Boston Trip – Exploring History, Culture, and Seafood

This trip to Boston was a blend of heart and heritage — part family visit, part exploration. With deep family ties in the area, we’ve returned to Boston many times over the years, but this visit had special meaning. We came to reconnect with loved ones, celebrate a life well-lived, and honor memories that make this city more than just a destination for us.

While some of our time was spent with family, we also carved out opportunities to rediscover Boston’s rich history, iconic landmarks, and diverse neighborhoods. From scenic walks through the Public Garden to exploring cobblestone alleys in Beacon Hill, we balanced quiet reflection with the joy of experiencing the city’s timeless character. This page highlights some of the places we revisited and new spots we explored along the way.

During our visit, we were struck by the number of people navigating Boston with walkers or wheelchairs — particularly along the Freedom Trail and through Boston Common. It was a clear reminder that the city, despite its age and historic infrastructure, continues to attract travelers of all abilities.

Boston has made meaningful strides in improving accessibility, especially in popular tourist areas. Many museums, historical landmarks, and civic spaces offer ramps, elevators, and alternative entrances for those with mobility concerns. However, some challenges remain. Cobblestone streets and uneven sidewalks, especially in areas like Beacon Hill, can make getting around more difficult. While Boston’s public transportation system has seen accessibility upgrades — including elevators in many subway stations — not every station is fully equipped. Buses, on the other hand, tend to be more accessible and can be a reliable option for travelers with limited mobility.

 Transportation:

• MBTA: The Massachusetts Bay Transportation Authority (MBTA) provides accessible buses, subway stations with elevators and ramps, and The RIDE, a paratransit service. We did not have the opportunity to ride the MBTA during this trip, but we did notice that some of the older trains required a step-up from ground level. This would have required us to fold-up our wheelchair and carry it into the MBTA car. It’s worth noting that while many improvements have been made, some of the older subway stations are still in the process of becoming fully ADA-compliant.
• Boston Logan Airport: Offers accessible facilities, including restrooms, elevators, and shuttle service. We flew into Boston Logan from Washington Dulles and had no difficulties within the airport.
• Wheelchair-accessible taxis and ride-sharing services: Available in Boston. We found that both Uber and traditional Taxi services would send a van that contained a wheelchair ramp upon request.

 Public Spaces and Attractions:

• Freedom Trail: We traversed the trail from the Faneuil Hall area to the Boston Commons area; there were numerous areas where one had to be careful due to cracks in the concrete. All corners on all sidewalks had ramps which made it easier to navigate through. There was the occasional cobblestoned area, but primarily it was standard concrete sidewalk.
• Museums and Cultural Institutions: we took an Uber to the Museum of Fine Arts and found that the Museum was very well laid out to make accessibility easier. Elevators were well marked and larger than normal, exhibits had very good passageways to allow wheelchair transit, etc.
• Boston Parks: We visited the Boston Commons and even though there was the occasional concrete crack or bump, we navigated the park from one end to the other without any issues.

We decided to stay at the Canopy by Hilton Boston Downtown due to the hotel's location being adjacent to the North End and Faneuil Hall. This provided us with walking access to areas that we planned to explore in more detail.

To view our experiences there, click here to view our Canopy Hotel page.

Walking the Freedom Trail from Faneuil Hall to the Boston Commons and back was a goal we set for ourselves during our trip planning. We had done this walk on previous trips to Boston and wanted to recreate it - only this time I was in a wheelchair. We had read that most of the trail was reasonably accessible, with a few areas that were either bumpy, cobblestoned or just diffcult.

The Boston Freedom Trail is a 2.5-mile (4.0 km) walking route that takes visitors on a journey through the city's significant role in the American Revolution and early U.S. history. Originally envisioned in the 1950s by journalist William Schofield to aid visitors in finding key historical landmarks, it was formally established in 1951. The trail is easily identifiable by a distinctive red line painted or bricked onto sidewalks and streets, guiding participants through Downtown, the North End, and Charlestown. Beyond its Revolutionary War focus, the Freedom Trail serves as a broader introduction to Boston's complex history, including subsequent social and political movements.

