If your big on going to the oldest bar in town... how about the "Oldest Bar in the country" Union Oyster house just outside Fanuiell Hall Boston makes that claim and est. 1820's it's pretty convincing.
Old Ironsides as mentioned above is a must see.
You could start at boston and drive North along the shore and not make it to the NH border in a weeks time if you stoped only for a few munites at every important nautical history spot.
There's the Salem derby warf and Friendship East Indiaman, PEM museaum, charter sails on Chebacco boat Fame, House of Seven Gables, Nahant beach, Swampscot beach, Chamberlain Alpha dory at Marblehead Hist.Soc. Marblehead light wich features prominently in hundreds of historic yachting photos, Manchester Yacht Club home club of Edwin Boardman and Sewanhaka cup champion scows Manchester and Massachusetts, Gloucester port, Phil Bolger and Friends boat design home office, Montgomerys yard home of the "Fish Class Cat", Centenial; first boat/dory to sail single handed across the Atlantic 1876, Rockport harbour/halibut point rock quary and Colonial era anchor on display, Wingasheek beach (beautifull) Essex Ma Ship building museaum, yards that turned out the famous Gloucester Fishing Schooners, also Chebacco Boat A.D. Story, Harold Burnhams Yard, Ipswich historic district More existing pre 1720 homes than any town in the country, Newbury Pert Lowell Co. oldest comercial dory shop in opperation builders of the Town Class sailing dory, My dory shop, I'm building a Banks dory hull from Gardners lines for Centennial, Newburyport Maritime Museaum, shoping, Newburyport launched hundreds of Fast Packets (clipper ships) and was building ships barks schooners 150'+ into the late 1800's, Amesbury Lowells Boat Shop founded 1790's dory builders, Salisbury great beach, amusments, food....
there that gets you to the NH border.
Portsmouth, Newcastle, Ordiorne State Park beach and WWII historic site are awsome,
Strawberry Banke in portsmouth is a old home museaum and has recently constructed a 60+ ft Piscataqua river Gundalow replica.
