Boston City Guide
Boston is such a beautiful city with so much to see and do!
My daughter Rebecca lived there for seven years and we loved getting to know Boston while she was there! From the Boston Harbor to beautiful museums to fabulous food, there is something for everyone! I asked Rebecca to put together a city guide for Boston since she knows the city so much better than I do and this is the ultimate guide for anyone who loves to travel in style! I hope you enjoy this guide and that it makes planning your next trip to Boston easier!
Stay
Fairmont Copley Plaza - The Fairmont is one of the most iconic hotels in Boston. First opening in 1912, the Fairmont has old-school elegance and charm but has kept the guest rooms updated with traditional elegant furnishings and art that adds a modern touch. They have a lovely lobby bar - the OAK Long Bar + Kitchen with great cocktails and delicious food including homemade pizza. The interior of the hotel is gorgeous and grand and the lobby is always buzzing with guests and events being hosted in the beautiful event spaces.
If you book a stay at the Fairmont, be sure to ask for a room overlooking Copley Square and enjoy one of the incredible breakfast options on the extensive room service menu while taking in beautiful city views.
Images below from pleasantholidays.com
The Newbury - Situated on the picturesque corner of Newbury and Arlington streets, the Newbury Boston is a newer hotel in the City. The historic building was originally the first-ever Ritz Carlton Hotel, opening in 1927 which later became the Taj Boston before the building was purchased and renovated between 2019-2021. The property has 286 rooms including 90 suites, some with wood-burning fireplaces and sweeping views of the downtown skyline across the Boston Common. All rooms are spacious and the suites offer impressive views, massive marble bathrooms with double sinks, and separate shower and tub.
This stylish boutique hotel has a beautiful rooftop restaurant on the 17th floor, Contessa. The food is excellent but the spot has become quite popular and books up weeks in advance so be sure to make a reservation! They also have a wonderful lobby bar -Street Bar where you can grab a cocktail before a night on the town!
Images below from thenewburyboston.com
The Langham Boston - In the heart of Boston’s Financial District, the Langham Boston offers style and comfort in this luxury hotel. The building was once Boston’s U.S. Federal Reserve Bank, originally built in 1922. Langham took over the building in the 1980s after the Federal Reserve moved down the street and the hotel operated for many years before closing for a two-year renovation in 2019. The hotel now offers even more beautiful rooms with rare comforts like velvety soft robes, cozy beds, and an impressive minibar stocked with local beers, craft ciders, and French wines.
The Langham has a beautiful cocktail bar and a delicious Italian restaurant in the former bank’s grand hall. The restaurant - Grana is a grandiose atrium adorned with French chandeliers, and original stone floors, and such a fun spot for breakfast, weekend brunch, 0r lunch.
Images before from langhamhotels.com
The Charles Hotel - If you are looking for a place to stay in Cambridge, look no further than The Charles Hotel. A long-standing favorite for academics, politicians, artists, and celebrities, the Charles Hotel is a true taste of New England. With handmade quilts hanging in common spaces, wainscoting, plaid carpeting, and wood paneling, your stay is sure to be cozy and comfortable. They offer 24-hour room service, (I recommend the pie of the day), and have an award-winning restaurant as well as a renowned jazz club, Regattabar, that hosts some of the top jazz musicians from around the world. The library is stocked with biographies that pay tribute to famous past guests including Barbra Streisand, Bill Clinton and Hillary Clinton, Ben Affleck, and even the Dalai Lama. With the charm of Harvard Square, amazing restaurants nearby and the beautiful Harvard Campus just steps away, The Charles Hotel is a wonderful place to stay!
Images below from booking.com
The Liberty - The Liberty is a beautiful and unique hotel within walking distance of the charming streets of Beacon Hill, the Public Gardens and Newbury Street but it has a very interesting history. The building was originally built as a jail in the mid-1800s and for nearly 140 years housed some of Boston's most notorious criminals. On Memorial Day weekend, 1990, the last prisoners were moved after revolting due to poor living conditions. After years of design work and remodeling while maintaining the architectural integrity and history of the building, The Liberty Boutique Hotel was opened in 2007 and became an overnight sensation.
Today, the former jail is a beautiful example of old meets new. The design is contemporary American with a gentle nod to the building's history with comfortable rooms complete with a mini-bar stocked with Veuve Clicquot and sweeping views of the Charles River. The hotel has a great open bar on the second floor and three restaurants, Alibi, Clink, and Scampo. With so much to do and see near by, this is a great place to stay if you are looking for a unique, yet luxurious experience.
Images below from libertyhotel.com
Eat
O Ya - This sophisticated Japanese and sushi spot is one of the best restaurants in the city. Nestled into a quiet street outside of Chinatown, O Ya offers the freshest and most authentic sushi and Japanese cuisine found in Boston. Local food critic Jolyon Helterman has described the food as having a similar effect as viewing art by Rothko as “sublime” and if that does not convince you this is a great spot, it is Blake Lively and Ryan Reynolds favorite restaurant in the city.
While the food and atmosphere are excellent, O Ya doesn't come cheap, as the signature 20-course omakase will run you $295. However, if you enjoy authentic sushi, a beautiful space, and exceptional service, O Ya is well worth the cost!
