Free Self-Guided Food & Walking Tour of Boston (2024)

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boston self-guided food tour eats in north end, downtown and beacon hill

Looking for a self-guided food tour of Boston?

You’re in the right place!

After a few days of intensive foodie discovery, I put together this easy walking route featuring the city’s best food and fun sights so you can get a taste of Boston! And the best part? It’s totally free!

Lace up your tennis shoes and grab your camera, we’re about to explore Boston’s best restaurants and most delicious eats. Don’t forget to come hungry!


This food tour contains a whole lot of food so I recommend splitting the items amongst a group. If you’re on a Boston solo travel adventure, you may want to break up the route across multiple days.

The best part of doing this on your own is that it’s super easy to customize! Take a look at the 7 different stops and bonus location so you can eat your way through Boston. Bon appetite!

Ultimate Boston Food Tour

If flexibility is what you’re after, a self-guided tour will offer just that! But if you’d rather mingle with new foodie friends or learn Boston’s history and foodie secrets from a local tour guide, the Ultimate Boston Food Tour is the way to go.

This 3-hour tour will take you from downtown to the North End, with a few stops along the Freedom Trail so you can soak up the city’s most delicious flavors and important sites, all at once!

Food Stop #1: Coffee – Tatte Cafe (Beacon Hill)

tatte cafe and honey halva latte

Start your self-guided food tour with coffee from Tatte Bakery & Cafe, a beloved local establishment known for its chic ambiance, robust coffee beans, and tasty treats. I truly can’t get enough of this spot! They have so much food you could eat here dozens of times during your stay in Boston.

The Beacon Hill location, nestled among the quaint narrow streets and charming brownstones is the perfect place to people-watch while fueling up for the day ahead.

WHAT TO ORDER: I recommend trying the house special, the Honey Halva Latte. It’s lightly sweetened and flavored with a dash of cardamom. Super pleasant and unique. Don’t be scared off by the cardamom. The flavor is pretty subtle.

Feel free to grab a pastry to share or nibble on. The menu here is pretty epic and it’s impossible to go wrong so order whatever catches your eye!

beacon hill food tour stop

WHAT TO SEE: Meandering through the gorgeous Beacon Hill streets was definitely a highlight of my time in Boston. Make sure to check out Louisburg Square and Acorn Street. This adorable cobblestone street has earned the title of most Instagrammable spot in Boston. (So, yes, expect a short line. Worth it, though!)

When you’re finished exploring Beacon Hill, head up Charles Street until you reach Boston Public Gardens. Head towards the bridge to admire the swan boat-filled pond surrounded by weeping willows.

Cut over towards the connected Boston Common space and exit the park at Tremont St.

Food Stop #2: Boston Cream Pie – Parker House Hotel (Downtown)

boston creme pie from parker house hotel

Dessert for breakfast? Don’t mind if I do! You can’t visit Boston without trying the official state dessert, the Boston Cream Pie. (Because apparently state desserts are a thing?)

Where better to try this culinary classic than at the OMNI Parker House Hotel, the very place it was invented? Brought to life in 1856 by French-Armenain chef M. Sanzian, this beloved dessert consists of sponge cake filled with creamy custard and topped with a chocolate glaze.

WHAT TO SEE: The Parker House Hotel is also a historic landmark, having hosted famous guests such as Charles Dickens and John F. Kennedy. After you finish up, take a stroll through its elegant halls and admire the grandeur of this 19th-century hotel.

PRO TIP: Keep in mind the restaurants at this hotel close between 2:00-4:00. There’s a coffee shop on-site where you can buy a Boston Cream Pie slice, but they typically sell out before 10am each day.

Here’s where our food tour intersects with Boston’s Freedom Trail! Make sure you check out these iconic sites:

  • Boston Massacre Site: Spot the cobblestone ring that marks the 1770 event where British soldiers killed five colonists during a confrontation, an incident that fueled the flames of the American Revolution. (Cross street of State & Devonshire)
  • Old State House: The city’s oldest surviving public building, once the center of political lifein colonial Boston. Inside, you can explore a range of exhibits and artifacts that tell the story of the American Revolution.


If you’re visiting Boston, consider checking out these other destinations in Massachusetts:


Food Stop #3: Lobster Roll, Clam Chowder & Pizza – Quincy Market (Downtown)

exterior of quincy market

Next, make your way to Quincy Market, a food lover’s paradise in the heart of downtown Boston. Once a bustling 19th-century commerce center, today, this food hall is home to almost every type of food imaginable.

