Have you been wanting to take a solo trip, but across the world seems too intimidating? Boston in the fall may be the perfect destination to build your confidence. Last fall I got to experience the beauty of the city with my best friend, but I regularly dream about taking a red-eye and going for a solo weekend getaway.
After experiencing Boston in the fall, I feel like it is the perfect city to dip your toes into solo travel. The fall brings the crisp air and beauty, and the history and coffee is enough to get you dreaming of returning for years to come. For a new solo traveler, it has a perfect balance of being within the United States still, but allows for an adventure and a learning curve. Boston was my favorite place to learn how to use public transportation such as the subway, and it helped me confidently navigate countries like Japan later on.
If you are like me and have never ridden a subway before, it can definitely be overwhelming. Google Maps was a life saver, because I could plan my routes ahead of time, and follow along as we approached each stop towards the final destination. But a safety reminder, don’t keep your eyes glued to your phone, don’t wear any earphones, and always be aware of your surroundings.
While you won’t get to experience the entire city in three to four nights, I highly recommend on the first day renting a bike and doing the Freedom Trail, it will show you so much of the city and the beauty of it. Take a break at the Union Oyster House, for my second favorite oysters I’ve ever had, and a delicious Old Fashioned. And finish the tour with dinner at Ciao Roma. If you want to feel like you have been transported to Italy, this is the perfect environment and I highly recommend the espresso martini.
For your second day, if you desire, take a short but beautiful ferry ride over to Salem and explore, especially in the fall. For me, we either needed more time in Salem, or to have planned it out better. Most of the tours aren’t on the cheap side, and the timing of them can cut into precious time. But if you can stop by Ye Olde Pepper Candy for some amazing treats, from America’s Oldest Candy store.
Once you get back to the city, and if you are anything like me and like history and spooky things (especially for a fall trip), find a local Ghost Tour. This has become my favorite travel hack in every city I visit, especially solo. These tours make it easy to meet other solo travelers, learn the history of the city, and just have an overall good time.
Boston may be one of my favorite cities I have visited, and I think it is extremely approachable for someone wanting to build confidence as a solo traveler. Is Boston somewhere you would like to explore in the future? If not, where is a dream solo destination in the United States?
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