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A Wicked Good Weekend in Boston!

This Christmas I got Debbie a trip to Boston for her birthday. I know, I know, that’s kind of cheating since it’s REALLY for her birthday, but I figured if I got the flights and hotels for Christmas, I could book something fun to do, or a really nice dinner for her birthday. When I started looking for a weekend getaway, I didn’t really have anywhere specific in mind – I just wanted it to be somewhere the two of us had never been together. I had seen ads for the site Weekend.com, and figured I’d try it to see what it came up with. The premise is you put in the weekends you want to go away, or just say any weekend in the next 6 months or year, and it will bring back the a number of places and the cheapest option to get to each. NOTE: weekend.com went out of business in 2023.

I ended up finding a great deal to Boston where we flew out of Fort Lauderdale Friday morning on Jet Blue, stayed two nights at the Hyatt Regency Boston, and flew back Sunday night for a total of $518. My lowest price was actually less than that, but I paid a little more to upgrade from Spirit on one of the legs so A) I would get a free carry-on bag and B) I would be flying round trip on Jet Blue in case the weather became a problem and one of the legs was cancelled. This price was for a personal bag and carry on only (no checked bag) but this was not a problem since we were only there for the weekend.

The weather in Boston on the Tuesday before we left was a balmy 60 degrees – but by the time we got there on Friday it was 25 degrees with a forecast of 15 degrees (-2 with the windchill) and 3-5 inches of snow on Saturday. If you know me, you know I am ALWAYS cold, so I began to panic and pulled out my super pants and shirt to bring with me. (This is what I call my thermal pants and shirt because they kept me nice and warm in New York when it was 35 degrees so I hoped they would work just as well in 15-degree weather!)

We took an Uber from the airport and arrived at our hotel at about 12:00 p.m. Luckily, they already had a room available for us, so we were able to check in immediately. The hotel was very nice and rated 4 stars. I looked at the price on a few sites like hotels.com or booking.com and the best price I saw was $331 for two nights after taxes and fees were applied so I felt great about the price I got through Weekend.com. The hotel itself was located in the Theater district which was perfect for us as we wanted to see a few shows while we were there. We were literally a stone’s throw from the Paramount and the Citizens Bank Opera House where Cats and Mean Girls were playing and there were tons of nice restaurants nearby. My only mishap occurred was when I opened my backpack to get dressed for walking around in the cold and I realized I had left my super pants at home! I almost cried until I got outside and realized my internal body temperature must be changing because I was fine in my sweatpants (there IS a perk to getting old lol!).

Most of the historical section of Boston is very walkable. We walked everywhere and I think the furthest we went was about a 20-minute walk. There are many cobblestone streets though, especially near Faneuil Hall that could be a problem for those with mobility issues. We stopped into the Back Deck restaurant for lunch on a whim since it was near the hotel, and though their menu sounded good, we weren’t really impressed. I went for Tomato Bisque and cornbread, but the cornbread was almost burnt, and their maple honey butter tasted a bit like plastic. Right outside the restaurant though was the Brattle Book Shop – and I love me a good bookstore! Something about the smell of books gets me every time. Brattle is a 3-story bookstore that has been operating since 1825. They have two floors of general used books; one floor of rare, signed, and collectible books; and $1, $3, and $5 sale carts that are outside year-round, weather dependent. At one point they even had a Great Gatsby signed by Fitzgerald dedicated to and annotated by T.S Eliot.

I love street art, and we had heard that Ink Block Park had some good murals, so we wandered over to see what was there.  There were a few good pieces, but there weren’t very many, so I was a little disappointed.  I think if you’re in the area great, but if not, it might not be worth the walk.  However the barista at Cuppacoffee made me a cup of hot chocolate with a cute flower design on it which made it totally worth it!

Next, we wandered over to the harbor and the site of the Boston Tea Party Museum. The museum has replica ships, 3-D reenactments of the Tea Party, the opportunity to take part in a town hall meeting and a film showing the events of the midnight ride. The price of admission is $29.99 which we thought was a bit steep, but even if you don’t enter the museum you can still visit the gift shop and Abigail’s Tea Room.

