When the tide began to turn in a positive direction during the pandemic, we made a vow to say yes to as many adventures as possible. Bucket list destinations and events were going to be given priority because life is so unpredictable, and we cannot let opportunities pass us by. This brings us to the impeccable timing of Andrea Bocelli announcing a US tour and tickets going on sale immediately after our “Say YES to everything” conversation. Andrea is Jen’s #1 must see concert, so naturally when she batted her eyes and said, “pretty please,” the tickets to Boston were purchased.

At our location in the tundra of New York State, Boston is either a 6 1/2 hour drive or a quick flight on a puddle jumper. We opted for the quick flight to make the most of our time there and make a weekend out of it. We were going in December so that meant holiday season and all that goes with it!

When deciding where to stay we had two priorities- walkability to all the major Christmas lights and distance to TD Garden. We quickly narrowed it down to the area near Faneuil Hall Marketplace and zeroed in on the Hilton Boston Downtown/Faneuil Hall. It checked all the boxes for us. Restaurant and bar located within the hotel, as well as options for breakfast. Most important for us was the primo location. Our favorite way to explore a city is by foot, so being centrally located is a must. We were a quarter of a mile from Quincy Market and just over a half mile from the Garden.

We must mention that another wonderful perk of Boston is the location of the airport. Most airports are at least a 30-minute drive to the city center. Not here. You are a quick ten-minute drive to downtown which made the flight all the more appealing to us. With the ease of Uber and Lyft it made sense to let someone else take the reins while we sat back, relaxed and enjoyed the view.

We approached this trip unlike any other. Meaning we did not have every detail planned out and “winged it.” Ok, we will be honest, our version of winging it still involves a smidgen of planning, but we are so proud of ourselves for being a little bit spontaneous, so go with it.

We were flying in Friday afternoon, had the concert Saturday night and the flight home was first thing Sunday morning. We did not have a ton of available time, but enough to see our top sights.

Getting There

Let’s take a moment to talk about the flight. We are big fans of the show Wings and the tiny Nantucket airport. It is adorable (in Jen’s words.). We were flying out of Saranac Lake and the similarities were abundant. Jen was searching for Joe and Brian to be our pilots and might have even yelled out for Faye. While the airport is small, it is a great jump off point and even has a lunch counter (queue the intro for Helen.)

TSA is a breeze without the huge lines, and we were staring at our six-passenger airplane from none other than Nantucket Airlines…. not even kidding. Jen really had to hold it together. With this type of flight everything is weighed. Everything. They must evenly distribute the weight perfectly or else there is trouble. They efficiently loaded us on quickly and took right off.

The plane is compact, loud and no refreshments brought by a stewardess. Heck, there wasn’t even an intercom system; the pilot just turned around to talk to us. The bumps are felt a little more potently than on the Boeing 737, but at least you can see the pilots directly in front of you. It they seem calm and in control then you have no reason to worry. At least that is what we told ourselves. An hour passed quickly, and we were safely landing at Logan International Airport. Joe and Brian did great!

Friday was all about old Irish Pubs and pretty lights. Jen printed out an article highlighting the biggest Christmas light displays in town to be our guide. First on the agenda – a drink to come down from that flight. Apart from Union street you will still find plenty of Irish pubs overflowing with charm. Fortunately for us we did not have to venture far from our hotel. Right around the corner was Mr. Dooley’s located on the corner of Broad and Batterymarch.

It was the perfect introduction to Boston. Christmas lights, garland adorned with ribbons and bows hung from every surface. Classic Christmas music was softly playing while we were wrapped up in the warmth of the atmosphere. We went at the perfect time to admire the charm before they became the daily hot spot from 5pm until close. After finding two seats at the bar we ordered some much needed refreshment.

We enjoyed everything about this place. The dark wood, the warm lighting, the bartender with an Irish accent, and the locals next to us discussing the hockey team that shall not be named. We could have stayed here all night and almost did, but first dinner.

With a friend’s recommendation we had early dinner reservations at L’Osteria, an Italian restaurant in the North End. Lights created another inviting atmosphere and the friendly staff made you feel welcome. The scallops were mouthwatering, and the fettuccine alfredo had the perfect blend of garlic and parmesan. Another spot we could have stayed forever enjoying each other’s company.

Christmas in Boston

With Jen’s article in hand for top spots we were off to Columbus Park to begin our Hallmark movie walk. At least that was what it was supposed to be. We had our walking GPS app up on Craig’s phone and began our sightseeing tour.

