date published: August 16, 2004

Boston Harbor has always been an important part of the Hub’s economy, but its precise role has varied over the years almost as much as the tide. In the city’s early days, the Harbor helped us prosper thanks to its status as a major colonial trading port. And while there was a time during the 1970s and ’80s when industrial pollution diminished much of the water’s splendor, these days the lively, thriving port is considered one of the cleanest major waterways in the U.S. and ships of all sorts crisscross its waters toting pleasure seekers and fisherman alike. So whether you’re a landlubber who enjoys the sea but prefers to keep the shore in sight, or a rugged sea dog ready for a taste of the unknown, there’s a treasure trove of options to get you out of the bustling metropolis and onto the water.

When most people think of Boston Harbor, they think of the Boston Tea Party. But our harbor has been much more than a dumping ground for the riotous acts of angry patriots; it is also home to more than 30 splendorous islands that make up the Boston Harbor Islands National Recreation Area. Just a 30-minute ferry ride from the city, these picturesque oases offer an abundance of recreational and historical activities. There’s the 39-acre George’s Island, where you’ll discover the pre-Civil War-era Fort Warren containing dozens of dark passageways and secret rooms. The fort, built during the first half of the 1800s to protect the harbor, was used as a prison during the Civil War and is rumored to be haunted by “The Lady in Black,” the ghost of a young bride who was caught trying to visit her husband (a prisoner on the island) and was hanged for spying. You can clamber all over the structure, then set up a picnic along the shores or grab a bite to eat at the snack bar. Afterwards, take a water taxi to one of the other islands, including Little Brewster, home of the oldest continuously operating lighthouse in the U.S., Boston Light; or Gallops and Lovells, where you can swim on sandy beaches, hike wind-swept dunes or take in views of the city skyline. Boston Harbor Cruises runs ferry service to George’s Island from Long Wharf.

If you want to turn your visit to the Harbor Islands into an overnight affair, permits are available for camping on several islands, including Grape, Bumpkin, Peddocks and Lovells islands. Both group and individual sites are available with a reservation, but reservations are not site-specific. Upon check-in, a park ranger assigns you a sleeping spot for the night.

Provincetown (a.k.a. P-Town) may be at the very tip of Cape Cod, but thanks to Bay State Cruise Lines and Boston Harbor Cruises, the famous resort town is only a quick cruise away, making it an ideal day trip for visitors hoping for a break from the city.

For the uninitiated, Provincetown is an eclectic blend of sandy beaches, restaurants, candy shops, unique boutiques and a lively and diverse community that welcomes all walks of life—from drag queens and bikers to families and fishermen, and everyone in between.

Travelers can choose between two cruise options: one speedy, one budget-friendly. The pricier, speedier ferry service—offered by both companies—makes the trip in a mere 90 minutes, maximizing the amount of time you can spend wandering P-Town’s main drag, Commercial Street, or sitting on the beach. Round-trip service costs approximately $48–58, with the last ferry departing for Boston as late as 8:30 p.m., Thursday–Sunday. For $19–29 round-trip, Bay State Cruises also offers a trip that leaves Boston Friday–Sunday at 9:30 a.m., arriving in P-Town after a three-hour cruise. This slower trip allows for only a short stay (the return trip departs at 3:30 p.m.), but the price and pace make it a good choice for families. You may even spot a whale or two on your trip.

Once you’ve pitched your tent and taken in your surroundings, you can hike trails or swim in the ocean (which is permitted on Bumpkin, Grape and Lovells islands). Grape also boasts an abundance of wild berries, making it a great destination for bird watchers. Unfortunately, travel between the islands is only possible during daylight hours, so you’ll have to plan ahead if you hope to explore more than one. The best part of camping on any island is that, with rates ranging from $5–15, the excursion is one of the city’s more affordable day trips.

Drifting on the ocean under city lights and twinkling stars is enough to turn an ordinary meal into an adventurous excursion the kids can appreciate and a romantic ride appealing to parents as well. Spirit of Boston Cruises (departs from the World Trade Center, 200 Seaport Blvd., 617-748-1499) offers a two-hour lunch cruise, complete with a show and sightseeing tour. Catch views of the city skyline while soaking up the sounds of Sinatra and other singers on this “Sentimental Journey.” In between songs, a narrator explains some of the various surrounding sights. The lunch buffet serves, appropriately enough, seafood favorites such as filet of sole and tuna salad.

