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Boston Harbor

Boston Harbor-image
© Shoreline Aerial Photography

It could only happen with the “Pats” in the Super Bowl — a commercial revolving around a car with “smaht pahk” in which a former Red Sox great is referred to as “your bigness.” Boston’s dialect is distinct. Some might say endearing. Its neighborhoods are diverse, and its residents are proud (especially of their sports teams). “Wicked pissah!” can describe something as awesome, and “No suh!” might be fired at something that is unbelievable. The streets do things their own way, too. There are no numbered blocks or easy-to-follow grids the likes of which you find in other large cities like New York and Washington. 

Yet Boston delivers the goods. It oozes culture from colleges and universities, restaurants, nightlife, shopping, museums, architecture and theater. All you have to do is find it. Boaters benefit from a totally revitalized harbor and surrounding area. Marinas and services are aplenty. There’s convenient public transportation adjacent to the waterfront, and the list of things to see and do is endless.

For starters, there’s the scenic Harborwalk with nearly 40 miles of pedestrian- and bike-friendly walkways to explore, with breathtaking views. On top of that, a series of parks, known collectively as the Rose Kennedy Greenway, were built to provide even more public green space and make the city more walkable. Located in Chinatown, the North End and the Wharf District, these parks include gardens, fountains, a tree-lined promenade and The Greenway Carousel.

That’s not to mention the inner harbor itself. Bustling and boater-friendly, Boston welcomes sailors with its quaint, historic charm and a dynamic new seaport district. The port, though, tends to be as traffic-prone as the city streets. So while you’re amping up for some “wicked fun pahtying,” keep a lookout for ferries, local boaters, commercial traffic, duck boats and — oh yes — the thrill seekers that roar around on the 70-foot, bow-toothed Codzilla!

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Things to See and Do

Twists and turns, nonsensical traffic patterns and lack of organization from one street to the next make your experience, let’s say, interesting. A good map — or your favorite app — is a must. Once armed with reliable navigation, you can find your way to famous (and infamous) historic sites, lush parks, world-class museums and arts organizations, and venues where some of the country’s most competitive sports teams play. There’s so much to do here that it’s difficult to condense, but we’ll give it a try.

First mention is Harborwalk because it is water-centric. The meandering pathway snakes for almost 40 miles around most of the shoreline from Chelsea and Charlestown to Dorchester — keep in mind that it’s not all contiguous, though. You can pick up the portion that you want to investigate just about anywhere on the city waterfront.

Speaking of outside roaming, there is nothing that says history quite like The Freedom Trail. You need only follow a 2.5-mile red-brick line that guides visitors to 16 historic sites that make up the Boston National Historical Park (617-242-5601). The trail starts at Boston Common, meanders through downtown Boston, passes through the North End, and finally crosses the Charles River. The national park’s headquarters is in Charlestown at 21 Second Ave.

Before even starting off on the Freedom Trail, you can sit or stroll around Boston Common, abutting Tremont and Beacon streets, for a classic Boston experience. While there, hop on a swan boat in the Public Garden and admire the ducks. As you will learn about this historic city, Boston boasts about being the birthplace of many things in America. Established in 1837, this was first public botanical garden in the United States. On the subject of botany, walk less than a mile to the southwest, or catch a cab, to Flores Mantilla (595 Tremont St.; 857-350-3001), where custom bunches of flowers are crafted with care and will certainly brighten any drab corners of your cruiser.

A half-mile side trip from the Common’s westernmost end will bring you to the Boston Public Library (700 Boylston St.; 617-536-5400) at Copley Square. The first free urban library in the country, the McKim Building was adorned by some of the greatest craftspeople, painters and sculptors of the 19th century. Call or visit www.bpl.org for information on free architectural tours.

Once on the Freedom Trail, you’ll pass the site of the Boston Massacre, where Bostonians and Redcoats clashed in 1770, before you come to Faneuil Hall (1 S. Market St.; 617-523-1300) and Quincy Market (4 S. Market St.; 617-523-1300). Whether or not you are following the trail, you will want to come here. A gift in 1742 from Boston’s wealthiest merchant Peter Faneuil, this popular mall is just a couple blocks from Long Wharf. Musicians, dancers, mimes and artists entertain all day outside the shops, restaurants, delis, bakeries and open areas. 

