Page Updated: January 12, 2024

Boston

Because of its rich historical significance to the U.S., we specifically planned this leg just for the city of Boston. It’s been a bucket list stop for us from the beginning!

All of our free time was spent between the areas of Charlestown, the Boston Common, the North End, and the South Boston Waterfront. We could do everything we did in leg 24 again, and I wouldn’t feel slighted. It’s our favorite city on the journey so far, and one of our favorite legs. I know we’ll be back to explore more of what Boston has to offer - even if it’s just to eat! Because everything we ate in Boston was ridiculously delicious!

We couldn’t find an Airbnb that worked for us within the Greater Boston area, so we booked one across the border in New Hampshire. A garage apartment connecting to our host, The Birch Suite was perfect and met all of our needs.

The wall of AirBnB guests was unique! Auto tags for Americans. Flags for foreigners. Really neat touch to the rental.

We are huge - HUGE - Halloween geeks. In a parallel universe, I’m sure we own a massive haunt and terrorize people for giggles.

We survived Halloween 2021 with the help of Silver Dollar City’s Pumpkins in the City. But historically our Halloween prep began in the summer months of June or July.

As Halloween ticked closer in year two of being on the road, we were really missing the vibe. By September 4th, I could stand it no longer and we picked up pumpkin lights to string on the rental decor. It’s never too early to decorated for Halloween!

THE LOCAL GRUB


BBQ Fries with

Burnt Ends

We’re judgy about bar-b-que. Naturally we had to check out Smoke Shop BBQ - Seaport — phenomenal! Great fair and the largest selection of whiskeys we’ve come across. We ate our way through Boston but made a point to visit here twice. It’s great! Will be stopping here every time we trip into Boston!


Grilled Swordfish Piccatta

Located in a historic former grain mill with wooden beams and exposed brick, Granary Tavern is located on Milk Street. The building drew us in. Local craft beers made us grab a seat. Swordfish on the menu made us order. Fresh and delicious!


We couldn’t leave Boston without stopping at Cheers! The Beacon Hall location provided exterior shots of the show, while the original bar set is located at Paramount Studios in Los Angeles. A reconstructed bar set can be found on the second floor of Boston’s Bull Finch Pub for looking a nostalgic Cheers experience.

Pub Skins

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scenes from the leg!

THE FUN STUFF

09/04/2022

A recreational park with baseball, football, and soccer fields - plus a playground and trails, Muldoon Park also has a fully wooded 18 basket disc golf course…

Muldoon Park

09/10/2022

Boston’s Freedom Trail is a 2.5 mile red brick ribbon that snakes through the streets and sidewalks of the city while passing a collection of 16 locations pivotal to….

The Freedom Trail

09/10/2022

Six glass spires etched with six million numbers, the New England Holocaust Memorial pays tribute to the six million Jews killed in the Holocaust….

New England Holocaust Memorial

09/10/2022

The oldest warship still afloat, USS Constitution - a.k.a. “Old Ironsides” - launched in 1797. After years of faithful service, and after several bouts of being…

USS Constitution

09/11/2022

The Boston Tea Party Ships & Museum offers a unique immersive experience of the events leading up to the American Revolution…

Boston Tea Party Ships & Museum

09/11/2022

A Fletcher-class destroyer - a class denoting destroyers built during World War II; USS Cassin Young was built in 1943, survived seven battles in WWII including two…

USS Cassin Young

09/11/2022

Boston’s Old Town Trolley Ghost and Gravestones Tour explores Beantown’s dark side. Led by a costumed “17th century gravedigger” providing exclusive…

Ghost & Gravestones Tour