Boston & Cape Cod and elsewhere trip in June

Question

I’m a 29 year old solo female planning to visit Massachusetts at the beginning of June and would love some advise on how long to spend there and things to do:

- I have been to Boston before but for work so I didn’t get to fully visit many things. How long do you think is ideal to stay? I like to be quite busy so I’m used to doing lots in one day

- I’d love to visit Cape Cod, again how long would you recommend for visiting?

- Is there anywhere else nearby to Boston and Cape Cod that you think would be worth adding to the trip? I’m not set on how many days I’ll be travelling in total and don’t want to miss anything!

Any advice is welcome, thanks in advance!

Answer

It sounds like a fantastic trip! Here’s how I would suggest planning your time in Massachusetts:

For Boston, since you’ve already been there for work, I would recommend spending 3 to 4 days. Boston is rich in history, culture, and great neighborhoods. Here are some things you can do in a busy itinerary:

Walk the Freedom Trail to see historic sites like the Massachusetts State House, Paul Revere's House, and Boston Common.
Visit the Museum of Fine Arts and the Isabella Stewart Gardner Museum if you enjoy art.
Explore neighborhoods like the North End (great food and history) and Back Bay for shopping.
Check out Fenway Park, even if you’re not a baseball fan, it’s a historic site.
Take a Harbor Cruise or visit the Boston Tea Party Ships & Museum for something more interactive.

If you’re someone who enjoys staying busy, you could fill a 4-day trip in Boston without issue. There’s a lot to see and do!

For Cape Cod, I recommend spending 2 to 3 days. The Cape offers a relaxing contrast to the bustle of Boston, with scenic beaches, quaint towns, and plenty of outdoor activities. Here's what you can do there:

Visit Provincetown at the tip of the Cape for unique shops, restaurants, and the stunning Pilgrim Monument.
Explore the Cape Cod National Seashore with beautiful coastal trails and lighthouses.
Visit Chatham, a charming town with great shopping and a lovely waterfront.
If you enjoy nature, try a whale watching tour in the waters off Provincetown.

You could base yourself in one town like Hyannis or Chatham and take day trips around the Cape. While the Cape has a slower pace, you can still stay quite busy with nature hikes and beach time, especially if you're into outdoor activities.

If you have a bit more time and want to explore beyond Boston and Cape Cod, there are a few great options:

Salem: Known for its witch trials history, Salem offers a mix of history, museums, and spooky fun. You can easily do a day trip from Boston.
Gloucester & Rockport: These picturesque fishing towns along the North Shore are perfect if you want a more laid-back experience with beautiful coastal views.
The Berkshires: About 2 hours west of Boston, the Berkshires offer hiking, art galleries, and outdoor music festivals. It’s a perfect area for a peaceful retreat in nature.

Since you're planning to travel solo and stay busy, a 7-10 day trip would give you time to explore Boston, the Cape, and a nearby destination. It would also provide enough time for spontaneous adventures without feeling rushed. Overall, I’d recommend planning for at least 7 days, especially if you're not sure whether to add another destination.

Have a fantastic trip, and enjoy your time in Massachusetts!