Images below from cntraveler.com
Contessa - This high-end Italian spot located in the Newbury Hotel has become Boston's new hot spot! Owned and operated by Major Food Group, the same company behind NYC's acclaimed Carbone, Contessa is just as delicious, beautiful, and equally as hard to score a coveted table so be sure to book in advance! With panoramic views of the Boston skyline, oversized pink fringed lamp shades, and touches of brass, emerald, and velvety rose furniture, Contessa is an Instagram-worthy dining experience! Not only is a beautiful, the food is delicious! Be sure to try the spicy lobster capellini and truffle pizza! They also have a wonderful brunch.
Images below from contessaristorante.com
Neptune Oyster - When in New England you have to have oysters or a lobster roll at least once during your visit and Neptune Oyster is the perfect spot! Located on Salem Street in the charming Italian district known as the North End, this well-known spot will often have a line down the street in the warmer months as Neptune take walk is walk-ins-only and is very small. The tiny interior has a nautical vibe with shiny subway tile, marble tabletops, and tin ceilings. They have wonderful seafood but are known for the oysters and be sure the at least try the lobster roll, hot with butter or cold lobster salad, Both are delicious and possibly the best in town! Pair with some salty fries and a glass of rose and have the perfect summer meal!
Images from neptuneoyster.com
Coppa - Nestled into the brick row home-lined streets of the South End, is Coppa, a delicious and hip bistro offering in-house cured meats, homemade pastas, and delicious small plates. The interior is cozy and warm with tightly packed tables filled with quests enjoying carefully rafter cocktails and glasses of natural wine. In the warmer months, you can dine alfresco on their charming front patio and enjoy delicious dishes from their menu that change with the seasons.
Images below from thefoodlens.com, cntraveler.com
Oleana - If you are planning on spending an evening in Cambridge, Oleana is the best spot for a delicious Mediterranean and Middle Eastern meal. It’s a great place to take a crowd because they have small plates and you will want to try everything but also great for an intimate meal for two. The vibe is warm, relaxed, and elegant and the menu is unmatched. If you visit in the warmer months, try to grab a seat on the back patio. It’s a beautiful space filled with flowers and string lights that feels like an escape from the city.
Images below from oleanarestaurant.com
Alden & Harlow - Another great Cambridge restaurant, just a few short blocks from the Charles Hotel, Alden and Harlow is a cozy and cool restaurant under Longfellow Bar. They offer unique spins on somewhat classic dishes like kale salad, steak tartar, and pastas, and if you go early you can get the secret burger which they only have limited quantities of each night but it absolutely delicious! They also have a wonderful bar with fantastic cocktails and a great wine list, a great place for a drink or meal in Harvard Square.
Images below from aldenharlow.com
Myers + Chang - Owned by local chef Joanne Chang, who opened Flour Bakery in Boston, she and her husband Christopher Myers opened Myers and Chang in 2007. The restaurant serves the specialties of China, Taiwan, Thailand, and Vietnam cuisine in a sleek and comfortable environment. Delectable noodle dishes, tuna poke, bao of all kinds, and the famous Mama Chang's pork and chive dumplings are just a few of the many menu items that are best enjoyed shared!
Images below from theinfatuation.com
Sportello - Located in the Seaport district, Barbara Lynch's Sportello is a modern yet homey Italian spot serving delicious food in a fun diner-style setting. Stools line a U-shaped counter that faces the kitchen with tables in the surrounding space. The food is a unique array of Italian flavors with dishes like spicy tomato soup, braised rabbit strozzapreti, and Spanish octopus. The environment is fun, everything is delicious and this is an excellent place for a meal in the Seaport!
Images below from sportelloboston.com
Shop
Newbury Street - Newbury Street is Boston’s shopping destination. The beautiful 19th-century brownstones that line the street are home to hundreds of retail locations, restaurants, and coffee shops. The street has everything from Chanel to Zara and is a must visit while in Boston.
Image below from pinterest.com
Charles Street - Located in Beacon Hill, this charming and historic street is lined with local boutiques and restaurants where you are sure to find unique pieces. Some favorites are Dress Boston, Ouimillie, and Vintage Taste.
Image below from pinterest.com
Prudential Center/ Copley Place - One block over from Newbury Street is Boylston Street where shopping continues and you will find the Prudential Center which connects to Copley Place, both high-end malls with every store you can think of. From Christian Louboutin and LOEWE to Sephora and J. Crew, there is something for everyone! The Prudential also has an Eataly, a grand Italian market that is a great place to pick up some Italian treats, have a meal, or just grab a glass of wine or a spritz and Rome around the store.
Experience
Isabella Stewart Gardner Museum - Once a grand and beautiful personal residence, the Isabella Stewart Gardner Museum displays the vast art collection of its eccentric founder, Isabelle Steward Gardner, who traveled the world, and had an eye for the finer luxuries in art and of ancient cultures. Set within a Venetian-style palazzo, surrounding a gorgeous courtyard, not only is the architecture impressive, but the residence houses masterpieces by Botticelli, Raphael, Titian, and John Singer Sargent. Stewart Gardner herself meticulously arranged the collection of more than 7,500 fine and decorative art objects, 2,700 books and manuscripts, and over 8,000 historic artifacts from around the world. The collection includes sculptures, furniture, textiles, metalworks, and ceramics, that she collected during her lifetime. The museum also hosts intimate concerts and talks in the courtyard for contemporary artists, musicians and scholars. This is a fabulous museum to visit in Boston.
