Travel Diary : A Long Fall Weekend in Boston, Massachusetts

Oh, Boston. Your sweet autumn sunshine and breezy, crisp air. Your curves hugged by the sea. Your decidant stories of years past.

Boston was a trip of foodie’s and history buff’s dreams come true. More specifically, my foodie and history buff dreams come true. I have had a Pinterest board dedicated to “Things to do in Boston” since college. It has always seemed to be the perfect collision of all of my favorite things; delicious food, delicious history, and delicious views.

I feel like I start most travel diaries saying “I’ve always wanted to go here” and honestly, I’ve always wanted to go everywhere. I love exploring new places. I love experiencing and trying new things. Most of all, I love being somewhere so rich in history. I love thinking about all of the historical events that have ever happened on the same soil that I am standing on.

Andrew lived in Boston for 3 months during a rotational program for his first job out of college. So we’ve talked about Boston and taking a trip there ever since we first started dating. For his birthday this year, in an attempt to not buy him more stuff and instead gift him experiences & memories, I thought a trip to Boston would be the perfect b-day celebration.

We left for Boston on Thursday afternoon and got to our hotel around 7:30 pm. We stayed at the Seaport Boston Hotel. It was a few blocks from where Andrew had lived so he was very familiar with the area.

A Late Dinner at The Barking Crab

As always, we were starved when we got to the hotel and immediately ventured out to find something for dinner. We were headed to North End and about to cross the bridge from Seaport into Downtown when we walked by The Barking Crab. It was a lot closer than where we were planning on going, was busy, and looked fun. They had open tables on the patio so we were sat immediately. We both ordered lobster rolls and drifted away into sweet, buttery, lobster heaven. Ok, that’s severely dramatic, but they were really freaking good.

Breakfast at Tatte

Early Friday morning, we sprung out of bed. Vacations in new cities are really the only time I ever “spring out of bed”. I am not a morning person at all so you know that I am excited to explore when a city turns me into a morning springer, but I digress. Our hotel was 2 blocks from a Tatte cafe & bakery. There are Tatte’s all over Boston and I highly recommend you pop into one. We split a breakfast bun, Andrew had the Egg in a Hole and I had the Prosciutto & Parmesan Scrambled Egg Plate.

Walk the Freedom Trail

After breakfast, we walked over the bridge into downtown and started to make our way to Boston Common to start walking the Freedom Trail. Walking, you’ll notice, was a recurring theme on this trip. This first day while walking the Freedom Trail we walked over 7 miles. We covered almost every stop on the Trail.

1. Boston Common
2. Massachusetts State House
3. Park Street Church
4. Granary Burying Ground
5. King’s Chapel and King’s Chapel Burying Ground
6. Boston Latin School Site/Statue of Benjamin Franklin
7. Old Corner Bookstore
8. Old South Meeting House
9. Old State House
10. Boston Massacre Site
11. Faneuil Hall
12. Paul Revere House
13. Old North Church
14. Copp’s Hill Burying Ground
15. USS Constitution
16. Bunker Hill Monument

Lunch at Quincy Market

While walking the trail we did get a little distracted at Faneuil Hall and stopped for lunch at Quincy Market. We both got a slice of pizza from Regina’s and it was delicioussss.

Cannoli’s & Sfogliatella from Mike’s Pastry

The last stop on the Freedom Trail that we covered was Paul Revere’s house. It’s in North End and dangerously close to Mike’s Pastry. After a full day of walking, we stopped walking the Freedom Tail there and treated ourselves to some pastries. We each got a cannoli (which we ate on a bench around the corner from Mike’s while waiting for an Uber lol), we also grabbed a Sfogliatella, a slice of Ricotta Pie, a Peanut Butter Fudge Brownie, and an Oreo Cupcake.

Dinner at Legal Seafood Harborside

After a long day of walking, we headed back to our hotel to get ready for a late dinner. We had reservations at Legal Seafood Harborside. Unfortunately, their 2nd floor has not reopened post-pandemic. So our “fancy” dinner for the trip turned into a casual dinner. The food was amazing anyways. I had Lobster Mac n Cheese which was surprisingly served in a lobster 😳 Andrew got Cioppino which is that heavenly bowl of seafood & broth in the photo to the left 😋😋😋

Walk & Shop on Newbury Street

Saturday morning our springing out of bed did not happen as quickly as it had Friday morning. We were exhausted from all the walking the day before, but had a ton of walking planned for Saturday too. We spent the day walking and shopping on Newbury Street. We grabbed brunch at Stephanie’s and then popped into a few stores that we don’t have near us in Charlotte, like Zara and Nordstrom Rack.

