The Dryftwell Guide to



Boston is the heart of Massachusetts because of its rich culture, American history, architectural beauty, and incredible seafood. The city is blessed with magnolias, historical monuments, mystical castles, and much more. You will see rich historical places and colonial architectural sights almost everywhere when you travel in the city’s old neighborhoods. Walk the Freedom Trail on the same steps of so many historical figures before us and end with a visit to the Cheers Bar known for their Bloody Mary’s. Boston is the home of Harvard University and you feel you are amongst some of the greatest minds in history when you enter the campus. The streets around the college are refreshing and alive with sharp young students who are eager to share their knowledge over a pint. Head down to the waterfront for a lobster roll, as well as a boat ride to see the city from a new vantage point.

Located right on the water, the city has a very calming and relaxing vibe. Parks, lakes and ocean fronts are abundant around and near the city. Fenway Park, home stadium to the Boston Red Sox, is located right on the Charles River. Make sure you catch a game if you’re in town during the season. 

When to go


In winter, Boston is cold, windy, and gloomy with temperatures commonly under freezing. But, the snow turns this city into a winter wonderland. People walking the streets bundled from head to toe enjoying the beautiful snow and street lights give the city a romantic vibe.  When you need to escape the cold you can visit the Skywalk Observatory Building to have a complete panoramic view of the city. Most of the tourist attractions and public places are very less crowded in winter so you may want to check out the Citi Performing Art Centers, Brattle Theaters. No matter the weather outside you can enjoy some great breweries including the Samuel Adams Brewery just outside the city center.


Boston is very energizing in the spring. Folks are coming out of their winter hibernation and there is excitement in the air. You can dine outside with your friends and family and have fun at the historical parks and lakes. Ride a bike or paddle a rowboat with your loved ones in one of the Boston lakes or Charles River to get the perfect local flavor. It’s the perfect time of year to visit Fenway Park, the first American baseball stadium built in 1912. Arrive a few hours before game time and explore Lansdowne Street or take a tour of the stadium. The Boston Common and Public Garden are great places to relax and experience the fragrance of fresh flowers of the season in full blossom and eat like a local at Davis Square.


Summer in Boston starts in June and lasts until the end of August. Boston typically has bright and sunny days and warm summer nights. Visit the Quincy Markets near the waterfront with artisanal shops for food, crafts, jewelry, and clothes. It feels like a huge farmers market. Boston offers you a perfect combination of sports, fun, and many outdoor and recreational activities and summer is the best time to take advantage of all Boston has to offer. You can get a sightseeing tour of the city and enjoy the summer cruising around Boston Harbor. To beat the heat during the daytime, you can escape to Boston Beach too.


You can enjoy the fall as Boston welcomes you with cool temperatures. Fall is the best season to visit the beautiful classic streets of Boston. You’ll find the perfect spot to sit in the Public Gardens. You can join the sightseeing tours of New England and Beacon Hill and experience cherry blossoms in public parks.


Boston has some of the most beautiful and attractive neighborhoods. There are a total of 23 neighborhoods all within reach either by a quick car ride, 20-minute walk or public transportation. The size of Boston is fairly small so it’s easy to explore the unique flair of each neighborhood, especially if you have a car or are willing to walk a bit.

Back Bay

Black Bay is the shopping and dining destination of Boston. It is a tiny little neighborhood and is considered one of the most expensive residential areas of the city. In the 19th century, the area was created to fill in Bay, thus the name Black Bay. You’ll find the perfect Victorian Brownstones, cafes, and Boston Public Library here. The best place to go for a day of shopping is Newbury Street, which has an abundance of both name-brand stores and boutiques as well as cafes to have a nice lunch. There are many art galleries, offices, and upscale hotels there too. Copley Square is centrally located in Boston. It is a beautiful plaza surrounded by stunning architecture and the best Boston Hotels. After visiting Copley Square, you can visit the Boston Common garden which is just two blocks east. It is the oldest park in the US with a lake and stunning greenery.

South End

Located just minutes away from Downtown and Back Bay, South End has now become the most visited Boston neighborhood. Many young people are attracted to this beautiful place because of the Victorian Brownstone buildings and the old-style homes. The thriving arts and the finest restaurants make you praise the beauty of this neighborhood. The South End is diverse and the home of different groups, including immigrants, young families, and professionals.

North End

North End is one of the best “Little Italys” in the United States. North End has endless “Mom and pop” restaurants established over 50 years ago. A perfect example is Mike’s Pastry, the home of the Cannoli that was established in 1946. Mike’s is a great place to stop in for an afternoon snack and it will blow your mind. Neptune’s Oyster has incredible seafood, quiet and will most likely be a line but worth the wait. While you are in the North End you can visit the Paul Revere house and soak up more US history. Of course pizza is a must and it is all good. On your way out of North End you can walk 5 minutes and grab a pint at the oldest bar in America, The Bell in Hand Tavern. The streets surrounding the bar are cobblestone and it looks as if you are living in the 1900’s.

Beacon Hill

A visit to Beacon Hill is like traveling back in time. One of the most picturesque areas of Boston with steep winding roads. Visit Acorn street and walk on a real cobblestone road made from 19th century brownstone. The street is maintained by the residents purely for the joy of living on one of the most beautiful streets in the United States. The gas lanterns hand lit daily give the illusion a horse drawn carriage is about to emerge from around the corner. There are multiple quaint streets within walking distance with antique shops and cafes to stop and enjoy an afternoon brunch. Once you visit this magical neighborhood of Boston you may wish you were born in a different time.

South Boston

With strong Irish American heritage, South Boston is also known as Sophie. Downtown skyline views, Dorchester Heights, and monuments can give you the best experience of your trip. Escape the city for a short time and visit the waterfront trails and grassy lawn that surround the Castle Land. There is also a lovely beach and has great views and is a great place to spend the day on a nice day.  Being as this neighborhood is strong with the Irish heritage, stop into Shenannigans Bar for a Guinness as a fun way to end a day of exploring.




Driving in Boston is not the best form of transportation due to cost and time constraints. The congestion and the cost of parking are quite high. And most parking is in garages, not in public parking areas. At peak hours, the congestion gets worse, so the cost of getting around gets more expensive and time-consuming. Most locals cover short distances by walking or cycling in Boston.

Public Transit

Buses are your friend in Boston. You can easily find buses and local transport, but you’ll need to be disciplined and have a schedule. The subway is also reliable and you can buy tickets to the Metro Station with a Charlie Card, which is free, rechargeable and the best way to cover the city. You can easily pick up a Charlie Card from any attendant in any metro station. The Massachusetts Bay Transportation Authority (MBTA) is the official name, but locals call it “The T.” If you ever want to take the T in Boston, don’t forget to check out maps and schedules at the official MBTA website.


Massachusetts is one of the most bike-friendly and walk-friendly states in the United States. So biking and walking is the ideal way to explore this magnificent city. Most locals walk around the city daily to go to work, to head out to happy hour or for fitness. If you want to try biking while you’re in town, you can sign up to get a new bike or even share a bike using Boston’s Bike sharing system. You can rent a bike on an hourly, daily, or weekly rate. What Boston lacks in vehicle parking it makes up for with bike parking as there are numerous safe places to lock your bike for extended periods.