Things to do while in Boston: Experiences, Sites, Eating, and Drinking

by | Jun 9, 2015 | Community news, Training

Things to do while in Boston: Experiences, Sites, Eating, and DrinkingMy first visit to Boston was actually a long weekend where I won a trip off the radio with airfare, hotel and tickets to a Celtics Game. Arlene Belliveau (former client from University of Massachusetts – Boston, and who is now serving as a consultant) packed more into a weekend of touring than most people can do in a week! I had another trip to Boston funded by a $500 savings bond I won from Hershey’s a long time ago. Can you tell it’s one of my favorite places!?!
Arlene and I put together a list of suggestions for those of you attending the User Conference. Hopefully you all can make time to explore the city!
Boston has so many things to see and do, we hope you’ll have extra time to sightsee! Arlene has been a natural tour guide to visitors from around the world and has a few recommendations that have been favorites of her guests over the years.
Boston Harbor Cruises has several great cruises to choose from but the sunset cruise is highly recommended. It provides a narrated tour of the harbor and hovers near the USS Constitution while they lower the flag and shoot off the cannon while to the right of boat you will see members of the coast guard at attention during the lowering of the flag.
You can spend an inexpensive day driving or taking a long walk over the Charlestown Bridge where you can see the Charlestown Naval Yard and tour the USS Constitution for a minimal cost at 24 5th Street, Charlestown, MA.
While in the cozy streets of Charlestown, lunch or drinks at the Warren Tavern is worth a stop. “The Warren Tavern is one of the most historic taverns in America. It is the oldest tavern in Massachusetts and was visited by many famous individuals including George Washington and Paul Revere.” It was one of the first buildings raised after Charlestown was sacked by the British. Paul Revere considered it one of his favorite watering holes and George Washington’s funeral speech was delivered here.
Boston’s North End is a mandatory stop for Arlene’s visitors and I can’t wait to go back to the area that at one time was populated over 80% by Italians. There are a huge number of Italian restaurants and coffee shops to choose from. Don’t miss Hanover Street where you’ll find Paul Revere Square and a short walk to the other end of the square and you’ll be at the Old North Church. They give a very brief informative talk on the history of the church made famous by “One if by land and two if by sea and I on the opposite shore shall be”!
Stroll back to Hanover Street through the square and almost directly across from the square is Saint Stephen’s Church. It was designed by Charles Bullfinch who also designed the Massachusetts State House. He’s regarded by many as the first native-born American architect. St. Stephen’s is where President Kennedy’s mother, Rose Kennedy, was baptized in 1890 and buried from in 1995.
Also on Hanover Street is Mike’s Pastry shop which is a big tourist spot with long lines. Personally, we recommend going on down the street on the opposite side where you’ll find Modern Pastry. We love this place! Try a Lobster Tail (pastry filled with custard) and several of the torrone and anything else that looks good (it all does). Accepts cash only.
On the North Square you can visit the Paul Revere House for $3.50 and walk on some of the original cobblestone roads.
You must eat in the North End. Ask the locals on the sidewalk or try one of these places where we’ve enjoyed great food: Massimino’s on Endicott Street (where they have a veal chop you have to know to ask for – it’s not on the menu and is very good); Artu’s on Prince Street; Giacomo’s or Lucia’s on Hanover Street; and L’Osteria on Salem Street.
End the day with a caffé mocha or espresso at Vittoria Café on Hanover Street. Best caffé mocha anywhere.
Faneuil Hall Market Place is a nice place to visit. Built in 1740 as a public market and meeting place, it’s now a site for street theatre and shopping. While walking, stop by the Holocaust Memorial Boston on Union Street. It’s small but moving.
Still hungry? Stop in at the Olde Union Oyster House – one of the oldest restaurants in Boston. Walk down to the Boston Stone on Marshall Street, a small alley just past the Union Oyster House. The stone is thought to be the geographic center for Boston surveyors dating back to 1737. This area represents the streets of the early 1700’s in Boston.
In the Seaport Area, Arlene has a few recommendations. Harpoon Brewery, 306 Northern Ave., gives brewery tours and has a German style beer hall. Temezcal, 250 Northern Ave., is a tequila cantina and sits right on the water. Legal Harborside is the area spot for Legal Seafood which has 3 different levels with 3 different menus on each level and roof top dining right on the water. Jerry Remys Seaport 250 Northern Ave., is a little bit of a Fenway Park experience by the sea. Jerry Remy is a favorite Red Sox broadcaster.
For those that are going to be around Fenway Park, try the Yard House at Fenway Triangle if you’re interested in a great back patio with 100s of beers on tap and a large menu. The Lower Depths, 476 Commonwealth Ave., serves Fenway Franks kicked up a notch and gourmet tots with a good beer selection. The Eastern Standard, 528 Commonwealth Ave., has seafood, a raw bar and good burgers. Erin Belliveau (Arlene’s daughter) highly recommends the Oyster sliders at the Island Creek Oyster Bar, 500 Commonwealth Ave. And then there’s the Bleacher Bar, 82A Lansdowne Street which is a place you want to pop into for a unique view of Fenway Park. Always crowded but a fun quick drink place.
And in another part of town, there’s Copley Square with the Trinity Church at 206 Clarendon Street which provides inexpensive and informative tours and includes beautiful stain glass and architecture. Across the square is the Boston Public Library which you can also tour or just walk in and look around. It’s definitely worth a visit. Then stroll to the Fairmont Hotel, an elegant historical hotel right on Copley Square and ask about the resident dog. The lobby is worth a look.
Shoppers will enjoy the Prudential and Copley Place in the Western Hotel. The Skywalk Observatory at the John Hancock Tower just off Copley Square provides a great view of the city.
If you leave Copley Square and walk down Boylston Street toward Arlington Street, take a stroll through the Boston Public Gardens. Have your camera ready, the flowers should be beautiful. And if you have your family, you MUST take a ride on the Swan Boats in the middle of the Public Gardens and ask someone to direct you to the Ducklings: Jack, Kack, Lack, Mack, Nack, Ouack, Pack, and Quack from the children’s book Make Way for Ducklings! This set of bronze ducks are along a pathway in the Public Gardens and are very close to the Cheers Bar from the TV show at 84 Beacon Street. Very small and very touristy but neat place to get your photo if you were a fan of the show.
You can walk up Beacon Street or as we know –Beacon Hill – to the front of the State House – or you can take a walk down Charles Street – interesting boutiques, coffee shops, antique and art stores. From Charles Street you can walk up Mount Vernon Street to Louisburg Square. It is one of the most expensive neighborhoods in the country – and one of the oldest in Boston – with original cobblestones. Former residents include: A Bronson Alcott and his daughter Louisa May; John Copley, the American painter; Charles Bullfinch, the architect of the State House; and currently former Senator and Secretary of State, John Kerry.
Boston is also famous for its Duck Tours which is a fun family outing. Check them out at
There are too many other historical sites and museums and restaurants to list here but hopefully these ideas will get you started. Bring your walking shoes and come hungry – you won’t be disappointed! And Arlene will be glad to tell you where to pahk your cah…


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