If you want to diverge from the trail, you can head east from the North End where you’ll find yourself back on the waterfront, passing many old shipping wharves that have been redeveloped as housing or commercial space while still maintaining public access. Long Wharf, at the eastern terminus of State Street, is a lively spot with excellent restaurants, high-end hotels, open space and landings for ferries and water taxis. It’s also home to Boston Waterboat Marina (617-523-1027), which you’ll find on our chart. Adjacent to Long Wharf, the New England Aquarium (1 Central Wharf; 617-973-5200) is a family favorite, with an outdoor harbor-seal exhibit, an indoor penguin habitat and a 200,000-gallon cylindrical saltwater tank — home to thousands of animals, including sea turtles 

Back on the historic trail, you’ll come to the Paul Revere House (19 N. Square; 617-523-2338) where the famous rider stopped to pick up his boots and overcoat before heading out on The Midnight Ride. Keep on the red-bricked trail to the Old North Church (193 Salem St.) in the North End, Boston’s Italian neighborhood. You should wander the blocks off Salem Street, where you’ll find hanging meats, live snails, squid in open barrels, olives in bulk, excellent restaurants, and the some of the best baked goods and ice cream in North America. It’s about a half-mile’s walk from the eastern shore’s marine facilities.

Constitution Marina

Farther along on The Freedom Trail, across the Charlestown Bridge (North Washington Street), the waterfront environs have changed dramatically over the decades. This is where the old Navy Yard built more than 200 warships, maintaining and repairing thousands until its closing in 1974. The National Park Service (21 Second Ave.; 617-242-5601) now maintains much of the yard that served the country for 175 years. Visit the USS Constitution (1 Constitution Road), the world’s oldest commissioned warship, which is still an active U.S. Navy vessel. “Old Ironsides” never lost a battle. The land-based USS Constitution Museum (617-426-1812) is just steps away, as is the USS Cassin Young, a destroyer representing the vessels built in the yard back in its heyday. Both the Constitution Marina (617-241-9640) and Charlestown Marina (617-242-2020) put you in the vicinity of these attractions.

Just over a quarter mile from the Charlestown marinas, you can climb 294 steps to the top of the Bunker Hill Monument (43 Monument Square; 617-242-5601) for a unique view of the area. The 221-foot granite obelisk, which is the final landmark along The Freedom Trail, marks the site of the Battle of Bunker Hill, fought in 1775. Head across the street to the Battle of Bunker Hill Museum (43 Monument Square; 617-242-5601) to find out just what happened here in 1775.

On the other side of the city, what locals call “Southie” for South Boston, the Seaport District has undergone extensive redevelopment. As you approach Boston by boat, you’ll see the distinctive glass front of the Moakley United States Courthouse (1 Courthouse Way), which has a walkway, docks for visiting ships, restaurants and a gallery. Just east of the courthouse is Fan Pier, with several fine restaurants and its eponymous marina (617-865-5757 ). On its eastern edge is the stunning Institute of Contemporary Art (25 Harbor Shore Drive; 617-478-3100), where you can see some truly innovative work. The Boston Convention and Exhibition Center (415 Summer St.; 617-954-2000) is among the largest of its kind in the Northeast and hosts a wide range of public events. If you’re in Boston during the winter, February is when the BCEC hosts the New England Boat Show.

At Fort Point Channel, bounding the Seaport District, you’ll find the Boston Children’s Museum (308 Congress St.; 617-426-6500), a must-stop if you have little ones in tow. The Friends of Fort Point Channel host events by the water all summer  long.

With some 35 schools, Boston is unequivocally a college town, a great place to have your high school student explore the likes of Harvard (1350 Massachusetts Ave.) and the Massachusetts Institute of Technology (77 Massachusetts Ave.), which are actually located in neighboring Cambridge, although most people consider that city as unofficially part of Beantown. Boston University (233 Bay State Road) and Northeastern University (360 Huntington Ave.) are on the other side of the Charles River. If you’re looking for Boston College (140 Commonwealth Ave.), it’s out west in Chestnut Hill, 6 miles as the seagull flies from the downtown waterfront.

