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1-5 Days Boston Itinerary

July 6, 2020 /

The capital of Massachusetts, Boston is the most well balanced city I have ever come across. There is something for everyone in this lovely city, which is as much a great place to live in as it is to travel. Known for it’s history, architecture, public gardens, churches, amazing food scene, proximity to the ocean, the serene Charles river, world renowned universities, famous Fenway stadium, stunning skyline views, plenty of activities & tours, excellent shopping opportunities and never ending array of bars, Boston has it all. There are enough people to enjoy people watching, but not the crazy crowds you come across in New York city. Having visited the city year round, I have a curated list of things to do based on different interests and time available. So there you go! Here is a suggested 1-5 days itinerary for Boston.

Day 1

Highlights: Duck Tour/Segway Tour/North End Tour/Freedom Trail, New England Aquarium, Boston Seaport

  • Boston Sea Port
  • Segway Tour
  • Boston Harbor

If you only have one day in Boston and wish to see most of the city in a glimpse, there is no better way to do it than a guided tour. While the Duck Tour, Trolley Tour and the Segway tour will show you all around the city, the North End Tour and the Freedom Trail are best for those with specific interests. Choose one of the below tours and enjoy your first or only day in Boston.

Boston Duck Tour: Considered as the best city tour out there, the ‘Duck’ which is a World War II style amphibious landing vehicle will show you around the city both on land and water. Add to it, the fun driver/guide with his/her overview of all the landmarks and you have the makings of an ultimate first day in the city. You could also go for the trolley tour instead but I liked how the duck tour vehicle drove into the water and converted our road drive into a boat ride.

Segway Tour: If you want to pursue a fun way to tour the city, nothing comes close to the Segway Tour. We had two options to choose from – 1 hour and 2 hour tours. We went for the 2 hour one and in the end, couldn’t be happier. You start off with a quick lesson and safety instructions on riding a Segway which a two-wheeled, self-balancing personal transporter. Perfect way to get introduced to the city and have an adventure at the same time!

  • North End Tour
  • Boston Seaport
  • Massachusetts State House

North End Food Tour: Also known as Boston’s Little Italy, North End was home to more than four million Italian immigrants who came to the country between late 80s and early 90s. The neighborhood boasts around 85 Italian restaurants today and has managed to retain the charm and authenticity of the earlier days. Our tour guide was a local who was raised in the neighborhood. During the 3 hour walking tour, we visited historic sites, hidden gems, local shops and tried scrumptuous Italian food at authentic restaurants and cafes around. What’s more? We ended our tour by buying some wine and visiting our guide’s mother at her wonderful home. She treated us to delicious homemade pasta Bolognese and cannolli. Yumm!

Freedom Trail Walking Tour: A 2.5 mile walking trail covering 16 historic landmarks that signify the American revolution. It includes museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers. While you can go for a self guided tour, it would be easier to have a trained guide who will give you the right facts and information.

After completing one of the tours above, grab a quick lunch and head to the New England Aquarium. With over a million visitors every year, the site also has an IMAX theatre and discounted prices for whale watching excursion which we will do on Day 2.
End your day by visiting the Boston Seaport at sunset and grabbing dinner/drinks in the neighborhood. Seaport had hands down the most beautiful views of Boston I have ever come across. We got some great shots during our engagement shoot. On our second visit, we were lucky enough to get a table with a view at The Barking Crab, a lively bar/restaurant with funky decor and delish cocktails!

Day 2 – Self Guided City Walking Tour

Highlights: Boston Public Library, Old South Church, Trinity Church, Boston Public Garden, Acorn Street, Lolita Cocina & Tequila Bar

  • Trinity Church
  • Boston Public Library
  • Old South Church

On your 2nd day in the city, we will go exploring on foot. This tried and tested self guided walking tour will help you truly capture the spirit of this city and save time.

Lets begin by visiting the Boston Public Library. One of the largest public libraries in United States, BPL has a collection of more than 23 million items and hosts exhibits every now and then. The exterior facade is as impressive as the interiors. This multi-level library resembles a palace in some parts and has modern architecture in others. The lobby has a grand staircase which leads to the Puvis de Chavannes Gallery. The main attraction is the stunning Bates Halls with its high vault ceiling and lovely green lamps on each table. The beautiful Abbey Room can be rented for private events. The Courtyard will take you back in time and has a tea room, one of the very few places serving high tea! The kids library on the modern side of the building is very charming and has fun events for kids from time to time.

