Letter T with Palm leaveshere is so much to love about Boston. It’s another big city with a lot of similarities to other big cities like San Francisco and New York, but with its own uniqueness. In this post, we list the top ten reasons to love Boston, ranging from its historical significance to the diversity of activities to engage in.

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Historical Significance

Reason 1 to love Boston - Historical significance
From Left to Right and Top to Bottom: George Washington statue in Boston Public Garden; Old State House; Ben Franklin statue at the Old City Hall; Fenway Park mural; Col. William Prescott statue at Bunker Hill Monument; Canons on the USS Constitution Ship; Freedom Trail marker; Paul Revere statue in front of the Old North Church

Boston is the birthplace of America and just about everywhere you look there is some historical landmark that helped shape Boston and America. It’s pretty cool to physically explore so many sights that you have read about in history books. Listed below are just a handful of the many historical locations Boston offers:

  • Boston Common – America’s first public park
  • Green Line of the “T” – the oldest metro system in America which was originally called the Tremont Street Subway
  • USS Constitution – America’s oldest naval vessel that still has an active U.S. Navy crew assigned to the ship.
  • Fenway Park – America’s oldest ballpark and home to the Boston Redsox
  • Samuel Adams Brewery – America’s original craft beer

Extremely Walkable City

Reason 2 to love Boston - Extremely Walkable CityWalkable
Map of the Freedom Trail with someone walking on the red bricks that identify you are on the Freedom Trail.

You can pretty much walk to everything in the city within 20 minutes. Apart from just walking the city and the beautiful neighborhoods that makeup Boston, there are many different trails that are enjoyable to stroll and take in Boston’s culture.

  • Freedom Trail – Begins at the Visitor Center in the Boston Common and extends 2.5 miles through Boston following a red brick trail that takes you to most of the historical landmarks in Boston that started the American Revolution. It’s great to do early in your trip to get a feel for how Boston is laid out. You can either do it on your own or join a tour where your guide dresses up in period costumes to inform you about all the historic sites that make up the trail.
  • Charles River Esplanade – Located in the Back Bay neighborhood, this walk is along the Charles River and expands 3 miles with great city views between the Boston University Bridge to the Museum of Science. It’s fun to watch all the water activities going on as you meander. Beware, there are lots of geese along this walk, so as you can imagine with that you need to watch your step since there’s a lot of geese poo, too.
  • Rose Fitzgerald Kennedy Greenway – 1.5 miles long extending from North End (right as you enter Little Italy) to Chinatown located near South Station. This used to be part of a highway but after the Big Dig it was turned into a large walkable green space made up of multiple parks that hosts several different events and attractions.
  • Boston Harbor Walk – As the name implies, this walk stretches 43 miles along the Boston harbor and connects eight different neighborhoods from East Boston to Dorchester. It’s still a work in progress that began in 1984 and once complete it will be a total of 47 miles. There are several things to do along the trail like stopping at one of the nine beaches, several museums, restaurants, and it even connects with the other trails mentioned above.
  • Memorial Drive – Every Sunday from the last Sunday in April through the second Sunday in November a portion of Memorial Drive between Western Avenue and Mount Auburn Street is closed off to vehicle traffic to allow for recreation. The views of the Charles River are wonderful. You can still enjoy the walkway that parallels Memorial Drive any day of the week, but even more so on Sundays.

Reliable Metro System

If you can’t walk to it within 20 minutes, then you can hop on the “T” and you’ll still be to your destination within 20 minutes. A car truly is not necessary in Boston.

The “T” has five different colored lines (Green, Red, Orange, Blue, and Silver) that get you to most of Boston’s neighborhoods.

Reason 3 to love Boston - Reliable Metro System
Map of Boston’s “T” subway system

As with most metro systems, it is pretty inexpensive with different ticket options to get the best bang for your buck. As of July 2019, the prices listed below are in effect:

  • One-way fare – $2.40 (CharlieCard) or $2.90 (CharlieTicket – also works on commuter rail and ferry)
  • 1-Day Pass – $12.75 for unlimited travel in a 24-hour period. Purchase this pass if you plan to make more than 5 one-way trips in a day. (Also works on commuter rail and ferry)
  • 7-Day Pass – $22.50 for unlimited travel for 7 days. Purchase this pass if you plan to make more than 8 one-way trips during your week stay. (Also works on commuter rail and ferry)
  • Monthly LinkPass – $90.00 for unlimited travel for 1 calendar month. (Does NOT work on commuter rail and ferry)

Most options can be purchased at any of the underground vending machines, but to be absolutely positive, check the MBTA’s website:   https://www.mbta.com/

Pro Tip: The Silver Line (SL1) from Logan Airport is FREE and gets you to the South Boston Waterfront or all the way to South Station where you can transfer to the Red Line.

