Boston Day Trips: Three Scenic Spots to Explore Beyond Beantown

There is plenty to do within the city limits of Boston, from sampling the city’s best eats to strolling the Freedom Trail. But you’ll find even more family fun when you venture out of the city on one of these three-day trips from Boston.

Boston is one of my favorite cities to explore. From the following my nose to the best seafood around the city to taking in a stand-up show or sampling the latest offerings from a great craft brewery, I’ve found seemingly endless things to do.

But visiting Boston and staying within the city limits is bit like ordering cannoli and just eating the creamy inside while eschewing the crispy shell. Part of the beauty of Boston is the fact that there are so many beautiful, historical places that are easily accessible from the city. When my parents decided to celebrate their 40th wedding anniversary by cruising from Boston to Nova Scotia with the family, we tacked on a few extra days to see Boston and its surrounds, uncovering three particularly memorable day trips.

Quick Tip:

Want to enjoy a day trip from Boston without organizing transportation or figuring out ferry schedules? A wide variety of tour operators offer excursions — from historic tours to leaf peeping jaunts.

Cape Cod

Perhaps one of the most famous day trips from Boston, Cape Cod is worth an even longer visit, time permitting. You can explore 15 picturesque towns on the peninsula, each with its own charms. Falmouth is beloved for its beaches; Sandwich is the oldest town on Cape Cod; Hyannis Port is now famous for its Kennedy connections; and Chatham is considered the quintessential Cape Cod fishing village.

Enjoy the sights by land by driving from town to town and stopping when the urge takes you — or cruise the Cape Cod canal for spectacular views of the coastline from the water. When we visited, we chose to spend time in Provincetown at the northern tip of the peninsula. The wonderful downtown area boasts quirky shops and art galleries, and we enjoyed feasting on classic local fare like lobster rolls, clam chowder and quahogs.

Quick Tip:

It’s technically not on Cape Cod, but Plymouth is an easy stop on the way back to Boston. If you haven’t see Plymouth Rock, it’s worth a visit, if only to hear the fascinating stories told by local park rangers.  

Martha’s Vineyard

I first heard about Martha’s Vineyard when a friend from New York described how she and her friends would rent a place there to get away from the city on summer weekends. Back then, I imagined an island of vineyards where everyone looked like Martha Stewart (I have a very literal brain). So I was pleasantly surprised when I actually visited the island!

After taking a ferry from Falmouth, we arrived on Martha’s Vineyard. Most visitors explore this 100-square-mile island by bus tour or by bikes. No matter what your mode of transport, don’t miss these highlights: the beautiful Aquinnah Cliffs, the Flying Horses Carousel (the oldest operating platform carousel in the country) and the gingerbread cottages at Oak Bluffs. If you have enough time, visiting the alpacas at the Island Alpaca Company is also memorable.

Quick Tip:

Though Martha’s Vineyard is “open” year-round, it’s primarily a summer destination. If you visit in the spring and summer, you’ll face larger crowds; in the fall and winter, you’ll encounter fewer tourists, but some businesses will be closed.


Salem may be super touristy, but it’s a fun and entertaining day trip from Boston. If you drive, it’s about 40 minutes from town. You can also take a scenic trip on the Salem Ferry between late May and Halloween, or take advantage of several bus and train options.

When I visited a week or two before Halloween, the historic town was in its element: people dressed up as witches of all shapes and sizes wandered down the Essex Street cobblestones, tarot card readers promised a glimpse into my future and all sorts of magic was brewing in the shop windows. I also enjoyed learning about the role of pirates in the city’s history, as well as seeing first-hand the House of the Seven Gables.

In the end, Boston’s a great city to explore, whether you’re traveling solo or with the entire family. But after you’ve done the duck boat tour and eaten your weight in ice cream, get out of town and explore the other fascinating sights around Boston.

Where to Stay:
Marriott Vacation Club PulseSM at Custom House, Boston

Katie C. is a freelance writer living in Denver, Colorado.