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New England Trip Itineraries

Escape to Boston for the Weekend

Destination(s): Boston

Day 1:Boston is a great city and small enough to get around by foot. The public transportation system known to locals as “The T” can easily take you from one end of the city to the other quickly and easily. For a weekend getaway to Beantown, grab a cup of coffee and start your first day of adventure off with a stroll through the beautiful Public Garden. In the warmer months, don’t miss a ride on the famous Swan Boats, a favorite of both kids and adults. Adjacent to the Public Garden is the Boston Common, the country’s oldest park. A visit to Boston would not be complete without a walk along the three-mile Freedom Trail. What makes the walk so special is that you can do it at your leisure, stopping along the way to catch some sights or take a break for lunch. Just follow the red painted bricks that will take you by 16 national historic sites, including churches, meeting houses and burial grounds. If you stay continuously on the trail, it should take a few hours to complete. Once you have finished, make your way over to Cheers and grab some lunch on a barstool where Norm used to sit on the famous TV show. Head back to your hotel room just up the street at the Beacon Hill Hotel, relax and take a shower. The hotel has a cozy restaurant which is great for a light bite before a night on the town. Walk over to Park Street train station and jump on the Green Line to Symphony T Station. Handel’s Messiah is playing tonight at Symphony Hall, home to the Boston Pops. When the show is over, take the T back to the hotel and get a good night sleep for tomorrow’s adventures. Day 2:Grab a cup of coffee at the hotel and head over to the train station again. Take the Green Line to the Prudential stop and head over to the Prudential Center Skywalk Observatory. You won’t believe the 360 degree views that can be found from this location. You’ll be able to see from Fenway Park all the way to Cambridge and beyond. Make your way past Boylston Street and up Lansdowne Street to the Boston Beer Works for lunch. Don’t miss their blueberry ale with floating blueberries and the sour cream and chive French fries but be sure to arrive early as this place gets “wicked” crowded before a Red Sox game. Stroll down Yawkey Way and visit Big League Tours for a behind the scenes tour of Fenway Park, the perfect start to a game. Finish up the day with a game at Fenway Park (Green Monster seats maybe?) and be sure to indulge in a steamed Fenway frank hotdog for the ultimate experience.Day 3:It’s your final day in the city so be sure to take it all in. From the hotel, you can walk through Government Center and over to Faneuil Hall. Also known as Quincy Marketplace, the shopping center is loaded with shops, restaurants and snacks. Head over to Durgin Park for lunch (Boston baked beans and Indian pudding are a must), the famed restaurant where the servers have attitudes! A visit to Boston would be incomplete without a stop at an Irish pub so head over to the Green Dragon Tavern for a quick pint before finishing up the day at Faneuil Hall. Located just a few steps from the marketplace is the North End, home to some of the best Italian food in the country. Relax with a cigar and cognac at Stanza dei Sigari on Hanover Street and end the trip with a slice of pie from Pizzeria Regina. read more about Escape to Boston for the Weekend

Boston Public Garden

Boston Public Garden

  • Arlington, Boylston, Charles and Beacon streets
  • tel:+1 617 522 1966
  • Visit website
  • Boston, 02116

Travelers entering the Boston Common will see Beacon Hill to the north, bustling Tremont Street to the east, Emerson College to the south, and gated greenery to the west. Beyond those gates is a well-manicured, but still approachable public garden. Lagoons, walking paths, bridges, statues and flowers galore make it the perfect spot for an afternoon stroll (or simply a path from the Common to Newbury Street). If you're looking for things to do with the kids, take the Swan Boats, and check out the Make Way for Ducklings sculpture in the northeast corner. read more about Boston Public Garden

Prudential Center Skywalk Observatory

Prudential Center Skywalk Observatory

  • 800 Boylston Street
  • 50th Floor, Prudential Center Tower
  • tel:+1 617 859 0648
  • Visit website
  • Boston, 02199
Durgin-Park

Durgin-Park

  • 340 Faneuil Hall Marketplace
  • tel:617/227-2038
  • Visit website
  • Boston, 02109
Boston Common

Boston Common

  • Beacon Street
  • Between Beacon, Park, Tremont, Boylston, and Charles Sts
  • tel:+1 800 7 3326 7866 (Tourist Information)
  • Visit website
  • Boston, 2203
Boston Beer Works

Boston Beer Works

Faneuil Hall

Faneuil Hall

  • Congress Street
  • Dock Sq (Congress St and North St)
  • tel:+1 800 7 3326 7866 (Tourist Info - Toll Free)
  • Visit website
  • Boston, 2203
Freedom Trail

Freedom Trail

  • 15 State Street
  • Suite 401
  • tel:+1 617 242 5642 / +1 617 242 5689
  • Visit website
  • Boston, 02109
Big League Tours

Big League Tours

  • 4 Yawkey Way
  • Fenway Park
  • tel:+1 317 534 2475 / +1 866 619 1748 (Toll free)
  • Visit website
  • Boston, 02215
Green Dragon Tavern

Green Dragon Tavern

  • 11 Marshall Street
  • tel:617 367 0055
  • Visit website
  • Boston, 02108
Cheers (Beacon Hill)

Cheers (Beacon Hill)

Fenway Park

Fenway Park

There's no place like Fenway. Whether you're a Red Sox fan or not, Fenway Park is a must-see. Built in 1912, it's the oldest baseball park in the country, and boasts the legendary Green Monster, which towers 37 feet in the air, threatening home run hopefuls. The manually-operated scoreboard paired with peanuts, Fenway Franks and historic fans, make this ballpark an epic timepiece. Can't make a game? Take a tour May through September. read more about Fenway Park

Stanza Dei Sigari

Stanza Dei Sigari

  • 292 Hanover Street
  • tel:617-227-0295
  • Visit website
  • Boston, 02113
Beacon Hill Hotel and Bistro

Beacon Hill Hotel and Bistro

  • 25 Charles Street
  • tel:+1 617 723-7575
  • Visit website
  • Boston, 02114
Handel & Haydn Society

Handel & Haydn Society

  • 300 Massachusetts Ave
  • tel:617/266-3605
  • Visit website
  • Boston, 02115
Pizzeria Regina

Pizzeria Regina