Many Serene Parks and Green Spaces

Reason 4 to love Boston - The many serene parks and green spacesre
A walk along the serene Charles Esplanade is a wonderful green space where you can plop down on a park bench and relax.

Boston’s parks and green spaces are incredibly stunning and relaxing. Emerald Necklace is the name given to the many parks that make up the Boston area:

  • Rose Fitzgerald Kennedy Greenway – Consists of multiple parks in the middle of Boston’s skyscrapers. Each park is different from the other. One includes a carousel, others include fountains and gardens, sculptures and other art installations, as well as, beer gardens and food truck events. There seems to also be something going on somewhere within the Greenway, so it’s a wonderful place to stop. We enjoyed the relaxing swings as you approach North End.
  • Christopher Columbus Waterfront Park – Located at Boston Harbor’s waterfront, it may not be as peaceful as some of the other parks as there is usually a lot of lively events going on here, but it’s still a fun public space to explore.
  • Norman B. Leventhal Park – Situated in the middle of Boston’s Financial District in Post Office Square, where a large parking garage used to sit is now a beautiful green space for all to enjoy the sculptural fountain and garden trellis with several park benches and tables.
  • Boston Common – Known as the center of Boston and can be compared to New York’s Central Park, but definitely not nearly as large. Here you will find public events like concerts, protests, and speeches. There’s also several monuments and statues in the park. As well as baseball fields, a playground for the little ones, and a Frog Pond that is a wading pool in the summer months and ice-skating rink in the winter months.
  • Boston Public Garden – Its centerpiece is a large pond with swan boats that’s outlined with majestic willow trees. Great place to relax and people watch as you meander through the multiple paths.
  • Commonwealth Avenue Mall – Located in the Back Bay neighborhood it’s a tree-covered park that is 1.3 miles long stretching from Boston Public Garden to Massachusetts Avenue with memorials and statues along the entire length and lined with the gorgeous brownstone brick houses on either side.
  • Copley Square – Also located in the Back Bay neighborhood with fountains, statues, and a large lawn area. The park has great views of the surrounding buildings, such as Trinity Church and the Boston Public Library.
  • Charles River Esplanade – Worth mentioning again since you can plop down just about anywhere along the walking/bike path that is lined with park benches and lawn to take in the scenery and relax.
  • Harvard Yard – Central area for students. Restaurants, shops, and bars surround this park. It’s also the meeting location if you plan to take a tour of the Harvard campus.

Other gorgeous parks included in the Emerald Necklace are Back Bay Fens, Riverway, Olmstead Park, Jamaica Pond, Arnold Arboretum, and Franklin Park.  You can find more detail on each of those parks at the City of Boston’s website.

Beautiful Architecture

Reason 5 to love Boston - Beautiful Archirecture
The historic Old North Church with beautiful brick architecture and a church spire that can be spotted all over the city.

As you can imagine with how old Boston is, the architecture ranges from old and new. We were amazed by just how striking the architecture was.  Specifically for us, we loved the amount of brick that is used in structures as this is not something we see often in California.

Some notable buildings with intriguing architecture include:

  • Boston Public Library
  • Trinity Church
  • Any of the Brownstone homes that you see in Beacon Hill or Back Bay neighborhoods
  • Liberty Hotel
  • South Station
  • Tremont Temple
  • Any historical building along the Freedom Trail (New and Old State Houses, Old North Church, King’s Chapel Church, etc.)

The way residents bring in color to liven up the architecture is pretty cool as well; most residents have a planter box of some sort with very colorful flowers.

Amazing Dining Options

Reason 6 to love Boston - Amazing Dining Options
Croissant Breakfast Sandwich from Tatte Bakery and Cafe

The amount of dining options is unreal and might we add, delicious! Your choices are endless with fare to please everyone. No matter where you’re at in the city you’ll find something wonderful to take away your hunger pangs (if that’s even possible with the amount of food you’re surrounded by).