WHAT TO ORDER: We’re hitting up two iconic Boston restaurants, Boston Chowda and Regina Pizzeria, to try some of the city’s most well-known local favorites.

lobster roll and clam chowder from boston chowda

Boston Chowda: This iconic eatery has been a staple of Boston’s culinary landscape for over 30 years and has won the award for “Best Clam Chowder” at the Boston Harborfest a number of times over the years.

My favorite part, though, is the authentic Boston accent and attitude their workers have.

  • Lobster Roll: These hearty sandwiches, packed with succulent, fresh-from-the-ocean lobster, are a must-try in Boston thanks to its proximity to prime lobster fishing waters. Choose between two main styles: the cold, mayo-based “Maine” style, and the warm, butter-drenched “Connecticut” style. (IMO: Connecticut is the way to go!)
  • Clam Chowder: Boston’s clam chowder is legendary, offering a soul-warming blend of fresh, local clams, creamy broth, and hearty potatoes. Trust me when I tell you this is not the microwavable soup you’ve had at home!
regina pizzeria

Regina Pizzeria: Founded in 1926, Regina Pizzeria has been serving up its world-renowned pies from the same North End location in Boston for nearly a century. It has earned its reputation as the best pizzeria in the city due to its commitment to tradition, using fresh, locally sourced ingredients, and its secret family recipe for a crunchy, flavorful crust.

  • Pizza Slice: I recommend a slice of the Margherita: a simple yet sublime blend of flavors with fresh basil, mozzarella, and Regina’s signature tomato sauce.
  • Panzarotti: If you’re feeling adventurous, try their famous “panzarotti” – a deep-fried pizza pocket filled with cheese and toppings of your choice.

Food Stop #4: Oysters & Boston Lager (Downtown/North End)

oysters and boston lager

For this next stop, we’ll let our food digest while we sip on the iconic Boston Lager and try some of the area’s fresh oysters.

As far as where to go, you’ve got a couple of options. Everything is located in the same area of downtown Boston so you can choose to do some of the sightseeing below either before or after drinks.

Choose from the bars below or try more than one:

  • Bell in Hand Tavern: America’s oldest continuously operating tavern that has hosted countless patrons since 1795.
  • Union Street Oyster House: An iconic landmark in Boston’s Freedom Trail, boasting the title of America’s oldest restaurant since 1826.
  • Neptune Oyster: a renowned seafood restaurant in Boston’s historic North End, known for its chic, vintage setting and offering some of the city’s freshest and most sumptuous oysters.
  • Sam Adams Tap Room: a prominent fixture in Boston’s historic Faneuil Hall, offering visitors an authentic brewery experience at the very heart of the city where the renowned Samuel Adams beer was born.

WHAT TO ORDER: As the original beer recipe that started the Samuel Adams brand in 1984, the Boston Lager is recognized as a classic American full-bodied lager. It is brewed with two-row malted barley to give it its caramel notes, and Bavarian Noble hops to provide a slight bitterness and floral, citrus aroma.

WHAT TO SEE: While you’re in the area (and trying to work up an appetite again!) check out some of these iconic spots.

  • Faneuil Hall: Faneuil Hall, a hub for shopping, dining, and street performances, was a significant meeting place for the advocates of American independence and features a museum and armory of the Artillery Company.
  • Boston Public Market: The indoor Boston Public Market, located in the historic Haymarket district, offers a variety of fresh local produce, seafood, meats, baked goods, and crafts from over 40 local farmers, fishermen, and food producers.
  • Paul Revere House: The Paul Revere House, the oldest surviving structure in downtown Boston, offers visitors the chance to explore the former home of this key figure in the American Revolution.
  • Old North Church: The Old North Church, known for signaling the approach of British troops and initiating Paul Revere’s “midnight ride,” continues to hold regular services and offers tours to visitors.
old state house along the walking route for freedom trail

Freedom Trail Tour

Skipping out on the historic sites of the Freedom Trail would mean missing out on the most essential Boston experience! Joining a local guide and storyteller is an engaging way to learn more about the Boston Tea Party and exciting tales of America’s other founding fathers. Plus, you’ll save time by getting a front-of-the-line pass! Total score.

Stop #5: Italian Pasta & Cold-Cuts (North End)

street corner near hanover street in boston's north end neighborhood

I hope you saved some room, because now we’re heading to the North End, otherwise known as Boston’s Little Italy. Before visiting I had no idea that Boston was home to a thriving community of Italian immigrants and their incredible restaurants.