Other city cultural spots include the world-renowned Museum of Fine Arts (465 Huntington Ave.; 617-267-9300); the Isabella Stuart Gardner Museum (25 Evans Way; 617-566-1401), which is just around the corner; the Museum of Science (1 Museum Of Science Driveway 617-723-2500) at the Craigie Drawbridge; and the Boston Pops, an offshoot of the Boston Symphony Orchestra at Symphony Hall (301 Massachusetts Ave.; 888-266-1200). The Charles River Esplanade is a 64-acre park that holds free events, and there is, of course, the home of the Red Sox, Fenway Park (4 Jersey St.; 617-226-6000), the oldest stadium in Major League Baseball. If you’re looking to catch a home run well over the Green Monster, put yourself on Lansdowne Street.

Head west to Back Bay if shopping is your desire. At the upscale boutiques along Newbury Street, you can empty your wallet in a wink. Newbury Street is also great for people-watching, and there are many places to dine.

If finding your own way is just too overwhelming, give your feet a rest and take a guided tour. Several leave from the Long Wharf area, including Old Town Trolley Tours (617-269-7010), which allow you to disembark and resume your tour as you please. Boston Duck Tours (617-267-DUCK) highlights its 80-minute loop around the city with a 20-minute ride on the Charles River in one of its renovated World War II amphibious landing vehicles (code-named DUKWs during the war, hence the name). Most “conDUCKtors” let children of all ages take a turn at the helm. The tours depart from the Museum of Science, the New England Aquarium and the Prudential Center (800 Boylston St.; 617-236-3100), which residents just call “The Prew,” an enclosed shopping and business building that has views of the city from its top floor. The Prudential Center is less than a mile east of Fenway Park.

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Restaurants and Provisions

In the dining department, Boston has what you crave, and then some. Visiting all those attractions builds up appetites, and restaurateurs have answered the call.

Whether it’s steak or lobster on your mind, you’ll be able to please your palate in the Seaport District, the budding waterfront area of South Boston. The Fan Pier development has brought some great choices to the mix. Just a block from the waterfront, Cisco Brewers (85 Northern Ave.; 617-356–7231) has an outdoor beer garden where you can also get craft cocktails, spirits and wine. Live music and food are nice accompaniments to your drinks. 

For upscale ambiance, Italian dining awaits at Strega Waterfront (1 Marina Park Drive, Boston; 617-345-3992) while Ocean Prime (140 Seaport Blvd.; 617- 670-1345) brings steak and seafood to the table. Proper attire is required at Del Frisco’s Double Eagle Steakhouse (250 Northern Ave.; 617-951-1368), a high-end inn that cooks up some fantastic slabs of meat. Visitors of Liberty Wharf can try the famous chowder at what is one of our favorites, Legal Sea Foods Harborside (270 Northern Ave.; 617-477-2900). If you miss this one, there are more than a dozen Legal Sea Foods scattered around greater Boston.

Head a few blocks inland from Fan Pier for tacos, including gluten-free, at Bartaco Seaport (25 Thompson Place; 617-819-8226), which has “not tacos” on the menu as well. A two-minute walk away toward Fort Point Channel, you’ll be in heaven with the treats at Flour Bakery and Café (12 Farnsworth St.; 617-338-4333). For some late-night fun in this area, pretend you’re Don Draper at the very retro Lucky’s Lounge (355 Congress St. 617-357-5825), a subterranean hot spot that stays open until 1 a.m. Early-to-bed folks will appreciate their happy hour specials, weekdays from 4 p.m. to 8 p.m.

Right on Fort Point Channel, coastal clam shack meets funky urban at the Barking Crab (88 Sleeper St.; 617-426-2722), where you can tie your dinghy next to the Northern Avenue Bridge. On the channel’s other side, James Hook & Co. (440 Atlantic Ave.; 617-423-5501) is a fishery where you can sit or grab your lobster and roll.

Patrons of the lovely Boston Yacht Haven (617-367-5050) are in for a treat — Commercial Wharf is right in the North End. You can stay at the marina and dine at the adjacent Boston Sail Loft (80 Atlantic Ave.; 617-227-7280), where you’ll find friendly bartenders and a casual American menu with great desserts, or opt to go Sicilian-style at The Daily Catch (65 Atlantic Avenue; 617-772-4400). They have the best squid ink pasta with garlic and clam sauce that you’ll ever come by. Their original restaurant (323 Hanover St.; 617-523-8567) is located a few blocks inland at the heart of this iconic neighborhood where the options for Italian fare are endless. Explore on your own, or ask locals for their favorites. Be aware that some places only accept cash. 

