Best Things To Do in Boston for First Time Visitors

Boston Sign

Boston is such an exciting city to visit, full of history, cultural experiences and stunning architecture. No matter how many times I visit, I always seem to find something new to love about it. Making your way around a new city can be a bit challenging. That’s why I created this awesome Guide to Boston!

If you’re wondering how to best spend your time in Boston…keep on reading!  This Ultimate Guide to Boston will give you insight into the very best places to visit, eat and stay to make your visit to Boston amazing. 

Whether it’s your first time visiting Boston or you want to explore a new area, we have you covered. 

Copley Square Architecture
Trinity Church in Copley Square

One of the things I find fascinating about Boston is how the historic buildings are intermingled with all the modern day skyscrapers, blending the new with the old. It always brings a feeling of pride at how far we’ve come as a country.

No where else in the United States can you experience such breadth of colonial history and remnants of our country’s beginnings.

Boston is truly a special place with rich history, beautiful parks, and some of America’s best museums.

Get an Overview of the City

When I visit a new city, I love to take one of the bus tours when I first get there. It’s the perfect way to orient yourself and get an idea of what areas you want to explore more.

There are plenty of options for touring around Boston. All of them will take you on a narrated tour around the city and point out all the historic sites but each one is a little different. 

Old Town Trolley Tour

Old Town Trolley Bus

Old Town Trolley Tour is the longest running tour of the city and one of the most popular. With 18 stops along the route, you’ll drive through the most popular areas of the city and hit all the important landmarks and attractions. Hop on and off at any stop along the way or stay on for the full loop (about 90 minutes). What’s great about this tour is the viewing platform on this bus is raised, giving you a great view, and you get unlimited re-boarding all day!  

A day pass is about $50 and includes discount tickets on a Harbor Cruise, Ghosts and Gravestones tour and the Tea Party Museum. You can purchase tickets in the booth near Long Wharf.

Boarding: Pickup in front of Marriott Long Wharf, Aquarium or Boston Common at Park Street.

Boston Duck Boat Tour

Duck Boat in Copley Square

When you take a Duck Boat Tour, you’ll tour the city streets and then take a splash into the Charles River. You won’t be able to miss these colorful WWII style amphibious landing vehicles roaming around the city. Each one is uniquely named so ask your “ConDucktor” which one you’re on. You may even get lucky and get a chance to drive one in the water.

A Duck Boat tour runs a continuous 90 minute loop and does not allow you to hop on or off. Before you hit the road be sure to practice your “quacking”.

Boarding: Pickup your Duck Boat at the Museum of Science, the Prudential Center or the New England Aquarium.  

City View 

CityView Trolley Tours is another Hop On/Hop Off option. While this tour has only 9 stops, they are all at the most popular destinations. A CityView Trolley Hop On/Hop Off ticket is valid for one complete loop. There is also an option for a non–stop 60 minute tour.  

Tickets can be purchased online or by phone. Just print your ticket or show your e– ticket on your phone. CityView Tours offers discounted Boston Harbor Sightseeing Cruise with the purchase of any trolley tour. 

Boarding: Pickup your CityView Trolley Tour at Stop#1 at Atlantic Avenue side of the
255 State Street Building. 

Ultimate Guide to Getting Around Boston

Best Areas to Visit in Boston

While Boston is the capital of Massachusetts, the city is relatively small, making it possible to see the city’s highlights in just a few days. The city is made up of different neighborhoods, each with their own unique personality, history, attractions, and vibe.

View of Downtown near Waterfront

The city’s most prominent tourist area is around Boston Common, Faneuil Hall and the Waterfront. This is where you will find some of the most popular historic sights and waterfront attractions. That said, there are lots of historic sites, museums and attractions all across the city.  

What are the Most Popular Areas of Boston?

Let’s explore the most popular areas of Boston so you can plan a visit that is best for you.    

