5 days in May

Question

We are two Irish women in our 50’s arriving in Boston on 5th May at the end of a 3 week driving holiday around New England. We are staying in Chelsea - and have been planning to keep the car ( parking included with the place). Looking for must see’s as it’s our first time. We will drive out to Harvard one afternoon, and we would love to see a game, doesn’t need to be in a big huge stadium - we’re not big sports fans - just want to experience a game somewhere, for the experience. Fenway park and the big stadiums look like it’s gonna be $400+ each - and that’s too expensive for what we want - so any suggestions for regional games would be appreciated.

We have a hop on hop off tour booked for our first day - if there’s any suggestions for things not to be missed - I’d love to hear them. Thank you!

Answer

Welcome to Boston! It sounds like you have an exciting trip ahead, and you’re already planning some great activities. Given that you’ll be in town for 5 days and staying in Chelsea, it’s great that you have access to parking, as Boston can be a bit tricky for driving and parking in the downtown area. Let me give you some suggestions on must-see attractions, as well as a few ideas for regional games that might suit your interests. I’ll also touch on some things to consider during your hop-on, hop-off tour and beyond.

Must-See Attractions in Boston

Since this is your first time in Boston, I’d recommend focusing on the highlights of the city, as well as some local gems:

Freedom Trail: This historic 2.5-mile walk takes you through 16 of Boston’s most significant historical sites, including the Massachusetts State House, Paul Revere’s House, and the Old North Church. It's a great way to immerse yourself in Boston’s history, and your hop-on, hop-off tour should cover part of this route.
Boston Common and Public Garden: These iconic parks are the perfect place to relax, enjoy nature, and take a stroll. You can also take a Swan Boat ride in the Public Garden, a popular and charming experience.
Harvard University: As you plan to visit, be sure to explore the Harvard campus in Cambridge, just a short drive from Boston. You can also wander around Harvard Square, which has great shops and cafes.
New England Aquarium: Located on the waterfront, the aquarium is home to an impressive array of marine life, including penguins, sea turtles, and the famous giant ocean tank. If you enjoy nature, this is a must-see!
Isabella Stewart Gardner Museum: If you appreciate art, this museum is a hidden gem. It features an incredible collection of European, Asian, and American art housed in a beautiful Venetian-style palace. The courtyard is absolutely stunning!
North End (Italian District): Take a stroll through Boston’s Little Italy. You can enjoy authentic Italian pastries from places like Mike’s Pastry (famous for its cannoli) or explore the historical sites in this neighborhood.
Beacon Hill: Another charming neighborhood to explore with its cobblestone streets, historic houses, and quaint shops. Don’t miss Acorn Street, often referred to as one of the most photographed streets in America!

Suggestions for a Regional Game Experience

Since you’re not looking for a major stadium experience, there are still plenty of ways to enjoy a live sports event in Boston without the hefty price tag:

Boston Red Sox at Fenway Park: Although you mentioned the high prices for tickets, Fenway Park does have some more affordable options, especially for weekday games or seats in the upper deck. If you’re flexible on seating, it might be worth checking out tickets for a regular season game.
Minor League Baseball: Consider checking out a game with the Worcester Red Sox (about an hour's drive from Boston), the Triple-A affiliate of the Red Sox. Their stadium, Polar Park, is new and offers a more affordable experience compared to Fenway. Tickets are generally much cheaper, and you can still enjoy a great atmosphere and some quality baseball.
Boston College Eagles: If you’re more interested in college sports, consider attending a Boston College baseball or lacrosse game. These events are often less expensive and are a fun way to experience a local sporting culture in a more intimate setting.
Boston Cannons (Lacrosse): If you’re open to something a little different, the Boston Cannons (professional lacrosse) play during the summer months. Their games are fun, fast-paced, and affordable compared to major league events.

Suggestions for Things Not to Miss During Your Hop-on, Hop-off Tour

With the hop-on, hop-off tour you’ve already booked, you’ll be able to get a good overview of the city. Here are a few stops you definitely don’t want to miss:

Boston Common and Public Garden: These two parks are central to Boston’s history and offer beautiful, scenic views. If you’re into walking, this is a great spot to get off and explore the area.
Quincy Market and Faneuil Hall: A historic market building and meeting hall, this area is a bustling spot for shopping, food, and street performances. It’s a great place to experience the energy of Boston and grab a bite to eat.
Boston Tea Party Ships and Museum: A must-see for history buffs! The museum gives a fun, interactive experience of the Boston Tea Party event that helped spark the American Revolution.
Seaport District: A newer area with great waterfront views, modern restaurants, and art galleries. This area is up-and-coming and worth a visit if you have time.
MIT Museum: If you have an interest in science and technology, make sure to explore the MIT Museum while you’re in Cambridge. It’s small but packed with interesting exhibits!

Final Thoughts

You’ve got a wonderful itinerary in the making, with a great mix of history, culture, and relaxation. Since you’re staying in Chelsea, it’ll be easy for you to drive into Boston, but be mindful that traffic can be busy during the day, especially on weekdays. Using public transportation (like the T) for some parts of your trip can also be a convenient option. Enjoy your time in Boston, and I’m sure you’ll find plenty of hidden gems during your 5-day stay!

Safe travels, and I hope you have an amazing time exploring Boston!

5 days in May

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