Shannon O'Brien Travel Itineraries

The best destinations

BOSTON - JUNE 3: Red Sox vs Athletics: Red Sox Pitcher Tim Wakefield throws a pitch to an Oakland Athletic. taken June 3, 2010 Fenway Park Boston, Massachusetts from the outfield bleachers.
BOSTON - JUNE 3: Red Sox vs Athletics: Red Sox Pitcher Tim Wakefield throws a pitch to an Oakland Athletic. taken June 3, 2010 Fenway Park Boston, Massachusetts from the outfield bleachers.

The Best of Massachusetts

#45 best destination in the world

Map view

Fenway Park, Boston

BOSTON - JUNE 3: Red Sox vs Athletics: Red Sox Pitcher Tim Wakefield throws a pitch to an Oakland Athletic. taken June 3, 2010 Fenway Park Boston, Massachusetts from the outfield bleachers.

Best time to visit: June-Oct

  • Fenway Park is a historic baseball stadium located in Boston, and the home of the Boston Red Sox since its opening in 1912, making it the oldest ballpark in Major League Baseball
  • Fenway Park is renowned for its unique features, including the iconic left-field wall known as the "Green Monster"
  • The park not only attracts fans for baseball games, but also offers visitor tours and special events

Boston Tea Party Ships & Museum

Boston, USA- March 08, 2019: The Boston Tea Party Ships and Museum is enlightening adventure as journey back in time to December 16, 1773, when the colonists marched on board the tea

Best time to visit: June-Oct

  • The Boston Tea Party Ships & Museum is a historical attraction located in Boston, and dedicated to the events of the Boston Tea Party, which was a pivotal moment leading up to the American Revolution
  • The museum offers an experience that includes live actors, interactive exhibits, and full-scale replica 18th-century sailing vessels
  • Visitors can engage in reenactments and hear stories from historical figures like Samuel Adams
  • It is situated on the Congress Street Bridge along the Fort Point Channel, close to the original site of the Boston Tea Party
  • The museum features restored tea ships, an interactive documentary, and Abigail’s Tea Room, where visitors can enjoy refreshments

Museum of Fine Arts Boston

Museum of Fine Arts in Boston Massachusetts.

Best time to visit: June-Oct

  • The Museum of Fine Arts is an art museum located in Boston, founded in 1870
  • It opened to the public on July 4, 1876, coinciding with the nation's centennial celebration
  • It is recognized as one of the largest and most comprehensive art museums in the world, featuring more than 100 galleries showcasing a diverse range of art, from ancient artifacts to contemporary pieces

#31 in Best Museums in the USA

North End, Boston

BOSTON, MA, USA - APRIL 20, 2020: The historic architecture of Boston in Massachusetts, USA at Little Italy neighborhood.

Best time to visit: June-Oct

  • The North End is a historic neighborhood in Boston, recognized as the city's oldest residential community
  • It has been inhabited since the early days of Boston's founding and is often referred to as "Little Italy"
  • The North End is known for its strong Italian-American community, which is reflected in the numerous Italian restaurants, cafés, and bakeries that line its streets
  • The neighborhood is home to several significant historical sites, including the colonial home of the American patriot Paul Revere; Old North Church, which is famous for its role in the American Revolution, particularly the signal lanterns that alerted Paul Revere of British troop movements; and Copp's Hill Burying Ground, which is one of Boston's oldest cemeteries

Freedom Trail, Boston

One of the Markers of The Freedom Trail, Boston, Massachusetts

Best time to visit: June-Oct

  • The Freedom Trail is a 2.5-mile (approximately 4 km) path through Boston, that connects 16 historically significant sites related to the American Revolution and the early history of the United States
  • The trail is marked by a distinctive red brick line, guiding visitors through some of Boston's oldest neighborhoods
  • Notable historic sites include the Boston Common, Massachusetts State House, Paul Revere House, Old North Church, and the USS Constitution
  • Each site along the trail tells a part of the story of America's fight for independence and the events leading up to it

#29 in Best Attractions in the USA

#15 in Best Easy Hikes in the USA

#5 in Best Landmarks in the USA

Boston Public Garden

George Washington Monument at Public Garden in Boston, Massachusetts.