Downtown & Waterfront

Best area for History and Sightseeing

Downtown is the heart of Boston’s historic center and one of the most popular areas. The Waterfront area offers stunning views of Boston Harbor and lots of possibilities for getting out on the water. These areas contain the city’s biggest concentration of historic sites and attractions, making it ideal for first time visitors

From the Downtown/Waterfront area, you can easily access its surrounding neighborhoods, including North End’s restaurants, Beacon Hill, Back Bay and the newly revitalized Seaport District. 

Faneuil Hall Marketplace
Faneuil Hall Marketplace

Things to Do in Boston’s Downtown & Waterfront Area

Faneuil Hall is where you will find cobblestone walkways, historic restaurants, street performers and a bustling marketplace filled with shops and novelty push carts. While Faneuil Hall may be a bit touristy, it is certainly an area first time visitors should explore and experience. Check out Top 10 Must–Do Activities When You Visit Faneuil Hall for the best things to do while you are there. 

Boston Harbor Walk – This 43 mile walkway runs along Boston’s waterfront communities. Look for the signs to pick it up near the Marriott Long Wharf to enjoy some panoramic views. 

Stop by the Boston Harbor Hotel to see the iconic American flag hanging in the atrium. 

Check out the Arctic Harbor seals swimming in front of the New England Aquarium and go inside for a visit if you have time. 

Book a Boston Harbor Cruise tour (Discounted if you take an Old Town Trolley Tour) or another boat tour. There is something that is sure to fit your mood whether it’s a sunset cruise,  an exhilarating ride on Codzilla or a cruise on a historic Schooner. Visit the booths along the Waterfront and the Long Wharf to find out what types of boat rides and cruises are available.

Codzilla

Rose Kennedy Greenway – Walk along this green-space in the center of the road between Faneuil Hall and the waterfront to see fountains, a vintage carousel, food trucks, popup beer and wine gardens and ever–changing public art.

Christopher Columbus Park
Christopher Columbus Park

Christopher Columbus Park – Have a picnic at this spacious green-space overlooking Boston Harbor or stroll under the wisteria trellis. 

Holocaust Memorial – Spend a moment at this beautiful and moving memorial dedicated to the Holocaust victims. (Union Street) 

Eateries near Boston’s Downtown & Waterfront Area

Tia's Waterfront Dining
Tia’s Waterfront Dining

There are loads of restaurants around the Downtown & Waterfront areas.  Some popular ones include:

The Chart House – Upscale seafood and steakhouse on the water (60 Long Wharf)

Tia’s – Waterfront dining adjacent to Marriott Long Wharf (200 Atlantic Ave.)

Central Wharf Co. – Located close to the waterfront, this sophisticated restaurant sits in a 200-year old building with exposed brick and serves great seafood and drinks. (160 Milk St.)

Mariel’s – An elegant restaurant with Cuban inspired menu and decor set in the historic Atlantic National Bank. (10 Post Office Sq.)

For more dining ideas around Faneuil Hall, including the historic restaurants nearby check out our Top 10 Must–Do Activities When You Visit Faneuil Hall  

Where to Stay near Boston’s Downtown & Waterfront Area

Staying in the Downtown and Waterfront area will be most convenient to visit all the popular historic attractions.

The historic Omni Parker House is a great choice as it is situated on the Freedom Trail in between the Boston Common and Faneuil Hall.

Other options include:

Back Bay

Best for Shopping and Architecture

Brownstones on Commonwealth Ave
Brownstones on Commonwealth Ave.

Boston’s Back Bay area is an upscale neighborhood known for its Victorian–era brownstone houses and beautiful architecture.

This bustling area maintains a bit of an urban feel with a sophisticated side and offers upscale shopping, incredible dining options and a vibrant nightlife. 

The Back Bay is located alongside the Charles River, and behind the Boston Public Garden. 

Things to Do in Boston’s Bay Bay Area

Copley Square in Boston’s Back Bay has some of Boston’s best historical places, art and architecture. The square is named after famed American artist John Singleton Copley, who is memorialized with a bronze statue in the square near Boylston Street. This is where you will find Trinity Church, Old South Church and the Boston Public Library.