The Freedom Trail features 16 historically significant sites, each an authentic treasure that has been preserved thanks to dedicated efforts. Among these are Boston Common, the oldest public park in the United States, and the Massachusetts State House. Visitors will also encounter prominent landmarks like the Granary Burying Ground, the final resting place of several signatories of the Declaration of Independence, and Faneuil Hall, often called the "Cradle of Liberty" for its role in pre-Revolutionary dissent. The trail continues to the historic North End, featuring sites like the Paul Revere House and the Old North Church, known for its signal that ignited Paul Revere's legendary ride. The trail concludes in Charlestown with the Bunker Hill Monument and the USS Constitution, the oldest commissioned warship still afloat.

Today, the Freedom Trail is a globally recognized attraction, drawing millions of visitors annually. It offers a compelling way to engage with American history, allowing individuals to literally walk in the footsteps of those who shaped the nation. Visitors can enjoy self-guided tours using maps or apps, or participate in guided tours led by costumed interpreters who bring the history to life. The trail caters to a wide audience, providing a valuable learning experience for families and individuals interested in the history of the American Revolution and beyond. While mostly accessible, some sections have stairs requiring alternate routes, especially for those using wheelchairs or strollers.

Although our primary goal was to enjoy the Van Gogh Exhibition, we were also interested in everything else this musuem had to offer. This is an easy museum to navigate in a wheelchair, as the access lanes in each exhibit area are spacious.

The Museum of Fine Arts (MFA) is a renowned art museum and is considered one of the most comprehensive art museums in the world. The MFA is open to a wide range of visitors and perspectives, aiming to inspire conversations and foster a sense of community through art.

 MFA Key Features

• Vast Collection: The MFA boasts a comprehensive collection of nearly 500,000 works of art, spanning ancient artifacts to contemporary pieces.
• Diverse Scope: The collection represents various cultures and time periods, including:
  • Art of the Americas: Features art from North, Central, and South America, spanning prehistoric times to the present day.
  • European Art: Highlights include masterpieces from the Middle Ages to the mid-20th century, with a focus on Dutch and Flemish painters and a large collection of Claude Monet paintings.
  • Asian Art: Offers a significant collection of Japanese, Chinese, Korean, and Indian art, considered one of the most distinguished in the Western world.
  • Ancient Egyptian and Nubian Art: Includes sculptures, sarcophagi, and jewelry from various periods.
  • Contemporary Art: Presents contemporary works in various media like painting, sculpture, photography, and more.
• Architectural Significance: The museum's building is a combination of neoclassical and modern wings, with the oldest section designed in 1909 in Beaux-Arts style and a newer West Wing (now the Linde Family Wing) designed by I.M. Pei.

 To see what others have said about the MFA, click here to view the Google Reviews;

Regina Pizzeria, located in the historic North End, is a landmark establishment renowned for its brick-oven pizza and storied past. Established in 1926 by Luigi D'Auria, it holds the distinction of being Boston's oldest pizzeria and has been a staple in the neighborhood for generations. Since the 1940s, the Polcari family has infused their own recipes and passion for quality ingredients into the operation, making Regina a beloved institution known for its thin-crust, Neapolitan-style pizzas. The original location at 11 1/2 Thacher Street is particularly well-known, embodying a sense of stepping back in time with its no-frills setting and dedication to traditional techniques.

What truly sets Regina Pizzeria apart is its unwavering commitment to producing a consistently excellent pizza, a hallmark of "Old School Boston" authenticity. The process involves a centuries-old oven, homemade dough aged 7-9 days, signature mozzarella, and a uniquely spiced tomato sauce featuring tomatoes grown specifically for the pizzeria. The atmosphere is lively and bustling, reflecting its status as a local favorite, drawing both loyal customers and tourists eager to experience a slice of history. While lines can form, the wait is considered worthwhile by many, offering a memorable dining experience focused on the quality of the pizza and the rich, authentic character of the North End location.

It is very famous in our family because Celeste's parents ate pizza from here often when they still lived in New England. Even after they relocated to Florida, they would often extoll the virtues of a pizza from Regina Pizzeria. Our goal of eating lunch here, was due in part to honoring Celeste's parents and in part because we knew the pizza was going to be great - and it was!

