Labor Day Weekend, the last hoorah of summer. Last long weekend to soak up the sun, enjoy the waves at the beach, and get fresh tan lines to hold on to when the cool breeze of Fall rolls in. With summer looking a little different this year and constantly spending my time outside lounging in the summer sun, I decided to stray from the typical beach party and barbecues that accompany the holiday weekend. Instead, my friends and I drove up to Massachusetts and spent a wonderful few days in Boston with an added day trip to Cape Cod.
Before I dive into the delicious food we drooled over, shops where we (almost) dropped pretty pennies in, and historical “must see” sights, I’m going to jump right to the point. Boston is where it’s at, folks. The city is absolutely beautiful with its smaller size yet big city feel, its modern and well kept neighborhoods and grounds, and a variety of districts that switch up the vibe. I’m not just highly recommending this city to you, but I am confidently telling you that I will pack my bags and move there one day - that’s how much I loved it. Hopefully that statement hooked you on this article because lucky for you, I’ve got a ton to share! Here’s our itinerary for three days in Boston and one to Cape Cod:
Day 1: Fort Point & North End
After half our day spent in the car traveling to Boston, we decided to take it easy in the afternoon and save the major sightseeing for a full day. Nonetheless, we still walked about 7 miles exploring the neighborhood where our hotel was located, as well as, the district we were in for dinner.
We walked from Downtown where our hotel was, through the Financial District, and across the Summer Street Bridge to Fort Point for drinks and apps as a welcome to the city. We dined at Lolita Fort Point which rests alongside the channel of water on a beautiful outdoor patio for fresh guacamole and chips and strawberry basil margaritas (they were absolutely delish). After lunch, we headed across the Congress Street Bridge and stopped at the Boston Tea Party Ships & Museum. Although the museum was closed due to covid (as you will see with some other sights later on), it was still interesting to be able to see where such a big event in history took place.
The rest of our afternoon was spent walking through the Financial District to the waterfront and alongside the harbor until we reached the North End where we dined for dinner and dessert. Sam, Quinn, and I are suckers for nothing less than exceptional Italian food, so you know we had to stop by Little Italy and try some of the best dishes and, of course, wine. Bricco Ristorante and Enoteca was honestly fantastic all around. From the service to the entrees, we enjoyed every aspect of our meal. I ordered the Scialatielli Amatriciana, which was the perfect amount of fresh pasta and spicy tomato sauce topped with pancetta. Are you craving a bowl yourself yet? The three of us, being wine connoisseurs and all, carefully selected a smooth Tuscan wine called “Tre” for its combination of reds. A blend of Sangiovese, Cabernet Sauvignon, and Merlot, the Tre was a perfect pairing with our meal and one I will definitely be purchasing for my next wine night with the ladies.
Following dinner, we walked down Hanover Street which lies in the heart of Little Italy to find the one and only, Mike’s Pastry shop. You could smell the freshly baked cannolis and cookies from this small bake shop before the doors even opened. From a wide variety of speciality cannolis, cookies, pastries, and desserts to choose from, Mike’s classic Chocolate Chip Cannoli was calling my name. One word: mouthwatering. That’s all I have to say. Keep up the great work, Mike’s. You’ve got the art of pastries absolutely mastered.
Day 2: Downtown & Seaport
We walked about 10 miles around Downtown Boston and to and from Seaport on our first full day in the city. If you couldn’t tell, we like to keep ourselves busy when we travel and we try to see everything we can. But what’s also important to mention is how walkable the city of Boston actually is. We had a very centrally located hotel which helped out a lot in terms of traveling to and from places ,and we were able to walk from Downtown to Seaport, Back Bay, and North End with no problems (even in platform sandals). Take a look at maps of Boston here to best plan your trip based off the activities and sights you want to include!
We started the day with freshly baked croissants and lattes from Tatte Bakery & Cafe located across from Boston Commons, which we soon after took a stroll through. Heading toward the North End and out of the park, we walked along the Freedom Trail. This trail is about 2.5 miles in length and highlights many historical aspects of the city. We were able to do a self-guided tour in the morning and before lunch we were able to see the following sights: the Massachusetts State House, Park Street Church, Granary Burying Ground, King’s Chapel, Benjamin Franklin Statue, Old City Hall, Old South Meeting House, The Site of the Boston Massacre, and the Old State House. While some tours inside of the museums and buildings were closed off due to current pandemic regulations, we were able to stand in a moment of history and read upon each sight. Also, I recommend stopping by the Brattle Book Shop, which is also in this area, to scope out the first editions, collectibles, and classic reads. This store is also super cute because it has an outdoor library, which is perfect for taking an Instagrammable photo.
