Our 5-day Boston City Guide shows you a step-by-step time line and itinerary for your stay in Boston. Follow it and get the best of your days in the city.
Take a look at other preplanned Boston City Guides:
1-day Boston City Guide >
3-day Boston City Guide >
The first day, you see some of the best - and certainly the most famous - that Boston has to offer.
Take Subway Red Line to Charles/MGH Station
walk to Public Garden
One of the best spots for a relaxing break in the middle of a city
A National Historic Landmark
Was the country's first public botanical garden
Read more about Public Garden
Take Subway Green Line (B, C, D) from Arlington Station to Kenmore Station
Take a walk to Fenway Park - 15’ in all
One of the best-known sports venues in the world
Every Red Sox game since May 15, 2003, has sold out - an MLB record
The only one of the original standard ballparks that's still being used
Read more about Fenway Park Tour
walk via Back Bay Fens to Museum of Fine Arts - 15’
One of the largest museums in the United States
Over one million visitors annually
Just opened its new Art of the Americas wing, and will add more sections throughout 2011
Read more about Museum of Fine Arts
Subway Green Line from Museum of Fine Arts Inbound Station to Copley Station Take a walk to Newbury Street - 20’
Fun place for high-end shopping
One of the most expensive streets in the world
It is the "Rodeo Drive of the East"
Read more about Newbury Street
walk to Freedom Trail, which begins in Boston Common
Take a walk to Boston Common
walk to Paul Revere House
walk to Old North Church - 5’
walk to North End Neighborhood
end of day 1
Today, you will head to the other side of the Charles River, where you'll find a fantastic assortment of university life, history, nature, and funky squares.
Subway Red Line to Kendall/MIT Station
Oldest institute of higher learning in the U.S.
One of the most prestigious universities in the world
A beautiful place to wander
Read more about Harvard University
walk to Harvard Museum of Natural History - 5’
walk to Cambridge Common - 5’
walk to Harvard Square - 5’
Over 8 million people visit every year
Many cultural events and festivals year-round
Over 80 shops, and nearly 100 eateries
Read more about Harvard Square
Take a walk on Brattle Street to Longfellow National Historic Site
walk to Mount Auburn Cemetery - 25’
walk to Charles River Reservation/Esplanade via Harvard Square - 35’
Subway Red Line from Harvard Square Station to Davis Square Station - 15’
Great place to get a sense of local life
Hosts many art events throughout the year
Read more about Davis Square
end of day 2
Boston is about so much more than the city itself - the surrounding region of New England is one of the most beautiful in the country.
Drive to Portsmouth, NH - 60’
Drive to Ogunquit, ME - 30’
Drive to Kennebunkport, ME - 20’
Drive to Portland Head Light - 45’
One of the most scenic lighthouses in the U.S.
Listed in the National Register of Historic Places
The most photographed lighthouse in North America
Read more about Portland Head Light
Drive to Portland, ME - 15’
end of day 3
While hardly any visitors to Boston pass up the Freedom Trail and the charming neighborhoods that covers, today you will get a chance to see some beautiful areas a little farther afield, that some would argue are even better.
Subway Orange Line to Green Street Station Take a walk to Arnold Arboretum
walk to Jamaica Pond - 15’
walk to Centre Street, Jamaica Plain - 5’
Take a walk to Samuel Adams Brewery
Subway Orange Line from Stony Brook Station to Ruggles Station. Take a walk to Isabella Stewart Gardner Museum - 25’
43 Bus from Ruggles Station to Tremont Street @ Waltham, South End Neighborhood - 20’
end of day 4
You simply can't pass up Cape Cod, a relaxing and beautiful way to end your trip to Boston. Citygoers head to the Cape in droves over summer, for its beaches and quaint towns, clam shacks scattered along the way.
Subway Silver Line to Court House Station (outbound) Take a walk to Bay State Criuse Company Ferry
end of day 5
Meet our Boston Local Expert:
Jeanette Mellinger hails from San Francisco, but has been living in the Boston area since September 2009. Some of her favorite things include urban hiking, running, taking photos, finding the best brunch spots, and hanging out with great company over a microbrew, bottle of wine, or coffee. Luckily, these things mean she's explored a lot of Boston so far, and can't wait to see more!