Viewliner Roomette on the Amtrak Silver Service. Of course the travel time would be a bit moreâ€¦ but the experience would be very different. Neither of us had traveled overnight on a train and I was stoked about the idea!
Although the train continued farther south, I wanted to round out the experience by de-training (that a thing?) in JAX and renting a car to drive the rest of the way. The drive is only about three hours to our final destination, but we decided to make it a two-day adventure. We wanted to smell the roses and also stay at a hotel right on the water. We had our quest locked in!
Buckle upâ€¦ it is time to first start the PLANE portion of our journey!