Boylston Street – the Boston Marathon Finish line is located on Boylston Street in front of the Old South Church. The Boston Marathon Memorial is a little further down on Boylston Street in front of Marathon Sports near Dartmouth Street. While wandering around Copley Square, don’t miss the Tortoise and the Hare statue, created by artist Nancy Schon, to recognize the many Boston Marathon race participants. 

Bates Reading Room - Boston Public Library
Bates Reading Room – Boston Public Library

Boston Public Library (700 Boylston St.) – The Boston Public Library’s McKim Building is an architectural masterpiece and should not be missed. Pop in to see the incredible architecture and paintings inside including the famous Bates Reading Room. The library is Free to visit. Closed on Sundays.

Trinity Church (206 Clarendon St.) – Founded in 1733, Boston’s Trinity Church is a National Historic Landmark. Each year over 70,000 people come to visit the church to see its elaborate exterior and ornate interior with beautiful stained glass windows. While visitors are welcome Thursday–Saturday 10:00 am – 5:00 pm, it is an active Episcopal church where parishioners gather daily to worship. Tickets for tours, concerts and music events can be purchased online. In springtime, hundreds of beautiful tulips will be in bloom in Copley Square, which is a site to see.  

Old South Church (645 Boylston St.)  The Old South Church is a magnificent work of Gothic Revival architecture which is open to the public to visit for Free

Commonwealth Avenue Mall
Commonwealth Avenue Mall

Commonwealth Ave – Wander down Commonwealth Avenue Mall to explore the statues and stately brownstone mansions along the way. This tree–lined green-space begins at the Arlington Street side of the Public Garden and offers a nice relaxing break from the action of Boylston Street.

Shopping – For some high–end luxury shopping, stop by Copley Place or the Prudential Center. Newbury Street is famed for its local boutiques and high–end shopping. On the eastern end, closest to the Public Garden you will find big–name designers like Gucci, Valentino, Chanel, Marc Jacobs, and Ralph Lauren. As you make your way down the street a few blocks, you’ll find more contemporary, affordable brands, including H&M. 

View Boston Observatory at the Prudential – The new observatory at the Prudential just opened in June 2023. Explore the 360 observation deck which offers a breathtaking view of Boston. 

Eateries near the Back Bay

OAK Long Bar & Kitchen at the Fairmont Copley Plaza
OAK Long Bar & Kitchen at the Fairmont Copley Plaza

The Oak Long Bar at Fairmont Copley Hotel has a stately atmosphere with dark wood which offers an elegant setting to enjoy drinks, raw bar and live entertainment. (138 St James Ave.)

Eataly – An Italian emporium filled with authentic Italian pasta, cheese, meats and pastries with an onsite restaurant and plenty of to–go options. (Prudential Center 800 Boylston Street)

Fire and Ice – An “all you can eat” experience where you choose the ingredients and it is cooked in front of you. (205 Berkeley Street)  

Sonsie is a very popular American bistro and wine bar on Newbury Street that has been around for over 25 years. (327 Newbury Street)

Where to Stay near Boston’s Back Bay Area

Beacon Hill 

Best for a Relaxed Upscale Vibe

Beacon Hill Mansions
Beacon Hill Mansions

The iconic Beacon Hill is Boston’s most prestigious neighborhood. Dating back to the early 19th century, this neighborhood was once home to Boston’s elite, including politicians, intellectuals, and prominent figures. As you wander through the picturesque streets lined with antique gas lamps and Victorian and Federal–style brick row houses, you will be transported to a bygone era. 

Beacon Hill gets its name from the beacon that once stood atop the hill, guiding sailors into Boston Harbor. The neighborhood is located off of Boston Common and borders the Downtown, Back Bay and Financial district. Staying in this area offers a quieter experience with attractions still nearby. Everything about this area emits romance. 

Things to Do in Boston’s Beacon Hill

Charles Street Boston
Charles Street

Charles Street – Take a stroll down this quaint street where you’ll find vintage boutiques, art galleries, eateries and charming antique shops.

