In the book, Penelope of Is This Seat Taken?, we see a lot of Boston, Massachusetts.

Boston is home! I went to school here and then stayed in the city for another 10 years. My family lives nearby, so I am always able to return.

Boston is the right size for exploring on foot and a well-rounded blend of historic comfort and ambition with an absolute amount of charm. Every neighborhood has a distinctive feel that it’s worth spending time in each.

Boston chefs have definitely stepped up to the plate in recent years and now the city is becoming a culinary destination too.

This is my guide to exploring Boston like a local!

The Best  Time to Visit

Boston changes depending on the season, which is a great reason to come back and visit.

It is cold in the winter. But with snow covering the ground and holiday festivities it can be a winter wonderland. So if you are willing to bundle up, there will be a fireplace lounge and a cup of hot chowder waiting for you.

Fall is when Boston really shines! The weather stays warm through October, because the tourists have left the breweries and apple orchards are in full swing, and the New England foliage is spectacular.

Layer is very important!

Getting Around 

Don’t rent a car! I’ve been living in the city for 10 years and I still get confused when driving the one-way streets, with no rhyme or reason.

The T is a convenient subway line. It is easy to use, and it is especially useful when traveling at rush hour or going to/from a game.

As an example, I use CharlieTicket to make subway travel cheaper. You can get on at any of the stations for the same price, regardless of which stop you get off at. You can buy additional tickets for more trips.

Otherwise this town was made for walking! If you stay in a central location most attractions are within a 30-minute walk. For nights out Ubers and Lyfts are always available.

Where to Stay


A landmark in Copley Square the Fairmont Copley Plaza is more of an opulent hotel option. You will feel right at home after being greeted by the staff and hotel’s canine ambassador Cori. The restaurant OAK Long Bar is also an excellent old-school setting with the perfect cocktails, breakfast rolls The best martinis in the city are served at this bar. I’m not saying there is anything wrong with my second grader. He is bright, inquisitive, and obviously loves to read. But it’s clear that he needs help in understanding how English works. I can’t help him yet

The Hotel Commonwealth is located in Kenmore Square, and it’s a great location for conferences and other events.

The Library is located at the old Liberty Hotel, which looks out on Boston Harbor. This building was once a prison for suffragettes and even Malcolm X. Its unique architecture and jail cells add an edge to this historic site. The hotel is beautiful.

Pay attention to the events that your little one attends throughout the week. Your child may see fashion shows during winter holidays, upside down Christmas trees in the spring, and elite parties in the summer.

The Envoy Hotel has a modern vibe and tends to skew younger. It is located in the innovative Seaport area, there are restaurants, cafes, movie theaters, bowling alleys, pop-up shops, and a marina to explore. The rooftop bar overlooking the city is a definite scene.


You can usually find rooms at the Boston Park Plaza for under $150 a night. Located steps away from the Boston Public Garden, most landmarks are within walking distance. The hotel has recently been restored and renovated so everything is very comfortable.

The rooms are small, but they can be expanded by hanging out in the lobby space or going to the top-of-the-line Lynx Fitness Club.


The Revolution is a new hotel in the trendy South End neighborhood. The rooms are small (bunk beds and communal baths are an option!) but are perfectly designed to accommodate guests. The lobby features really cool decor and street art that celebrates all of Boston’s rich history. “firsts.”

What to Do + Local Highlights

Take a Walk Along the Freedom Trail

Walk the Freedom Trail. You can do this with a quirky costumed guide or just follow the red brick path. There are many interesting sights along this 2.5-mile walk. These include Old North Church, Paul Revere’s House, some old burial sites, the USS Constitution, and Bunker Hill Monument.

This The harbor is a popular place for tourists, but even if you aren’t a history buff, you will come across attractive parks, street performers, beautiful Harbor views and some of the best food in the city.

See the Museums

Boston has world-class museums. The Museum of Fine Arts and the Boston Tea Party Ships & Museum are both wonderful places to visit, but the Isabella Stuart Gardner Museum is the most unique! It was the home of an eccentric socialite who collected and commissioned art from all over the world.

She left her home to Boston, but she wanted her collection to be preserved. The exemption is that the frames were not damaged by the famous art heist in 1903, still unsolved.

The museum is open every third Thursday of the month, and it features activities, food, and drinks for all ages. The courtyard is stunning at night, so come to see it!

Visit the Boston Public Library

The Boston Public Library is my favorite place in the city. Get through the Dartmouth Street door and make a grand entrance! From there, Bates Hall and the Sargent Gallery are must-see rooms.

You can relax in the stunning Courtyard or Map Room Tea Lounge. Visitors can also relax in the stunning Courtyard or Map Room Tea Lounge which recently expanded to include a bar.

 Explore “New Boston”

The Seaport is Boston’s new “city within a city.” Almost everything has been built in the last 10 years and it is a cool juxtaposition from Boston’s historic sites just across the way.

You will find trendy restaurants, a movie theater, a bowling alley, a marina and a mix of outdoor pop-ups. The Boston Harborwalk follows the water ‘s edge for 43 miles and is particularly scenic around sunset.

The Underground Tunnel System

The Big Dig is the name of the historic and expensive underground tunnel system project in Boston. It was completed in 2007 and the old elevated roadway became a greenway.

There are always art installations, food vendors, craft vendors, and beer gardens in the area. It’s a great way to go into the North End or the Seaport area.

Hang Out at Fenway

Go to Fenway Park! Even if you are not a Red Sox fan, you’ll still have a unique energy here. It’s the oldest major league ballpark still in use, so history and nostalgia play a factor. Daily tours of the park are also offered.

