The perfect 3 day itinerary to Boston, Massachusetts

(Last Updated On: May 22, 2023)

Boston is one of the oldest cities on the east coast – with so much history and culture, you’ll fall in love whenever you visit. It is also known for it’s serious sporting ties (Boston Celtics and Bruins to name a few!) and it’s contribution to the America Revolution with the Boston Tea Party. During our fall trip to new England, we were able to squeeze in a weekend in Boston, right before we drove to Vermont for the fall colors and I’m so glad we did.

If you are planning a weekend in Boston and wondering what to do when you get there, this itinerary is for you!

While there is always so much to do and see in Boston, 3 days is definitely enough to see the main highlights and some of the favorite local spots, too! Through this blog post, I’ve structured a 3 day itinerary to hit some iconic tourist attractions and also get a taste of some amazing Boston restaurants and nightlife.

Everything you need to know before you go:

When to Go: Late April through June and September through November are the best times to visit Boston. Visiting Boston during spring is a great idea as you’ll get to enjoy outdoor dining options.
Where to Stay: I recommend staying in downtown Boston or Beacon hill neighborhood as it is super close to all restaurants, bars and shopping.
How to Get Around: Fly into Logan International Airport and catch the free shuttle to the blue line. The city is well connected via public transportation system – subway and buses and is an easy way to get around the city. (plus no hassle to find parking spots)

Day 1

Brunch at The Lookout Rooftop Bar

The best way to start your New England Trip? A cocktail in hand and toasting to some of the best views. Hit this place for best panoramic views of the city skyline and Boston Harbor, while you sip on delicious craft cocktails. I really loved their Winter Paloma(their specialty) and Pumpkin Coquito cocktails.

Stroll through Boston Common and Boston Public Garden

Enjoy an evening stroll through Boston Public Garden, one of my favorite places in the city: quiet and beautiful! It is the first public botanical garden in America and an excellent spot to meander, relax and enjoy a bit of peace amidst the hustle and bustle of the city. Around late April, the gardens are bursting with flowers and spring colors – truly a sight to sore eyes.

Ride a swan paddle boat in the garden’s pond , to enjoy some mesmerizing views of the city from the water.

Across the Public garden is Boston Common- the heart and soul of Boston. The park is gorgeous to walk through–be sure to stop by the carousel and to take in the views of the gold-domed Massachusetts State House while you’re there! They also have an ice skating rink in winter and a spray pool for kids to play in summer.

Hop on a Boston Tea Party Ship and tour the Museum.

Take a journey back in time to the famous Boston Tea Party, an incident that changed the course of American history. You can take a self guided tour of this floating museum to explore authentically restored tea ships, see one of the two remaining tea chests from the 1700s, learn how the Boston Tea Party kick-started the American Revolution and throw the fated tea into Boston Harbor.

Learn more about Boston Tea Party Ships & Museum here

Dinner at Ruka Restobar

If you came to Boston and did not try a Seafood restaurant, you have not lived the whole experience of the city. Boston has tons of Seafood Restaurant options – Atlantic Fish Co, Neptune Oyster, Row 34 are a few popular ones.

Another seafood restaurant worth checking out is Ruka Restobar – Located in the The Godfrey Hotel, this Restaurant is a wonderful blend of Peruvian-Japanese-Chinese flavors. The cultural motif decor, live sushi bar, an electric menu of food & cocktail and buzzing ambiance will definitely please your heart and taste buds.

We tried their King Tupac & Phoenix Sunrise (sushi options) , Kimchee Fried Rice and Pork Yakisoba and loved the burst of flavors in each dish. I highly recommend this place for a romantic dinner date.

Day 2

Breakfast at Tatte Bakery & Cafe

Start your day with a sweet nibble at Boston’s famous cafe chain- Tatte. Tatte Bakery & Cafe has several locations around Boston, but the Beacon Hill location is easy to reach.

Treat yourself to delicious sweets, tasty sandwiches and creamiest pastries that look too beautiful to eat. It is also a great place for a snack or quick lunch while you’re running around trying to see Boston in 3 days.

Checkout out Harvard University Campus

Harvard University was founded in 1636 and is the oldest college in America. It is a university rich with culture, history and tradition and definitely a must visit on your travel list. I would recommend taking a free student-led tour to get the most out of your visit because there are so many fascinating stories about the buildings and people who graduated from Harvard.

We spent our morning touring the campus, admiring the architecture of the buildings, checking out the beautiful library and finally picnicking on the Harvard law yard – reliving our student days. After exploring Harvard, you can walk along the Charles river and hit M.I.T, if you are in mood to visit yet another top academic institution in the world.

