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Preplanned City Guides and Travel Itineraries

5-day Boston City Guide

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 Guide3-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
09:00-09:20 Beacon Hill Neighborhood (Park and outdoors, Free)

Why visit

  • One of the most desirable neighborhoods in Boston
  • A National Historic Landmark
  • Home to the pub that became the inspiration for the TV show, Cheers
Read more about Beacon Hill Neighborhood

Photo: bluebike

Take a walk to Public Garden
09:20-09:35 Public Garden (Park and outdoors, Free)

Why visit

  • 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

Photo: Philocrites

Take Subway Green Line (B, C, D) from Arlington Station to Kenmore Station
Take a walk to Fenway Park - 15’ in all
09:50-11:00 Fenway Park Tour (Park and outdoors, 12 $)

Why visit

  • 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

Photo: jack heddon

Take a walk via Back Bay Fens to Museum of Fine Arts - 15’
11:15-13:00 Museum of Fine Arts (Museum, 20 $)

Why visit

  • 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

Photo: pobrecito33

Take Subway Green Line from Museum of Fine Arts Inbound Station to Copley Station
Take a walk to Newbury Street - 20’
13:20-14:50 Newbury Street (Park and outdoors, Free)

Why visit

  • 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
Take a walk to Freedom Trail, which begins in Boston Common
14:50-15:00 Boston Common (Park and outdoors, Free)

Why visit

  • One of the oldest city parks in the US
  • Great spot during any season
Read more about Boston Common
Lunch time
Take a walk to Boston Common
15:00-16:45 Freedom Trail (Park and outdoors, Free)

Why visit

  • Great collection of American Revolution sites
  • A Boston National Historical Park
Read more about Freedom Trail

Photo: kberberi

Take a walk to Paul Revere House
16:45-17:00 The Paul Revere House (Monument, 3.5 $)

Why visit

  • Downtown Boston's oldest building
  • A National Historic Landmark
Read more about The Paul Revere House
Take a walk to Old North Church - 5’
17:05-17:15 Old North Church (Church, Free)

Why visit

  • The oldest standing church building in Boston
  • The signal that started the American Revolution was sent from here
Read more about Old North Church

Photo: jbcurio

Take a walk to North End Neighborhood
17:15-18:00 North End Neighborhood (Park and outdoors, Free)

Why visit

  • Boston's Little Italy
  • The oldest residential community of the city
  • Great spot to stop for delicious Italian food
Read more about North End Neighborhood

Photo: copelaes

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.

Take Subway Red Line to Kendall/MIT Station
09:00-09:45 Harvard University (Monument, Free)

Why visit

  • 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

Photo: kleintjef

Take a walk to Harvard Museum of Natural History - 5’
09:50-11:20 Harvard Museum of Natural History (Monument, 9 $)

Why visit

  • Incredibly diverse collection of life on earth
  • The University's most visited museum
  • Collection of highly-realistic glass models of plants
Read more about Harvard Museum of Natural History
Talk a walk to Cambridge Common - 5’
11:25-11:35 Cambridge Common (Park and outdoors, Free)

Why visit

  • Great green space
  • One of the best spots to bring your picnic
Read more about Cambridge Common

Photo: nsub1

Take a walk to Harvard Square - 5’
11:40-12:30 Harvard Square (Park and outdoors, Free)

Why visit

  • 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

Photo: wallyg

Lunch time
Take a walk on Brattle Street to Longfellow National Historic Site
13:30-14:00 Longfellow National Historic Site (Monument, Free)

Why visit

  • National Historic Site
  • Great representative of local history
Read more about Longfellow National Historic Site

Photo: dbaron

Take a walk to Mount Auburn Cemetery - 25’
14:25-15:15 Mount Auburn Cemetery (Park and outdoors, Free)

Why visit

  • National Historic Landmark
  • Started the American public parks and gardens movement
  • Has a collection of over 5,000 trees
Read more about Mount Auburn Cemetery
walk to Charles River Reservation/Esplanade via Harvard Square - 35’
15:50-17:00 Charles River Reservation/Esplanade (Park and outdoors, Free)

Why visit

  • Abundance of on-land activities
  • Great spot for water sports
  • One of the most spectacular Fourth of July shows
Read more about Charles River Reservation/Esplanade

