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  • Writer's pictureSamantha Diaz

The Ultimate Travel Guide to Boston, Massachusetts

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Hey everyone! I'm excited to share my Boston travel guide with you all. Many of you have been asking for recommendations on what to do in this amazing city. The great thing about Boston is that it's a perfect destination, even if you're not a big fan of big cities. With its small size, you can easily explore numerous hidden gems in just a long weekend. Although exploring Boston thoroughly takes more than 24 hours, I have a feeling that even after a day, you'll be craving for more time!

Calling all history buffs, culture vultures, and foodies! Boston is the ultimate dream destination for you. This vibrant city boasts an incredible food scene, expansive green spaces, charming neighborhoods, and top-notch museums. What makes Boston even more appealing is that it offers all the perks of a big metropolis without the overwhelming hustle and bustle of New York. Just hop on the subway, and you can easily navigate your way around. But don't forget to pack comfortable shoes, because if you're up for it, walking is a fantastic option. Boston's compact layout and sidewalks on both sides of every street make it an ideal pedestrian-friendly city. Get ready to immerse yourself in the rich history, cultural wonders, and delectable cuisine that Boston has to offer!

In this travel guide, I'll be covering the best places to stay, where to find delicious food, and what activities to enjoy. I'll also highlight some of my favorite spots in the city so you can experience the best of what Boston has to offer! If you have any specific requests or questions about anything related to Boston, feel free to ask me. I'm here to help make your Boston trip unforgettable!


Do I need a rental car when visiting Boston?

No! One of the best things about Boston is that it’s a very small city that’s easy to navigate. If you’re coming from the airport, you can either take a cab or an Uber. The Silver Line train is also free to South Station when you leave the airport. I find that Ubers are less expensive than taxis when leaving the airport, and they are more convenient because you don't have to wait for one at the airport or stop along the way.

Getting Around Boston

Don’t rent a car! The MBTA (Boston’s public transportation system) is the oldest subway in the nation, but it’s also straightforward and especially convenient during rush hour or to/from a game. I suggest buying a roundtrip CharlieTicket from a subway vending machine to start. The fare cost is the same regardless of which stop you get off at. You can always add more money for additional trips. Otherwise, this town was made for walking! The city is extremely compact, and if you stay in a central location, most attractions are within a 30-minute walk. For nights out, Ubers and Lyfts are always available.

Things to Do in Boston, Massachusetts

Walk Along the Freedom Trail

The Freedom Trail is a 2.5-mile walking route through downtown Boston, Massachusetts. The path leads you to past attractions relating to the city's founding, as well as the events of the Revolutionary War. There are markers and signs along the way to help you follow the trail. The Freedom Trail begins in Boston Common, America's oldest public park, and ends at Bunker Hill Monument. You can pick up a map and guide at Faneuil Hall or the Boston Common Visitor Center at 139 Tremont Street. Admission is charged for some sites along the trail, but others are free.

Along the way, you’ll visit 16 historic Boston landmarks:

  1. Boston Common: Where the first white settler set up a farm and America's oldest city park is located, dating back to 1634.

  2. Massachusetts State House: The State House is a federal-style building with an iconic gold dome that celebrates independence and was designed by America’s first. professional architect Charles Bulfinch is a major landmark in Boston.

  3. Park Street Church: Where William Lloyd Garrison called for the end of slavery in the United States.

  4. Granary Burying Ground: The final resting place of famous Patriots, including Paul Revere.

  5. King’s Chapel Burying Ground: The graveyard used by Loyalists.

  6. Benjamin Franklin statue and a mosaic commemorating Boston’s first public school at Old City Hall, where the Boston Public Library now stands.

  7. Old Corner Bookstore: Once the epicenter of Boston's literary scene.

  8. Old South Meeting House: Where the Patriots led the Boston Tea Party.

  9. Old State House: The seat of the colonial government of the British Empire.

  10. Site of the Boston Massacre: When British troops fired on (or "attacked") tax protestors.

  11. Faneuil Hall: Boston’s most popular marketplace is also a National Historic Landmark where Patriots once gathered to protest British taxation.