 To see what others have said about Regina Pizzeria, click here to view the Google Reviews;

Our goal in visiting Boston's North End was straight forward; we wanted to explore the old North Church area, visit Paul Revere's home, and eat lunch at the Regina Pizzeria. And explore everything in between.

The North End is one of the most vibrant and historically significant neighborhoods in Boston. It is renowned for being Boston's oldest residential community, with a continuous European settlement since the 1630s.

 Key aspects of the North End:

• Italian-American Cultural Hub: It is widely recognized as Boston's "Little Italy," with a strong Italian-American presence and a delightful atmosphere reminiscent of old-world cafes and restaurants.
• Historic Significance: The North End played a crucial role during the American Revolution. Important historical sites such as the Paul Revere House (Boston's oldest wooden house) and the Old North Church (Boston's oldest surviving church building) are located here. These sites are connected by the Freedom Trail.
• Culinary Destination: The narrow, lively streets, particularly Hanover and Salem Streets, are filled with numerous Italian restaurants, bakeries, and shops, attracting both locals and tourists seeking authentic Italian cuisine and sweets. Popular pastry shops like Mike's Pastry and Modern Pastry are famous for their cannoli. We can personally vouch for the Bova Bakery, as we had cannolis from there our first night and they were amazing!
• Unique Character: The neighborhood boasts a charming, old-world feel with its historic architecture, including tenement buildings built in the late 19th and early 20th centuries. Despite facing challenges like the Central Artery construction in the 1950s and recent gentrification, the North End maintains its strong sense of community and cultural heritage, especially through its Italian establishments and traditions.
• Points of Interest: Visitors can explore various sites beyond restaurants and bakeries, such as Copp's Hill Burying Ground (Boston's second-oldest cemetery), the Paul Revere Mall (also known as the Prado), and the Christopher Columbus Waterfront Park. Recreational spaces like the Mirabella Pool and bocce ball courts offer further opportunities for enjoyment.

 North End Accessibility The sidewalks are narrow in many places, with the occasional concrete cracks. The crowds make it challenging and some sidewalks are very narrow, but overall this is an interesting area to explore and we did not find any areas that were impossible to navigate.

 To see what others have said about the North End, click here to view the Google Reviews;

Boston is a city defined by its connection to the sea — and nowhere is that more deliciously evident than in its seafood. For our family, seafood in Boston isn't just a meal; it's a tradition that spans generations and geography.

Our most recent trip began with dinner at the downtown Boston Legal Sea Foods, a name that holds a special place in our hearts. Celeste’s mother was a longtime fan, and when a Legal location opened in Sarasota, it became a favorite stop — a comforting reminder of Boston’s culinary roots transplanted to the Gulf Coast. But being back at the original, just steps from the harbor, brought that connection full circle. The fresh catch, the bustling atmosphere, and the view of the water set the tone for our time in the city.

Boston’s seafood legacy runs deep. Decades ago, we had the unforgettable experience of dining at Anthony’s Pier Four, once perched proudly on the harbor and long considered one of Boston’s iconic seafood destinations. Though the restaurant is gone, the memory of that incredible lobster dinner — the best we’ve ever had — still lingers. It was the kind of meal that defines a city’s flavor.

Today, the seafood scene in Boston remains world-class, from the classic clam chowder to perfectly grilled swordfish and overstuffed lobster rolls. Whether you're dining in the historic Seaport District, grabbing oysters at Quincy Market, or discovering tucked-away spots in the North End, you’re never far from something fresh, local, and steeped in tradition.

If you're a seafood lover — or just curious what makes Boston’s reputation so enduring — don't miss the chance to experience it firsthand. For us, it’s a taste of the city’s history, its harbor, and a lot of family memories rolled into every bite.

 Seafood in Boston:

Boston is synonymous with fresh seafood, and for us, no trip to the city feels complete without indulging in a classic New England seafood meal. We kicked off our Boston visit with dinner at the downtown Legal Sea Foods restaurant — a modern favorite that continues to live up to its reputation. The atmosphere was lively, the service excellent, and the food? As fresh and satisfying as we remembered.

