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2 day Boston Itinerary: Perfect Weekend Trip

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Looking for a perfect weekend getaway in New England? Get this epic 2 day Boston itinerary to check out this city steeped in history, culture, and culinary.

A unique mix of the old classic and a bit of the charming modern, has made Boston the only city in the United States that can boast of incredible history, rich culture, and the most number of college students one can find in a single place anywhere in North America.

The best part for a first time visitor, or even for any tourist for that matter, is that Boston is very very accessible. So irrespective of it is by foot or by the excellent public subway transportation system known as the “T”, it doesn’t necessitate the need for a car at all to explore the delightful sights, food, and history of this coastal city.

So whether you are walking the Freedom Trail for the first time or exploring some of the city’s finest art museums like the Isabella Stewart Gardner, here is the ultimate two day itinerary, along with some tour advice, that can lay claim that you have experienced the best of Beantown, the most colloquially used label for Boston.

2 Day Boston Itinerary: Planning Tips and Sightseeing Ideas

Boston Old State House building in Massachusetts USA
Boston Old State House building in Massachusetts USA

Hotel recommendations

The jumble of residential and commercial districts, each with a unique personality of its own, is basically what Boston represents. You don’t have to pay a princely sum to stay in Boston unless you are looking for something lux which evidently comes at a price.

Overlooking the bustling harbor, the city stretches all the way west along with the River Charles, showcasing many waterfront attractions and historic sights. So it is difficult to single out a perfect place to stay as in reality there are so many excellent options.

  • Luxury Hotels

The Ritz-Carlton Hotel

Omni Parker House

Harbor Hotel

Mandarin Oriental

  • Family Hotels:

Hyatt Regency

Four Seasons

Marriott Long Wharf

The Godfrey Hotel

  • Mid-range Hotels:

Harborside Inn

Aloft Seaport District

Kimptown Marlow

Seaport Hotel and World Trade Center

  • Economy Hotels:

Hi Hostel

Irving House at Harvard

The Inn on Arsenal

Recommended Tours

The business district of Boston is crammed with historical sights and colonial architecture and other landmarks. As many as sixteen revolutionary attractions can be visited by the Freedom Trail, which is a 3.8km long walk starting from Boston Common to the Downtown neighborhood and beyond.

The nearby Boston Harbor, which at one time was the maritime hub of the country, offers a range of activities like whale watching tours, boating and a visit to the New England Aquarium.

Every neighborhood of Boston excels in providing a dining experience to dream off. Though it is not easy to choose one that stands apart from the others, the North End is the place to enjoy Italian food, while Chinatown is great for dumplings, dim sums, and other Asian dishes.

Seafood is a big draw in Boston, and the Seaport District is the centre of the fishing industry of the city. Food markets which are famous are the longest running outdoor Haymarket and Greenway Farmers Market as well as the indoor Boston Public Market.

Not surprisingly, the best nightlife hubs are near the universities, mostly in Kenmore Square and Lansdowne Street. For first time visitors, Downtown Boston is the ideal starting point. If you are in a romantic mood, head to Beacon Hill with its irresistible air of romance with gaslit street lamps and flower-decked window sills.

Families can jump off their tour from the Rose Kennedy Greenway, Boston Harbor Islands, Children’s Museum as well as the Boston Tea Party ships. For moving about, hop on to the ‘T’ where kids under 12 can ride for free. Boston’s best-known shopping strip is Newbury Street and the two massive shopping outlets of Copley Place and Prudential Center.

Day 1 of 2 day Boston Itinerary

The first thing to do is to get the Go Boston Card which allows you free entry and avoidable queues to most of the city’s major attractions. A huge benefit for those who have just two days to explore Boston. (Some of the highlights mentioned here may not be appealing during the winters when indoor attractions may hold a greater charm).

DAY ONE (Morning)

Start your first day with an amazing morning meal at South Street Diner which welcomes it’s hungry patrons with breakfast staples 24×7. I found their Diner Special of three eggs, French toast, fries and choice of bacon, beef has, ham or sausage a clear winner.

Since you have only 48 hours to tick off the most popular attractions and you are uncertain about the weather, I would recommend starting your trip from the Boston Common. Locals flock here on a sunny day and this oldest park of America offers great people-watching opportunities. Indeed, this is one green pocket that the city holds in high esteem.

