Boston in a few days

Your perfect guide for a memorable first visit to the historic city. 

It has been over 10 years since I last visited Boston, and I still look back on that trip with great fondness. Of course, I still have the photos, and I have been wanting to write about the city. However, with so much time having passed, I needed a little help. My friend Debbie, who was born in Boston and still visits regularly, helped me put this article together. So not only from a first-time visitor but also from a local some information about Boston in a few days. 

Transportation

• We flew from Chicago to Logan Airport, as we planned to visit Cape Cod, we took a rental car. Logan Airport offers several rental car companies. You can take the free Rental Car Center shuttle from the terminals. 

• The same shuttle takes you to the Airport Station on the Blue Line, which leads to downtown Boston.

• Taxis, Uber, and Lyft are available at designated ride-share pick-up zones at the airport. Regular taxis outside each terminal. The ride to downtown Boston typically costs around $25–$40. (prices I checked via AI) and a third category, the water taxi. You can take a free shuttle to the Logan Dock, where water taxis can take you across Boston Harbor to downtown. What a way to arrive 

• While not the most direct choice, if you are adventurous and you travel with a backpack, some paths allow you to walk or bike from the airport into Boston.

Where to stay

We stayed in Boston’s vibrant Theater District, right in the heart of downtown. It’s an excellent starting point for exploring the city on foot and transforms into a lively hub in the evenings, thanks to its theaters, pubs, wine bars, and restaurants. For our stay, we chose the Courtyard by Marriott Boston Downtown.

What to visit

Neighborhoods 

Boston was founded in 1630 by the English, but also with a high percentage of Irish Americans. As Debbie described there are different neighborhoods, imagine a patchwork quilt, each reflecting the city’s immigrant history and cultural diversity. This is not a history class so I will not mention them all but some close to downtown. 

North End (Italian) 

North End, Boston’s ‘Little Italy’, is a maze of narrow streets home to some of the city’s oldest buildings and, of course, the home of delicious Italian food. 

South Boston or Southie (Irish) 

Residential area with a strong Irish American background. The waterfront walking paths and lawn surrounding the 19th-century Fort Independence on Castle Island attract joggers and picnickers.  

Beacon Hill (wealthy) 

Beacon Hill is one of Boston’s most picturesque and affluent neighborhoods, known for its cobblestone streets and gaslit lanterns. This neighborhood is also home to Boston Common, America’s oldest park that continues to be a stage for free speech and public assembly. The public park with the swan boats and the Victorian botanical style feels very English. 

Duck tour 

Boston is the capital and largest city of the U.S. state of Massachusetts. It is also considered the official capital of New England. And you know, if you have read my other travel blogs, that I like to start with a “red bus tour.” In Boston you can take a Duck Tour, a fantastic way to get an overview of Boston’s history and landmarks in a short time. The “DUCK,” a colorful amphibious vehicle, starts on land and transitions into a boat to cruise along the Charles River. The guides are entertaining and knowledgeable, and it is great to see the city skyline from the waterside. Tours typically run from March through November, depending on the weather.

Some of the buildings we saw along the way. 

Quincy Market/Faneuil Hall 

A bustling marketplace and historic meeting hall near the waterfront and today’s Government Center. Opened in 1742, it served as the site of several famous speeches by Samuel Adams, James Otis, and other patriots advocating for independence from Great Britain. Inside, you’ll find a lively atmosphere, making it a great spot to grab a drink or a bite to eat.

If you want to visit a farmers’ market, you can go to Haymarket. Close to Faneuil Hall for fresh fruits, vegetables, and seafood. 

Shopping Newbury Street, Boylston Street, Charles Street

Newbury Street is the most iconic shopping street in Boston with its Brownstones and upscale vibe, and a mix of high-end brands and independent boutiques. 

Boylston Street runs parallel to Newbury Street and features larger stores, department stores, and popular chains. 

In Charles Street you will find antique shops, small boutiques, and locally owned stores. It is perfect for unique finds and one-of-a-kind gifts. 

Waterfront 

Boston’s waterfront offers a picturesque setting for a stroll, with harbor views, historic landmarks, and vibrant spots to explore along the way. The wonderful thing about the waterfront is that there are multiple places to start your walk, depending on your interests and where you are in the city. 

New England Holocaust Memorial 

The New England Holocaust Memorial is a poignant tribute to the Jewish victims of the Holocaust.  

The memorial consists of six glass towers, each representing a different major extermination camp: Majdanek, Chełmno, Sobibor, Treblinka, Bełżec and Auschwitz-Birkenau. You can walk under these towers. Six million numbers are etched in the glass. I found it very impressive.

Freedom Trail 

The Freedom Trail is a historical walk through the city center of Boston. The trail is four kilometers long and passes 16 sites of national historic significance, including the Boston Common, the Old State House, and the Old North Church. The Freedom Trail was conceived by William Schofield, a local journalist who proposed in 1951 to connect major attractions with a pedestrian route. (I did not walk it myself, but it is on my list for my next visit). 

Bonus Tips

Harvard

A visit to Harvard in Cambridge, just across the river, is an absolute must. We took the Harvard tour led by Harvard students, which offered fascinating insights into the university’s history and culture. If you’re interested, you can also take a similar tour at MIT, another world-renowned institution nearby. For more information, check out Trademark Tours.

Miscellaneous

Giant steaming tea kettle, a landmark since the 1800s

Legal Seafoods, for a table filled with various seafood dishes, including lobster tails, grilled fish with lemon. Get a taste of New England. 

• It’s easy to travel from Boston to Cape Cod and Martha’s Vineyard. Cape Cod is about 70–90 miles south of Boston, and you can reach it by car, bus, or ferry. And from Cape Cod it is easy to visit Martha’s Vineyard. (In a later blog more about these destinations).  

• Boston served as a destination for many people escaping slavery on the underground railroad. Read the Underground railroad by Colson Whitehead.

Boston is a city that blends rich history with vibrant modern life, from the historic streets of Beacon Hill to the lively waterfront and the prestigious halls of Harvard. Whether you are exploring its diverse neighborhoods, enjoying a Duck Tour, or taking a scenic trip to Cape Cod, there is something for everyone. If you have not experienced Boston yet, start planning your trip—you will not be disappointed! 

Enjoy Boston in a few days!

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