Boston – the mere mention of the name evokes images of the old colonial times, Fenway park, the elevated expressway (oops, that’s gone, courtesy of the Big Dig) and the Pop’s fourth of July concert.  There is much more that makes the greater Boston area so vibrant – and just a few important tips to learn before visiting. 

Boston itself is a core city composed of about a dozen distinct neighborhoods.   Unlike cities in the Midwest, as Boston grew, it retained the original boundaries rather than growing by annexing  neighbors.  As a result, Boston proper is quite small and this makes it a great walking city.    Some of the famous attractions are located in neighborhoods with such strong identity that they seem to be in different towns.  As an example, they say that the USS Constitution (“old ironsides”) is  located in Charlestown but Charlestown is really  part of Boston. 

North and south of the city are many attractions associates with the area such as the port of Gloucester and Plymouth rock.  Farther to the east is Cape Cod, gateway to the funky and diverse arts community of Provincetown ( where the Pilgrims first landed)  and the islands of Nantucket and Martha’s Vineyard.  To the west are the suburban locations of the origins of the revolutionary war in Lexington and Concord.  Farther to the north is the beauty of coastal Maine.   There is enough to see in the greater Boston area to fill a month of vacation, even more.

Let’s get started!  

How to get Around

The airport in Boston is Logan International. It is located on a panhandle in the harbor and connected to the city mostly by tunnels for cars and trains ( the subway or MBTA - the “T” for short). Logan is a medium size airport that is extremely busy due to its role as the easternmost gateway to the USA.  Driving from Logan is somewhat unforgiving.   Make a navigation mistake and you will pay – not with your life but with confusion and considerable delay.  Making matters more interesting is the fact than GPS signals are blocked by the tunnels so the GPS is useless when you need it most as you exit the tunnels. 

There are many more north south roads from Boston than there are to the west.  Immediately north  are not the best towns  -   lower middle class residential with high density and traffic.  This includes Somerville, Revere,  Malden, Saugus and Lynn.  Immediately to the south, the towns are less “inner city”  but also quite dense and with similar traffic woes.   This included Milton, Quincy and Braintree.    Near the city, Brookline, Cambridge and Newton are upscale along the lines of Greenwich village in New York and with similar traffic.    Busy suburb start about 10 miles from the city center – Andover, Lexington, Needham,  Arlington.  A little farther out are the more quiet suburbs – Wayland, Concord, Sudbury, Weston, Norwood, Billerica.   The subway ( the “T)  runs only about 10 miles out of the city.  Beyond that, commuter trains run from the far suburbs to large stations where one transfers to the T.    Train stations of any type are unusual to the west of the city.   Driving from a suburb such as Andover into the city takes between a half hour to an hour plus, depending on the time of day.  Because many roads originated as cow paths, knowing how to get around can be a little tricky.  In the city, a good strategy is to get in, dump the car and proceed by foot or the T.   Most attractions outside of the city are best reached by car.

Parking in Boston is either expensive or impossible.  As always, there are tricks.   A little know underground parking garage exists under the Boston Common (the large park near the Capital Building).   Get there early enough and this is a cheap, practical  place to park for the day - and with central location as well.    Also, the  Alewife brook T station is a good portal to the city by car.   Still, driving to some area attractions can be difficult unless you know the ropes.     

The part of Boston of interest to tourists is quite small physically.

Where to Stay

There are at least three or four very different choices for location and style of accommodations in and near Boston  In greater Boston.   they include upscale hotels downtown in the city,   chain motels in the suburbs north of the city (the “north shore”), larger premium chain hotels in large towns a few miles  to the west of the city and country inns and chain motels further to the west ( about 20 miles, in towns like Sudbury and Concord).   Each has plusses and minuses.  Generally, the closer you get to the city, the more expensive the accommodation.  Areas within 10-15 miles of the city are densely populated, urban and, in many cases, a little gritty.  Farther from the city to the west or north, areas become more suburban or even semi-rural.   Here are a few examples and typical room rates.

Downtown Boston

     The Omni Parker house $299

     The Langham Hotel $316

North Shore chain motels

                Holiday Inn express Saugus $127

                Hampton Inn Woburn $110

Premium chains nearby Boston, to the west

                Crowne Plaza Newton $197

                Sheraton Needham $209

Country inns and chain motels in the suburbs farther to the west

                Colonial Inn Concord $145 – located in the village, with plenty of restaurants and good shopping

                Wayside Inn Sudbury $140 – located in the woods and isolated, with a working Grist Mill

                Red Roof Inn Framingham $72  -  close to the highway and that’s about it

As is always the case, nicer properties are more  pricey and, except for chain motels, closer proximity to the city costs more.    Bargains do exist but be sure to double check the trip advisor ratings to avoid an unpleasant surprise.   

A Boston Day Trip

            The Freedom trail – see the graves of Samuel Adams, John Hancock, Paul Revere and the Old North Church (“one of by land, two if by sea”)

            Old Ironsides – part of the Boston harbor cruise

            Faneuil Hall/Quincy market – food and fun on the waterfront

            Cheers – aka the Bull and Finch Pub – people seem to love it – go figure!

Whale watch – best time is from April to October – about $45 for a three hour cruise  to Stellwagen Bank where the Whales feed.  Cruises leave from downtown Boston or from Gloucester, the fishing port north of the city.