The park is conveniently located next to the Public Garden, which offers visitors pedal boats in the shape of giant swans to move around a beautiful lake. These boats operate only in summer and spring and I found taking one a great and enjoyable ride. Keep an eye for the ducklings when walking through the Common. 

The blossoms were in full force when I visited the garden in summer which made for some wonderful photographs.

A great way to familiarise yourself with the history of the city is by walking the Freedom Trail, which luckily starts from the Boston Common itself. This 3.8 km long walk can take around two hours to complete and gives you an insight into some historical landmarks and points of interest such as Massachusetts State House, Park Street Church, Granary Burying Ground (this historic burying ground has nearly 2300 markers), home of the free speech Faneuil House and the oldest structure in Boston Paul Revere House among others.

Even though I am not a history buff, I found the trail very enjoyable, especially the section which highlights the different neighborhoods of Boston. I would recommend taking the 90 minutes of Boston’s Freedom Trail Walk into History Tour which details the tumultuous period of 15 years that culminated in the American Revolution.

DAY ONE(Afternoon)

Your hectic sightseeing and long morning walk mean you have hard-earned a tasty lunch. I found the Quincy Market to be a nice option as, apart from being touristy, it was housed in an impressive building. This is the best place to try out one of the local delicacies like clam chowder. 

The food is a bit expensive, but the price is offset by the stunning setting and expansive menu.

Once sated, a short twenty minutes on the red subway line will take you to the neighboring city of Cambridge and one of the most well-known landmarks of the area, Harvard University. While I found it easy to wander around on my own, you can opt for a guided tour with a real time student for a more in-depth experience.


As the first day draws to a close, it is time to relax in the tacky atmosphere prevailing in the North End, Boston’s Italian neighborhood. Before you bite into the chunky pasta, try out the excellent cocktail menu at Ward 8 Bar & Restaurant, weather permitting, as it has an outdoor seating area. Even by US standards, Boston’s portion sizes are huge, so try and share food to make eating out a little economical.

Day 2 of 2 day Boston Itinerary


Someone recommended Boston Public Market to me and I found it to be far far better than Quincy where I had my breakfast the first morning. The setting may not be as good, but the selection of food with an emphasis on local produce makes it an incredible breakfast option.

After finishing your morning meal, head to the Museum of Fine Arts, another essential stopover on the two day itinerary. The place is massive so keep the rest of the morning devoted to exploring it. I found the video narrative of the chronological history of the world quite fascinating as was the impressive collection of contemporary and modern art. The admission fee is a bit stiff, but the museum is a must-see on any trip to Boston.

For lunch, I would recommend the best ever vegan food at By Chloe, which has a couple of branches in the city. Their vegan burgers are absolutely unbeatable as are the Caesar Salad and the delicious desserts.

If you are looking for Instagram happy photo opportunities, your next port of call has to be the Isabella Stewart Gardner Museum. You have to shell up an admission fee of $25 but the collection here is extremely absorbing, to say the least.

On your final meal in Boston, treat yourself to something tantalizing that will resonate in your memory long after you have reached home. Stillwater, located in the Financial District, stands out with its whimsical menu of bagel popcorn and vegan pork rinds.

When night falls in Beantown on your last day, treat yourself to some live drama performances at the Shubert Theatre. If you are into dancing or want to mingle, the Theatre District boasts of some fine nightclubs with the best DJs driving the crowds to a frenzy till the early morning hours.

Extra Travel Tips

  • There are certain sections on the Freedom Trail which have uneven terrain, so comfortable walking shoes are a must. I got caught in a downpour, so I carried an umbrella or rain jacket. To make the most of your limited time visit their website for all the important information.
  • If you are looking for an alternative way to unwind after a long day of walking, opt for a sunset sailing trip from Boston Harbor on any one evening of your two day itinerary. Dinner is not available, but you can purchase food and beverages onboard.
  • Feel free to pack some cannolis to try back at home from Mike’s Pastry. These pastry tubes are filled with buttercream in different sizes and flavors and are a favorite with the locals and I found them absolutely delicious.
  • The locals love baseball, but if you don’t know anything about the sport you should give Fenway Park a miss.
  • If you relish tea, then the fully restored Boston Tea Party Ships & Museum is a must on your list. Here visitors are shown a reenactment of the famous tea party, complete with guides and costumes.
  • If you want to experience the brewing process do not miss out on a visit to the Sam Adams Brewery where you can sample aged beers with local cheese. Limited edition beers with live music can be enjoyed in their Beer Garden or the Taproom.


