Have you been to Boston? It is a place I have always wanted to visit, but until recently never had.

Getting there involved an unexpected adventure. I was reading and had the flight tracker showing on my seatback screen and noticed that we did a little u-turn on the flight pattern. I didn’t think too much about it and went back to reading. I looked up a few minutes later and noticed that the plane was literally flying in a loose figure 8 pattern! It was a bit disconcerting to be honest. Soon enough the pilot announced that we had been put in a holding pattern over northern Virginia as New York airspace was “closed.” We circled for so long that we now needed gas so we were landing in Pittsburgh to refuel!

We were refueled and ready to take off in record time, but then we had to wait about 45 minutes to get clearance for take off. We ended up landing in Boston at about 4:20 which was 2.5 hours delayed. Definitely could have been worse. We were told that the whole issue was due to a small weather disturbance over the New York area. The pilot said in more than 40 years of flying he could only recall about 4 times where he was diverted to another airport. A query to the Facebook Skymiles Life page has a consensus that this is becoming the norm due to Air Traffic Control shortages.

Day 1

Do you prefer AirBnBs or hotels? We usually end up at a hotel, but we found an adorable AirBnB this time, located in the Back Bay neighborhood of Boston. Much internet researching told me this was the best place for first time visitors to stay because of its central location. I can’t argue with that. We walked to Newbury Street and Fenway, and felt very central to other neighborhoods but we did Uber, and subway/tram our way around a few times.

Here is the link to our AirBnB. It was super clean, and exactly as pictured.

After dropping off our bags, we headed out to explore the area we were in with a plan to grab dinner wherever looked good. Our first stop was an Irish pub called The BeBop. We would have been happy to stay awhile, the live music was great. We ended up leaving cash on the table and moving on after we finished our first beers because we couldn’t get the server to come over and take our food order. No biggie, we were refreshed and lubricated for more exploring.

We found the famous Newbury Street by accident and walked a good portion of the street and popped into a few shops, including an awesome grocery called DeLuca’s.

There were so many options for dinner! We decided on Sonsie. Set up like a Parisian cafe with rows of indoor tables facing out, and completely open to the street. We were able to get a table for two on the street, which was the only outdoor vacant table, so it felt meant to be. I should point out that is graduation weekend and there are literally three dozen colleges in Boston so the city was hopping the entire weekend!

Hubby ordered a waygu burger and I ordered a lobster roll. Everything was great. I wouldn’t say the food was outstanding but it was really good. The atmosphere and the service were great, and I loved my rose Cava. Yay for our first night in Boston.

Day 2

A 9:00 a.m. tour of Fenway park began our day. It is not just the husband that loves baseball, I am a fan too. After decades of watching two daughters play softball, I finally learned some of the rules and became a legitimate fan. The oldest ballpark in America y’all! Built in 1912. And if my fellow Atlantans don’t know, the Braves organization began here in Boston. Highly recommend the tour for baseball fans and history buffs.

From here we Ubered over to Boston Commons. We explored the Commons a bit, this is where the Freedom Trail begins. We explored a cemetery with graves dating back to the 1700’s. The cemetery is directly over the first subway tracks built in the United States. Feeling the trains rumble underneath my feet made me wonder how these coffins stayed put for 300 years. Yikes.

We walked across the street to the Boston Public Gardens. Possibly my favorite thing of the whole weekend. Spring was in full bloom in Boston, and not only were gardens beautiful with blooms, there were baby ducklings everywhere.

There are swan boats to ride around the lake in the gardens. We probably should have ridden a boat but we were just happy to meander the grounds and sit and watch everything. A dear friend shared a picture of her Grandmother riding the swan boats, so cool to see the same things happening in the same spot decades later. The area is surrounded by the Beacon Hill neighborhood with beautiful brownstone homes, that had gorgeous tiny little gardens out front.

Did you know that ether was discovered at Massachusetts General Hospital in Boston in 1847? A huge milestone in human history and modern surgical medicine.

The famous Cheers pub from the TV show was nearby here so went there for lunch. We were thinking this would be a cheesy little tourist stop – and it was that – but it was also really fun and our food was great too. We had a Bull & Finch IPA, named after the original name of the bar. Imagine our surprise when we got home on Tuesday evening and saw that George Wendt, who played Norm from Cheers had passed away.

We walked the 1.5 miles to our AirBnB for an afternoon respite before heading to Fenway for the Braves v. Red Sox game. Let me just say that singing Sweet Caroline in Fenway Park was a moment I will cherish.

The Braves were leading for most of the game and then the Red Soxs tied in the 8th and hit a walk off home run in the 8th. That was quite the bummer for Braves fans, but then again we saw a walk off homerun at Fenway, so you know, all in all a great experience!

A Fenway jumbo hotdog and Cokes was dinner for tonight. I really regret not getting an ice-cream Sunday in a miniature baseball cap after I realized I put 17,660 steps and 12.4 miles in according to my Oura app!