For dinner we met up with a friend’s daughter, Kendall, for our highly anticipated meal at Stillwater. The restaurant was only two blocks from our hotel and describes itself as:

“Tucked in Downtown Boston, Stillwater is a restaurant that serves comfort food with a twist — it’s a lively space filled with fancified classics and fresh cocktails. At the helm of the kitchen is local gourmet junk food expert and Food Network’s Chopped Gold Medal Games Champion Chef Sarah Wade”. I’m here to tell you – it was pretty darned good! We had a little bit of everything – including:

Biscuits and Butter: Warm homemade crumbly bleu cheese thyme biscuits, whipped chicken drippings butter
Deviled Eggs: The creamiest deviled eggs, smoked paprika, crispy chicken skin, chives
Smoked Pulled Pork Sandwich: House Smoked Pork, Homemade Honey BBQ Sauce, Creamy Slaw and Pickles on Texas Toast.
Ritz Chicken: Ritz cracker crusted fried chicken thighs, whipped potatoes, charred three onion butter, cress
Smoked Pork Mac & Cheese: House smoked pork, the best mac & cheese, buttered ritz cracker crumbs
Jelly Donut Creme Brulee: Classic creme brûlée, strawberry compote, caramelized peanut butter sugar, peanut brittle
Cheese Cake: Ricotta donuts atop Oreo cookie cheesecake

My favorite was the smoked pork Mac & Cheese – sooooo good.

After dinner we waddled (and I mean waddled!) over to the Lyric theater to see a production of Cake written by Bekah Brunstetter. The Lyric is an older, smaller theater located on Clarendon Street.  In Cake, Della is a traditional Southern baker who is asked by her deceased best friend’s daughter to make the cake for her wedding.  The daughter however is marrying another woman which conflicts with Della’s traditional Southern values.  I thought the show was cute and entertaining. The actress who played Della was amazing in the part.  I’m not sure how I felt about the ending as everything wasn’t fully resolved – but I guess that’s real life. 

Saturday morning we woke up to 15 degrees which according to the weather felt like -2!.  We had a food tour scheduled at 1:00 p.m., so we decided to snuggle up for the morning and didn’t even leave the room until about 11:00 a.m.!  Even though we were going on a food tour, our first stop was at the Omni Parker house – where Parker House Rolls and the Boston Crème Pie originated.  The waiters didn’t seem too surprised that we came in wanting only pie, so it must happen often.  It was delicious!!

We chose Nummy food tours because it included a bit of history while visiting stops on Boston’s famous Freedom Trail, and because there were two lobster dishes.  Debbie’s only goal for the trip was to have a delicious lobster roll, which we figured would be pretty easy to do.  Our tour guide Chloe was amazing and had a lot of knowledge about Boston’s history.  As luck would have it, we were the only two signed up for the tour that day, so we got our own private tour.

We started off at the Massachusetts state house and went by the “General Hooker Entrance”.  No this is not where the term hooker was conceived, this is a tribute to Civil War General Joseph Hooker.  However, according to Chloe this part of the trail was very popular with frat boys on her tour and they all had to stop to get selfies lol!

The first food stop on our tour was at Mooo restaurant which is a renowned steak house in Boston.  Today however it was all about the lobster.  We were served an appetizer of Parker House rolls, and the best lobster bisque I have ever tasted.  It was a Maine bisque with Brandy, Cognac and Butter Fleuron.  To. Die. For.  I honestly think this was the best meal I had in Boston – and I thought I didn’t even like Lobster Bisque!

Next, we walked past the Omni Parker house (where we had to sheepishly admit we had already had dessert before the tour) and Chloe filled us in on some of its history.  We found out that in the corner restaurant at the Omni, The Last Resort, JFK proposed to Jackie and Malcolm X worked as a bus boy. 

Around the corner was the Granary Burying ground.  Granary began interring people in 1660, and though there are about 2,345 headstones, it is believed there about 5,000 people buried here.  The gravestones were later moved into actual rows to accommodate pedestrian walkways and lawn mowers, so although there may be a gravestone, someone else might lie underneath.  There are a number of famous Bostonians buried here, including Samuel Adams, John Hancock and Paul Revere.  Across the street from Granary is the Bean Town Pub, whose motto is “The only pub in the world where you can drink a cold Sam Adams across from a cold Sam Adams”!  Interestingly, Chloe told us that the picture on Sam Adams bottles was actually Paul Revere, as the company thought his face was more pleasing – though some argue that is just a bit of folklore. 

