1-5 Days Boston Itinerary
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
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
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!
65 Comments
Hillary Swetz
You nailed it! New England native here, and you listed 99% of my favorites (especially cannolis. Oh man. I have to go to Logan to pick family up from the airport next week and I am DYING to grab a cannoli before their flight arrives.)
Maybe it’s my country-bumpkin-ness, but I also have fun taking a ride on the T at least once if I’m spending time in Boston. I get to swipe my Charlie Card and have “Charlie on the MTA” stuck in my head for a few hours. 😛
Also, SPORTS! Obviously, we know everyone hates the Patriots, but you can watch the Red Sox or the Boston Marathon or any of the college football/hockey games if you time your visit right.
Lekha C.
Thank you so much Hillary! Means a lot coming from a local.. I love riding the T too. I have only watched a BU College hockey game and had a great time. I hope to catch a game at Fenway Stadium and write about my experience 🙂
Jill Robbins
What a great guide! I have never been to Boston and I love how you’ve broken it all down depending on how much time someone has to visit.
Lekha C.
Thank you so much! That was the idea. This is the first time I tried this kind of post, glad to know it hit the mark 🙂
ravina
Really Great!
Lekha C.
Thank you!
Kim
I live so close (Toronto) but have never been, looks like so much fun! I’ll have to make the trip!
Lekha C.
You will love it. I was supposed to be in Toronto this month. Unfortunately had to cancel all travel plans. You can make a nice road trip out of this, stopping in the Finger Lakes region on your way 🙂
Shay
This looks like such a fun getaway, and I love your pictures! That trattoria looks AMAZING, and now I’m desperately craving some Boston creme pie!
Lekha C.
Thank you so much! The food is indeed lovely, I can’t stop thinking about the Tiramisu lol
Emmeline
Oh man! I’m bummed I didn’t know about the North End Food Tour last time I was in Boston. I’ll have to go back when I can 🙂 Thanks for the guide, I love that city.
Lekha C.
Thank you. That tour was indeed a great find! Do try it out next time you are in the city. 🙂
Francesca
Boston is seriously such a fun city! I love visiting any time of the year. I still need to hit the museum of fine arts. I love walking the Freedom Trail!
Lekha C.
I couldn’t agree more. When we rented our apartment, it was keeping in mind that we are close to Boston. MFA also hosts events including late nights with music and cocktails!
Rhonda Albom
Yes, Boston is so much fun. I have walked the Freedom trail but hubby has done much more as he went to Uni in Cambridge. He agrees that Legal Sea Foods is a classic not to be missed and also suggests the little Italian restaurants in the North End.
Lekha C.
It must have been so much fun going to university in Cambridge. I am glad he seconds my opinion 🙂 Means a lot coming from someone who has lived so close to the city!
AllyTravels.com
Nice post – can’t wait to check out the Segway tours the next time I visit Boston!
Lekha C.
It’s the most fun I ever had on a city tour! You will love it.
Kelly
I am planning on visiting Boston from Canada (once the borders open), so this post is perfect for me! I have done a segway tour in Chicago and it was so much fun, so it’s good to know that there is also one in Boston. I will do it for sure!
Lekha C.
Hey that’s great! I didn’t know they had them in Chicago too. I hope the borders open soon and you get to visit Boston! I would have been in Toronto this month had it not been for this situation..
Devin Held
I went to Boston for a weekend once for a conference. I definitely didn’t explore enough by the looks of it from your blog! Thanks for sharing.
Lekha C.
You should definitely explore more next time you are in the city! Like I said, it has something for everyone 🙂
Patrici
So much to do and see in Boston! I didn’t know about whale watching, that’s exciting!
Lekha C.
Absolutely. While there are whale watching tours from some other towns in Massachusetts as well, this one departs from Boston Harbor! It was easier to add it to my itinerary..
Emma
I love Boston. I’ve been twice in the last couple of years and keep finding fun things to do. Since that you’ve mentioned too, plus you’ve given me some great ideas for my next trip
Lekha C.
I am glad this post helped you find some new things to do next time you are in the city. Thank you!