Photo: Martin Hapl

Take Subway Red Line from Harvard Square Station to Davis Square Station - 15’
17:15-18:00 Davis Square (Park and outdoors, Free)

Why visit

  • Great place to get a sense of local life
  • Popular neighborhood
  • Hosts many art events throughout the year
Read more about Davis Square

Photo: timsackton

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’
09:00-10:30 Portsmouth, New Hampshire (Park and outdoors, Free)

Why visit

  • The third oldest city in the U.S.
  • New Hampshire's loveliest colonial town
  • A collection of beautiful historical buildings
Read more about Portsmouth, New Hampshire
Drive to Ogunquit, ME - 30’
11:00-13:00 Ogunquit, Maine (Park and outdoors, Free)

Why visit

  • Three miles of beautiful sandy beach
  • One of the coast's most popular tourist towns
  • Great, fresh seafood
Read more about Ogunquit, Maine

Photo: RSzepan

Drive to Kennebunkport, ME - 20’
13:20-15:15 Kennebunkport, Maine (Park and outdoors, Free)

Why visit

  • Popular seaside tourist destination
  • Art galleries, cute inns, and beautiful views
  • Summer residence of the Bush family
Read more about Kennebunkport, Maine

Photo: IronMal

Drive to Portland Head Light - 45’
16:00-17:00 Portland Head Light (Monument, Free)

Why visit

  • 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

Photo: brentdanley

Drive to Portland, ME - 15’
17:15-19:15 Portland, Maine (Park and outdoors, Free)

Why visit

  • Lively waterfront
  • Vibrant downtown
  • Great food destination
Read more about Portland, Maine

Photo: kariek

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.

Take Subway Orange Line to Green Street Station
Take a walk to Arnold Arboretum
10:00-11:30 Arnold Arboretum (Park and outdoors, Free)

Why visit

  • World-renowned plant collection
  • National Historic Site
  • National Historic Landmark
Read more about Arnold Arboretum

Photo: msandman

Take a walk to Jamaica Pond - 15’
11:45-12:25 Jamaica Pond (Park and outdoors, Free)

Why visit

  • Part of Boston's Emerald Necklace
  • Home to plenty of recreation
  • Great fishing spot
Read more about Jamaica Pond
Take a walk to Centre Street, Jamaica Plain - 5’
12:30-13:45 Centre Street, Jamaica Plain Neighborhood (Park and outdoors, Free)

Why visit

  • Warm neighborhood feel
  • Great dining options
  • Home to a portion of the Emerald Necklace
Read more about Centre Street, Jamaica Plain Neighborhood
Take a walk to Samuel Adams Brewery
13:45-14:50 Samuel Adams Brewery Tour (Museum, Free)

Why visit

  • Over 30 different beer styles
  • Entertaining tour for all ages
  • Over 21, the tour comes with tastings
Read more about Samuel Adams Brewery Tour

Photo: katkamin

Take Subway Orange Line from Stony Brook Station to Ruggles Station.
Take a walk to Isabella Stewart Gardner Museum - 25’
15:15-17:00 Isabella Stewart Gardner Museum (Museum, 12 $)

Why visit

  • Collection of over 2,500 works
  • Beautiful courtyard garden
  • Regular concert evenings
Read more about Isabella Stewart Gardner Museum

Photo: ochus b

Take 43 Bus from Ruggles Station to Tremont Street @ Waltham, South End Neighborhood - 20’
17:20-18:00 South End Neighborhood (Park and outdoors, Free)

Why visit

  • Victorian brick row houses
  • Boston Landmark District
  • Listed in the National Register of Historic Places
Read more about South End Neighborhood
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.

Take Subway Silver Line to Court House Station (outbound)
Take a walk to Bay State Criuse Company Ferry
08:30-10:00 Ferry to Provincetown (Park and outdoors, 49 $)

Why visit

  • Sunbathing on the sundeck
  • Photos galore of the Cape Cod Bay
Read more about Ferry to Provincetown

Photo: anarchitect

10:00-19:30 Provincetown, Cape Cod (Park and outdoors, Free)

Why visit

  • Two of the best beaches in the U. S.
  • America's oldest art colony
  • Birthplace of American playwriting
  • Great festivals
Read more about Provincetown, Cape Cod
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!

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