I’ve heard that New York City’s Little Italy is nothing but tourist traps these days, and after eating Boston Italian, I’m certain that’s correct. The food here seriously blew me away. I’ve never been a big fan of red sauce Italian, but now I know that’s only because I’d never had the good stuff!

italian grocery store in little italy

Salumeria Italiana: First, I recommend stopping in this adorable Italian grocery and sandwich shop. This shop is a true gem that’s been around since 1962. Split a sandwich, order charcuterie for a midnight snack or simply peruse the assortment of noodles, olive oil, and other sauces.

linguine with mussels and fracomo sauce from giacomo's in north end

Giacomo’s: I chose this cozy Hanover Street mainstay off a gut-feeling and boy am I glad I did. Little did I know, Giacomo’s is one of the most sought after restaurants in Boston, often with a line out the door seven days a week. I went at an odd time and was able to walk right in.

I tried the linguine with fracomo sauce and mussels and the fried mozzarella marinara. After one bite, my concept of good Italian has been forever changed! I couldn’t recommend this spot more.

Alternative Options: If the line is simply too long, I’ve heard great things about Mamma Maria and Daily Catch. But honestly, if you go anywhere on Hanover Street, you’re pretty much guaranteed a great meal!

PRO TIP: Keep in mind most of the restaurants in Boston’s North End are cash only. There are plenty of ATMs around, though.

Food Stop #6: Cannoli – Mike’s Pastry vs Modern Pastry (North End)

cannoli and the line outside mike's pastry shop

Ready for another line or two? I promise it’s worth it!

In the heart of Boston’s North End, a friendly competition known as the ‘Cannoli Wars’ rages on Hanover Street. Two famed Italian bakeries, Mike’s Pastry and Modern Pastry, vie for the title of ‘Best Cannoli in Boston’. Each shop has its devoted followers, and the debate over which establishment serves the superior cannoli is a cherished piece of local culture.

While Mike’s Pastry is known for its larger, creamier cannoli with a wide variety of flavors, Modern Pastry is revered for its smaller, crispier version that stays true to the traditional recipe. My personal favorite is Modern Pastry. Try both out for yourself and let me know if you agree!

Food Stop #7: Lookout Rooftop Bar

view from lookout rooftop bar on food tour

Whew, what a day! You saw some of Boston’s best sights and ate the best food this city has to offer! Now it’s on to our last stop for a sunset drink with an epic view of the Boston skyline.

I recommend walking down to Commercial Street and taking in the sights of the harbor while you make your way to Lookout Rooftop Bar in the Seaport District. If you’re into photography, stop by Fan Pier to snap a photo of the city view.

Sitting atop the Envoy Hotel, this is the best rooftop bar in Boston. Occupying almost the entire rooftop, there’s plenty of space and the view of downtown is truly unforgettable. Settle in and sip on a cocktail or beer as the sun goes down. It’s the perfect way to end your epic self-guided food tour of Boston.

Bonus Stop: Chinatown

chinatown main gate and macarons from bao bao bakery

Hot pot. Ramen. Hand-pulled noodles. Sushi. Dim Sum. I could go on. Boston’s Chinatown is a somewhat under-the-radar desintation, but this neighborhood truly has it all. Plus, Chinatown’s bakeries are all the rage.

It would be a crime for any foodie to visit Boston and skip out on Chinatown! So, of course, I had to include a few great places to explore. Here are some of the most highly recommended spots in Chinatown:

  • Hei La Moon Dim Sum: Dim sum is a traditional Chinese cuisine, typically served in bite-sized portions and accompanied by tea, featuring a diverse array of dumplings, buns, rolls, and other treats. I recommend trying the Shrimp Shumai or the Steamed Pork Buns.
  • Bao Bao Bakery & Cafe: Order the pineapple bun and thank me later.
  • Clay Pot Cafe: Try the clay pot rice that people in Hong Kong line up for hours to get a taste of, a rice-based casserole with various toppings and crunchy socarrat-esque bottom layer, similar to Spain‘s famous paella.
  • Mei Sum Bakery: For a little taste of Portugal, head to this local bakery and order the egg tart, a yummy take on the famous Portuguese pastel de nata.

PRO TIP: If you’re craving Bejing-style roast duck, keep in mind you have to order it in advance at most restaurants, but Peach Farm is the one exception!

Boston Self-Guided Food Tour Map

Use this map to help get from place to place while enjoying your free self-guided food and walking tour of Boston!



Sydney is a solo travel expert who’s extensively explored Spain, Portugal, Morocco, California, and more! She creates travel guides and itineraries to share everything she's learned about the Iberian peninsula through personal experience and exploration.

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1 thought on “Free Self-Guided Food & Walking Tour of Boston (2024)”

  1. Hello thank you for your article, I also travel a lot (I have this chance ,-)) but I do not yet know this city that I dream of discovering so thank you for your detailed page and look forward to leaving. Good luck. Take care ,-) Sarah


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