Spring Travel 2010: Movie-Inspired Trips From Philadelphia: A Smart Holiday: Boston

If you liked Good Will Hunting, you’ll love a trip to … Boston

At its heart, Good Will Hunting, the 1997 film that propelled Matt Damon and Ben Affleck to stardom, is a love triangle. Will, played by Damon, is a freakishly gifted South Boston tough caught between love for ideas, love for his tribe and love for a girl. (Guess which wins?) Along the way, the movie offers glimpses of a city that will strike any Philadelphian as a sort of funhouse version of our own — how we might have turned out had it been rabble-rousing Puritans and not consensus-seeking Quakers who laid down our cobblestone streets, built our wharves, and occupied our taverns when the British started passing the Intolerable Acts.

The Set
It would be difficult to find a better view of the sun rising over Boston Harbor than from one of the sleek rooms at the year-old Fairmont Battery Wharf. Standout amenities include 42-inch LCD televisions, a digital safe with an outlet inside for recharging electronics, and windows that actually open, plus the hotel’s restaurant, Sensing, which serves inventive Nouveau French fare. Or flash back to a more classically elegant time at the Omni Parker House on School Street — you can just picture Cary Grant chasing Katharine Hepburn through the lush, paneled lobby in some high-society screwball comedy.
Fairmont Battery Wharf, 3 Battery Wharf. From $319 per night, plus $42 for valet parking. 800-257-7544.
Omni Parker House, 60 School Street. From $150 per night, plus $40 for valet parking. 617-227-8600.

The Script
Yes, they’re hokey. Yes, everyone will know you’re a tourist. But the 90-minute historical walking tours run by the Freedom Trail Foundation are amusingly informative and offer a smart overview of the 18th-century city that fomented the American Revolution. The $6-$12 Walk Into History tour leaves from Faneuil Hall several times a day; other routes include an African-American Patriots tour and a Historic Pub Crawl tour. When your guide releases you, take the subway (called the T) to Cambridge and see more of MIT’s architecture and amazing public sculpture collection (Calder, Nevelson) than Matt Damon ever did (most of the movie’s college scenes were shot in Toronto) on a self-guided campus tour. Also: Chic Newbury Street has shopping you can’t find at KOP. Treat yourself.
The Freedom Trail Foundation.
MIT self-guided campus tour.

The Food Scene

For a civilized weekday lunch or afternoon tea, ferret out the Courtyard Restaurant at the Boston Public Library, a high-ceilinged oasis that overlooks a hidden courtyard straight out of a Roman villa — but first, call for reservations. For dinner, locals are obsessing over Barbara Lynch’s new Sportello — an Italian diner concept with polentas and pastas — and the South End’s Coppa, also Italian, but intimate and wine-focused. Of course, if you want classic Boston, it’s oysters at tiny, lauded Neptune.
Courtyard Restaurant at the Boston Public Library, 700 Boylston Street, 617-859-2251.
Sportello, 348 Congress Street, 617-737-1234.
Coppa, 253 Shawmut Avenue, 617-391-0902.
Neptune, 63 Salem Street, 617-742-3474. 

The Photo Op

Not far from the end of the pedestrian bridge on the Arlington Street side of the very pretty Boston Public Garden sits the bench on which the shrink played by Robin Williams (who won an Oscar for his performance) first pierces Will’s emotional armor. Tip: The free Audissey Guide iPod tour of the garden makes the bench simple to find — it’s stop number 5. There are also Audissey Guides for downtown, the Harborwalk and Fort Point Channel.

Getting There
Amtrak completes the 30th-Street-to-South-Station run in about six hours (from about $160 round-trip) — five if you spring for the Acela (from about $280 round-trip). One of US Airways’s 16 daily nonstop flights from PHL will whisk you to Boston in about an hour and a quarter (plus three hours in security lines) for less than $200. Or hit the highway: It’s about 300 miles — five hours if all the stars are aligned and it’s 3 a.m. Six otherwise. Eight on a bad day.

What To Get Before You Go

Sleek (and windproof) jacket: Boston is generally chilly — and quite windy — until late in spring, so if you go before May, you’ll be glad to have a good waterproof, windproof top layer. Patagonia and North Face make lots that look good and do the job.
REI, multiple locations.  

Great walking shoes: With its curving Colonial streets, gorgeous swaths of parkland and unhinged native drivers, Boston demands to be walked. Cole Haan’s Air Bria line of stylish walking shoes incorporates Nike Air cushioning technology to keep you comfortable for all 294 steps of the Bunker Hill Monument.
Cole Haan, 1600 Walnut Street, 215-985-5801, and the Plaza at King of Prussia, 610-992-1062.