Freedom Trail, Salem Witches & Pirates | Solo Trip to Boston, Massachusetts
Boston Skyline
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Want more Boston? Follow along with the vlog of my weekend long adventure in Boston, Massachusetts .
I had the most amazing solo weekend in Boston and Salem, and I'm still buzzing from it! There's something so freeing about exploring a new city on your own timeline. There is no compromising on where to eat lunch or how long to spend at each stop. I packed so much into just a few days, from walking the historic Freedom Trail to diving deep into Salem's witchy vibes. Honestly, this trip reminded me why I love solo travel so much. you end up having conversations and experiences you never would have otherwise.
Boston State House
The Freedom Trail
My adventure began in Boston, a city steeped in American history. The Freedom Trail is Boston's coolest history lesson disguised as a fun walk through the city. It's a 2.5-mile red line (made of bricks and paint) that you can follow with your eyes down to the ground as it connects 16 amazing historical spots from the colonial days and Revolutionary War. The trail kicks off at Boston Common and winds its way through downtown and over to Charlestown, hitting all the must-see places like where the Boston Tea Party was planned, Paul Revere's house, and the church where those famous lanterns were hung.
I joined a guided tour, and our knowledgeable guide painted vivid pictures of the past as we wandered through iconic sites like the Massachusetts State House, Paul Revere’s House, and Old North Church. Each stop on the trail told a story, from revolutionary battles to the birth of a nation, and being solo allowed me to fully immerse myself in the narratives without distractions.
As a solo traveler, you have the luxury of stopping for photos whenever inspiration strikes, and the Freedom Trail is packed with Instagram-worthy moments. The golden dome of the Massachusetts State House is a must-capture shot. It's especially stunning during golden hour when the dome seems to glow against the sky. Head to the cobblestone streets around Paul Revere's House for those quintessential Boston vibes; the narrow, lamp-lit Revere Street creates the perfect historical backdrop.
Tip: Wear comfortable shoes! Boston is definitely walkable, but those cobblestone streets in some areas can be tough on your feet after a few hours. The Freedom Trail covers so many famous spots, and you'll want to explore every corner.
Paul Revere Statue
Transportation: Boston's subway system (called the MBTA or "the T") is pretty great for getting around. I bought a 7-day LinkPass for $22.50, and it was totally worth it since I was hopping on and off buses and trains constantly. The app is super helpful for real-time updates. But you don’t necessarily have to get a pass. Boston has a “tap to ride” system as well, so you can just tap your credit card or phone’s mobile pay for each ride.
Boston Public Library
While not technically on the Freedom Trail, the Boston Public Library is an absolute gem that deserves a spot on any Boston itinerary. This stunning Renaissance Revival building in Copley Square is like stepping into a palace. The famous Bates Hall reading room with its barrel-vaulted ceiling that'll make you feel like you're in a Harry Potter movie. Even if you're not much of a library person, the courtyard is perfect for a peaceful break from sightseeing, and it's completely free to explore.
Boston Skyline from Castle Island
Castle Island
I lucked out with my Airbnb choice in South Boston (Southie). This neighborhood turned out to be the perfect home base for a solo traveler exploring Boston. Southie has this amazing blend of authentic local charm and convenience that you just can't get in the touristy downtown areas. It's super walkable and safe, which is exactly what you want when you're exploring on your own. Plus, you're just a short bus ride to all the major attractions, but far enough away that you can escape the crowds and tourist prices when you want to grab dinner or a coffee.
A short walk from my Airbnb was the picturesque Castle Island. The island, with its historic fortifications and stunning views of Boston Harbor, is the perfect spot for a solo traveler seeking a bit of tranquility. I strolled along the waterfront paths, enjoyed the fresh sea breeze, and marveled at the historical Fort Independence. It was a peaceful escape from the city’s hustle, and the views were nothing short of spectacular.
Tip: Bring a book or a journal. The peaceful surroundings provide a great opportunity for some reflective downtime.
The Social Aspect
This was probably my biggest worry before going: would I feel lonely? I was so busy I barely had time to feel lonely, but here are some ways I ended up connecting with people:
Join group tours – Even though you're traveling solo, group walking tours are a great way to meet other travelers. I ended up making friends with a couple I met on my Freedom Trail tour.
Sit at the bar when dining alone – Bartenders in Boston are genuinely friendly and often became my impromptu city guides. Plus, you might end up chatting with other solo diners.
Stay in social accommodations – If you're open to hostels or boutique hotels with common areas, these can be great for meeting people.
The Witch House
Salem, Massachusetts
A short train ride from Boston took me to Salem, a town famously associated with the 1692 witch trials. Salem’s rich history is woven into its modern fabric, with museums, historic homes, and charming streets that seem to echo the past. The Salem Witch Museum and The Witch House were particularly intriguing, offering insights into the trials and the town’s colonial past.
Salem also has a quirky, eclectic vibe. I enjoyed wandering through its shops, and soaking up the unique atmosphere. Whether you’re interested in the macabre or simply want to enjoy the town’s charming ambiance, Salem is a fascinating destination that offers something for everyone.
Pirate Museum
Located in the heart of this historic city, the Pirate Museum offers a captivating journey through the true tale of “Black Sam” Bellamy and his capture of the slave ship Whydah. Explore authentic artifacts, interactive exhibits, and the chance to touch Real Pirate Treasure. This museum is fun for the whole family!
Tip: Map out your top attractions to visit ahead of time. Salem has so many historical sites. Some are within walking distance and others require a car or bus ride.
Final Thoughs
I was nervous about doing a big city trip alone, but Boston turned out to be the perfect place to build my confidence. It's manageable in size, the people are generally helpful (despite the reputation for being cold, but I found the opposite!), and there's so much to see that you're never bored.
The key is to over-prepare just a little bit , know your route, have backup plans, and trust yourself. You've got this! Some of my best memories from this trip happened because I was alone and open to unexpected experiences.