Next we cross the road (2 mins walk) and reach the Old South Church, a national historic landmark with Victorian Gothic architecture. The 350 years old church sitting right in the heart of this modern city is a sight to behold. They claim to be a vibrant, theologically progressive Christian church, diverse in age and culture. It is beautiful from inside and there is no entrance fee.

Even if you don’t get a chance to go inside, it is on our way to the next destination, the Trinity Church ( 2 mins walk).
A parish of the Episcopal Diocese of Massachusetts, Trinity Church is located at Copley Square in Back Bay neighborhood. A masterpiece of American Architecture, it is considered one of the most significant buildings in the country. The national historic landmark is an excellent example of Richardsonian Romanesque architecture. Colorful interiors including stained glass windows, mosaics, wall murals are warm and inviting.

  • Back Bay
  • Acorn Street
  • Marshall Street

Time to grab some lunch! Head to Earl’s Kitchen + Bar at the Prudential Center (7 mins walk) and have their Korean Chicken Wings! Wash it down with their mules (sometimes available at $5) if you are in mood for a drink. The garlic parmesan fries are the best and the ambience is lovely.

Perfect time to take an afternoon walk through Boston Public Garden (13 minutes walk to entrance). Part of the Emerald Necklace system of parks, it was the first public botanical garden and was established in 1837. The lagoon in the garden has beautiful swans during the summers, you can even take a swan boat ride and enjoy this dreamy location. The most popular sighting would be the “Make Way for Ducklings” statues inspired by Robert McCluskey’s book. Appreciate the beautiful trees, plants, flowers, statues, fountains and the bridge. You get to see beautiful tulips in spring and fall foliage during Autumn. Being there always brings me peace and I look forward to those visits when in the city.

Let’s move on.. It’s time to visit the most photographed street in America! Acorn street (5 minutes walk) in the Beacon Hill Neighborhood is paved with real cobblestone and lined with historic redbrick houses which will take you back in time. The Beacon Hill Neighborhood itself is the most expensive neighborhood to live in the city. Instagram is flooded with pictures from this street and we were lucky enough to capture a part of our engagement shoot there.

After having spent a wonderful day walking the city, you must be tired by now. Time to end the day by going for dinner and drinks at the most beautiful bar/restaurant in the city, Lolita Cocina & Tequila Bar (18-24 minutes walk). There are 2 locations – Back Bay and Fort Point. I prefer the Fort Point one as it also provides stunning views of the city skyline from outside. The gothic bar is truly a piece of art and the food/drinks are excellent. You will be served cotton candy with your check, a sweet ending to your 2nd day in Boston.

If you happen to be in Boston during spring, do look out for the cherry blossoms around city. While there are dedicated Cherry Blossom festivals, you will be sure to find full bloom along the Charles River Esplanade during the peak season of April.

Day 3

Highlights: Boston Harbor, Whale Watching, Quincy Market/Faneuil Hall, North End

  • Trattoria Il Panino
  • Quincy Market
  • Whale Watching Cruise

We will begin Day 3 with brunch at Quincy Market. With 18 restaurants and 35 eateries consisting of various cuisines, it is like the best food hall out there. You get to try Boston specialities like lobster rolls, clam chowder, clams, pizza , Boston cream pie plus get to indulge in international cuisine at reasonable prices. Don’t be tempted by all the shopping around yet as we will come back for the same. You may also head directly to Boston Harbor (our next stop) and try some amazing seafood at Legal Sea Foods, a fine dining chain in this region. We had a cup of lobster bisque and clam chowder followed by lobster roll two ways!

After a satisfying breakfast/brunch, let’s take a walk to the Boston Harbor. You will be greeted by serene waterfront views. In case you are in mood for some Mimosas, there are a few restaurants with outdoor seating as well. Don’t be surprised if you see a wedding party having a photo shoot. This also happens to be a significant site in American history as it was the location of Boston Tea Party.

The whale watching tour (booked in advance Spring through Fall) will depart from the harbor and you may want to queue up in time. The cruise is comfortable with indoor seating and a bar on site. It was exciting for us as we had never seen whales in their natural habitat. The captain announced when whales came in sight and we all rushed out to the deck to see those beautiful massive creatures. Some of them came so close to our cruise, it left us stunned. We also saw a mama whale with her kid and what seemed to be like a lesson going on! It took us around 3.5 hours to get back and it was time well spent.

