The Waterfront

Start: Old State House Museum (T: Orange or Blue Line to State).

Finish: John Joseph Moakley U.S. Courthouse.

Time: 2-5 hours, depending on how much time you spend in shops and museums.

Best Time: Mid-morning to early afternoon.

Worst Time: Mid-afternoon or later. Most attractions will be closing, and you'll be wandering through rush-hour traffic.

One of America's legendary seaports, Boston draws much of its considerable appeal from its proximity to the water. This tour takes you near and along the shoreline of the colonial town and the modern city.

The same building holds the subway station and your first stop, the:

1. Old State House Museum

The little brick building at 206 Washington St. was erected in 1713, replacing the Boston Town House. Back then, the shore was just a couple of blocks away, and this was a tall building. Exit and turn toward the water (downhill), passing the subway entrance. The Boston Massacre Site is a circle of cobblestones that sits on a triangular traffic island beneath the balcony.

Down the shallow hill to your left is Faneuil Hall. Now landlocked, it stood on the water before the harbor began to fill with silt and garbage. The filling-in was completed (using earth) and new streets laid out as part of the Quincy Market project of 1826. Ahead of you, sloping gently toward Boston Harbor, is State Street. This was King Street until 1784 (fairly late considering the antiroyal sentiment that inspired the change), and it ran right out into the harbor.

With the Old State House at your back, follow State Street toward the water. Note that the 40-story glass skyscraper at the corner of Congress Street, Exchange Place, encloses the facade of its predecessor, the Boston Stock Exchange (1891). On State Street just before Kilby Street, a plaque marks the former site of the:

2. Bunch of Grapes Tavern

Constructed in 1712, the tavern entertained both independence-minded colonists and their royalist counterparts before and during the Revolutionary War. After the British symbols (including the lion and unicorn from the Old State House) were removed from most of the public buildings in town in July 1776, they were made into a bonfire here. The Ohio Company, which settled that state, was formed here in 1786.

Where Kilby Street and Merchants Row meet on either side of State Street, pause and step out of the way of other pedestrians. This is the:

3. Shoreline of Colonial Boston

The construction of Long Wharf began here in 1709. At its greatest, Boston's main wharf was 1,743 feet long and 104 feet wide, extending so far into the harbor that the water at the end was 17 feet deep.

Continue on State Street, crossing Broad Street, developed in 1805-07 as part of a plan to improve the waterfront. Charles Bulfinch helped design 60 of the brick warehouses that stood here, some of which survive today. Pause at the corner of State and India streets and look up at the:

4. Custom House

Construction took a full decade, from 1837-47; the foundation alone, which sits on some 3,000 wooden piles resting on bedrock, took 3 years to build. The tower, added in 1911-15, was for many years the tallest structure in town. The building is now a Marriott time-share property. Admire the colorful clocks on all four sides of the tower, but don't count on them to tell the correct time.

5. Take a Break

Faneuil Hall Marketplace is a block away. If the weather is fine, head to the enormous food court inside Quincy Market for a snack or meal to go, then take it across the street to the Greenway.

Leave through the archway at the east end of the complex, in Marketplace Center (look for the Gap). Filling the space between the market and the harbor, where traffic on an ugly interstate highway once roared about 20 feet above street level, is the:

6. Rose Fitzgerald Kennedy Greenway

This lovely park occupies 15 acres of prime real estate, arranged like no park you've ever seen before—it's 1 mile long and a block or less wide. The major legacy of the $15-billion Big Dig highway-construction project, this constantly evolving institution features gorgeous plants and flowers along with dramatic public art. Check the Greenway's website to see whether any events are scheduled during your visit. Formally opened in 2008, the Greenway consists of four sections: North End, Wharf District, Dewey Square, and Chinatown. You're standing in the Wharf District.

Across the way, to your right as you face the harbor, is the Boston Marriott Long Wharf hotel. Cross the John F. Fitzgerald Surface Road, the Greenway, and Atlantic Avenue and step out of the flow of the crowd to take in:

7. Long Wharf

Boston's principal wharf opened for business in 1710. This is the embarkation point for many sightseeing cruises, as well as the MBTA ferry to Charlestown. Even at its busiest, it's not nearly as crowded and frantic as it was in its 18th- and 19th-century heyday, when Boston was one of the most important ports in the country. Near the end of the wharf is a granite building, dating from 1846, that was used by Customs appraisers. Now it houses offices and residences. At the very end of the wharf is a small plaza that may be covered in construction equipment during your visit. If you're able to gain access to the very end of the wharf, the view is worth the effort.

Return to the Marriott and stand with the lobby behind you. Walk 1 block (with Legal Sea Foods on your right) on Old Atlantic Avenue to the:

8. New England Aquarium

The aquarium opened in 1969. Peter Chermayeff, then with Cambridge Seven Associates, designed the structure, which echoes the waves of the adjacent harbor. You don't have to buy a ticket to check out the harbor seals, who frolic in an exhibit near the entrance..

Continue to walk along the waterfront for the equivalent of 2 blocks. On your right, you'll pass the residential Harbor Towers, designed by I. M. Pei and opened in 1971. This is India Wharf, which adjoins your next stop:

9. Rowes Wharf

Turn left as you reach the first red-brick building in this complex and follow the walkway that encircles it, along the water. The hotel-office-residential development bears the name of John Rowe (known as "Merchant" Rowe), who donated the Sacred Cod that hangs in the State House. The wharf was constructed after a fire in 1760 and has long been used as a ferry terminal. It's probably better known today for the dramatic arch in the center of the Boston Harbor Hotel (1985), designed by the Chicago architecture firm Skidmore, Owings, and Merrill. Enjoy the peek-a-boo view of the Greenway through the arch as you walk past the hotel and the boats in the marina and at the docks.

At the end of this little promenade is a short staircase that leads up to the:

10. Northern Avenue Bridge

An iron-turntable bridge built in 1908, the pedestrian-only bridge is a favorite with bridge aficionados -- if "through truss swing span" means something to you, make sure you have your camera -- and makes a good place to pause and look around. Beneath you is Fort Point Channel, which separates downtown from South Boston. A stone's throw away is the Evelyn Moakley Bridge, the vehicular access point to the Seaport District and an important piece of the Big Dig. Behind you, at the corner of Atlantic Avenue, is the First District Headquarters of the U.S. Coast Guard. The Massachusetts, the first commissioned revenue cutter, was based here. (Revenue cutters were the forerunners of the U.S. Coast Guard.)

Cross the Northern Avenue Bridge. You're on Old Northern Avenue, but the formal address of your destination is 1 Courthouse Way. This is the:

11. John Joseph Moakley U.S. Courthouse

Dedicated in 2001, the courthouse bears the name of a longtime Massachusetts congressman who was instrumental in securing funding for the Big Dig. Henry N. Cobb of Pei Cobb Freed & Partners designed the deceptively plain structure. Follow the Harborwalk around to the back to take in the centerpiece of the design, an 88-foot-tall wall of glass that opens the interior of the courthouse to the harbor. During business hours, the public is welcome to enter the building, take in the dramatic views, and even have a meal or snack overlooking the water in the second-floor cafeteria. You can't bring in your cellphone (the guards in the lobby will take it away and return it as you leave), and adults must show two forms of ID to enter.

The park outside the courthouse makes a good place to stop and plan your next stop. From here, both the Boston Children's Museum and the Institute of Contemporary Art are within easy walking distance. You can return to the Greenway and work up an appetite by following it south to Chinatown or north to the North End. Or take public transportation -- the Silver Line Courthouse stop is nearby, and South Station is about 15 minutes away on foot -- to your next destination.

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.