A weekend guide to Boston

words Al Woods

Thinking about taking a trip to Boston? I don’t blame you. It’s a bustling, thriving city without all the junk that comes with growing too big, and it’s super easy to get to both through national and international flights and through a short road trip from New York City. But what exactly should you get up to while you’re there?

If you’ve been wondering about that, have no fear. Here are just a few of our highlights and a sample itinerary for a weekend visit to the stunning city.

guide to Boston

A weekend guide to Boston

1.       Friday

Friday is the day you’re most likely to arrive, and so the day will mostly be dedicated to checking into your hotel and getting to know the local bars and restaurants. If you get a chance, it can be worth either deliberately getting lost or going on a guided walking, bus or boat tour.

In the evening, it’s time to party, unless you’re travelling with kids in which case perhaps it’s worth checking out a movie instead. Otherwise, Boston is a lively town that really comes to life on a Friday night, so why not sample the sights and sounds? Just remember to drink in moderation.

boston guide

2.       Saturday

Saturday will be your main day in the city, and so it’s the perfect opportunity for you to tick off whatever you want to tick off. Perhaps you want to browse the masterpieces at the Museum of Fine Arts, or perhaps you’d prefer to take a tour of Fenway Park.

Another option for your Saturday is to head off on a day trip to nearby Martha’s Vineyard. It’s one of only five place names in the US to have an apostrophe (which is technically against the law), and it’s also home to a bunch of fantastic restaurants and eateries. If you’re into food tourism, you’ll like Martha’s Vineyard.

3.       Sunday

As your final day in the city, Sunday is the time for you to tick off anything that you might have missed on your other days in the city, as well as to pick up some souvenirs and to revisit any of your favorite bars and restaurants.

Once you’re ready to leave the city, it’s up to you how you head home. Boston is a great starting point for road trips, and it also has excellent international flight connections. Another option is to take a cruise from Boston, with plenty of national and international cruises on offer as well as specialist deals for foodies, couples, retirees and more.


This three-day itinerary is a good place to start, but you should also feel free to adapt it as needed to make it better suit your needs. The most important thing of all is to make the most of your time there. Happy travels!


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