Our seafood tradition in Boston goes way back. Years ago, we had the best lobster dinner of our lives at the now-closed but iconic Anthony’s Pier 4 on the Boston Harbor. It was a family favorite and a special memory we still talk about today. Celeste’s mom, a seafood lover herself, was thrilled when Legal Sea Foods opened a location in Sarasota — proof of just how deep the Boston seafood legacy runs.

While we haven't dined at every seafood spot in town, we’ve rounded up a short list of top recommendations based on local acclaim and consistent reviews. Please note that the restaurant name is linked to their website and the "external link icon" is linked to that restaurant's Google Reviews;

• Legal Sea Foods – Multiple locations, reliably fresh, and a great intro to Boston seafood culture.
• Neptune Oyster – Tiny, always packed, but widely praised for its lobster rolls and oysters.
• Union Oyster House – A National Historic Landmark and the oldest restaurant in Boston, serving seafood since 1826.
• Row 34 – Industrial chic vibes and a menu full of oysters, beer, and innovation.
• The Barking Crab – Casual, open-air seafood shack experience right on the water.

Some of these restaurants we’ve personally enjoyed (like Legal Sea Foods and the late, great Anthony’s Pier 4), while others are top-rated local favorites we've researched to help visitors plan an amazing seafood experience in Boston. For a wider look, check out Boston’s top-rated seafood restaurants on Google.

Boston is a city steeped in history, culture, and charm — a place where you can walk the same cobblestone streets as American revolutionaries, explore vibrant waterfronts, and dive deep into some of the best museums in the country. Whether it’s your first visit or your tenth, there’s always something new to discover.

In the annals of human affection, few loves burn as brightly, or as chillily, as that of a New Englander for their ice cream. It's a devotion forged in the crucible of long, dark winters and tempered by the fleeting, humid summers, making every scoop a testament to enduring hope and the triumph of dairy.

One might imagine that a region accustomed to blizzards and the kind of wind that strips the paint off houses would shun anything cold. One would be wrong. So profoundly, deliciously wrong. The New Englander doesn't merely like ice cream; they integrate it into the very fabric of their being. It's a culinary constant, a comforting presence whether shoveling snow in February or swatting mosquitoes in July.

And OMG, the ice cream itself! It's not just frozen sugar water; it's an edible heirloom, a creamy monument to generations of dairy farmers and inventive parlor owners. Here, "homemade" isn't a marketing ploy; it's a sacred trust. The milk, often sourced from contented cows gazing out at picturesque stone walls, possesses a richness that translates into a depth of flavor bordering on the spiritual.

Forget your airy, whipped pretenders; New England ice cream boasts a density that requires serious spoon-work. Each scoop is a concentrated payload of pure, unadulterated joy. The flavors, while often traditional – your deep, dark chocolates; your vibrant, sun-drenched strawberries; your maple-walnut that tastes like a sugaring-off party in your mouth – are executed with an artisanal precision that elevates them to an art form.

Indeed, the semi-humorous aspect lies in the sheer, unwavering commitment. A New Englander will brave a Nor'easter for a double scoop of their favorite flavor. They will discuss the merits of various local creameries with the intensity of a political debate. And they will, without fail, offer you a bite, knowing full well that once you taste the creamy perfection, you too will be irrevocably drawn into the sweet, cold embrace of New England's most enduring love affair. Just try not to get brain freeze – it's a rite of passage, but a surprisingly painful one.

Boston offers a wide variety of excellent ice cream shops. Some top contenders include Toscanini's, known for unique flavors like burnt caramel and B3, and J.P. Licks, a popular local chain with classic options and a build-your-own topping bar. Other highly-regarded spots include Honeycomb Creamery, known for rich and refreshing flavors, and Ron's Gourmet, a classic choice in Hyde Park and Dedham. Please note that each ice cream shop "name" is a link to their website;

• Top-rated and Award-Winning Ice Cream Shops:

   Toscanini's Ice Cream: Known for its gourmet ice cream and unique, frequently changing flavors like Mango Sticky Rice and Carrot Cake. They have won "Best Ice Cream" multiple times, including in 2024, according to Boston Magazine. The "B3" flavor (brownie, brown sugar, brown butter) is particularly recommended.