Image below from gardnermuseum.org
Museum of Fine Arts, Boston - The MFA’s has a vast collection of art and artifacts with works spanning centuries, styles and artist. The museum is know to have one of the best collections of Korean art outside the Korean peninsula, the only permanent exhibition space for ancient coins in the United States, one of the world’s largest holdings of ancient Egyptian treasures, and a comprehensive collection of work by John Singer Sargent. Don’t miss the Claude Monet gallery in the European Wing, with one of the greatest collections of the Impressionist’s work outside of France and be sure to check out the special exhibits. There is always something interesting and unique you won’t want to miss.
Boston Public Library - In Copley Square right off Newbury Street is the beautiful Boston Public Library. It’s the oldest municipally-funded public library in the country and its McKim Building is considered the masterwork of iconic Gilded Age architect Charles Follen McKim. The library holds tours each day as well as lectures and special exhibits. If you are interested in architecture be sure to check out the Art & Architecture Tours, which show some features tiled arches by famed Spanish builder Rafael Guastavino, and the first mural commission from John Singer Sargeant. The museum is home to far more than books and the architecture alone is worth visiting!
Images below from godfreyhotelboston.com, pinterest.com, bpl.org
Public Garden - When the weather is nice, the Public Garden is one of the best places to visit in the city! Grab a coffee and stroll through the beautiful landscaping, visit the lagoon that snakes almost the entire length of the garden and is where the famed Swan Boats have been peddled for over a century. If you are lucky you may even spot some of the beautiful live swans that float peacefully in the ponds.
Images below from hotels.com
High Street Place - Located in the Financial District, High Street Place is a food hall of sorts but on an upscale level. Think beer gardens, wine bars a James Beard finalist restaurant, plus an eclectic mix of some of Boston’s most discerning foodie favorites from across the city. Some favorite options include bagels and pastrami from Brookline's favorite Jewish deli, Mamaleh’s; doughnuts from Blackbird; and Bubble Bath, a Champagne bar complete with a Moët & Chandon vending machine. Grab a seat inside or out, visit with friends, or enjoy a game on the top-notch entertainment system. High Street is the perfect palace to stop in for lunch or a drink while exploring the city, especially if you can’t decide what you want to eat!
Images below from highstreetplace.com
The Freedom Trail - If you are looking to take in some of the rich American history in Boston, The Freedom Trail is a great attraction. It begins at the Boston Common, the oldest public park in the United States, following a red brick path lined with 16 historic landmarks, which paint a picture of Boston’s revolutionary history. The trail is about 2.5 miles long and winds its way through the city. You’ll see revolutionary sites in a modern setting as you walk alongside commuters and other tourists. If you are just looking to take in a few key sites, prioritize the North End section of the trail, home to landmarks like the Paul Revere House, Old North Church, and Copp’s Hill Burial Ground, in a historic neighborhood that’s known as Boston’s Little Italy.
Images below from picfair.com, cntraveler.com, thefreedomtrail.org
Fenway Park - Fenway Park, known as America’s “Most Beloved Ballpark” is a must-visit during baseball season, even if you aren’t a baseball fan. Home of the Red Sox, who play there each year from late March through October, offers behind-the-scenes tours in the off-season and also hosts summer concerts. It’s one of the oldest and smallest MLB parks in the country and is nestled right into the middle of the city. Grab a ticket, a beer, and a hotdog and sing “Sweet Caroline” during the eighth inning and you are sure to feel the joy and comradery that makes Fenway Park so special.
Images below from istockphoto.com
South End - The South End is one of the most charming neighborhoods in Boston. Residential areas are lined with beautiful brownstones and historic plaques that show off the neighborhood's rich past. There is an abundance of art galleries, boutiques and delicious restaurants, each quaint and wonderful. On Sundays, you can visit SoWa Open Market where you will find loads of food trucks and entertainment as well as SoWa Vintage Market and Farmer's Market, and a number of one-of-a-kind boutiques and design showrooms. After a meal in South End stop by Beehive for a cocktail and lively local jazz or visit DeLux Cafe, one of Boston's best dive bars, for a delicious late-night burger in a cozy and casual setting.
Images below from cntraveler.com, bostonuncovered.com, greatruns.co
Seaport District - Boston Seaport is one of the city's fastest-growing neighborhoods that has a different look and feel than any other area of Boston. Once a no-man's land, the Seapost has quickly grown into a modern development, with Boston’s priciest sky-scraping condos, large office buildings and top retailers. You will also find the Institute of Contemporary Art, rooftop bars, and great restaurants. Be sure to take a walk along the waterfront for beautiful views of the Boston Harbor, sprinkled with sailboats and gorgeous summer sunsets.
Images below from www.expedia.ca
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