Odyssey Cruises (Rowes Wharf, 1-888-741-0281) embarks on several different trips daily and provides a more upscale dining experience on board its modern, elegant yacht. A children’s meal rate is available for the lunch and brunch cruises, making them the best bet for families. But when night falls, adults will enjoy dancing to live jazz music and Top 40 hits on one of the lower levels, or heading to the observation deck to sip cocktails under the stars while taking in views of the city. A four-course meal is served on the dinner cruise, and the trip can be commemorated by the staff photographer. 

Some of Boston’s best nightlife can be found out on the water. For Latin lovers, Boston Harbor Cruises spices things up with its Salsa Harbor Cruise series. Every Sunday beginning at 6 p.m., guests gather at Long Wharf, where beginner salsa lessons are provided for those who need the practice. Then everyone boards the ship for a three-hour cruise featuring dancing and a buffet dinner. When the boat returns to port, the partying and dancing continue at the nightclub Sanctuary on nearby State Street, free of charge.

Dinner theater fans will want to consider Boston Harbor Cruises’ Mystery Cruise, which departs Long Wharf on Fridays and Saturdays at 7:30 p.m. While touring the inner harbor, guests enjoy a gourmet dinner from Ristorante Marino. But the real fun comes from the on-board comedic improv actors, who incorporate their audience members into a whodunit mystery. Witness a murder, search the boat, question the characters and, if all goes well, solve the crime before returning to shore.

While military history buffs can have the perfect field day on George’s Island and Fort Warren, they won’t want to end their trip there. Boston Harbor Cruises runs two sightseeing cruises, one to the Charlestown Navy Yard—home of the U.S.S Constitution—and the other a 90-minute historic cruise that is sure to teach even locals a thing or two they didn’t know about Boston Harbor. There’s even a Sunset Cruise available that concludes with a front-row seat for “Old Ironsides’” end-of-the-day cannon serenade. Massachusetts Bay Lines offers a similar tour of the harbor’s historical points aboard one of its replica steamships. The 55-minute narrated excursion includes a tour of the U.S.S. Constitution.

The inner harbor may once again be home to a wide array of wildlife, but in order to enjoy firsthand some of the most majestic, peaceful and titanic creatures of the ocean deep, visitors need to travel farther offshore. Local whale-watch excursions bring peepers out to Stellwagen Bank—a national marine sanctuary that is home to a variety of ocean mammals including dolphins, seals, finback and minke whales, and even the crowd-pleasing humpback whale. Tours depart from the waterfront and are run by several different companies, including Boston Harbor Cruises (One Long Wharf, 617-227-4321), Massachusetts Bay Lines (Rowes Wharf, 617-542-8000) and the New England Aquarium (Central Wharf, 617-973-5206). Most trips take approximately three hours and are considered among the most exhilarating nature-loving experiences available in Boston (see Whale Watch listings in Sightseeing, for times and rates). Because the summer months are a time when there’s an influx of whales feeding and mating on the bank, most companies guarantee a sighting.

back to homepage
With the sun slowly setting on Boston Harbor, the crew of the Liberty Clipper, one of the schooners owned by the Liberty Fleet of Tall Ships, moved into position as eager patrons lined up to embark on a cruise of the harbor. “Welcome aboard,” the captain called from above with a smile, dwarfed by the hulking masts rising behind him. As people staked out their spots on deck or lined up at the bar for a pre-sail beverage, the well-tanned crew pulled up the lines in preparation for the voyage ahead.

All of the Liberty ships, designed to replicate 19th-century clipper ships, can carry upwards of 100 passengers and boast an impeccably manicured wood-and-steel finish and billowing white sails. And sail they do, making daily trips out of Boston Harbor, including featured excursions such as Friday night lobster dinners and Sunday brunch sails.

What makes the Liberty Clipper experience special is its unique view of Boston. Not only are you offered a spectacular view of the skyline, the two- to three-hour cruises take guests away from the hustle and bustle of the city, giving them a taste of the tranquility that Boston’s waters held in the city’s earliest days. Passengers are also encouraged to test their seamanship and join the crew in raising the sails. “When I say heave, you say ho,” the captain bellows, bringing to mind the Old World vessels that once criss-crossed the globe. A journey aboard the Liberty Clipper will thrill avid boating enthusiasts, but landlubbers shouldn’t fear either—a trip aboard a tall ship is almost always smooth sailing.
—Matt Karr