Day 3

Today I was determined to ride the subway. I love subways and like to check them out in cities that have safe and usable ones. We slept in a bit and then headed out to find the Massachusets Street station which was only about 1/2 mile walk from our stay. We took this over to the Old State House with the plan of checking out Quincy Market, Fenhuiel Hall, and then walking the Freedom Trail.

We made it to the markets and then my phone lost it’s signal, and despite the sidewalks being marked with the Freedom Trail pathway, we walked in a big block that got us back to where we started. At this point we called an Uber and had it take us to the Boston Monument on Beacon Hill, the farthest point on the trail.

Truly the history in this city is amazing. It is hard to wrap your head around sometimes. We walked from here to the USS Constitution, where we explored all decks on the on the ship. This was genuinely wild to see how these sailors lived on this vessel. We continued on the Freedom Trail which is very conveniently marked on the sidewalk in most places. Sadly, I took 0 pictures of Old Iron Sides.

This took us over to the North End which is also known as the Little Italy of Boston, where Italian immigrants settled and developed the city into what it is today. After seeing another cemetery, the Old North Church, and Paul Revere’s house, we needed some sustenance. Did I mention this was a crazy busy weekend in Boston with all the graduations?

We ended up landing at a tiny little Italian restaurant called Antico Forno where we scored a seat at the bar. A drink and antipasto plate (i.e., Italian charcuterie) were just what we needed. We headed back to the AirBnb for a rest and to decided on dinner. We realized that we left a package we had bought at the restaurant. I called and they still had it so we decided to head back to the North End for dinner.

We picked up our package from Antico Forno and thought about staying for dinner – all of the food and the pizzas looked delicious. We made the unfortunate error to try and find something new.

We chose a quaint looking little Italian restaurant down the street called L’Osteria. It was busy so we thought it can’t be bad. Did I mention it was graduation weekend?

This was the worst meal we had in Boston and possibly the worst Italian meal we have had ever. I will spare you every detail but the wine was horrible, the Bolognese sauce tasted like Beefaroni, my sausage was tough and rubbery. You get the idea. The best thing was my espresso martini and I really think it was a ready to drink canned cocktail. Oh well! Just makes you appreciate the good meals even more right?

After dinner we stopped at Modern (also known as Mike’s) Bakery on the recommendation of friends who grew up here. The line, at 8:30 at night was out the door and down the street! We waited. What a great place. So many options. I wish I had taken pictures of our goodies, but we went back to our AirBnB and ate them. A nice ending to a crappy dinner lol!

Martha’s Vineyard

We got up at 5:00 a.m. and caught our 6:10 shuttle ride to Cape Cod. We were with a group of 16 other people enroute to Wood’s Hole, Massachusetts. We stopped in Falmouth to visit a newly renovated light house.

And we saw ocean swans! Who knew??

The ferry to Martha’s Vineyard was huge! It hauled humans and vehicles, including full size tractor trailer trucks! After a 45 minute ride we arrived in Oak Bluffs.

There are three “big” cities on the island. Two of them have ferry service: Oak Bluffs and Vineyard Haven. The third is Edgartown and we decided to head there first. This was not only a Monday, but right before Memorial Day weekend which begins the season for Martha’s Vineyard. Everything was quiet but humming with the activities of preparing for the summer crowds.

We stumbled upon the cutest little oyster bar and after seeing the Dirty Filthy Rich martini – olives stuffed with caviar – on the menu, we decided we had to visit this place.

We did not order the martinis but we did get two glasses of Sancerre and 10 oysters with a bump of caviar on the side.

Funny story. While I was ordering a sweat bee flew in my mouth causing me to literally choke and spit it out right in front of our poor sweet server! Not before it stung my lip either! I was so embarrassed, but our server was the best human ever and claimed that she actually saw it go in my mouth. She brought me some ice and we soldiered on.

Everything here was so delicious! The best thing was the kimchee to put on the oysters, had not had that with oysters and it was so good! We did think it easily overpowered them so just the tiniest little dab did the trick. And the caviar was an excellent addition.

From here we headed to Vineyard Haven. Another cute town with shops and restaurants, we meandered a bit before heading back to Oak Bluffs.

At this point we realized that the three towns all had some unique offerings, but also a lot of the same. The most interesting thing about Oak Bluffs was the gingerbread houses that stood where tents previously stood in a religious community that centered around a large tabernacle. Crazy history here dating back to 1835 and the Methodist church. It is still an active non-profit organization today although the homes have private ownership and can be rented for summer guests.

By the time we got back on the ferry at 3:45, it was really windy and downright cold. We were happy to be on the enclosed ferry where it was warm. By the time we got off of our shuttle in Boston it was 7:00 p.m. A long day, but definitely worth it. What a beautiful slice of America Cape Cod and Martha’s Vineyard are.

It was also incredibly windy and cold in Boston. Like hard to walk against – windy. We stopped at a restaurant called Dillon’s because it looked cute and was on the way back to our AirBnb. This resulted in lobster roll number two for me, and a perfect ending to a long weekend in an amazing city.