   Crescent Ridge Dairy: Awarded "Best Ice Cream" by Boston Magazine in 2023, 2022, and 2019. Their Black Raspberry flavor won first place at the World Dairy Expo in 2022.

   J.P. Licks: A popular local chain celebrated for its homemade ice cream, unique flavors (like Peanut Butter Oreo), and generous portions. They were recognized as "Best Ice Cream" by Boston Magazine in 2021.

• Shops with Unique Flavor Options:

   Amorino Gelato: An Italian gelato shop famous for shaping its gelato and sorbet into flowers. They offer unlimited flavors per bowl.

   Van Leeuwen Ice Cream: Has multiple locations throughout Boston, known for unusual and rich flavors, with both dairy and vegan options available.

   North End Creamery: A small-batch shop with a focus on homemade flavors like cookies and cream, mint chip, and rum raisin.

• Other Notable Ice Cream Shops:

   Kimball Farm : Kimball Farm was voted best ice cream stand in Massachusetts in 2010 by USA Today. It also placed second in a "Best Of Mass Ice Cream" contest and in a Boston.com reader poll. This shop was my first introduction to New England ice cream, and I still enjoy returning here whenever I can.

   Emack & Bolio's Ice Cream: Emack & Bolio's is an ice cream chain known for its creative flavors, unique toppings, and rock-and-roll inspired atmosphere. Founded in Boston in 1975, it's a popular destination for ice cream lovers seeking adventurous combinations and a fun experience.

   Chill on Park: Features unique flavors like lavender honey and maple walnut, with a variety of options including sundaes and milkshakes.

• Special Mention Ice Cream Shop:

   Cape Cod Creamery: Cape Cod Creamery in Hyannis Port, MA, is a popular, family-owned ice cream shop known for its high-quality, homemade ice cream with flavors inspired by Cape Cod towns. It's a favorite among locals and visitors, praised for its delicious ice cream, friendly service, and Cape Cod-themed atmosphere. We can vouch for this shop, as we visited them during our Cape Cod explorations.

As of July 2025, Boston is ranked as one of the top 25 Hotel markets in the United States. There are 73 hotels located within the City of Boston in the following “Chain Scales”: 14 luxury hotels, 29 upper upscale hotels, 9 upscale hotels, 13 upper midscale hotels, 2 midscale hotels, 2 economy hotels, and 4 that are unclassified. We mention these numbers because it illustrates the diffculty in finding an accommodation that fits your requirements.

The Google Travel website allows us to create lists of hotels based upon varous "search filters" and we are going to utilize "price range" and "highest rated" as the search filters. Please note further that when we say "rated" we are referring to Google Review Ratings;

• Price range less than $200 per night:
• Price range between $201 and $400 per night:
• Price range greater than $401 per night:
• Highest rated (ignoring price) that are wheelchair accessible:
• Accommodations with parking (ignoring price):
• All Boston accommodations (no search filters):

If you want to perform your own research, then you could start with the last item above and apply your own search filters. We would suggest that if you are driving, downtown Boston is not an easy place to find parking that is reasonably priced. Here is a link to a Google Map displaying "public parking in downtown Boston"

There are approximately 1,803 restaurants in Boston (as of July 2025). The city offers a diverse range of dining options, including Italian, Mexican, and Pizza, among others. Boston is known for its lively dining scene with options for every taste and budget. So there is no "one single answer" to the question "where is the best place to eat in Boston". The answer depends upon your desired cuisine, the desired price, distance, etc, etc. So we are going to help you with your search by categoring a set of responses to that question about "where to eat in Boston" by providing you with a link to a set of Google Search Result pages for various cuisines. Each result list will already be sorted by Google based upon their Google Review Ratings. (Remember you can have Google re-sort these lists using their filters on the search results page);

• Seafood Restaurants in Boston:
• Italian Restaurants in Boston:
• Chinese Restaurants in Boston:
• Mexican Restaurants in Boston:
• American Restaurants in Boston:

• Steak Restaurants in Boston:
• Barbeque Restaurants in Boston:
• French Restaurants in Boston:
• Indian Restaurants in Boston:
• Thai Restaurants in Boston:

OK, so you've finished your meal and you want to walk a bit and find some good Italian Pastries, you are in luck because the North End has a very good selection. Here is a link to the "highest rated Italian Pastries in the North End" If you find that there is a line at Mike's Pastry (and there is almost always a line there), then consider visiting either the Modern Pastry Shop or Bova's Bakery. We can recommend Bova's as we've had cannolis there and they were fantastic!

