Our adventures began six years ago when Amber signed up for a cheap flight notification service she saw on social media.  We both had traveled a bit before – family vacations, work trips or day trips that were close to the places we had lived but nothing where we had got on a plane together and went somewhere – just the two of us with our own plan. 

The first deal we got was for Boston, Massachusetts.  Amber has been an avid Boston Red Sox fan for the last 30 years so when the opportunity to finally see the Red Sox at Fenway Park.  It was fate. A sign from the universe that we needed to go.  We quickly checked the Red Sox schedule and found the cheapest flight to correlate, but after booking, we realized the team would be on the road during our trip, and no game would be happening while we were there.

There was no turning back. We planned an amazing first trip that taught us a lot about who we are as travelers.  Boston has become a special place to us and our main hub for yearly trips.  We’ve truly come to love the New England Coast and everything it has to offer. 

 A Day in Boston

With the Red Sox game off the docket, we began our planning for our first trip.

Sun Country has a daily flight out of Minneapolis to Boston that we use for most of our trips.  We love our Minneapolis-based company Sun Country because it’s affordable and allows us to go to so many places that are of interest to us.  The MSP->BOS is an early flight (6:50 am) so it is not for the faint of heart, but it gets you to Boston by 11 am giving you most of the day to explore. 

For accommodations, we booked our first Airbnb for this trip which was a small one bedroom in Watertown, MA close to public transportation and free parking. We rented a car so that we had the freedom to go where ever so free parking was a major plus for us.  We went with Airbnb to save on cost and we were unfamiliar of the area at the time.

With our early flight and arrival to Boston, we knew that we would not be able to check into our place till later that afternoon.  We also did not want to worry about finding a parking spot and carting around our luggage as we explored downtown Boston.  Our solution, which ended up being one of our favorite things we did in Boston, was the Boston Water Taxi to Rowes Wharf.  The taxis provide an on-demand service between the Logan Airport Stop and Rowes Wharf.  Tickets are $45 round trip (per person), and they will securely store your luggage at the Rowes Wharf office location.  You can prebook your tickets or purchase a ticket on board.  The airport offers a free shuttle that runs from each terminal to the water taxi dock.  The bus picks you up right outside baggage claim.  Be sure to get on the Massport shuttle bus #66.  The coolest part of the taxi ride is that you get some of the best views of Boston Harbor. 

Once we docked, we secured our luggage in storge and made our way into the city.  Rowes Wharf puts you in a great starting spot to begin your sightseeing.  Being hungry from our travels, our first stop was at the Trillium Garden on The Greenway, which is located right off the wharf.  It’s a seasonal beer garden featuring craft ales, wine and food trucks.  It was a busy little place, and we were lucky to find a spot to sit to enjoy our picks from the Bacon Truck.

Our first stop after lunch was at the Boston Tea Party Ships and Museum.  We did not go in but took some photos and videos of the paying customers throwing the tea into the bay.  The cost for going in was $35 per person and included a fully guided tour with activities. 

Next, we hopped on the Freedom Trail, the 2.5-mile-long path that runs through Boston and passes by 16 locations of significance to the history of the United States. If you are a history buff this is a great free way to take in everything. The National Park Service even has a free audio tour that you can listen to stories about each site. Some of our favorite stops included King’s Chapel Burying Ground (which is said to be the oldest graveyard in the city), The Old South Meeting House (the organizing location of the Boston Tea Party), Boston common (the oldest city park in the United States), the Old State House, and Granary Burying Ground where Samuel Adams, John Hancock and Paul Revere are buried. 

While we were close to Boston Common, we stopped over at the Cheers Bar to take a photo outside the famous 90s sitcom bar. Located off the park on Beacon Street the bar is full of nostalgia and touristy fun.

Cheers has a special place in our hearts as it where Amber gained her love for the Boston Red Sox. In the show, bar owner Sam Malone was a relief pitcher for the Red Sox for five years. She didn’t want to be a Minnesota Twins fan like everyone around her growing up, so she chose the only other team she knew at that time and it was the Red Sox. Thirty years later and the Red Sox are still her longest love.

We finished the day at Christopher Columbus Waterfront Park.  It’s beautiful, covered archway and views of the bay were a great ending to a busy day exploring the city.  When we were ready, we made or way back to the water taxi station, picked up our bags from storage, and rode the water taxi back to the airport dock to get our rental car.  So simple and easy! We recommend this to all our friends wanting to visit. 

Feeling the hunger in our stomachs we stopped at a small little Italian restaurant on the way to our Airbnb – Fiorella’s Trattoria.  It was a simple little place that came with good reviews.  We enjoyed the chicken gnocchi fra diavolo and the chicken parmigiana.  Both were done well with lots of flavor. 

We finished the day feeling like we had seen everything we needed to see in downtown Boston. Now to seeing what day trips we can take.