The 260-foot trellis in Columbus Park is breathtaking. It is completely covered in blue and white lights. It is truly a vision and a must see for any light lover. The surrounding trees are even covered to add to the experience. Make your way past the many selfie takers to try and capture a selfie of your own. Hopefully, you will stumble upon a couple willing to take your picture in trade for taking theirs. We sat down on one of the many benches to soak in the beauty. Take a walk down by the water’s edge to see the lighted trellis with the city as its personal backdrop.

After you feel you have spent enough time go across the street to Faneuil Hall Marketplace to see the tree in Quincy Market and the shops with their own holiday displays. We took this opportunity to grab hot chocolate and fresh baked chocolate chip cookies from one of the many vendors.

Now that we truly looked like a Hallmark movie with our cocoa and cookies, we continued to Boston Common. Sounds easy enough with our handy dandy walking app. Plus, we look like a movie, so it should play out like a movie. Right? Anyone that has used the walking app knows where this is heading. Boston city streets are a labyrinth not meant to be navigated by just anyone. No, they are meant to trap and confuse so you will never find your way out. The app flipped and rerouted because it also did not know where we were. Some nice Bostonians took pity on the tourists and offered some much-needed assistance.

The trouble and time it took to reach Boston Common was worth every second. We came in from Tremont Street and were greeted with the Boston Christmas Tree, which is the city’s official tree. It was given to Boston by the people of Nova Scotia to thank them for their assistance with the 1917 Halifax Explosion and has been lit every year since 1941. We love the history that is so rich in this city. Surrounding this tree in the Common are countless trees covered in lights. We spent time looking around in full admiration.

We continue on the walkway following the lights to the ice skating on Frog Pond. Even with the unseasonably warm weather they were still able to make some ice for those wishing to hop on. The rink is surrounded by light covered trees and a stunning view of the city. The area is bustling with locals and tourists alike enjoying everything the holiday season has to offer.

We climbed up the Flag Staff Hill to take a closer look at the Soldiers and Sailors Monument. Even at night the detail in the statue was easy to appreciate. This raised point also gave an unmatchable view of the lit city, which led Jen to say to Craig, “What is that?!” Down the other side of the hill was the start of a trail of lights. We pulled out the Christmas light article and that darn app again to figure out what that could be.

Back story – when we started off one of the hot spots was Commonwealth Avenue Mall, but it was over two miles away from our hotel, so we scratched that off the list. We figured we would try to hit it the following day or on our next trip.

“Ummm…. is that Commonwealth Avenue Mall?” (Not a shopping mall, but a walkway.)

“No, it can’t possibly be. We were not going to walk that far today.”

“Let’s go check it out since this stupid walking app isn’t working and my battery is at 4%.”

As we approach the crosswalk, we are greeted by a wrought iron gate decorated by a wreath and see a bridge covered in lights. Beyond the bridge is nothing our words can describe. We were indeed at Commonwealth Avenue Mall, and we were venturing into an enchanted forest. The walkway is lined with trees and those trees are blanketed in white lights. It is unlike anything we have ever seen. We walked a little over a mile in before we decided to turn back to our hotel. There was no end in sight. While there were others walking the path it did not feel crowded or congested. Everyone set their own leisurely pace taking it in. What a wonder in the city of Boston!

All we had to do at this point was walk back to our hotel. We debated an Uber but elected to walk to extend our own personal Hallmark movie. It can only get better, right? Back to the nightmare app to guide our way home. This time we decided to get a general idea of the street names before we blindly followed. After a few correct turns we had confidence seeping from our bones we had no business exuding. As a labyrinth typically does, it allows your simple beginnings to lure you into the trap fast approaching.

As the distance to the Hilton shortened, so did the streets and so did our boasting. The street names on our app did not appear and the sirens passing by became more frequent. We were circling the drain and could not find our way out. Finally, a haven, a street name we recognized and knew! We smile at each other and laugh that we almost got lost. Rounding the corner onto our street we are smacked with police tape and several police cruisers with lights flashing, A police officer is clearing the street and tells us to turn around and get out of here.

Jen politely asks if we can cross the street and continue on our way, which he quickly turns down. Again, he says, “Get out of here.” Ok, Officer. Point taken. In any other city you can just walk around the block and be back on your way, but the labyrinth swallows us back in. To join us on our journey was another officer with his flashlight to the ground walking briskly. It did not take us long to figure out what he was doing after he said, “There is so much blood! This trail is never ending!” What is a trip to the city without a blood trail?! Did you even go if this doesn’t happen?