Acorn Street –  Stroll down the most photographed street in Boston.  This quaint, cobblestone street is just a few blocks from the Public Gardens off Charles Street. 

Louisburg Square – This historic square, with its gas street lamps and cobblestone streets, is the most affluent section of Beacon Hill. Look for #19 which is the home to former Secretary of State John Kerry and #10, where author Louisa May Alcott lived until her death in 1888. 

Boston Public Garden – The Boston Public Garden was established in 1837 and is America’s first botanical garden. This Victorian–style garden, designed by Frederick Law Olmsted, is a tranquil green-space and the perfect place to relax.  

Swan Boats at Boston Public Garden
Swan Boats at Boston Public Garden
  • Meander around the sprawling tree-lined walkways and enjoy the beautiful flowers, weeping willows and other interesting trees throughout the park and surrounding the lagoon.
  • Take a walk over the Victorian Foot–Bridge.
  • Ride the famous Swan Boats around the lagoon (Mid– April through September).
  • See the famous George Washington statue (Arlington Street side).
  • Don’t miss the Make way for Ducklings statues (Charles Street side). You may even see them dressed up.

Boston Common – The Boston Common is considered to be the oldest public park in the United States. Originally, it was used for cattle grazing and even held public hangings. Today, the Boston Common is a popular green-space enjoyed year round by visitors and locals alike. 

The Boston Common is also the official start of the Freedom Trail. To learn more about the Boston Common and the Freedom Trail, see my Ultimate Guide to Boston’s Freedom Trail from a Local.

Boston Common

Charles River Esplanade – The Charles River Esplanade is a three–mile, 64–acre park that runs along the Charles River. To get there from the Public Garden you can take David G. Mugar Way (from the corner of Arlington/Beacon Street) and go over the Arthur Fiddler Bridge to the Esplanade. This is a great place to watch the sunset.

Events are held at the Hatch Shell, including the Fourth of July celebration with the Boston Pops Fireworks Spectacular. 

Eateries near Beacon Hill

Cheers Restaurant and Pub is the bar that inspired the hit TV comedy “Cheers”, starring Ted Danson (86 Beacon Street). Today, it is a popular tourist spot which serves up character inspired menu items and sells “Cheers” merchandise. Everybody may not know your name here (like the show), but it will be fun to visit. 

Alibai – Enjoy a cocktail or listen to some music at this trendy cocktail lounge, located in the old Charles Street Jail at the Liberty Hotel (215 Charles St.).

21st Amendment is a pub located next to the State House which serves up traditional pub food (150 Bowdoin St.). This eatery, named after the constitutional amendment, is still popular with politicos, lobbyists, and local media, but it also attracts tourists and Beacon Hill residents.

Carrie Nation Cocktail Club and Speakeasy
Carrie Nation Cocktail Club and Speakeasy

Carrie Nation Restaurant and Cocktail Club is a 1920 style speakeasy, located a few blocks behind the State House (11 Beacon St.). Dine in the main space or sneak back to the swanky lounge with plush leather seating, dark polished wood and billiards. 

Where to Stay near Beacon Hill

North End

Best for Italian Cuisine and Summer Street Festivals

The North End is a maze of narrow streets with some of the city’s oldest buildings and a few famous historic sites. Known as Boston’s “Little Italy” because of its large Italian population, the North End definitely lives up to its reputation.

There are amazing Italian restaurants, cafes and bakeries everywhere you turn and it is a very popular destination for Bostonian’s and visitors alike. 

Hanover Street - North End Boston
Hanover Street – North End Boston

The North End is an easy walk from Boston’s Waterfront. You can either follow the Freedom Trail markers or pick up Richmond St. at the end of the trellis structure in Christopher Columbus Park near Joe’s Bar and Grille. Just head straight down Richmond St. to Hanover St. which is the main street with the most restaurants.

Things to Do in Boston’s North End

The main draw of the North End is its famous Italian cuisine. This area is definitely a must-experience part of Boston. While you will find amazing cafes, bars, and restaurants throughout the neighborhood, the main concentration of eateries is on Hanover and Salem Streets.  

