A Boston Itinerary
If you are planning a trip to Boston, follow our Boston itinerary below
Boston MA has skyscrapers that you'd expect from an American city, a picture-perfect harbour, and so many amazing places to shop and eat. Boston MA is a great place to explore for a day. There is a definite buzz walking around the city, so get yourself ready to go and experience it!
If you are planning to solo travel Boston whether that’s for a weekend solo trip to Boston or just a day, discover our Boston itinerary to make the most of your solo Boston trip.
N.b. By booking through this page for your Boston solo travel, you are helping to improve the lives of vulnerable girls about the globe. Thanks for helping.
Okay, so whilst it is a bit cliché for America but on your Boston solo trip, you have to try the bagels served at the South End Buttery. They have so many different breakfast choices and amazing coffee; the perfect way to fuel yourself for a day of exploring.
From the South End you can follow Tremont Street which will lead you directly to Boston Common – the first-ever public park in the USA. If you walk around the park you will get a great view of the city’s financial district and Massachusetts State House. * Check rates & availability: Boston Freedom Trail Walking Tour
Parallel to Boston Common is Washington Street, which is the best place for some retail therapy, especially at the giant Macy’s, and is the ideal location to grab a mid-morning coffee. Or take a short walking tour along Movie Mile to see this area with others. * Check rates & availability: Boston walking tour
To continue your solo travel to Boston, from Washington Street you can walk towards the Government Center, which is home to the Faneuil Hall Marketplace, the best place to buy your Boston jumpers and t-shirts! Boston Public Market is about a five-minute walk away from Faneuil Hall, and has all kinds of options for lunch, from falafels to pizza to bagels (again!).
It is also a great place to sample some local beers and ales, and immerse yourself in the culture, but make sure you have your ID handy! You can explore historical Boston on a walking tour whilst seeing the Public Market and the Old North Church and enjoying donuts whilst discovering local history. * Check rates for Boston Underground Donut Tour
One of the solo things to do in Boston is to wander around the harbour. It is breathtaking – literally, if it’s as windy as it was when I visited. From the Wharf, head towards Back Bay and aim for the Prudential Building; it’s the second tallest building in Boston so is pretty hard to miss.
If you prefer to learn about the USA's revolutionary history on a guided tour, you can combine Back Bay with the Freedom Trail on a walking tour. * Check rates & availability: 2 Hour Back Bay Tour
If you do decide to include the tower, you could spend a day in the Prudential Tower itself, as there are so many shops (including a massive Sephora!), restaurants, and bars. But the real gem is on the 50th floor of the Pru: the Skywalk Observatory.
This is the highest observation deck in New England, and gives you a panoramic view of Boston and surrounding areas. It really is the best way to experience the city and one of the best things to do in Boston by yourself, as you can see Fenway Park and even Harvard University, which you otherwise might not be able to see in just one day. You can even do a guided tour of this famous university with one of the students! (check availability here). Discover what else Boston is known for.
Fenway Park in Boston, the iconic home of the Red Sox, is a must-visit spot for sports fans. It's not just about baseball; it's about soaking up the history and vibes. You can't miss the famous Green Monster! Take a tour and dive into the stories of legendary players, feel the excitement of game days, and bask in the park's timeless charm. Whether you're a hardcore fan or just curious, Fenway Park is a place where sports magic happens. * Check rates and availability: Boston Fenway Park
Where To Dine
If you are feeling peckish, check out EATALY which is located in the Prudential Center. As you may have guessed, it specialises in all things Italian, including absolutely amazing freshly-made pizza – totally worth it! It also has four restaurants to choose from so will suit any budget, and has loads of cool things to buy as souvenirs or presents.
Choosing a place for dinner is going to be difficult, as wherever you are in Boston there are great options for food. I would recommend heading back towards the North End, which you can do via cab or subway. The North End is known for its Italian-American population, so if a big bowl of pasta is what you fancy after a long day of exploring, this is the place to be.
Or take a sunset cruise along Boston Harbour to see the city come to life when the sun sets. From Rowes Wharf you'll get to see the city's famous landmarks as well as the historic USS Constitution. * Check rates and availability: Harbour cruise
From The North End you are about a mile away from South Station, which is Boston’s busiest transport hub and will get you to the airport or help you on your way to your next destination.
If you do have longer in the USA, you can catch a coach to so many other places from South Station for a very reasonable price, so just check out the other states you plan to visit before you go! Getting to New York only takes about 4 hours on the coach, so if you fancy it check out this guide for free things to do in a day!
Get Your Guide – If you're unsure of things to do in Boston solo, Get Your Guide helps you to find top-rated day tours and activities in Boston. Choose from the original and world-famous Boston duck tour, a ghost and gravestones tour, or the Boston sightseeing trolley tour.
There are several to choose from including a whale-watching catamaran cruise off the coast of Boston, and it’s really simple to use. Just check the reviews, price and availability then book online. Read my Get Your Guide review or click the link below for all their tours.* Check all Get Your Guide tours, prices and availability
Viator – Viator are similar to Get Your Guide. They are an American company and a tour platform with more than 345,000 tours and worldwide activities. They also offer a food and history North End Freedom Trail walking tour, and a Martha’s Vineyard day trip with a ferry and island tour option. Read my Viator review or click the link for all their tours. * Check all Viator tours, prices and availability
Where To Stay in Boston
From installing low-flow toilets, showerheads, and aerators, to giving left-over food to employees and upgrading their recycling practices, it’s no wonder that the Lenox Hotel was designated by Condé Nast as one of America’s “greenest” luxury hotels. They are very transparent when it comes to their green and sustainable practices. * Check rates and availability for Lenox Hotel
Stay in this stylish 4-star hotel which was once a former police headquarters. There's a fitness centre to work out, a lobby lounge to work in, and a bar to relax and socialise in. Plus the beds are super comfy. You're just a short walk away from the Boston Common and Copley Square and just 5 minutes away from the Boston Bay train station too. * Check rates and availability for Hotel AKA Back Bay
Close to Boston Commons Park and a Subway station, this 4-star eco hotel does not only serve stunning views but also social commitments. It's also a 15 minute walk to shops and restaurants and close to the Granary Burial Grounds. There's a minibar in your room, a cocktail bar and a gym to work off those calories. Plus you can bring your pet too! * Check rates and availability: Hotel AKA Boston Common
Social Impact Programs
EatOkra – Brooklyn-based startup EatOkra is a mobile app for finding black-owned restaurants. The app contains information and ratings for local black-owned restaurants in Boston and elsewhere in the US. It is a great way to discover new places to eat and support local black-owned businesses.
Books to read before travelling to Boston:
Only In Boston: A Guide to Unique Locations, Hidden Corners and Unusual Objects by Duncan J. D. Smith.
Boston Food Crawls: Touring the Neighborhoods One Bite & Libation at a Time by J. Q. Louise.