Talia
Neve been to Boston but looks amazing and will put it on my list. Saving this blog post for my next trip!
Lekha C.
Thank you! I hope you get to visit soon..
May Durkee
I love Boston! Very good guide! Would love to go back sometimes soon to explore what I wasn’t able to when I visited.
Lekha C.
Thank you very much! I hope you get to visit again..
Alessia
Absolutely lovely post! I haven’t been to Boston yet but I will save this itinerary for when I will be able to visit! 🙂
Lekha C.
Thank you so much! hope you get to visit soon..
Kooky Loves to Travel
Self-guided tours are the best! great post!
Lekha C.
I couldn’t agree more. Thank you!
Linn
I love Boston! This is such a great itinerary and I’ll save it for my next trip as I didn’t get to do it all last time. Thanks for writing this!
Lekha C.
Thank you so much! I am glad you liked it 🙂
Mayi Mac
I’ve been to Boston only once and even though my stay was short, I had lots of fun. I have been meaning to go back and stay at least 5 days so this itinerary is very useful. I am going to park this until I can travel to the US. I enjoyed the Freedom trail even though it was kinda cold, seeing the stunning buildings and architecture was worth it.
Lekha C.
I am glad you loved the city! You will definitely have a great time if you are able to plan 5 days next time you are in Boston. Thank you:)
Mayuri
Such a detailed itinerary, saving for my future travel plans to the States! Lovely photos xoxo
Lekha C.
Thank you very much! Hope you get to travel soon.
Paige @ The Best Paige In The Book
Boston is such a cool city to visit! I loved going on the duck tour when I was there, but the Segways sounds like they’d be super fun!
Lekha C.
Segway was really fun! It gave us an opportunity to see the city in new light 🙂
Sara
Such an awesome post! Boston has always been on my US bucket list so thanks for the post I will definitely be referencing it
Lekha C.
I am glad you liked it Sara and hope you have a great time in Boston!
Jessi
Looks like an awesome trip and itinerary! I love self guided walking tours, too! Thanks so much for sharing! Pinning for later when I can travel 😭
Lekha C.
Thank you! I hope we all get to travel soon 🙂
Ana
Love your packed itinerary! From whale watching to the museum, I’d like to try it all. Your photos tell a beautiful story. Thanks for sharing your trip and all the many great stops along the way. I’ll pin for future reference.
Lekha C.
Thank you so much. You made my day!
Ashlee
This is the perfect way to see Boston! I’ve been there many times and all the sights you listed are amazing.
Lekha C.
I am glad you liked the itinerary. Thank you!
Ashleigh
I need to try that Tiramisu from Cafe Vittoria!
Lekha C.
You will love it! It was the best I had 🙂
Linda M Purcell
I used to live there a long time ago. I loved it. Wish I could visit again. Maybe sometime soon.
Lekha C.
I hope we all get to travel soon!
Shelley
Boston is so beautiful! I went once, soooo many years ago, but your blog brought me back. Thanks for the 1-day guided tour recommendations, I love the idea of a segway tour, but those scare me so much… so maybe I’d stick to the duck tour lol.
Lekha C.
Oh I am sure if you give in to the fear you’ll love it 🙂 Regardless of which tour you choose, it will be definitely fun!
Cass
Never been to Boston as this post really gave me a flavour of it. Great guide!
Lekha C.
Thank you very much! I hope you’ll love it 🙂
Melissa
Those self hosted city tours are always my faves. I love creating my own route using Google Maps and recommendations from others. 🙂
Lekha C.
I do the same! They are the best 🙂
Fiona
I have only even seen Boston in TV shows but it looks amazing and some of these things to do look so good! I would love to go to Boston!
Lekha C.
I am sure you will love it more in person!
Digitaldaybook
Boston is such a unique city. I love the duck tour haha as cliche as that is
Karen
I live in Western Mass so get to Boston on occasion for a visit. You absolutely included all of the great places to see in Boston. I learned about a few more I didn’t know about. My favorite Boston experiences are the Aquarium and of course a whale watch.
Lekha C.
The whale watch is indeed very thrilling. I have explored a couple of new places as well, hopefully will get a chance to include them in the blog soon!