Courthouse Docks in Boston
City Breaks | 5 minutes

See the Best of Boston in 4 Days

If you’re in Boston for a short stay and want to pack as much as possible  into your trip, we have some great suggestions to suit all interests:

  • Eat, Drink & Be Merry:  Boston Brew Tours, Sam Adams, The Burren Pub, The North End’s Italian Restaurants, Mike’s Pastry, Fan Pier’s Seafood Restaurants.
  • Learn: The Freedom Trail, The Museum of Fine Art, Isabella Stuart Gardner Museum, The State House,  The John F. Kennedy Presidential Library, The Institute of Contemporary Art.
  • Shop: Assembly Row, Newbury Street, the Prudential Centre.
  • Watch: The Boston Red Sox, Whale Watching Tours.

Boston is America’s walking city, so no matter where you’re staying, all the best sites are reachable on foot. The “T”, as locals refer to it, is the mass transit system which covers much of the city and its outlying areas. If you feel like giving your feet a break, a one day pass can be purchased for $11.00 or get your value’s worth with a week-long pass for $18.00. These passes are valid on all city buses and subway lines. There’s even a free T service to downtown Boston from the airport via the Silver Line! If you want to make sure you burn off some calories while you’re here, Hubway is a pedal-cycle rental system that offers reasonable daily and multi-day passes.  Grab a bike in Boston, Somerville, Cambridge or Brookline and explore to your heart’s content!  Once you’ve seen all you wish to see, simply return the bike to any Hubway station with a free space.

Boston Holidays - Boston Brew Tours

The beer drinker can spend an entire day indulging in the sudsy brew, while at the same time learning about how it’s made.  Boston Brew Tours give both day and evening guided tours, where you can sample some of the best craft beers at a number of local breweries.  If that isn’t enough, supplement your tour with a stop at Sam Adams – the home of the Boston Beer Museum.

If you’re feeling homesick, go where the Irish Bostonians go. Try the Burren Pub for its rich old world style and traditional Irish music – the owners are Irish musicians.  The Burren is located in Somerville’s Davis Square – you’ll have to take the T’s Red Line to get there, but they say that the Shepherd’s Pie is just like mum makes!

Boston Holidays - Mike's PastryAfter your excursion through Boston’s beer offerings, it’s time to stretch those legs! The brick-lined route of the Freedom Trail is a 4 km stretch that takes in 16 historically significant sites — each one an authentic treasure. Explore museums and meetinghouses, churches, and burial grounds. Learn about the brave people who shaped the nation. Cap off the evening with dinner at one of the North End’s great Italian restaurants.  You’ll want to save room for a stop at Mike’s Pastry or Modern Pastry for an authentic Italian dessert. We’ll let you decide who has the best cannoli!


Click here for a full-screen map of Boston highlighting all the places and attractions mentioned in this blog.

The history and art enthusiast won’t be disappointed in the city of Boston!  The Museum of Fine Art is the perfect place to start the day. With a collection of over 450,000 works of art, the MFA welcomes more than one million visitors a year.  A quick five-minute stroll through The Fens will lead you to the Isabella Stuart Gardner Museum.  Between the courtyard garden and the surrounding galleries, the Gardner is a feast for the senses.

Continue your journey to the State House – the seat of Massachusetts’ government. Housed in a building that’s over 200 years old, see where important state laws are made in a historic setting. Hop on the T to visit the John F. Kennedy Presidential Library and Museum.  Here you’ll find exhibits detailing his early life, his presidential campaign and of course the clothing and other items owned by his wife, Jackie Bouvier Kennedy.

Boston Holidays - ICA Museum

Once you’ve had your fill of history, the obvious choice for your next stop is the Institute of Contemporary Art. Exhibitions encompass static art, performance, film and video with programmes for both adults and families. Round out the day with dinner at one of the fantastic seafood restaurants at Fan Pier).

Boston Holidays - Newbury Street - Shopping The bargainista and the luxury maven can splash their cash at several retail centres – from discount outlets to high-end, luxury designer shops. After a morning stroll through the Rose Kennedy Greenway (a linear park that meanders through Chinatown, the North End and the Financial District), take the T on the orange line to Assembly Row, the area’s newest outlet shopping centre. Just an 8-minute journey from downtown Boston, this vibrant district is filled with designer shops, restaurants and entertainment – such as the LEGOLAND discovery centre with a 62,000 sq foot movie complex.

Once you’ve scoured the shops for the best bargains, blow your savings on some pricier purchases!  Boston’s Newbury Street is a fashionista’s dream with designers from Marc Jacobs to Alexander Wang and everything in between. One block over is Boylston Street, where you’ll find the Prudential centre or “the Pru”, as locals call it. Take the elevator to the 50th floor for a 360⁰ view of the city from the Skywalk Observatory – it’s breathtaking!

The Sports Fanatic can’t leave without taking in a game at Fenway park – home of the Boston Red Sox! Built by Irish immigrant Charles E. Logue, it’s an enduring landmark where Redsox legends Fisk, Rice, Yaz and Williams made baseball history. Tours of the legendary stadium can be organised through Fenway Park Tours. End your trip on a high crest by taking a cruise on the harbour to catch a glimpse of Moby Dick…or maybe settle for a humpback whale or two! Boston Harbour Cruises offers whale watching tours throughout the day.

Boston Holidays - Fenway Park - Red Sox

As you can see, there’s so much to explore.  If you’ve been inspired to visit the home of  “tea parties”, Harvard and salt-water taffy, take a look at the great Boston holidays on offer on Clickand.com, all including flights from Ireland and a choice of accommodation.

With special thanks to our Bostonian friends Lee Statham (Presidential Library & Museum), Patricia Purdue (Massachusetts Office of Travel & Tourism), Nancy Gardella (Martha’s Vineyard Chamber of Commerce), and Catherine Doran (Greater Boston Convention & Visitors Bureau) for their local knowledge and expertise.


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