Living near the Freedom Trail, I meet my beloved Frommer's Boston readers all the time. After I assure them that I'm not selling anything or trying to enlist them in a cult (why so suspicious, readers?), they usually make one of two comments. They want to know where they can find a public bathroom, or they want to praise the guide's suggested itineraries.

Read on for strategies that can help you organize your time. These itineraries include sightseeing destinations, snack and meal suggestions, shopping pointers, and dinner-and-a-movie alternatives. Two tips: Wear comfortable shoes, and don't ignore the breaks built into each itinerary, which can help you feel more like a relaxed insider and less like a crazed participant in a scavenger hunt.

Suggested Evening Itineraries

If you're traveling as a family, you may be checking the TV listings for your evening plans. If not -- or if you had the foresight to book a sitter -- here are some suggestions.

  • Dinner in the North End, and coffee and dessert at a caffè. Afterward, enjoy the view from Copp's Hill Terrace, between Charter and Commercial streets overlooking the harbor, or take in a show at the Improv Asylum. Wind down with a drink at the Cheers bar at Quincy Market.
  • Dinner at Legal Sea Foods in the Prudential Center, followed (or preceded) by a visit to the 50th-floor Prudential Center Skywalk or a drink in the lounge at Top of the Hub, on the 52nd floor. If heights aren't your thing, lift a glass at the Oak Bar in the Fairmont Copley Plaza Hotel.
  • Summer only: Assemble a picnic and head to the Hatch Shell for music or a movie, to Boston Common for a play, or to City Hall Plaza for a concert.
  • Winter only: A Boston Symphony Orchestra or Boston Ballet performance, then a late supper at Brasserie Jo or dessert at Finale.
  • Dinner at Sel de la Terre on State Street or around the corner at Legal Sea Foods, then a stroll along the harbor. Hit the North End or the food court at Faneuil Hall Marketplace for dessert.
  • Dinner at Brasserie Jo, then a Huntington Theatre Company performance or music at Wally's Cafe (or both).
  • Dinner at the Boston location of Jasper White's Summer Shack, a stroll on Newbury Street, and a nightcap at the Bristol Lounge in the Four Seasons Hotel or the Bar at Taj Boston.
  • Shopping at the Coop or the Harvard Book Store, then dinner at Mr. Bartley's Burger Cottage. Contemplate Harvard Yard from the Widener Library steps, and finish up with ice cream at JP Licks or Lizzy's, or a show at Club Passim (or both).
  • Dinner at the East Coast Grill or Oleana, followed by music at Scullers Jazz Club, the Regattabar, or Ryles Jazz Club.
  • Dinner at Baraka Café, ice cream at Toscanini's, and music at the Middle East or T. T. the Bear's Place.
  • A movie at the Kendall Square Cinema before or after dinner at Hungry Mother or Oleana, then music at the Cantab Lounge.
  • Dinner at Redbones or Johnny D's Uptown Restaurant & Music Club, and a show at Johnny D's or the Somerville Theater.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.