At the end of the Freedom Trail, we found ourselves at Faneuil Hall Marketplace, commonly known as Quincy Market. This area is definitely a must-see as it seemed to always be buzzing with locals and tourists, being that it is one of the most popular places to visit in the city. Composed of the three markets North, South and Quincy, the Faneuil Hall Marketplace has tons to see. The North and South Markets are primarily for shopping and have a row of retail shops on each side of the visitor as they stroll through the market. On the contrary, the Quincy Market is the spot to be for food. Walking through the hall, there are food vendors aligning the sides of the market with just about every cuisine you can imagine. We tried the New England clam chowder soup from Boston Chowda Co. and it was phenomenal. After a late lunch at the market, we headed back to the hotel to get glammed up for our night escapade to Seaport.
Being that our first full day also aligned with Sam’s birthday, we decided there was no better way to celebrate being back together than a good ol’ bar crawl. Due to covid restrictions in the state of MA, guests are required to have food with drink purchases which soon turned our bar crawl into one with many appetizers as well. We began the night at Drink which is an underground bar in Seaport that specializes in crafting concoctions for its guests based on what alcohol and cocktails they enjoy. Being a creature of habit, I loyally devoted myself to the timeless mojito (which was fantastic, by the way). Sam and Quinn however, shared their favorite drinks and spirits with our waitress and she surprised them with hand-crafted bevs. After leaving Drink, we headed towards the waterfront and drank massive margaritas at Temazcal Cantina. In full seriousness, the margarita glass was as big as my head. But that didn’t stop us from enjoying a few because they were de-lic-ous. Our drinks paired exceptionally well with chips and fresh guac, salsa, and black bean spread as well. A couple of margaritas later, we decided to end the night with a rooftop view of the Boston Harbor at Legal Harborside. A beautiful restaurant to watch the sunset over the water and East Boston, Legal Harborside made for a picturesque view and a great way to end the night of celebrations.
Day 3: Cape Cod
Taking a day trip to Cape Cod from Boston is a simple 1 hour drive, making it completely doable for even a half day of activities. But not on LDW, of course, with heavy traffic from beachgoers and holiday getaway cars of families ready to enjoy a day on the water. Nonetheless, even with the delays we encountered, we still had time for a packed day on the Cape.
Our first stop was in Chatham to see our great friend who is a local, and not to mention a fantastic tour guide, Sarah Simpson. From the small town of Chatham, we made our way up the arm of the peninsula and drove through a handful of beachy towns such as Orleans, Eastham, and Wellfleet until we arrived in Provincetown. P-town is at the tip of the Cape facing inward toward the Cape Cod Bay with beautiful views of marshes and calm waters. This town is known for being a big art scene with tons of galleries to stroll into, as well as, a foodie haven with fresh lobster rolls and mouth watering sweet shops. Provincetown’s Commercial Street is where you can find the liveliness of locals and tourists, as this is where all the restaurants and shops are located. We strolled up and down this path throughout the afternoon, hopping in and out of apparel and accessories stores, jewelry shops, and vintage boutiques until we found perfect souvenirs to bring back home with us. In the midst of exploring, we had to stop and try a New England lobster roll because you’re crazy if you don’t have one when in Massachusetts. Sorry, I don’t make the rules! Upon getting takeout at The Lobster Pot of lobster rolls and potato salad, we sat on a bench overlooking the Provincetown Harbor and devoured a (surprise) very delicious lawbsta roll.
On the way out of P-town, Sarah took us to the Provincetown Causeway at golden hour. Not only did the time of day make the scene look handpicked from a movie, but the seascape itself was a dream. The Causeway is essentially a jetty that runs from the very end of Commercial Street across the harbor to Wood End and the Long Point Light House at the very tip of the Cape. This is a beautiful walk literally across water with views of the marsh to your right, P-town to your left, and the lighthouse ahead.