Carmelina’s (307 Hanover St.; 617-742-0020) is an Italian dining experience so sought after that reservations need to be made well in advance. A few blocks over on Salem Street, you can pretend you’re in Italy at the intimate Ristorante Euno (119 Salem St.; 617-573-9406), which is open daily except Monday. Try any of the homemade pastas and sauces. Mamma Maria (3 North Square; 617-523-0077) is steps from Paul Revere’s house and has five private dining rooms set in a 29th century row house.

Pizza? Let’s talk about pizza. Head northeast for the locally famous Regina Pizzeria (11 ½ Thacher St.; 617-227-0765). This is the original location of the pizzerias that are throughout the city. To the south is the more low-key Ernesto’s (69 Salem St.; 617-523-1373). Both are award-winning and will not disappoint. 

Next to Boston Waterboat Marina (617-523-1027) on Long Wharf is the always reliable Chart House (60 Long Wharf; 617-227-1576), which occupies the historic Gardiner Building (circa 1760). John Hancock once kept an office there. All in the family are welcome, but please respect their dress code: no baseball hats, graphic T-shirts or cut-off shorts.

It’s just a few blocks from Long Wharf to Faneuil Hall and Quincy Market, where there are numerous kiosks for quick eats and sweet treats, trendy restaurants that stay open late for drinks, and some longtime Boston establishments.

Downtown, meat-lovers will want to head to Ruth’s Chris (45 School St.; 617-742-8401) in the Old City Hall building, or Mooo (15 Beacon St.; 617-670-2515) on the edge of Beacon Hill. If Mooo is your choice, wash down your cow chow with some vintage cocktails at neighboring Carrie Nation (11 Beacon St.; 617-227-3100), a restaurant and cocktail club that channels the spirit of a 1920s speakeasy.

Across the mouth of the Charles River, several good dining choices are in walking distance of Charlestown Marina (617-242-2020) and Constitution Marina (617-241-9640). At Pier 6 (18th St.; 617-337-0054), enjoy a breathtaking view of the city while you sip a stellar cocktail and nibble on an appetizer — try the crab cakes or ceviche. They stay open until late fall. From Constitution Marina, head up Warren Street toward Dexter Row, then make a left onto Pleasant Street, toward Main Street, to the Warren Tavern (2 Pleasant St.; 617-241-8142). It has been around since 1780 — long enough to boast that “George Washington drank here.” If he drank a lot, he must have slept here, too. Paul Revere reportedly lifted a tankard here as well. They’ve got a great Sunday brunch as well as lunch and dinner.

Then there’s the good ol’ Eastie neighborhood, aka East Boston. Boaters who are fortunate to be staying at Boston Harbor Shipyard & Marina (617-561-1400) are treated to a magnificent view of the city, and even better local food. The area is full of old school charm and houses an eclectic group of businesses, such as Downeast Cider House (256 Marginal St.; 857-301-8881), which is across the street from Boston Harbor Shipyard & Marina.

Wander farther away from the water for some other options in East Boston. Trendy outdoor dining inspired by the nautical history of the area can be found at Cunard Tavern (24 Orleans St.; 617-567-7609). About a mile from Boston Harbor Shipyard & Marina is the famous Santarpio’s Pizza (111 Chelsea St.; 617-567-9871), with mouth-watering pies. There’s also Rino’s Place (258 Saratoga St.; 617-567-7412), an East Boston hallmark with home-cooked Italian fare that rivals the North End’s best. They only take reservations for parties of six or more so get there early or be prepared to linger on the outside street corner while you wait. The area’s large Latino population brings in some authentic eateries like Angela’s Café (131 Lexington St.; 617-567-4972) with Poblano cuisine and Mi Pueblito (333 Border St.; 617-569-3787), serving a mix of Mexican, Guatemalan, and Salvadoran dishes.

Next door to Eastie is up and coming Chelsea, where you’ll find Ciao! Pizza and Pasta (59 Williams St.; 617-286-9346) near the Marina at Admiral’s Hill (617-889-4002). It gets rave reviews for its wood-fired pizza, and sweetens the pie for dessert. You’ll also find bakeries, coffee shops and other conveniences close to the marina — just ask the dockmaster to point you in the right direction.