Our walking app was apparently set to “follow the blood trail” because we are taking every turn the officer takes. We finally decided to hop over the blood to get back towards our hotel. Let’s say that again……. we hopped over a trail of blood…… to get to our hotel. Fortunately we parted ways before the officer found the source and made our way to the safety of our hotel.

When our heads hit our pillows, it was lights out for us. We had just walked over 8 miles. We had only been there for a few hours and our expectations had already been exceeded. Irish Pub – check. Christmas lights – check. Crime scene – check.

The Freedom Trail

Saturday was the day of the concert, but we had the entire day to find things to occupy our time. We started with breakfast at the Tradesman Coffee Shop & Lounge, located within our hotel. Hands down the best breakfast sandwich either of us have ever had. After some much needed caffeine and nourishment, we were ready to tackle the Freedom Trail.

The Freedom Trail is 2.5 miles of history in the city of Boston. We are going to give you a huge helpful hint – put away the map and walking app. The trail is engrained in the sidewalk and walkways with red bricks. Follow the red brick road (you know where we were going with that.) The red brick takes you to every point of interest and is marked perfectly. Even when there is a detour, the city paints a red line for you to follow.

Due to our location, we began at the Old State House. We did not enter, but if you wish to you can go in and look around. It is not hard to pick out as it is an old brick building that appears to be being swallowed up by the modern city buildings around it. Right next to the state house is the Boston Massacre site that is remembered with a large marker.

From here we followed the trail to Faneuil Hall and down the famous Union Street that is lined with historic Irish pubs. From here you will pass the Boston Public Market filled with fresh fish, fruits and vegetables from numerous vendors. Continue until you hit Paul Revere’s House. For $5 you can go inside and allow one of the many experts to give you the history within those walls. As children we heard the tale of Paul Revere over and over. It was an incredible experience to step foot in his home and marvel at his life. Who knew he had 16 children?!

Next stop was the Old North Church made famous the night of Paul Revere’s Midnight Ride and the two lanterns to warn the British were coming by sea (one if by land, two if by sea.) We sat in one of the personal seating sections to read about the famous parishioners that once attended services there. We gazed upon the window marked with a torch that was used as an escape from the British patrol on that famous night.

Continuing the red brick trail brought us to Copp’s Hill Burying Ground which dates to 1659. This was the oldest cemetery we have ever walked through in the United States. The stone markers are showing their age and their remarkable resilience against the elements atop this hill.

Our final stop is the USS Constitution across the Charles River. Approaching the Charleston Bridge set our panic button in motion because the construction was everywhere. Fortunately the city of Boston painted a red line for us to follow for the detour. Once across we were back on the original trail and the top of the USS Constitution was in our sights.

This ship is the world’s oldest ship of any type still afloat. It was launched in 1797 during the time of President George Washington. It is in the Charlestown Navy yard and tours are run by US Navy sailors. Their knowledge is vast and plentiful giving you a rich history of the ship. The ship reminds you of the time of pirates roaming the seas and even Captain Jack trying to overtake this looking for rum. We highly recommend taking the time to hop aboard and visiting the gift shop that has great souvenirs.

Uber is the greatest invention since sliced bread. We walked just outside the grounds of the shipyard and requested a car to pick us up and deliver us to another must stop for a late lunch. The Green Dragon Tavern was the meeting place for Paul Revere and John Hancock, along with all the members of the Sons of Liberty planning the revolution and war for independence. Obviously we had to eat here. Another incredible Irish Pub just off Union Street. And Jen got her lobster roll (amazing). It was the perfect spot to end our history journey in Boston.

Time for the concert. We are not even going to attempt to put into words what Andrea Bocelli’s concert was like. Stunning. Amazing. Breathtaking. They just don’t do it justice. If you have the opportunity, GO! His voice cannot be compared, and his talent blows everyone out of the water. He picks the perfect special guests to compliment his performance and flow of the music. Amazing.

The show ended at 10:30 and due to the mass of people leaving the venue we opted to walk back to the hotel since we finally had a sense of direction around this city. We were on a high from his performance and chose to have a late-night snack at Vintage Restaurant and Lounge located directly across the street from our hotel. Best pizza we have ever had, and great staff closed out our incredible weekend getaway. Thank you, Boston, we will be back!

Thanks for reading! And remember, #NeverStopPlanning.

Jen and Craig

You can read about more of our adventures here and here.