Shop at Newbury Street

Newbury Street is an area in Boston that has many stores and restaurants. The high-end designers are closer to Arlington Street and tend to be less formal as you walk west.

In the Winter

Wander the Gardens

This is also the beginning of the Boston Public Garden, a well-maintained oasis with willow trees and a small lagoon. The Swan Boats and the “Make Way for Ducklings” statues add an endearing quirkiness to the garden.

Across the street is a place where there are fields for tennis courts and a gazebo for outdoor concerts.

Acorn Street in Beacon Hill

Visit the historic neighborhood of Beacon Hill.

Beacon Hill is a historic residential neighborhood that has the State House located prominently at the top. Across the street from the State House is one of the best-kept secrets – the Boston Athenaeum – a library with a history dating back to 1807.

Founded in 1807, this independent library is five floors of rare book collections, historic art and the dreamiest nooks and crannies. Tours and day passes are available.

Walk through Beacon Hill to see brick sidewalks and cobblestone streets. Keep an eye out for Louisberg Square and Acorn Street, two historic landmarks!

Walk Along the Waterfront Promenade

Along the Charles River are walkways or “promenades” that go between bridges. Visitors can walk along these paths to Cambridge, or they can rent sailboats and kayaks from Community Boating.

Walk through the South End neighborhood.

If you venture to the less-touristy neighborhood of the South End, you will be treated to beautiful homes, award-winning restaurants and specialty stores.

I recommend stopping by the SOWA Open Market that is held every Sunday with food trucks, local vendors, beer garden, and antique stores. On the first Friday of each month, there is a popular SOWA artists studio open house. In December, there is a popular Winter Festival market.

Things You Have to Eat

It should be no surprise that seafood should be a priority during your Boston visit.

Lobster Roll

A good lobster roll will have a buttered and grilled bun packed with fresh New England lobster meat, not much else! Though the Boston way is made with a cold mayo-based roll, you can also elect for a warm butter version at most places.

Clam Chowder

Clam chowder is the real deal in Boston. It has a rich creamy milk base and is loaded with clams and potatoes. For oysters, you can’t go wrong with any from Cape Cod or Duxbury.

Island Creek Oyster Bar and Saltie Girl are two excellent locations for all of the above!

Visit Boston’s Little Italy for an extensive sampling of Italian foods.

You can’t visit the city without having a meal in the North End. The acclaimed version of Little Italy is Boston’s Italian food. With dozens of authentic mom and pop gems, you’re bound to find an amazing pasta dish.

A cannoli is the best dessert in the city after dinner. There are two main competitors on Hanover Street, but I prefer Mike’s Pastry.

Three Cheers for Craft Beer

Boston already has a strong beer scene with Sam Adams and Harpoon, but craft breweries are popping up all over the city too. During the summer, beer gardens are a great place to mingle. Cheers! Advertisements

Where to Eat

For Breakfast

The best way to start the day is with a Mike and Patty’s breakfast sandwich. For a cafe experience, Flour has excellent pastries. And of course there’s always Dunkin’ Donuts.

Recently, artisan doughnut shops have started popping up in the city. My favorite one is Blackbird Doughnuts. Their flavors are fresh and fun but without the toppings overkill.

The Beehive is the place to go for breakfast or dinner in the South End. The bohemian-esque restaurant features a stage with local jazz musicians and entertainers on a nightly basis.

For Lunch + Light Bites

Make a reservation at the Island Creek Oyster Bar before or after a Red Sox game. This restaurant is great and their seafood dishes are perfect.

If you are in the mood for a lobster roll, stop at Pauli’s in the North End. They have many different varieties of lobster rolls, all of which are very large and priced reasonably.

For Dinner + Drinks

A local is a favorite of a tapas restaurant and bar. Everything they have is delicious and can be shared. They do not take reservations, so get there early!

Fox & the Knife is a restaurant run by a kickass female chef and an all-female team in South Boston. Chef Karen Akunowicz’s delicious appetizer-style menu is inspired by her time in Modena, Italy.

ReelHouse is a beautiful waterfront restaurant in East Boston. Its patio and view make this an ideal destination for sunset dinners and drinks. During the summer, a complimentary boat shuttle will take you to sister restaurant Pier 4 in Charlestown!

Bogie’s Place is an adults only restaurant located behind JM Curley’s (which has a great burger!). The steak and cocktails are the highlights of this cozy, private bar. This place will impress your date.

 When you’ve worked up an appetite exploring the beautiful Back Bay and shopping in Newbury Street Piattini’s is a reliable spot for a panini and salad. For something a little more upscale Sonsie is a longtime staple with bistro-style seating in the front. Both are reliable Great for people watching!

Helpful Tips + Fun Facts

The people of Boston love sports. The residents take great pride in the city nicknamed “Title Town” after so many championship wins. The bars play the Sox, Bruins, Celtics or Patriots games loud and proud.

South Boston or “Southie” is often depicted as gritty and mob dominant thanks to movies like The Departed and Black Mass. I have had out-of-town friends request a visit to South Boston but are disappointed when they see young adults refined bars and recently renovated townhouses.

If it helps, you The Boston accent is heard here.

So many day trips are within reach of Boston. Head to the Cape for the beach and lighthouses, or south to Newport for mansions or north to White Mountains during leaf-peeping season.

Here is some more information to help plan your trip:

  • What to Know When Visiting BostonDay Hikes Near Boston10-Day New England Road Trip from Boston

Penelope is an avid traveler with a sense of adventure. She has researched and selected activities to make sure that explorers will enjoy every minute of their trip. Her website Is This Seat Taken? provides daily itineraries, including activity suggestions, local food spots, transportation options, and tips for making the most of your time.