Gelato from Amorino

Midway through Newbury Street, we stopped at Amorino’s for gelato. They top their gelato with macarons which is definitely my kind of dessert. They also scoop the gelato into petals around the cone. It’s adorable, but melts quickly so be prepared to eat fast lol.

Lunch at the Gourmet Dumpling House

If you only take one restaurant recommendation from this entire post, let it be The Gourmet Dumpling House in Chinatown. The restaurant is quite small. We went for lunch and it was jam-packed, but we were sat right away. We actually shared a small 4 top with 2 girls. The service is quick and the kitchen is even quicker. We ordered the mini juicy dumplings, the pork buns, and pan-fried dumplings. The dumplings come out scalding hot, I was a bit overzealous and burnt my mouth trying to cram dumplings into my mouth before they cooled.

Sailboat Sunset Cruise on the Boston Harbor

The day after we booked our flights, I started searching for things to do in Boston. I really wanted to take a boat ride of some sort on the Harbor. I ended up finding the Boston Harbor Champagne Sunset Sail from Rowes Wharf. We sailed on the Harbor from 5 pm – 7 pm and watched the sun set behind the city. There were several drink options, including seasonal apple & pumpkin spice ciders. It was really relaxing, romantic, and a ton of fun. We booked our tickets through Get Your Guide and they have an app that sent reminders, stored our tickets, and made it really easy to pull them up for check-in.

Day Trip to Salem

Sunday, we spent the day in Salem. It was only a 30 minute uber to get there. Since we decided so spur of the moment to go we didn’t get to book the more popular tours. We ended up seeing a play at the Old Town Hall and then walked the town ourselves and went to see each building that was used in the filming of Hocus Pocus. Hocus Pocus is my favorite Halloween movie so this was tons of fun. We basically sang “I Put A Spell on You” the whole day. If you are wanting to do your own Hocus Pocus tour like we did, here are all of the stops.

Hocus Pocus Filming Sites in Salem, Massachusetts :

• Salem Commons, 30 Washington Sq. (Where Allison hands Max his number back)
• Old Town Hall, 32 Derby Square (Where Max’s Parents attended a Halloween Party)
• Phillips School, 86 Essex St (Max’s Highschool)
• The Ropes Mansion, 318 Essex St (Allison’s House)
• 4 Ocean Ave (Max & Dani’s House, this is a private residence so please be respectful.)
• Pioneer Village, Forest River Park (Thackery Binx’s House)
• Old Burial Hill, Marblehead MA (Where Max is bullied out of his shoes)

In between all of the spooky site-seeing, we stopped at the Lobster Shanty. This restaurant has been on Diners, Drive-Ins, & Dives twice and there was a line waiting for it to open at noon, so we knew it had to be good. I had another lobster roll. I only give honest food reviews here so I will tell you that it was not my favvvvooritee lobster roll. Mainly because it had celery. I don’t hate celery, but for whatever reason did not love it on my lobster roll. Andrew got the Lobster Casserole which was basically lobster swimming in a dish of butter topped with Ritz Cracker crumbs….I regret to say, he made the better lunch decision and I should have copied him and got the casserole too. 😅😂

After lunch, we stopped at The House of Seven Gables. They were sold out for the tours inside of the house, but we got to explore the other homes on the property and the gardens. My number one tip if you are going to Salem in October, PLAN AHEAD. 😊

Bike Around The City

Monday was our last day in Boston and we tried to get as much out of it as we possibly could. We had breakfast/brunch at Flour Bakery + Cafe and then headed back to the hotel to check out and valet our luggage with the front desk. It was still pretty early and check-out was at noon, but our flight wasn’t until 4:45 pm so we had plenty of time to continue exploring. We walked down to Trader Joe’s and compared Boston’s Trader Joe’s to ours at home. Boston obviously won lol. Next, we strolled along the Smith Family Waterfront.

Eventually, we decided to rent bikes. We biked from Seaport to North End. Biking was a really fun way to see the city. We probably biked for 30 minutes and then grabbed some lunch in North End. I did a really quick google search for “Best Pizza in North End” and Galleria Umberto Rosticceria came up. We grabbed slices of pizza and Arancini and it was the most perfect final meal in Boston.

I hope you guys enjoyed this travel diary! I know it was a long one, but I didn’t want to miss anything. There is SO much to do & see in Boston. I highly recommend a trip in the fall. The weather was absolutely perfect. We are already talking about going back.

If you have any Boston recommendations for our next trip, please comment below! I’d love to hear them!

Love always,