Now if you would like to spend some time shopping or looking around, Quincy Market or Fanuil Hall Marketplace has a multitude of options. The market is festive during the holidays with Christmas decorations all around. There is also a Ghirardelli Icecream and Chocolate shop on premises for those with a sweet tooth.

The last destination for today where you will also be having a lovely Italian dinner is the North End. As specified in the Day 1 itinerary, Boston’s Little Italy has around 85 Italian restaurants and cafes. We started by having a cappuccino and the best tiramisu in town at Boston’s oldest Italian cafe known as Cafe Vittoria. This was followed by dinner at Mare Oyster Bar. This hidden gem is one of my favorite restaurants in Boston. Start off with some wine and oysters followed by Wild Mushroom Spaghetti (with truffles) for main course. As an alternative, you could head to Trattoria Il Panino and try their Gnocchi Alla Sorrentina! While you may be tempted to get some dessert, wait a little longer and head to Mike’s pastry for delicious Cannolis. Founded in 1946, this bakery has people lining up in long queues to pickup their famous cannollis. You will never find such a wide variety of flavors anywhere! Time to wrap up another eventful day..

Day 4

Highlights: Harvard University, Massachusetts Institute of Technology, Harvard Bridge, Skywalk Observatory

Harvard University
Top of the Hub

Massachusetts Institute of Technology

One of the top universities in United States, Harvard University was established in 1636. It is the oldest institution of higher education in the country. While you can go for a self guided tour, I would advise going for one of the student led tours. Some of the libraries are open to public and often host exhibits. Harvard is like a world in itself and you can grab a meal at one of the student hang-out cafes after the tour and enjoy the student vibe.

Next we will head to Massachusetts Institute of Technology. One of the best institutes of technology, MIT campus is situated alongside the Charles River. Unlike Harvard, you can actually walk the corridors of MIT and take a glance at the class rooms and labs. There is also a very interesting exhibit of vintage science equipment open to public.

It’s time to walk the Harvard Bridge now. Also known as MIT bridge, it is the longest bridge over the Charles River connecting Boston and Cambridge. The bridge is known for it’s smoot measurements, an informal unit of measurement named after Oliver Smoot. The beautiful views of the river and city on both sides are a pleasant experience. This bridge will also take you halfway to our last destination, the Skywalk Observatory.

One of the highest observation decks in the city, Skywalk Observatory has beautiful high rise views of the city skyline. The same building used to have a restaurant called ‘Top of the Hub’ that offered comparable views. By dining here, we were able to save money on entrance fee plus enjoy a good meal with live music. The restaurant has closed until further notice recently. Like any high rise, sunset would be the best time to enjoy the views both before and after sunset. There are a number of restaurants in the neighborhood. Grab some dinner & drinks and end another interesting day in the city.

Day 5

Highlights: Boston Museum of Fine Arts, Spirit of Boston Lunch Cruise, Boston Opera House

Boston Opera House
Museum of Fine Arts
Spirit of Boston

Museum of Fine Arts Boston was established in 1870 and is the 17th largest art museum in the world. With more than 500,000 works of art, the museum is visited by a million visitors every year. The diverse artwork ranges from the prehistoric times to modern day.

I booked the ‘Spirit of Boston’ lunch cruise as a surprise for my husband’s birthday. The vessel was gorgeous with indoor dining and outdoor deck seating. The buffet style lunch was delicious and the skyline & harbor views from the deck were lovely. We also spotted a cruise-liner up close with some maintenance in progress. They had arranged a small birthday cake/dessert for my husband which was a nice touch. If you are looking for a more formal experience, book the Odyssey dinner cruise. It is a little more expensive but comes with a 3-course meal and cocktails included.

Last but not the least, it’s time to catch a show at Boston Opera House. I went on a self date to watch ‘The Nutcracker’ ballet during the holiday season. It was a terrific experience and left me completely mesmerized. The Opera house first opened in 1928 and hosts Broadway shows and ballet performances! Grab a nice dinner during your last night in the city.

I hope you enjoy your stay in Boston and love the city as much as we do!

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