Luke’s Lobster was our next food stop, and it first opened its doors in 2009.  Luke’s works directly with fishermen to hand pick the best seafood, bring it straight to their own seafood company and then shipping directly to their shacks. Cutting out the middleman means better tasting lobster, crab and shrimp for you to enjoy and a fairer price for their fishermen.  We had a lobster roll here which Luke’s serves Maine style (On a buttered and toasted split top New England style bun, with a swipe of mayo, and ¼ lb chilled lobster topped with lemon butter and seasoning). A lobster roll with a side and a drink will cost you $20 which is a fantastic price.  Deb was set on a hot lobster roll being her best meal this trip, but I have to admit, this may have been even better than the one we would end up getting on Sunday.    

Next up was the Bell-In-Hand Tavern, American’s oldest tavern with its first pour in 1795.  The tavern became a gathering place for printers and politicians, sailors and students, it quickly became the most famous alehouse in the city.  JFK even used to write here.  We were served a French Turkey sandwich with bacon, brie, lettuce, fig spread and mayo, along with a side of Boston Baked Beans.  I’m not a bean gal, but Deb said they were really good.  I did enjoy the sandwich though.  

We passed Quincy Market and Faneuil Hall on our way to the Boston Public Market knowing we would come back and visit them when the tour was done.  The BPM is a food hall reminiscent of Chelsea Market in New York.  They have 35 artisans and food producers under one roof offering fresh foods, crafts and specialty items.  The first stall we visited was Red Apple Farm, a 100-year old 4th generation family farm where we had some of their hot apple cider donuts and then were off to the Popover lady where I had an Everything Popover which was seasoned simliar to an Everything bagel.  I think of all the things we had on our tour the Popover was my least favorite, it was just kind of plain – not that it was bad, but everything else was SO good.   

Our last stop on the food tour was the Union Oyster House which has the distinction of being the oldest restaurant in America serving food since 1826.  Here we had Indian Pudding which is apparently very big in Boston.  Traditional American Indian Pudding is a baked custard pudding made with cornmeal, milk, eggs, and sweetened with molasses.  It has the texture of grits, and almost tastes like you’re eating a melted gingerbread man.  I’m told many people love it, but for some reason this one was just meh for me.   

Following the tour, we walked across the street to see the Holocaust Survivor Memorial.  Founded by Stephan Ross, a Holocaust survivor, and erected in 1995, the memorial consists of six glass towers that visitors can walk through. Each tower symbolizes a different major extermination camp.  Engraved on the outside walls of each tower are groups of numbers representing the six million Jews murdered in the Holocaust. Inscribed on the inner walls are quotes from survivors of each camp. Underneath the towers, steam rises up through metal grates from a dark floor with twinkling lights on it. Reading the quotes was absolutely heartbreaking.

From here we walked over to the Paul Revere House, where Revere lived when he embarked on his famous ride on April 18, 1775.  There are actually three buildings on the property which serve as a museum of life in the 1700’s.  Admission is $5 for adults, and it is cash only.  Nearby you can find the Skinny house, or the Spite house as some call it.  Located at 44 Hull street it is the narrowest house in Boston.  Spite house is 4 stories high, with the walls being 10.4 feet apart at it’s widest, and 6.2 feet at it’s skinniest.  Legend has it two brothers inherited land from their deceased father. While one brother was away serving in the military, the other built a large home, leaving the soldier only a shred of property that he felt certain was too tiny to build on. When the soldier returned, he found his inheritance depleted and built the narrow house to spite his brother by blocking the sunlight and ruining his view.  While we were there we saw our first flurries of snow start falling.

On our way back to Fanueil Hall and Quincy Market we decided to compare two of the most famous cannolis in the city.  First up was Mike’s Pastry on Hanover Street which is a Boston institution.  Mike’s claims to have created the Cannoli in 1946 and if you go, be prepared to wait a little bit.  Most times there will be dozens of people in line waiting to get one of Mike’s cannolis or other tasty desserts.  We bought a Ricotta canolli for comparison purposes, and a Nutella one just ‘cause it looked amazing!  Our second shop was Bova’s which has been serving baked goods for over 80 years and is open 24 hours serving up Boston’s baked goods around the clock.  Here we got another ricotta cannoli to do our test taste.  Our winner was Mike’s.  The cannolis at Mike’s were larger, and had a sweeter ricotta, though both were pretty darn good!