Listed below are just some of the areas/places you can go to find amazing food establishments:

  • Union Oyster House is America’s oldest restaurant and is located in a quint area with cobblestone streets right before you enter North End. The most popular dish is their New England Clam Chowder.
  • Faneuil Hall Marketplace, Quincy Market, North Market, and South Market are all located in the same area and provide loads of options. It’s very touristy so expect lots of crowds. It was a complete madhouse when we went on a June Saturday.
  • Boston Public Market is an indoor market that houses several vendors offering local food.
  • North End Neighborhood for family-owned Italian eateries and bakeries with cannolis.
  • Warren’s Tavern is the oldest tavern in Massachusetts. Located very close to Bunker Hill in Charlestown. Surprisingly for being such a touristy location, their food was actually pretty good.
  • Massachusetts Avenue in Cambridge has TONS of options and the closer you get to Harvard the number of possibilities quadruple.
  • Newbury Street in Back Bay provides several dining establishments on a mile-long stretch of Brownstones.
  • Liberty Hotel is an upscale hotel with 5 restaurants. This hotel and its restaurants are unique in that it was once a prison and has maintained the jailhouse theme since converting to a hotel.
  • Tatte Bakery and Café, Thinking Cup, Caffé Nero, and Flour Café and Bakery are all great places to get your coffee fix and each has multiple locations across the city.
  • Tasty Burger has multiple locations with amazing hamburgers and fries. We might be from California where In-N-Out is all the rave, but we honestly think Tasty Burger is so much better. Don’t hate us.
  • Parker’s Bar (casual) or Parker’s Restaurant (fine dining) for the original Boston Cream Pie.
  • No. 9 Park for an exceptional fine dining experience.
  • New Jumbo Seafood Restaurant in Chinatown for late, late-night eats. Probably the best Chinese food we’ve ever had.

We’re not joking when we say the selection is infinite, so only use the above list as a guide.

Cleaner Than Other Big Cities

Reason 7 to love Boston - Cleaner than other big cities

Boston appeared to be a lot cleaner and less cluttered than other bigger cities we’ve been to. For instance, the streets don’t have newspaper stands cluttering every corner. Also, even though you’d spot some homeless, it didn’t seem as big of a problem as it is in California.

Great Jump-off Point for Other Nearby Getaways

Reason 8 to love Boston - Great Jump-off Point for Other Nearby Getaways
Boston’s South Station train information sign.

If you have time, or you want to escape the big city for a day or two, you can easily hop on a ferry from Boston Harbor Cruises.

  • Ferry to Provincetown, Cape Cod costs $93 round trip and takes about 90 minutes each way.
  • Ferry to Salem costs $45 round trip and takes about 60 minutes each way.

If driving is more your speed, the locations below are also great getaways from the big city:

  • Portsmouth, New Hampshire is a little over a 1-hour drive.
  • Newport, Rhode Island is a 90-minute drive
  • Portland, Maine is a 2-hour drive
  • Kennebunkport, Maine is a 2-hour drive
  • Manchester, Vermont is a 3-hour drive

There’s also the option of taking the train:

  • Amtrak Downeaster has stops in New Hampshire and Maine, with the furthest stop being Brunswick, Maine which takes 3.5 hours from Boston.
  • Amtrak Acela has stops in Rhode Island, Connecticut, New York, New Jersey, Pennsylvania, Delaware, and Maryland. The furthest stop being Washington D.C. which takes 7 hours from Boston.

We took Amtrak from Boston to New York City (4 hours) and was impressed with how comfortable the ride was. We had plenty of legroom and seats reclined back nicely without taking away space from those sitting behind us.

Diversity in Activities

Reason 9 to love Boston - Diversity in Activities
Tour guide for the Fenway Park Tour with attendees seated in the Green Monster.

There’s so much to do in Boston and the variety is astounding. You likely won’t be able to do them all.