The Freedom Trail also winds through the North End where you can see the Paul Revere House (Site 12), Old North Church (Site 13) and the Copp’s Burying Ground (Site 14).  

Ultimate Guide to Boston’s Freedom Trail from a Local

Eateries in the North End

There are SO many great restaurants in the North End so you won’t go hungry but they do get very crowded. Making reservations is highly recommended, especially during the high season.

Some of the most historic and popular restaurants include:  

Cantina Italiana is the oldest restaurant in the North End serving classic Italian dishes since 1931.

Mamma Maria is a popular restaurant with rave reviews in the middle of North Square next to the Paul Revere House.

Ristorante Limoncello – Family owned with southern Italian recipes. 

Trattoria il Panino – Boston’s first original Trattoria offering fresh pasta with a late night menu. 

La Famiglia Giorgio’s – Family sized portions of all the classics.

Vinoteca di Monica Ristorante and Pasta Shop – A great selection of traditional favorites and home made pasta. Visit their Pasta Shop next door to get some to bring home. 

After Dinner Delights

Stop in Caffè Vittoria to enjoy a cappuccino, macchiato, latte or signature cocktail after dinner. This is Boston’s first traditional Italian café which opened in 1929.

Mike's Pastry

Save room to treat yourself to a cannoli or other treat at Mike’s Pastry or Modern Pastry –  either place is sure to satisfy your sweet cravings but be sure to bring CASH and be prepared to wait in line which at times is around the corner – but it goes fast and worth the wait.

Where to Stay near the North End

Charlestown

Best for Maritime and Colonial History 

Charlestown is a quaint waterfront town with Irish–American roots and a rich maritime history. 

The neighborhood features charming historical buildings and narrow streets that offer a glimpse into Boston’s colonial past. Most visitors come to Charlestown to finish off the last two stops of the Freedom Trail, but this area has much more to explore. 

Ultimate Guide to Boston’s Freedom Trail from a Local

Charlestown is on the northern side of the city and about a 30 minute walk from the North End. If you’re not up for walking, you can pick up a ferry from Long Wharf at the Waterfront that will bring you over to the Charlestown Navy Yard. 

Things to do in Charlestown

Charlestown Navy Yard: Take a stroll along the waterfront and explore the Charlestown Navy Yard and see the dry docks. Stop to admire the statues and sculpture art that is scattered around the Navy Yard. 

USS Constitution (Freedom Trail site #15) –  Tour “Old Ironsides”, the oldest commissioned warship afloat in the world. Admission is Free. 

USS Constitution at Charlestown Navy Yard

USS Cassin Young –  Explore a historic navy destroyer which served in World War II. Admission is Free.  

USS Constitution Museum: Stop in the museum to learn about the history of “Old Ironsides” and the United States Navy through interactive exhibits, artifacts, and engaging displays. 

Bunker Hill Monument (Freedom Trail site #16) –  Head over to Bunker Hill to climb the 294 steps to the top of the iconic Bunker Hill Monument to get panoramic views of Boston. 

Eateries near Charlestown

The Anchor is a fun wine and beer garden next to the Navy Yard. Enjoy free comedy on Sunday nights starting in May. (1 Shipyard Park)

The Warren Tavern is one of the most historic taverns in America. Step into this cozy restaurant for a cold one or for some great chowder or lobster mac & cheese. (2 Pleasant St,)

Pier 6 – An upscale restaurant that offers fresh seafood and other New England favorites with waterfront views. (1 8th St)

Where to Stay near Charlestown

Charlestown is a little off–the–beaten–path from the main sightseeing attractions with limited options for accommodations. 

Residence Inn by Marriott Boston Harbor on Tudor Wharf

Looking for a unique and more affordable place to stay while you’re in Boston? Consider staying on a yacht or houseboat where you get lulled to sleep by the gentle waves and wake up to incredible views of Boston Harbor. Check out Bed and Breakfast Afloat at Constitution Marina and Green Turtle to see if this is for you. 