We were so full after our food tour that we decided to skip dinner and head to our evening’s entertainment, the Blue Man Group.  We weren’t up for Cats again and were a week too early for Mean Girls, so we decided to give it a try.  I mean it has been around forever, so it had to be good right?  I’m not so sure lol! I’m glad we did it because it’s practically an institution, but I almost felt too mature to be there.  I think a rowdy frat would be right at home.  Don’t get me wrong, the percussion and visuals were amazing, but some of the bits went on a little too long. I’d describe it as comedy/mime type show with great techno effects.  At the end they filled the whole room up with tissue paper and I sent my kids a picture saying, “I have no idea what’s happening here” lol! 

The snow started in earnest that night and we ended up getting about 5-inches. so we had a lovely walk in the snow on our way home.  I’m sure for locals it’s a pain in the ass, but for this Florida girl it was a nice change of scenery.  

The following morning, we took an Uber to Cambridge, and had breakfast at Brookline Lunch.  Brookline is a little hole in the wall food joint serving food since 1937, which looks like it hasn’t had a good cleaning in a long while.  The interior is cute however, with a brick wall lined with movie posters and photo memorabilia.  I had a really good Eggs Benedict with a heaping pile of roasted potatoes and vegetables.  The cuisine is Mediterranean-American with large portions and delicious food.  We arrived at about 10, and when we left there was a long outside of folks waiting to get in.   

After we ate, we wandered over to Graffiti Alley to see some street art.  Graffiti Alley is a small covered alley located at 565 Massachusetts Avenue connecting it to City Parking Lot #5.  The entire alley is covered in some great art, but it is very small so unless you’re already in the area I don’t know if I’d make a trip to see it.  (I think we’re spoiled living next to Wynwood and all the Street Art there)

We came back to Boston to walk down Newbury and Boylston streets to window shop at the high-end stores like Burberry, Cartier and Hermes.  Along Boylston street we found the Boston Marathon Memorial.  The monument marks the spot where two pressure cooker bombs detonated in 2013 during the Boston Marathon, killing three people and wounding more than 260 others. It includes three stone pillars, and four bronze and glass spires.  The pillars are made of stone gathered from places around Boston significant to the bombing victims.  One representing 8-year-old Boston resident Martin Richard was taken from Franklin Park in his family’s Dorchester neighborhood. Another that is fused to it honors 23-year-old Boston University graduate student Lingzi Lu and was donated by her school.  And the third pillar for 29-year-old Medford native Krystle Campbell comes from Spectacle Island in Boston Harbor. Its inscription reads: “All we have lost is brightly lost.”

We walked through Boston Common which looked like a Winter Wonderland because of the snow.  One day we’d like to come back and ride the duck boats, but that was not meant to be today because the lake was frozen over.  It did mean however that the ice-skating rinks were open and we watched the brave souls who were whirling around the rink.

In our quest for a hot lobster roll we had a decision to make.  We had heard that a couple of places like Saltie Girl or Row 34 both had excellent rolls, but they were in the neighborhood of $40 each.  I’m sure the experience there was great, but we were looking for something a little cheaper for lunch.  On the same list was James Hook & Co.  JHC is one of the largest seafood wholesale distributors in New England, and this family run business has been serving Boston since 1925.  Located right next to the Boston Tea Party museum, JHC has a small shanty restaurant on the property where they serve the lunch crowd.  The regular lobster roll with mayo is $21.99, while the regular lobster roll with drawn butter is $25.99.  Served hot on a steaming bun piled with lobster – this was definitely the way to go!  A couple of lobster rolls and some clam chowder and Debbie’s hot lobster roll fix was satisfied.  Of COURSE, I got the butter since that’s my favorite part lol!  Deb even got Clam Chowder on the side.  If you’re just looking for a good lobster roll at a great price – this is your place!

Unfortunately after our lobster it was time to go. We took an Uber back to the airport, but we’ll definitely be back to see more of Massachusetts some day.

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