  • Explore the many museums – To name a few there’s the Museum of Science, New England Aquarium, Boston Tea Party Ships and Museum, Mapparium at the Mark Baker Eddy Library, Isabella Stewart Gardner Museum, and the Harvard Museum of Natural History
  • Sail or kayak the Charles River – You can rent both sailboats and kayaks from Community Boating Inc. which is located right along the Charles River Esplanade. They also teach you how to sail if you’ve never done it.
  • Shop til’ you drop – If shopping is your thing you won’t be disappointed with all the shopping opportunities around the city. Some very popular shopping areas are on Charles Street and Newbury Street boutique shops, Prudential Center shops, and the Faneuil Hall Marketplace.
  • Enjoy a show in the Theater District – There are at least a dozen different theater venues, so you’re sure to find a production that satisfies your taste.
  • Lounge on the beach – Boston isn’t known as a beach town, but there are a few beaches in Dorchester which is on the outskirts of South Boston. One notable beach is Carson Beach that offers a 3-mile stretch of beach with swimming access and a bathhouse. Facilities include restrooms, rinsing showers, grills, picnic tables, and a boardwalk among others.
  • Be a spectator at a sports game – Bostonians love their sports and there’s no better way to immerse yourself in Boston’s culture than by attending one of their beloved major league sports games like a Redsox baseball game at Fenway Park, Celtics basketball game or Bruins hockey game at TD Garden.
  • Partake in one (or more) of the tours around town – Each tour shows a different aspect of the city’s culture whether it be the Old Town Trolley tour, Fenway Park tour, Charles River tours, Student-led tours of MIT and Harvard campuses, or brewery tours of Samuel Adams and Harpoon breweries.
  • Get your drink on – You have many choices to imbibe in some alcoholic beverages from rooftop bars and other bars, pubs, taverns, and breweries.
  • Stroll the city by biking or walking – As noted in an above section there are several trails to enjoy, as well as, the different neighborhood streets to appreciate.
  • Indulge in all the culinary goodness and eat all the things – Refer to the dining section above where we identify several places you can experience the gastropub culture of Boston.

See what we mean by the different types of activities you can engage in during your visit?!?! It’s incredible!

Attractive Neighborhoods

Reason 10 to love Boston - Attractive Neighborhoods
Beautiful Acorn Street in the Beacon Hill Neighborhood.

You can’t do any of the above without getting out in the lovely neighborhoods of Boston. There are 23 neighborhoods that makeup Boston’s 48 square miles. Each neighborhood is unique and so fun to explore. All have amazing food, gorgeous sights, and many activities.

We weren’t able to visit all of Boston’s neighborhoods during our stay, but listed below are the ones we were able to explore:

  • Charlestown – Located in the Boston Harbor and includes the end of Freedom Trail sights (Bunker Hill Monument and the USS Constitution Naval Ship), Warren Tavern, and the Museum of Science.
  • North End – Known as Little Italy with family-owned Italian restaurants and cannolis. There are more Freedom Trail sights as you walk along the narrow streets in this neighborhood.
  • Downtown – The heart of Boston and includes the Financial District and Theater District. It’s quite interesting as you meander through downtown to come across colonial burying grounds and other historical landmarks among the many tall skyscrapers.
  • Beacon Hill – This whole neighborhood has a European feel to it. You can admire the lovely cobblestone street on Acorn Street or plop into one of the Charles Street shops.
  • Back Bay – Boston’s high-end neighborhood with picturesque brownstones and lavish shopping on Newbury Street. This area got its name because it used to be part of the bay, but in the early 1800s the bay was filled in with land.
  • Fenway – Most notable for Fenway Park, where the Boston Red Sox call home and the oldest ballpark in America. The Fenway neighborhood also consists of several colleges, so there’s a large student population in this area. We can’t forget to mention the beautiful Isabella Stewart Gardner Art Museum is in Fenway as well.
  • South Boston – Includes the new up and coming area called the Seaport District which is along the waterfront and has many new hip restaurants, bars, and hotels. It’s also home to the Harpoon Brewery.
  • Cambridge – Technically not a neighborhood of Boston, but a neighboring city across the Charles River where the elite colleges Harvard and MIT are located. As mentioned in the dining area, there are endless opportunities of restaurants along Massachusetts Avenue.

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We were completely amazed by just how much we loved Boston; it definitely exceeded our expectations. We spent a little over a week in Boston and there’s still so much that we didn’t get to see.  It’s a city you can keep going back to and get something different out of it each time you go.

Hopefully, this post has encouraged you to venture to Boston and see all the things you, too, can love about Boston.

If you have been to Boston, is there something you particularly loved? Let us know in the comments section below or shoot us an email.

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We are RJ and Megan Barrett- A husband and wife team who are passionate for all things travel!
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Jake Armstrong
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