Sample Boston itineraries

Start at Boston Common and join a small-group Freedom Trail tour. In two and a half hours you will see the State House, the Granary Burying Ground, the Old State House, the Boston Massacre site and Faneuil Hall, with a guide who brings the 1770s to life.

Follow the red line into the North End, Boston's Little Italy, for lunch.

• Pizzeria Regina North End
  Brick-oven pizza on Thacher Street since 1926
• Giacomo's North End
  Tiny, beloved and famous for its pasta. Expect a line.

Continue on the trail to the Paul Revere House and Old North Church, then walk across the bridge to Charlestown to board the USS Constitution. Take the ferry back downtown for a great view of the skyline. Pick up a cannoli on the way and choose your side in the Mike's vs. Modern debate.

• Mike's Pastry or Modern Pastry Hanover Street
  The great cannoli rivalry
• Caffe Vittoria Hanover Street
  Espresso in an old-world cafe

Dinner where Bostonians have eaten oysters for two centuries, or at the North End's favorite raw bar.

• Union Oyster House Near Faneuil Hall
  America's oldest continuously operating restaurant, since 1826
• Neptune Oyster North End
  Small, buzzy and known for its hot buttered lobster roll

Wander the cobblestone lanes of Beacon Hill (do not miss Acorn Street), then cross into the Public Garden to see the Make Way for Ducklings statues and, in season, ride the Swan Boats.

• The Paramount Charles Street, Beacon Hill
  A neighborhood breakfast and brunch institution
• Tatte Bakery Charles Street and around town
  Pastries and coffee in a bright, busy cafe

Hop on a duck boat for the city's most famous tour. It rolls past the landmarks, then drives straight into the Charles River.

Stroll Newbury Street's shops and cafes, then see Copley Square: Trinity Church and the Boston Public Library, whose courtyard is one of the city's hidden gems. For a bird's-eye view, head up to View Boston at the top of the Prudential Center.

• Saltie Girl Back Bay
  Seafood and an enormous tinned-fish menu
• Atlantic Fish Co. Boylston Street
  A classic Back Bay seafood room

Take a harbor sunset cruise from the waterfront, then have dinner in the Seaport.

• Row 34 Fort Point, Seaport
  Oysters and local beer in a converted warehouse
• Legal Harborside Seaport
  Three floors of seafood with harbor views

Ride the Red Line to Harvard Square and take a student-led tour of Harvard Yard, then browse the bookstores and cafes around the square. If you have time, walk down Massachusetts Avenue to see MIT.

• Alden & Harlow Harvard Square
  Creative small plates in a basement dining room

Head back across the river to Fenway Park. The tour takes you onto the field level and up on top of the Green Monster.

In season, stay for a Red Sox game. Otherwise, catch the Celtics or Bruins at TD Garden, or grab a burger near the park.

• Bleacher Bar Lansdowne Street
  A bar built into Fenway's outfield wall, with a window onto the field
• Tasty Burger Fenway
  A casual local burger favorite

Join a food and history tour that combines tastings with the stories of the North End, the Freedom Trail and Beacon Hill.

Throw tea into the harbor yourself at the Boston Tea Party Ships & Museum, then wander the Rose Kennedy Greenway or browse the stalls of the Boston Public Market.

Have dinner in the South End, Boston's restaurant row, or try dim sum and dumplings in Chinatown. Finish with a Boston cream pie where it was invented.

• Toro South End
  Lively Spanish tapas
• Myers + Chang South End
  Playful Asian small plates
• Gourmet Dumpling House Chinatown
  Soup dumplings and scallion pancakes
• Omni Parker House Downtown
  Birthplace of the Boston cream pie and Parker House rolls

Take the ferry to Salem and explore the witch trials story, the Peabody Essex Museum and the House of the Seven Gables. October is magical, and very busy.

• Turner's Seafood at Lyceum Hall Salem
  Seafood in a historic hall where Alexander Graham Bell once lectured

Stand on Lexington Green and Concord's Old North Bridge, where the Revolution began on April 19, 1775, then visit Walden Pond and Louisa May Alcott's Orchard House.

Board Mayflower II, visit Plimoth Patuxet Museums and see Plymouth Rock, with a stop in Quincy, home of two presidents, on the way.

Back in Boston, toast your trip with a classic Italian dinner in the North End.

• Mamma Maria North Square, North End
  Upscale Italian in a townhouse facing the Paul Revere House