Salem – about 30 minutes to the north of Boston

The House of the 7 Gables – the home that inspired Nathaniel Hawthorne to write the famous 1851 novel

            Witch museums – too many to count

            Haunted houses – see "Witch museums" above

            Cemetery – resting place of Richard Moore an original Mayflower passenger and John Hathorne, the judge at the Salem witch trials

            PEM – the Peabody Essex Museum – often has unique exhibitions

Parts of Salem are quaint but remember that it is a city with a population of 40,000 so parts of it are semi urban.

Gloucester/whale watch – see the working fishing port shown in the movie The Perfect Storm, the famous statue of the fisherman and have some seafood.  Don’t expect Disneyland, this place is a real fishing port!  Gloucester is one of the two places to board a whale watch boat, the other being downtown Boston.

Newport mansions in nearby Rhode island are the summer “cottages” of the Astor’s and Vanderbilt’s and 8 other wealthy turn of the century families.  You can tour as many or as few as you like.   If you never wanted to be filthy rich, think again!.   Newport is still the in place for the very rich – just walk around the harbor and look at the yachts. It is an easy day trip from Boston and the suburbs.

Provincetown, Cape Cod National Seashore

A significant drive (or boat ride) from Boston but come on, they write songs about Cape Cod!  After the bridge over the canal, the cape is composed of a series of small towns, some of which are a little, shall we say, touristy.  You will find no shortage of t shirts or salt water taffy.  The outer cape is more unspoiled.  Much of the outer cape is preserved as the national Seashore.   Many of the beaches are 10-15 feet below the level of the surrounding sand dunes, making for a feeling of closeness to the sea.   There is raw beauty in the beaches and dunes although not the slap you in the face kind one sees at Bryce Canyon.  Provincetown is located at the very tip of cape cod – the end of the land shaped like a giant shrimp.  It is a great place to shop – everything from original art to old license plates.   In season, the restaurants are great.  Many, but not all, of the guest houses and inns cater to a homosexual crowd.  P-Town isn’t like any other place on earth.

 The Wayside Inn Sudbury

The Wayside Inn dates back to 1716, and  it is reputed to be America’s  oldest continuously operating inn and was the inspiration for the collection of poems Tales of a Wayside Inn  by Henry Wadsworth Longfellow.  In addition to the Inn itself, the grounds include a functioning reproduction grist mill, a chapel and the original little red school house, subject of the incident leading the famous nursery rhyme Mary had a little lamb.  The Inn is always open and the other buildings are open occasionally.


A well preserved new England town center, including many examples of early American architecture, shops, churches and interesting restaurants.  Buried in the nearby Sleepy Hollow Cemetery are Louisa May Alcott, Ralph Waldo Emerson, henry David Thoreau and Nathaniel Hawthorne.  Nearby also is Walden Pond and a reproduction of the 10 x 15 foot cabin  in which he lived for two years and about which he wrote Walden.

Martha’s Vineyard

Located just off the coast of Falmouth on Cape Cod, Martha’s Vineyard is an island reached by a 45 minute ferry ride.  The year round population of 15,000 explodes to 100,000 in the warm weather so it is a good place to visit off season.  You don’t need a car as there are tour van services available ( check ahead to see what date they start).   It can be a busy but practical day trip.    Hotels are available but expensive.  Attractions include the cliffs of Gay Head


Thirty miles out to sea, Nantucket is like an 1800’s whaling center frozen in time.  From the cobblestone streets to the churches and the harbor, visiting Nantucket is a unique experience.   It can be expensive in season and affordable off season but beware, get too far from the normal season and many restaurants won’t be open.  Don’t miss the island tour van and the Whaling museum.  Even if you don’t think you have interest in the history of whaling, you will. 

The Yorks Maine

OK, so you think Maine is too far from Massachusetts to be included in a Boston trip.  Actually, the intervening New Hampshire seacoast is tiny  (just a few miles) so southern Maine is quite close to Massachusetts.  Two hours from the western suburbs, find the Yorks – York Village, York Harbor and York beach.  There is no one killer attraction – you go to the Yorks  to spend a night and wake up to fishing boats in a foggy cove ( the Dockside hotel) or to the expanse of the beach (the Cutty Sark hotel) and then crawl up the coast soaking up the ambiance.  In or around York is the home of Stonewall Kitchen where you can tour the plant and sample nearly everything at the company headquarters store. Before York, on the highway, are many outlet stores with bargains galore.  Just to the north is the postcard beautiful Perkins Cove and a walkway called the Marginal Way on hills overlooking the ocean.  Next is Nubble light (where I took the lighthouse photo).  Beyond that is the Bush compound in Kennebunk and then Fort Williams Park and Portland Light.  Mostly, you go up the coast for the views and the excuse to eat seafood.


Located to the southeast of Boston is Plymouth,  the pilgrims second landing and the place where they settled.  Here, you can tour an exact replica of the Mayflower and visit Plimoth Plantation, an historically correct recreation of the settler’s village and also of the native Americans.  In the English section, reenactors stick to their roles in speech and actions as they explain how the settlers lived.  Take their photo and they are likely to ask “ is that rock with the flash of sunlight the work of the devil?”

Old Sturbridge Village

Located to the west in Sturbridge is a historically correct recreation of an entire New England town, including farm and fields, from the 1830’s.  Similar to Plimoth Plantation except much larger and of course of a different period.

Other Interesting Attractions

     The Boston Common

     The Swan Boats in the Boston Public Garden

     Boston Duck Boats ( like the Dells!)


            The Arnold Arboretum in Boston

            The Garden in the Woods in Framingham

            Tower Hill Botanical gardens in Boylston