DAY 1
The first day, you see some of the best - and certainly the most famous - that Boston has to offer.
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
Photo: bluebike
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
Photo: Philocrites
Take a walk to Fenway Park - 15’ in all
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
Photo: jack heddon
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
Photo: pobrecito33
Take a walk to Newbury Street - 20’
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"
Photo: Nicolas Karim
Why visit
- One of the oldest city parks in the US
- Great spot during any season
Photo: GreenNetizen
Take a walk to Boston Common
Why visit
- Great collection of American Revolution sites
- A Boston National Historical Park
Photo: kberberi
Why visit
- Downtown Boston's oldest building
- A National Historic Landmark
Photo: Dennis Wright
Why visit
- The oldest standing church building in Boston
- The signal that started the American Revolution was sent from here
Photo: jbcurio
Why visit
- Boston's Little Italy
- The oldest residential community of the city
- Great spot to stop for delicious Italian food
Photo: copelaes
DAY 2
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.
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
Photo: kleintjef
Why visit
- Incredibly diverse collection of life on earth
- The University's most visited museum
- Collection of highly-realistic glass models of plants
Photo: Erik Mallinson
Why visit
- Great green space
- One of the best spots to bring your picnic
Photo: nsub1
Why visit
- Over 8 million people visit every year
- Many cultural events and festivals year-round
- Over 80 shops, and nearly 100 eateries
Photo: wallyg
Take a walk on Brattle Street to Longfellow National Historic Site
Why visit
- National Historic Site
- Great representative of local history
Photo: dbaron
Why visit
- National Historic Landmark
- Started the American public parks and gardens movement
- Has a collection of over 5,000 trees
Photo: friendsofmountauburn
Why visit
- Abundance of on-land activities
- Great spot for water sports
- One of the most spectacular Fourth of July shows
Photo: Martin Hapl
Why visit
- Great place to get a sense of local life
- Popular neighborhood
- Hosts many art events throughout the year
Photo: timsackton
DAY 3
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.
Why visit
- The third oldest city in the U.S.
- New Hampshire's loveliest colonial town
- A collection of beautiful historical buildings
Photo: Elizabeth Thomsen
Why visit
- Three miles of beautiful sandy beach
- One of the coast's most popular tourist towns
- Great, fresh seafood
Photo: RSzepan
Why visit
- Popular seaside tourist destination
- Art galleries, cute inns, and beautiful views
- Summer residence of the Bush family
Photo: IronMal
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
Photo: brentdanley
Photo: kariek
DAY 4
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 a walk to Arnold Arboretum
Why visit
- World-renowned plant collection
- National Historic Site
- National Historic Landmark
Photo: msandman
Why visit
- Part of Boston's Emerald Necklace
- Home to plenty of recreation
- Great fishing spot
Photo: andrewjosephkatz
Why visit
- Warm neighborhood feel
- Great dining options
- Home to a portion of the Emerald Necklace
Photo: John_Stephen_Dwyer
Take a walk to Samuel Adams Brewery
Why visit
- Over 30 different beer styles
- Entertaining tour for all ages
- Over 21, the tour comes with tastings
Photo: katkamin
Take a walk to Isabella Stewart Gardner Museum - 25’
Why visit
- Collection of over 2,500 works
- Beautiful courtyard garden
- Regular concert evenings
Photo: ochus b
Why visit
- Victorian brick row houses
- Boston Landmark District
- Listed in the National Register of Historic Places
Photo: Robert Blackie
DAY 5
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 a walk to Bay State Criuse Company Ferry
Why visit
- Sunbathing on the sundeck
- Photos galore of the Cape Cod Bay
Photo: anarchitect
Why visit
- Two of the best beaches in the U. S.
- America's oldest art colony
- Birthplace of American playwriting
- Great festivals
Photo: laura padgett
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!