Seaport District

Best for a Modern City Experience 

Boston’s Seaport district has undergone a huge rejuvenation over the last couple years and has been transformed into a bustling area with a cosmopolitan vibe.

Take a ride down Seaport Boulevard and you will feel the energy with the high rise hotels, restaurants and colorful art sculptures scattered along the roadways. For anyone who has not been to this section of Boston for a few years, you will be amazed at the difference. I know I was!

The Seaport is shiny and new so you won’t get the real feel of historic Boston staying in this area. It is also a little removed from the main sightseeing attractions. If you have time, definitely venture over to experience this new area once you explore the historic areas of Boston. 

Things to do in Boston’s Seaport District

Seaport Boulevard
Seaport Boulevard

Seaport Boulevard: Stroll along the glitzy Seaport Boulevard to explore the sleek restaurants, bars and colorful public art scattered about. This newly revitalized area evokes a sense of energy with its high rise hotels and countless options for fun.  

 The Lawn on DStop by Boston’s “Back Yard” for some outdoor fun with lawn games, illuminated swings, bocce ball and new Pickleball court. (420 D St,)  

The Pavillion – An outdoor amphitheater that hosts live performances and events from May through October. (290 Northern Ave,)

Institute of Contemporary Art – Visit the ICA to see some interesting exhibits. (25 Harbor Shore Drive)

Boston Tea Party Ships and Museum – Step back in time and enjoy a dramatic and interactive reenactment of Boston’s famous Tea Party. (306 Congress St.)

Open Air Market –  If you will be visiting during the holiday season, be sure to visit the SnowPort Holiday Market. This outdoor market is host to over 200 local artisans and vendors where you can pick up some unique gifts. SnowPort was such a success, there is also a Summer Market as well.

Eateries near Boston’s Seaport District

James Hook & Co. – This little shack on the edge of Seaport Boulevard has been serving the freshest lobster and New England favorites since 1925 and is said to have the best lobster roll in town.  (440 Atlantic Ave,) 

Lookout Rooftop and Bar – This Seaport restaurant atop of the Envoy Hotel offers killer panoramic views of the city as well as delicious options for small bites. Head downstairs to The Outlook which offers a full menu. (70 Sleeper St)

Row 34 is a hot spot with exceptional seafood, specializing in locally sourced oysters with its shucking station.  (383 Congress St.)   

Lucky’s Lounge – A speak–easy style underground bar which serves up an assortment of casual eats and comfort food in a lively atmosphere. While there is an address, there is no sign out front. (355 Congress St.)

The Barking Crab – The Barking Crab is a landmark Boston restaurant. This casual waterfront eatery offers fresh, local seafood and is a popular place for boaters to dock and eat. (88 Sleeper St.)

Where to Stay in Boston’s Seaport District

Stay in the Seaport District if you are looking for more of a modern city experience and not planning on exploring many of Boston’s historic sites. There is plenty to do in this area but you will have to travel to get to the main tourist areas.

Fenway– Kenmore Area

Best for Visiting Fenway Park and Nightlife

The Fenway– Kenmore area is home to Fenway Park, the home ballpark for the Red Sox, and the iconic Citgo sign which lights up Kenmore Square. While Fenway Park draws large crowds to this area, it is also where you will find some of the best museums.

With its large concentration of universities and lively restaurants, music venues and nightlife, this urban area of Boston is high energy and has a younger population. 

Things to do in Boston’s Fenway–Kenmore Area

Fenway Park (4 Jersey St,) – Fenway Park is the oldest ballpark in Major League Baseball and has been home to the Red Sox since 1912.

If the Red Sox are in town and you love baseball, try to get tickets to watch a game at this historic ballpark. You can also take the Fenway Park Tour to get up close and learn all about the history and legendary players. 

Boston Citgo Sign – This iconic landmark that overlooks Kenmore Square can be seen all around the city and has become a treasured beacon in the city since 1940. The sign changed to its current logo in 1965, lighting up the sky with neon lights. In 1983, it almost had its demise, but us Bostonians were outraged and protested. Thankfully, the sign was saved with a long–term commitment to protect it for decades to come. 