  12. Paul Revere House: the house of the esteemed patriot, Paul Revere.

  13. Old North Church: Revere launched his famous Midnight Ride from this church. He arranged to have lanterns perched on the steeple to warn that the Redcoats were coming.

  14. Copp’s Hill Burying Ground: The man who hung the lantern rests here.

  15. USS Constitution: The historic ship known as Old Ironsides is now a free museum, offering visitors a chance to explore the past.

  16. Bunker Hill Monument: A granite obelisk marks the spot where American Patriots fought British soldiers in the first pitched battle of the American Revolution.

To take a guided tour of the Freedom Trail and other historical sites, click this button below.

Fenway Park

No trip to Boston is complete without experiencing a Red Sox game at Fenway Park, the oldest and most iconic baseball stadium in Major League Baseball. The Fenway-Kenmore neighborhood around the park offers a vibrant atmosphere before and after the game.

TD Garden

TD Garden, located nearby, is the home of the Boston Celtics and Boston Bruins, hosting thrilling sports events and concerts. The area is also filled with restaurants, bars, shops, and attractions like the Emerald Necklace parks and renowned museums. Don't miss out on the unforgettable experience of Fenway Park and its lively surroundings!

Boston Public Library

For an architectural and historical treat, a visit to the Boston Public Library is a must. The library's courtyard, in my opinion, is one of the most stunning spots in the city. While exploring, you may stumble upon a hidden gem, The Courtyard Restaurant. It's not as widely known, but they offer a delightful afternoon tea experience. It's perfect for a fun girls' trip, although it might not be as appealing to the guys unless they're up for a relaxing time!

Newbury Street

Newbury Street is a bustling hub in Boston, renowned for its vibrant shopping scene. The street is lined with an array of restaurants and shops on both sides, making it a must-visit destination. Even if shopping isn't your priority, it's still worth exploring for the fantastic people-watching opportunities and to indulge in delicious dining options.

North End

The North End is the epitome of Boston's culture and charm. This vibrant neighborhood encompasses everything that defines the essence of the city for me. The friendly locals will warmly greet you at every turn, while the neighborhood's reputation as "Little Italy" promises a delectable culinary experience. If you venture to the outskirts, you'll be rewarded with breathtaking ocean views. Moreover, the North End is steeped in rich history, adding another layer of fascination to this beloved neighborhood. It's no wonder I hold the North End so close to my heart.

Beacon Hill

Beacon Hill, without a doubt, holds an irresistible charm that makes it one of Boston's most enchanting areas. And if you're seeking pure cuteness, look no further than Acorn Street, which could easily contend for the title of the most adorable street in the entire United States. In Beacon Hill, you'll find everything you love about a city—historic significance, architectural beauty, and an undeniable charm—all nestled within a quaint neighborhood. Stepping foot in Beacon Hill feels like a delightful journey back in time, with its cobblestone streets, delightful flower boxes, and elegant row houses crafted from beautiful brick. While there are fantastic restaurants and charming shops in Beacon Hill, we recommend taking a leisurely stroll to appreciate the neighborhood's stunning homes. Wander along the likes of Acorn Street, Pinckney Street, Marlborough Street, and Myrtle Street, and you'll quickly understand that Beacon Hill offers much more than just dining and shopping—it's a treasure trove of architectural wonders waiting to be explored.

Coffee Shops in Boston, Massachusetts

Tatte Bakery and Café

When it comes to my go-to casual coffee spot in Boston, Tatte takes the crown. With its numerous locations scattered throughout the city, this place is adored by both locals and tourists of all ages. Not only is Tatte incredibly Instagram-worthy, but it also offers a stellar selection of coffee, pastries, egg sandwiches, avocado toast, and much more. Just like "latte," I pronounce it as Tatte. If you're looking for the perfect brunch spot, this is my top recommendation. With its widespread presence, you're likely to find a Tatte location within a mile of wherever you're staying.

