Whether you come for the US revolutionary history, the esteemed institutions of higher education or a tasty lobster roll, spending a perfect weekend in Boston is always within reach.

A statue of George Washington is illuminated by soft light posts at dusk in a public garden in Boston; perfect weekend Boston
History comes alive when strolling the streets of Boston © Sean Pavone / Getty Images



Begin your explorations at Boston Common, an intersection of neighborhoods both contemporary and historic. The Massachusetts State House towers over the Common from the northeast corner; fountains and statues dot the park; and Bostonians bustle to and fro. From here, it’s a one-mile walk to your dining destination, following the Freedom Trail.

This red-brick path passes some of the landmarks of the colonists’ fight for independence from the British crown. Look for the Granary Burying Ground, the final resting place of many revolutionary heroes; the Old South Meeting House, where rabble-rousers instigated the Boston Tea Party; and the Old State House, site of the 'Boston Massacre,' the first violent skirmish of the revolution. Faneuil Hall is the 18th-century meeting and market place that is now the center of Boston tourism action.

Stroll across the North End Park and into the eponymous neighborhood, where the sounds and scents of Italy drift through the doorways. Boston’s Italian heritage will tantalize your senses as you wander through the streets crammed with restaurants, bakeries and cafes. Join the line for an affordable feast at Giacomo’s Ristorante or make a reservation for an intimate affair at Pomodoro. The grand finale is cannoli from Modern Pastry Shop.



Rise and shine and learn the best way to see Boston is on two wheels. Rent a bicycle at Urban Adventours or Blue Bikes. Pedal along the Charles River Esplanade for flowering trees and shady paths. Or cross to the north side of the river (Cambridge) for city views and academic ambiance. Along the Charles River Bike Path, it’s about 5 miles one way to Harvard Square.

You’ll ride past the Massachusetts Institute of Technology (MIT), where you can stop to tour the campus’s impressive collection of modern architecture and public art. Or, continue two miles west to Harvard Square to explore the original Ivy League institution, not to mention the bookstores, record shops, clubs and cafes that fill the streets around it.  The options for refreshment are plentiful, including Café Pamplona in Harvard Sq and Roxy’s Grilled Cheese near MIT.

A large humpback whale emerges from the water; Perfect weekend Boston
Enjoy a day of whale watching in the wild during a weekend in Boston © Shahaira / Getty Images


Head back downtown in time to hop on a New England Aquarium Whale Watch (last boat leaves at noon, 2:30pm or 5:30pm depending on the season; reserve in advance). Feel the ocean breeze and enjoy the scenery as you journey out to Stellwagen Bank, a rich feeding ground for marine mammals and birds. Onboard naturalists point out humpbacks, finbacks, minkes, pilot whales and right whales, as well as dolphins, sharks and more. Whale sightings are guaranteed.


Debarking from the cruise at Central Wharf, you’re perfectly placed for a stroll along the Rose Kennedy Greenway, a strip of manicured parkland that snakes through downtown Boston. Take a ride on the Carousel, cool off in the Rings Fountain and admire the lush gardens and eclectic art, as you make your way to the Seaport District.

This seaside neighborhood was the old fishing district, centered on gritty Fisherman’s Wharf. It’s been snazzied-up in recent years, but it’s still the best place to sample the city’s freshest seafood. Here’s your chance to slurp some oysters, savor some chowder or devour a lobster roll. You’ll find a myriad of options for waterfront dining or rooftop drinking; we like Legal Harborside or Barking Crab for the former, Lookout Rooftop Bar or Trillium Fort Point for the latter. The wonderful views of the Boston Harbor and city skyline are hard to beat.

A row of classic Victorian-themed apartments with red brick walls and sidewalks, elegant stone steps and iron railings. There is a light purple plant next to stairs and a row of trees lining the sidewalks; Perfect weekend Boston.
Stroll through South End to marvel at the beautiful Victorian-themed row of apartments © Jorge Antonio / Getty Images



Reserve a table for Sunday jazz brunch at the Beehive. Feast on decadent food like eggs shakshuka (poached eggs with tomatoes, peppers and spices). Sip a concoction from the Bellini bar. And enjoy music courtesy of faculty and students from the local Berklee School of Music.


After brunch, stroll through the South End, admiring the Victorian row houses and English gardens.  South of Washington St, residential changes to post-industrial. Now known as SoWa, this is Boston’s vibrant art district, crammed with studios and galleries and – on Sundays – a giant art market. SoWa Open Market is the city’s largest gathering place for makers of all types, and you’ll find everything from handmade jewelry and designer clothing to artisanal soaps and pottery. Just in time for you to pick up a one-of-a-kind souvenir to remember your weekend in quirky, creative Boston.

Where to Stay

The Revolution Hotel offers a new concept in affordable lodging. The guest rooms are small but fresh, and furnished with fluffy pillows, quality linens and high-tech gadgetry. Shared bathrooms are spotless, and well stocked with plush towels and high-end toiletries. (En suite bathrooms are also available.) Art-filled common spaces and the South End location make this place a fantastic option for the budget-conscious traveler.

Alternatively, go upscale at No 284, a boutique hotel housed in a Back Bay brownstone. Luxurious amenities, original art and contemporary design are perfect complements to this classy location on Commonwealth Ave.

How to get there

Logan International Airport is 15 to 20 minutes away from downtown Boston. The free Silver Line bus takes passengers to South Station, from where the T (Boston’s metro system, $2.40 to $2.90) goes almost anywhere in Boston. Alternatively, a free airport shuttle bus takes passengers to the Airport T-station.

You might also like

Get more travel inspiration, tips and exclusive offers sent straight to your inbox with our weekly newsletter.


Explore related stories

Features - GettyImages-158426900_medium


Ultimate Ecuador: plan your perfect adventure

Jan 7, 2016 • 4 min read