Lunch at Sulmona Restaurant

Located in the heart of Kendall Square in Cambridge, this restaurant was one of my favorite spots in the city. The contemporary decor, creative cocktails and super yummy food options is definitely a hit. It’s a great place to brunch with friends or hangout over cocktails.

Must try: Pizettes(Pepperoni & Carne), Italian Skillet Pancake, Hanger Steak Eggs Benedict

Cocktails: Sulmona Bloody Mary, Pineapple Mimosa and Bloody Caesar.

Visit the Trinity Church and Back Bay

Trinity Church, located in Copley Square is an architectural wonder and was even named one of the ten most architecturally significant buildings in the United States. Within the spectrum of worship styles in the Anglican tradition, Trinity Church has historically been considered a Broad Church parish and is also home to several high-level choirs.

You can take a self-tour of the church to know more.

You can also visit the Boston Public Library at the Copley Square, to catch up on some reading or just admire its ornate architecture and gorgeous statues in every corner.

After that head to Back Bay- one of Boston’s trendiest addresses. Stunning mansions, high-end shopping, bustling restaurants and quaint shops with Harry Potter memorabilia – if that’s not enough, go checkout the hype for yourselves.

Dinner at Terra at Eataly Boston

After a day of exploring, its time to checkout the wonderful Italian dining paradise in Boston – Eataly.

Eataly is a vibrant Italian marketplace that features an array of cafes, counters, groceries, restaurants, and a cooking school. We picked Terra – a restaurant inspired by earth and fire, for our date night.

As soon as we entered the restaurant, I fell in love with the vibe of the place – A dining room filled with tropical plants and greens with a wood-burning Italian grill at the center, where Chef Dan Bazzinotti cooks over open flames. Everything from herb-infused cocktails, rare wines, perfectly cooked steak and pork chops was a treat to our senses. SOO GOOD – I cant stop raving about this place.

Must try: Pappardelle con Anatra, Braciola di Maiale, Agnello allo scottadito

Cocktails: Ravanello Affumicato, Fico Old Fasioned

Day 3

Take the Freedom Trail Tour

One thing Boston you cannot miss is the Freedom Trail: the famous 2.5-mile trail covers 16 historical sights related to American history in Boston, and is easily one of the most popular things to do in the city.

You can either do self-guided tour around the Beacon hill neighborhood or take one of the tours- Freedom Trail Tour, which lasts 90 minutes and stops at 11 of the trail’s 16 spots. The walking trail begins in Boston Common and you’ll get to hear the story of the Boston Massacre as you progress through the Old South Meeting House, and stop to admire the Massachusetts State House and Massachusetts 54th Infantry Memorial. I advice you to wear comfortable shoes because you will walk a ton.

Take an insta worthy photo at the Acorn Street

Stop by the Acorn Street – One of the most photographed streets in the states. Beacon hill neighborhood offers a reminiscent ride back to colonial Boston – cobblestone streets, row houses, historic structures dating back to the 1700s and classic New England Charm.

Acorn Street was once home to artisans and the servants of Beacon Hill’s elite. The historic structures that line the south side date back to the late 1700s and early 1800s, while on the north side of the street, the area’s famous hidden gardens are sheltered behind brick walls.

Residents take great pride in their homes and go all out for the holidays and Halloween, decorating their windows and stairways with subtle red ribbons and spooky decor – also a great time to visit.

Lunch at Citrus and Salt

Craving some tacos and Marg? Here’s a lunch spot for you! Citrus and Salt is a creative Baja Coast-inspired restaurant serving Mexican eats & cocktails in vibrant, beach-y dining room. Their fish tacos were incredibly crispy, flaky and flavorful.

Sunset at the Boston Harbor

A continuous 34 mile trail along Boston’s coastline is definitely worth taking a stroll at sunset or checking out for a little bit.

Dinner & Drinks at the YOTEL Boston

Cocktails with a view? I’ll take it any day! For the last spot in your Boston itinerary, hit the Deck 12 – YOTEL Boston’s rooftop bar to devour some tasty snacks and raise your glasses to say “Cheers!” to yet another great view of the city.

Other restaurants worth checking out:

Krasi – Greek restaurant
Contessa – Rooftop dining in Back Bay

Boston is different in every season, which is a fantastic reason to come back and visit.

Heads up: the winter is very cold! But with snow on the ground and holiday festivities, it is definitely a winter wonderland. So,if you are willing to layer up, the city will have a fireplace lounge and a hot cup of chowder waiting for you.