Modern Pastry

For pastry and coffee enthusiasts, there's no better place than Modern Pastry. This beloved family-owned bakery has been delighting taste buds since 1930 when the Picariello family brought their Italian recipes and warm hospitality to Boston. Honoring traditions from over 150 years ago, they continue to employ old-world methods that have made them a cherished establishment in the North End. While the bakery is often bustling, they offer both table service and to-go orders. If you're in need of a well-deserved break after exploring Boston, I recommend grabbing a seat at one of their bistro tables. Treat yourself to their delectable pastries alongside a cup of coffee and savor a truly satisfying experience.

Flour Bakery + Cafe

Prepare to be delighted by Flour bakery + cafe, a wonderfully quirky establishment founded by the talented Joanne Chang back in 2000. With multiple locations sprinkled throughout the city, Flour seamlessly combines French and American culinary techniques to bring you an irresistible array of pastries, cookies, tarts, as well as satisfying sandwiches, soups, and salads for those moments when your taste buds crave savory delights. It's no surprise that Flour has garnered global acclaim, earning accolades from renowned culinary and travel publications. Celebrity chef Bobby Flay himself counts among the many admirers of Chang's delectable sticky buns. Not only is Chang a James Beard Award-winning Outstanding Baker, but she has also graciously shared her expertise through five remarkable cookbooks. The beauty of Flour's numerous locations is that you'll likely find one nestled in almost any neighborhood you're exploring, ensuring that a delightful Flour experience is always within reach during your sightseeing adventures.

Where to Eat in Boston, Massachusetts


Immerse yourself in the Parisian charm of Frenchie, a French-inspired restaurant that exudes a delightful ambiance. With a lovely outdoor patio, it's the perfect spot to savor their signature frosé, a refreshing frozen rosé cocktail served on tap during the summer. Gather your girlfriends and indulge in their delectable Nutella crepe. And let's not forget about their irresistible coffee—it's simply delicious.

Union Oyster House

For the ultimate dining experience in Boston, a visit to Union Oyster House is a must. As the oldest continuously operating restaurant in the United States, it has welcomed influential revolutionaries, politicians, and celebrities over its two-century history. From John F. Kennedy, who frequented the establishment every Sunday, to Meryl Streep, this iconic restaurant has hosted many notable figures. And there's a good reason for its enduring popularity—the food is incredible. Sample their famous oysters and treat yourself to one of their hearty seafood dishes. In fact, it was recognized as the North American Best Landmark Restaurant in 2020 by the World Culinary Awards.

Bricco Salumeria & Pasta Shop

In the North End, where many Italian Americans settled, you'll find Bricco Salumeria & Pasta Shop—a testament to Boston's Italian heritage. Founded by Frank DePasquale, who hails from a town near the Amalfi Coast, this establishment offers an array of authentic Italian products, from imported meats to olive oil and cheese. Whether you're picking up supplies for a homemade Italian dinner or stopping in for a sandwich, Bricco won't disappoint. Indulge in their Italian sandwich, filled with mortadella, Genoa salami, and soppressata, all nestled in freshly made bread.


When in Boston, a visit to Toro is a must. This Spanish-inspired restaurant, helmed by Ken Oringer and James Beard Award-winning chef Jamie Bissonnette, offers a delectable tapas-style menu with a focus on Barcelona-inspired plates. Grab a friend or two and revel in a shared dining experience, savoring a variety of their enticing dishes.

Neptune Oyster

For oyster enthusiasts, Neptune Oyster in the North End is an absolute gem. Known for serving some of the freshest seafood in Boston, with a specialization in East Coast oysters, it's a haven for seafood lovers. In fact, they were semifinalists for the James Beard Award for Outstanding Restaurant in 2020. As the seats are highly sought after and reservations are not accepted, I recommend arriving early, putting your name on the list, and taking the opportunity to explore the neighborhood. Nearby, history buffs will appreciate the Paul Revere House, offering insights into the American Revolution.