The MGM Music Hall is Boston’s newest live music venue in the Fenway area which hosts top pop artists like Bruce Springsteen, Bruno Mars and James Taylor. (2 Lansdowne St.) 

Museum of Fine Arts – The MFA is a world–class museum and one of the largest art museums in the country. The collection encompasses nearly 500,000 works of art, including art from ancient Egyptian to contemporary. It also hosts works by renowned artists like Monet, Van Gogh, and Rembrandt. (465 Huntington Ave.)

Isabella Stewart Gardner Museum – This unique museum showcases the personal art collection of Isabella Stewart Gardner with a gorgeous courtyard garden. It is also famous for the 1990 Art Heist where 13 paintings were stolen and never recovered. Today, empty frames still hang as a reminder of the loss of these precious works of art. (25 Evans Way) 

Courtyard Garden at the Isabella Stewart Gardner Museum
Courtyard Garden at the Isabella Stewart Gardner Museum

Symphony Hall – Experience world–class performances at Symphony Hall, the home of the Boston Symphony Orchestra. (301 Massachusetts Ave) 

Landsdowne Street – One of Boston’s most lively night time destinations where you will find lots of restaurants, clubs, bars and gaming rooms making it popular with the college crowd. 

Back Bay Fens – Stroll through this sprawling green-space which is part of the Emerald Necklace, designed by Frederick Law Olmsted. 

Christian Science Center Plaza – This impressive plaza with its reflective pool is the world headquarters of the Christian Science Church. Stop in the Mary Baker Eddy Library to see its world–famous Mapparium, an amazing 3D illuminated perspective of the globe. (Intersection of Massachusetts Ave, Clearway St, Belvidere St, and Huntington Ave.)

Eateries in Fenway–Kenmore Area

Cask ‘n Flagon – A legendary Fenway hangout since 1969 which is usually packed with Sox fans before and after games. (62 Brookline Ave.) 

Bleacher Bar – This upscale sports bar located inside Fenway Park overlooks the outfield. Plan it right and you can enjoy some great food while you get to watch the game for free!  (82A Lansdowne St,)

Loretta’s Last Call –  Get your country fix here with live music, weekly line–dancing, and other fun events. Loretta’s serves up country classics with a late night donut shop until 2:00am. (1 Lansdowne St.)

TimeOut Market –  Not sure what you want to eat? Time Out Market has you covered. This eatery offers selections from around the world including Italian, Mediterranean, Asian, and American influences. (401 Park St.) 

Where to Stay near Fenway–Kenmore Area

Staying in this area is not really recommended for First Time visitors since it is so far away from the heart of the city and historic sites and attractions. If you plan to take in a baseball game or visit one of the museums in the area, make it a day trip.

That said, here are a few suggestions just in case this is the spot for you. For all you Rock n’ Roll music lovers, check out the Verb.  

Best Time to Visit Boston

Boston is an amazing city to visit no matter what time of year. While Summer is the most popular time, the city awakens with beautiful flowers in the Spring and transforms into vibrant fall colors in the autumn. Winter can be cold and snowy but it can be magical as well with all the holiday glitter.

Bottom Line

A visit to Boston is an absolute must! It is truly amazing to learn about its history and admire the incredible architecture all around the city. As you explore the city, you’ll find each neighborhood is unique and offers a very different experience.

For First Time Visitors, the Downtown Waterfront area is where you will likely want to spend much of your time since that is where the majority of the historic sites are located.

The other must-see areas for a first timer would be Copley Square and the Beacon Hill area, including the tranquil Boston Public Garden and Boston Common. Of course, you will also need to experience at least one authentic Italian dinner in the North End while you are in town. Just be sure to make reservations and bring cash for a famous cannoli.

We can’t wait for you to come visit…Happy travels.

Explore More…

Ultimate Guide to Getting Around Boston

Ultimate Guide to Boston’s Freedom Trail from a Local

Top 10 Must–Do Activities When You Visit Faneuil Hall

Watch the Reenactments of the Battles of Lexington and Concord

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.