Boston is a compact city, which makes it highly walkable — but also incredibly frustrating if you’re trying to drive. The street layout is a historic maze of one-ways, traffic circles, and unexpected dead ends, many of which date back to the colonial era. GPS apps help, but they can’t always account for sudden detours, confusing signage, or aggressive local driving styles.

Parking is another headache. Street parking is limited, often permit-only, and garages can be expensive or hard to find near popular attractions. If you're staying downtown, your best bet is to park once and explore on foot or via public transit.

Boston’s MBTA system ("the T") is the oldest subway in the U.S., and while some lines are aging, it remains an efficient way to get around. Trains and buses cover most of the city and neighboring areas like Cambridge, with single-fare options and day passes available for visitors. Rideshare services like Uber and Lyft are also widely available and convenient for reaching spots the T doesn't easily serve.

In short, unless you’re planning day trips outside the city, you won’t need a car to enjoy Boston — and you’ll likely be glad you didn’t bring one.

Boston’s public transportation network, operated by the MBTA and affectionately known as “the T,” includes subway lines, buses, commuter rail, and even ferries — making it easy to explore the city and surrounding areas without a car.

Subway & Bus Service:

The subway is the fastest way to cover long distances across the city, with color-coded lines that are fairly intuitive once you get the hang of them. Riders can purchase fares using a reusable CharlieCard (best for longer stays) or a CharlieTicket (ideal for short-term use). The MBTA mTicket App allows users to plan trips, check schedules in real time, and pay for fares directly from their phones. Buses are generally reliable and offer better accessibility than many of the older subway stations.

Commuter Rail:

If you're planning a day trip to places like Salem, Concord, or even Providence, the MBTA's Commuter Rail system is a comfortable option. While service is less frequent than the subway, the trains are spacious and scenic. Tickets can be purchased through the same mTicket app, keeping things simple and convenient. Celeste and I used to ride the Fitchburg Line into Boston from Ayers, MA. We parked our car at the Ayers station and then once we got to Boston, we would ride the "T" to whatever destination we wanted to get to.

The RIDE:

For individuals with disabilities who cannot use the bus, subway, or trolley, the MBTA offers a door-to-door shared ride service called The RIDE.

Ferry Service – A Scenic Surprise:

One of Boston’s most underrated transportation options is its ferry network. The ferry route from Long Wharf to Hingham in particular offers an affordable and unexpectedly scenic cruise through Boston Harbor. It’s a great way to beat the traffic while enjoying skyline views and sea breezes — and for the price of a standard transit fare, it’s an experience in itself.

For unlimited subway, bus, and ferry rides in a single day, consider purchasing a CharlieCard day pass, especially if you’re planning to explore multiple neighborhoods or take a round-trip ferry.

Consider downloading apps like MBTA Go to check real-time schedules and plan your trips efficiently. You can also use apps like ParkBoston to pay for metered parking.

Boston is an interesting place to visit, however it is important to plan your trip there in order to make the trip as enjoyable as possible. Since it would be almost impossible for any single web page to tell you everything there is to know about Boston, here are some informative links for you to utilize for your own research - many of these we utilized for our own trip;

• Just Traveling Thru Travel Planning Tips
• Youtube Search Results list for "Boston, MA"
• Google search results list for "Accommodations in Boston, MA"
• Google search results list for "Restaurants in Boston, MA"
• Google search results list for "Boston, MA Shopping"
• The creation of some portions of this page's narrative text were assisted by OpenAI. (2025). ChatGPT [Large language model].
• Visit our Youtube Channel
• Our Image Gallery for Boston
• Wikipedia Article for Boston

• Google Image Gallery for Boston
• Google Reviews for Boston, MA

 Boston Tours via GetYourGuide  Boston Tours & Excursions via Viator