Lemoncillo is a delightful addition to the list of Boston's culinary gems. This charming Italian restaurant offers a warm and inviting atmosphere, coupled with a menu that celebrates the flavors of Italy. Lemoncillo is known for its skillfully crafted dishes that showcase fresh ingredients and traditional recipes. From homemade pasta to mouthwatering seafood and delectable desserts, their menu promises a memorable dining experience. With attentive service and a cozy ambiance, Lemoncillo provides the perfect setting for a romantic dinner or a gathering with friends. Don't miss the opportunity to indulge in their exquisite Italian cuisine during your visit to Boston.

Where to Stay in Boston, Massachusetts

Navigating Boston is a breeze with its convenient public transportation system, taxis, and ride-sharing apps. When choosing a place to stay in Boston, it's essential to consider your trip's purpose and preferences. The Back Bay area is perfect for those with a packed itinerary as it boasts a central location near popular tourist attractions and excellent dining options. This area is highly recommended for young couples, food enthusiasts, and anyone looking to make the most of their time in the city. Back Bay's convenient positioning makes it an ideal base for exploring all that Boston has to offer.

If you're traveling with children, older family members, or interested in experiencing tourist hotspots like the Boston Aquarium, Faneuil Hall, Quincy Market, the North End, or the Waterfront, staying near the Financial District, North End, or Waterfront area might be more suitable. However, it's worth noting that Boston's compact size allows for easy exploration, regardless of the neighborhood you choose to stay in.

Below are some highly acclaimed hotels in the city, each receiving over 4-star ratings on TripAdvisor. While I haven't had the opportunity to personally stay at these hotels yet, they come highly recommended by fellow travelers and are known for their exceptional locations and service. When I get the chance to experience them myself, I'll provide you with a comprehensive review, which I believe will be the best source of information.

  • The Ritz-Carlton

  • Lenox Hotel

  • W Boston

  • InterContinental Boston

  • The Revere Hotel

  • Mandarin Oriental Boston

  • The Westin Copley Place

  • Loews Hotel Boston

  • Boston Harbor Hotel

  • The Envoy Hotel

  • The Colonnade Hotel

  • Boston Park Plaza

  • Taj Boston

  • Kimpton Nine Zero Hotel

Choose from this esteemed selection of hotels to ensure a memorable stay in Boston.

Best Time to Visit Boston, Massachusetts

Boston is particularly enchanting during the months of September, October, and November. Fall foliage paints the city in stunning hues, making it a perfect time to visit if you appreciate the beauty of changing leaves. For cooler temperatures, October is an ideal month to explore the city. However, if you're planning a trip in November, it's worth noting that the weather can vary from year to year. Some years may bring warmer temperatures, while others can be cooler. It's wise to pack a range of clothing options to accommodate both warm and cool weather during your visit.

Additionally, if you have a sweet tooth and love donuts, make sure to stop by Red Apple Farm. Their apple cider donuts, available year-round at their shop inside the Boston Public Market, are a delectable treat that should not be missed. Insider tip: Don't leave without indulging in these delightful treats while you're in Boston!

Discover the captivating charm, rich history, and culinary delights of Boston, Massachusetts! From exploring historical landmarks to indulging in a vibrant food scene, this city has it all. Whether you're a history buff, a culture enthusiast, or a foodie seeking new culinary adventures, Boston is sure to captivate your senses. Don't miss out on the chance to immerse yourself in this extraordinary city. Grab your guide and embark on an unforgettable journey through the wonders of Boston!


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Hi, Thanks for stopping by!

I'm Samantha! A photographer and I believe that every picture has a story. As a blogger, I share my travel stories with everyone. I think it's important to document my travels and share my experiences with others. I've been to some amazing places and I've seen some incredible things. I want to share my stories and photos with the world.

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