Last, as a farewell tour of Cape Cod, Sarah drove us back down the peninsula to Thumpertown Beach in Eastham for a fiery sunset. Any travel blog and local will eagerly share with you that sunsets on the Cape are something special, and after viewing one myself I wholeheartedly agree. Chasing the sun before it set over the bay’s horizon, we quickly ran down to the water to photograph the scene mentally and physically because that’s a memory you never want to forget. A painted sky above, hanging out with great company, and wading in the shallow waters after a hot summer day - you can picture the scene right now! With sailboats sitting in the sand banks of low tide just in line with the sun setting, the nautical silhouettes we photographed were that of a dream. Highly recommend making time for the sunset anywhere looking over the Cape Cod Bay when you visit. I can see why Sarah ends most of her days with nature’s beautiful watercolor paintings on these shores. Before heading back to the city, we treated ourselves to fresh homemade ice cream at the Ice Cream Cafe in Orleans which was the sweet cherry on top of an amazing day.
One of the many beach views on Cape Cod, featuring me and Sarah.
Day 4: Back Bay
On our final day in Boston, we had nothing shy of a jam packed schedule as today we were exploring the city’s Back Bay area. First stop was the Boston Public Garden which we walked through so we could take the scenic route to Back Bay, and y’all was it beautiful. Well maintained grounds, trees hanging over the center pond, and views of the buildings peaking through the colored leaves - this is definitely a place I would sit with a good cup of coffee and an even better book for hours on end. After admiring the natural beauty of the garden, we switched gears real quick to gawk at the materialistic charm of Newbury Street, as well as, the character of its architecture. A shopaholic’s dream, Newbury St. is known for its high end retail shops and luxury goods. Burberry, Ralph Lauren, Chanel, Cartier, Bulgari, Longchamp Paris, Valentino, Ted Baker London. Similar to the 5th Ave shopping in NYC, you name the store and Newbury probably has one waiting for you. Tough to resist swiping your credit card and maxing it out on this street, no doubt, but we remained strong and powered through. The one purchase we did make here was for food, absolutely no surprise there if you know us. With a very high recommendation from a local (shoutout Meghan Krikorian, thank you hun), we brunched at Stephanies on Newbury St. Fantastic service, amazing breakfast food, fresh coffee, and all the energy we needed for our busy day ahead.
Up next, we walked through the Back Bay district to find the adorable Copley Square which sits right across from the Boston Public Library. Copley Square is a great place to take a seat and take in the city, especially after all the walking you’ll do. Although the Boston Public Library was closed due to covid and we were not allowed to enter, this is one of many popular tourist sights as the interior is elegantly designed. Definitely wish we could’ve seen it in person, but maybe you’ll have better luck! Further down the street from those sights is the Prudential Center Mall, which you know we had to stop into. Tons of great stores to check out here as well if you’re in the mood to burn a hole in your pocket and spend some cash. Although strolling through this neighborhood and taking it easy was all we had planned for this day, our schedule took a large turn when we walked down to Fenway Park.
If you’re not planning on visiting Fenway Park during your time in Boston, rearrange your schedule like we did. Fenway is not just a normal stadium, it's actually the oldest MLB stadium still in use today. The stadium has so much character because of its age and it is one of two MLB stadiums that continues to use a manually operated scoreboard. Talk about a blast from the past, am I right? When we arrived at Fenway, we seriously only planned on snapping a few photos for our brothers and fathers who are baseball fanatics. However, that plan took a full 180 when we heard the roar of the stadium’s audio track playing cheering vocals. We had ourselves a game to watch! Although the stadium isn’t allowing fans to enter due to health protocols, we were lucky enough to have watched the game from start to end on television at bars on the same street. First, we slid into a table and grabbed a beer at Max & Leo’s Pizza to get in the baseball spirit. And to get in the Boston spirit, I had a Samuel Adams Summer Ale (light beer, pairs well with Sox games). After, we headed over to the Bleacher Bar to finish watching the game from an even better viewpoint. This bar is located behind center field of Fenway and has a huge window opening out to the stadium for those dining to see the game. It was such a unique concept, one I wish my home team sure had in their stadium (hi Yankees), to be so close to the players on the field with only a wall in between. Not to mention, this is the absolute closest thing we’re going to get when it comes to watching live sports in an arena. All in all, it was a very fun way to spend our last day in the city.
As a farewell to Boston, we were sure to buy some merch and hold onto our little pieces of the city until our next visit, whenever that may be. Boston is something special and I am so thankful to have had the opportunity to explore it with my best friends, even in such different times for tourism like the ones we face this year. As one of my beloved authors Colleen Hoover once wrote in a favorite book of mine, “everything is better in Boston” - and I agree.
View facing away from the Boston Harbor in the Christopher Columbus Waterfront Park, featuring me.