Best time to visit: June-Oct

  • The Boston Public Garden is a historic park located in the center of Boston, adjacent to Boston Common
  • Established in 1837, it holds the distinction of being the first public botanical garden in the United States
  • The garden features carefully landscaped areas, including a lagoon, walking paths, and a variety of flower beds
  • A highlight of the garden includes the opportunity to operate the iconic Swan Boats on the lagoon
  • The park was designed by Frederick Law Olmsted, who is also known for designing Central Park in New York City

Boston Public Library

Boston, USA - May 27, 2016: Locals study and read books in the Reading Room at McKim Building of Boston Public Library

Best time to visit: June-Oct

  • The Boston Public Library is a prominent municipal public library system located in Boston
  • Established in 1848, it was the first large free municipal library in the United States, and has played a significant role in the development of public libraries across the country
  • The library holds over 23 million items, making it one of the largest library collections in the nation

John F. Kennedy Presidential Library and Museum, Boston

Boston, Massachusetts - May 25, 2018: A re-creation of the 1960 U.S. Presidential election results at the John F Kennedy Presidential Library and Museum.

Best time to visit: June-Oct

  • The John F. Kennedy Presidential Library and Museum is dedicated to the memory of John F. Kennedy, the 35th President of the United States
  • Located in Boston, it serves as both a presidential library and a museum, showcasing the life, legacy, and presidency of JFK
  • Visitors can explore exhibits that detail significant events from Kennedy's presidency, including the Cold War, civil rights, and space exploration

Harvard University, Cambridge

Cambridge, MA, USA - March 15, 2024: View of the architecture of the famous Harvard University in Cambridge, Massachusetts, USA showcasing it brick buildings with some students and locals passing by .

Best time to visit: June-Oct

  • Harvard University is a prestigious private Ivy League research university located in Cambridge
  • Founded in 1636, it is recognized as the oldest institution of higher education in the United States
  • A famous landmark located in Harvard Yard, where visitors often take photos and rub the statue's foot for good luck

Coast Guard Beach, Eastham

Golden Sunrise on Coast Guard Beach in Cape Cod National Seashore at Eastham Massachusetts
  • Coast Guard Beach is a beach located in Eastham, that is part of the Cape Cod National Seashore
  • The beach is well-known for activities such as surfing and boogie boarding
  • The nearby visitor center offers a shuttle service to this bustling locale

#61 in Best Beaches in the USA

Good Harbor Beach, Gloucester

Good Harbor Beach and Salt Island aerial view in summer in Gloucester, Cape Ann, Massachusetts MA, USA.
  • Good Harbor Beach is a beach located in Gloucester, known for its white sand and gentle surf
  • The beach boasts a curved shoreline with fine, clean sand, making it an ideal spot for sunbathing
  • It is renowned for various activities, including swimming, body surfing, and boogie boarding
  • At low tide, visitors can walk out to Salt Island

#49 in Best Beaches in the USA

Aquinnah Cliffs, Martha's Vineyard

Aquinnah Clifffs Overlook and Gay Head Light during summer at Martha’s Vineyard, MA
  • The Aquinnah Cliffs, formerly known as Gay Head, are a natural feature located on Martha's Vineyard
  • The cliffs rise approximately 150 feet above the Atlantic Ocean and are composed of colorful clay and sandstone, formed during the last glacial period
  • The area also includes the historic Gay Head Lighthouse, which visitors can enjoy along with its scenic overlooks and trails
  • The cliffs hold historical importance for the native Wampanoag people, who have inhabited the region for centuries

Nantucket Whaling Museum

NANTUCKET, MASSACHUSETTS - August 22, 2015: Complete skeleton of a 46-foot (14 meter) bull Sperm whale suspended from the ceiling of the Nantucket Whaling Museum, originally a candle factory

Best time to visit: March-April, Sept-Oct

  • The Nantucket Whaling Museum is a prominent museum located in Nantucket, dedicated to preserving and interpreting the history of whaling and its impact on the island's culture
  • The museum houses a variety of exhibits that include a 46-foot sperm whale skeleton, a massive Fresnel lens used in lighthouses, artifacts from the whaling industry, such as scrimshaw and whaling tools, and a restored 1847 candle factory
  • The museum includes a rooftop deck that offers views of Nantucket harbor

House of the Seven Gables, Salem

A flower garden at the house of the seven gables in Salem Massachusetts on a sunny day.

Best time to visit: Sept-Nov

  • The House of the Seven Gables, also known as the Turner-Ingersoll Mansion, is a historic seaside mansion located in Salem
  • Built in 1668 by sea captain John Turner I, it is one of the oldest surviving timber-framed houses in North America, featuring 17 rooms and over 8,000 square feet of space
  • The house gained literary fame as the inspiration for Nathaniel Hawthorne's novel, "The House of the Seven Gables," published in 1851