If you are done with your Boston sightseeing or looking to get away from the city there are some great places to visit with families and friends.

  • Salem: This pedestrian friendly city lies just 25 miles from Boston and is a great hit with tourists of all ages. Salem is rich in folklore and architecture and comes into its own during the Halloween period.
  • Martha’s Vineyard: A hotspot of the rich and famous, Martha’s Vineyard is located just south of Cape Cod. The scenic beaches and the breathtaking landscapes make it a perfect getaway from Boston, usually in the summer months.
  • Rockport: Located north of Boston and just an hour’s drive away, Rockport is a lovely coastal town, complete with beautiful beaches and lush green forests.
  • Whale watching cruise: If you want to experience the best of the marine wildlife of New England take a whale watching cruise in a high speed catamaran. This three and a half hour tour is perfect for spotting fin and humpback whales apart from dolphins in the company of a trained naturalist.
  • New Hampshire: Fall foliage is renowned in New England and this full day tour makes it easy to explore the region’s scenic beauty. Visitors can travel to the White Mountains with photo stops on the Kancamagus Highway on this seamless tour.


Boston is one such city that experiences all the four seasons. While the winter time can be bone chilling, the summers can turn out to be hot and humid. So here is an essential list for what to pack for Boston, no matter the time of the year.

  • Reusable Water Bottle: While tap water is safe and very tasty, carry a reusable water bottle not only to enjoy it but also to avoid the use of plastic everytime you get thirsty. They have a built-in UV light which eliminates the need to clean it every now and then.
  • Daypack: An ergonomic daypack to keep all your essentials safe and close at hand. Anyway, a backpack would look totally in place in Boston being home to as many as 35 colleges.
  • Painkillers: You never know when your body is fatigued with excess activity or cocktails from the bars around Boston. Having ibuprofen or aspirin is always a good idea.
  • Sanitizing Wipes: Checking into new hotel rooms from time to time involves coming in contact with high touch areas. Always have some wet wipes on you to kill any germs that may be lurking.
  • Boots: Boston is an extremely walkable city, so it is important to have a comfortable pair of walking boots which can contend with rain, snow, slush or other elements. Additionally, they should be waterproof, have good support and traction.
  • Rain Jacket: An easy to fold rain jacket that is waterproof and wind resistant. If possible, it should fit into your pocket when not in use 
  • Layers: Weather can turn foul in Boston even during a nice sunny day in the Fall season. Be prepared for such eventualities by packing a number of performance layers.
  • Sunscreen and Sunglasses: There will be lots of warm and sunny days, so be prepared with adequate protection.


Sky-high rental values have made Boston one of the most expensive of all cities in the US. Thankfully, this trend has had no effect on tourism and Boston is quite affordable($80-100 per day), providing proper guidance is followed.

Lodging, without doubt, is the most expensive, followed by food and drink which vary widely from place to place. Your best option would be to hit the suburbs of East or South Boston for cheaper offerings.

If you want to use public transport, consider buying a daily pass if you are going to be in transit often. Follow this advice to stretch your dollar to the limit.

  • Buy booze from the store and have a few drinks beforehand instead of wasting money on full-priced drinks at the bar.
  • Cooking and eating at home will save you loads of cash.


Boston is pretty safe as compared to contemporary crime standards anywhere else in the States. Though petty crimes are a part and parcel of any city, beware of pickpockets in busy nightlife areas and on public transport. Use a security belt to keep your valuables safe no matter where you go. They are perfect for hiding a wad of cash and copies of important documents.


Two days in Boston is not a lot of time but will surely give you a good feel of the place. There are few cities in the world where the airport is just three miles away from the city center which saves considerable time given that you have just 48 hours. 

That said, you can easily visit around five attractions per day and still have enough time to enjoy three great meals, knowing how good the food is in Boston.

About the Guest Writer: Jo is the creator of the travel blog WanderwithJo. She is a globetrotter based in India. Follow her adventures on Instagram

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