02/04/2012 01:31 am ET | Updated Feb 04, 2012

Mayors' Super Bowl Bets: How Small Businesses Could Have Helped

The annual tradition of opposing mayors making a Super Bowl bet is taking place once again. This year, Mayors Mike Bloomberg of New York City and Thomas Menino of Boston made it a little more interesting, as the gamblers say, by putting together prize packages for one lucky family in the opposing team's respective hometown. If the Patriots win, four people get to live it up in New York City, and vice versa if the Giants are victorious.

The problem is that the prizes -- how should we put this -- suck. They suck as bad as the Super Bowl games used to in the 1980s. A Duck Tour ride? Four tickets to the Phantom of the Opera? As the old joke goes, what's second prize? Eight tickets? These gifts are the kind that appeal only to the fanny-pack brigade and characters looking for that one last shot at love in whatever holiday rom-com Gary Marshall belches up this year.

Yes, there are appealing things in each package, but the whole thing feels like it was put together by the "Corporate Committee to Show You Things You Probably Already Know About." The selections don't capture the unique entrepreneurial places and experiences that make Boston and New York City great -- or boost the small businesses that are the core of these cities' character.

We've decided to rectify the situation by letting our imagination run wild and proposing our ideal revamp of the bets. And while we didn't throw in anything as glamorous as a photo op with the mayor (what's second prize? Two photos?), we think the winners of our theoretical Super Bowl bet -- and local entrepreneurs -- would have a whole lot more fun if Bloomberg and Menino took these suggestions to heart.

If the Giants win:

  • Congratulations, Giants lovers! We're putting our winners up in a suite at the Clarendon Square Inn, an 1860s home turned six-story bed and breakfast. Located in the South End, but not "Southie," the Clarendon offers you a plush bed, a soaking tub for two, a marble fireplace, a tranquil back deck, and rooftop hot tub with city views.
  • A tour of Harpoon Brewery where the company motto is "Love Beer. Love Life." You'll get to love both while sampling the beermaker's great UFO Raspberry Hefeweizen and specialty 100 Barrel Series.
  • You can walk the Freedom Trail on your own. To get a totally unique perspective on The Hub, we're setting you up with a Venetian gondola ride on the Charles River, via Boston Gondola Tours. Take in a sunset on one of the authentic private gondolas and we'll throw in roses, strawberries and an accordion accompaniment.
  • After you make it back to land, drinks and appetizers will be feted at the Island Creek Oyster Bar. Owners Jeremy Sewall and Skip Bennett ensure fresh seafood, caught by local fisherman, lands right on your table.
  • Dueling dinners are served at Sibling Rivalry, where chef brothers David and Bob Kinkead offer different takes on a common ingredient like the "Fowl" entrees: David's Crispy Pressed Half Duck and Bob's Spit-Roasted Half Chicken. Fraternal friction never tasted so good.
  • Anyone can take in the world's great works of art, but few asthetes take time out to ponder the crappy stuff. That's why you'll be perusing the walls at MOBA, the Museum of Bad Art. Aficionados can soak in terrible wonders like "Sunday on the Pot With George," "Sad Baby," and Da-Vinci-wouldn't-approve "Mana Lisa." Afterward, walk down the block to discuss what you've seen -- or try and forget -- over wine and crispy fried lobster legs at Isabella.
  • Nothing says you're a Patriot, the original kind, quite like a Tricorne hat. You can outfit the entire family at Salmagundi, a one-of-a-kind store that stocks some 7,000 lids. If your tastes run a little less Tea Party-ish, husband and wife owners Andria Rapagnola and Jessen Fitzpatrick will find something in their incredible collection to ensure you're behatted in style.
  • Boston and the Irish go together like fish and chips, but the less said about the "authentic" downtown spots the better. We'll pick up your bar tab as you get your pint on at Plough & Stars, a 42-year-old Cambridge institution with live music, Irish breakfast, a fine selection of whiskey from the Cooley Distillery, and Craic-heads of all walks of life. This is the place to go where you want everyone to know your name.
  • For reasons we can't fathom, Bostonians are loyal to Dunkin' Donuts. To satiate your pastry craving, we'll fill your belly with delicacies from Joanne Chang's Flour and even throw in a sticky buns class to impress the New York foodies back home.
  • No better way to wrap up a sporting weekend than with a little exercise. And by little, we mean the beloved New England sport of candlepin bowling. For the uninitiated, the pins are cylindrical (like a candle, get it?) and the balls have a top weight of 2 lb. 7 oz. So bowl a few games on us at the erstwhile Sacco's Bowl Haven, which opened in 1939 and still has the blue-collar vibe of its bowling heyday. However, today's pinheads demand better grub, so Flatbread Company took over, overhauled the menu with its gourmet pizza, but smartly left the lanes alone. Pizza and candlepin? What better way to celebrate the fact that the Giants beat the Patriots yet again, and the even more astonishing fact that Eli has more Super Bowl rings than Peyton?

If the Patriots win:

  • Congratulations, Pats fans! You've just won a stay at the Canal Park Inn, a cozy bed and breakfast in the heart of bustling downtown Manhattan. Located in Tribeca, Canal Park is surrounded by top-flight eateries, and just a stone's throw from the sunsets-over-the-Statue-of-Liberty at the Hudson River Park. The inn is in a landmarked 1826 canal house where each room is named for a family that lived there in 1850. You'll be bunking down in the Batby Suite, which includes a private deck, offering an oasis of calm in the sea of action.
  • In New York, sweatpants don't count as clothes you wear in public, so we're going to outfit your entire family. Since 1938, Paul Stuart has been keeping the men of Gotham well-dressed in clothing only available in its stores. Women can get all trendy in the "Ultimate Closet" at Scoop NYC, and the little ones can do the same at Bundle. As for the teens ... we wouldn't even try. We'll hand you a wad of cash so you can go shopping alone.
  • In recent years, New York City has had an explosion in craft breweries and we're going to take you on a tri-borough suds tasting extravaganza. You'll make your way from brewery-to-brewery in a classic 1970s taxi piloted by the Checker Guy. First up, the Pale Ale at the Bronx Brewery, which just opened last August and is already available at some 30-plus watering holes. Next, you'll hit the Harlem Brewing Company for a Sugar Hill Ale from Jazz Age-loving brewer Celeste Beatty. Final stop, Brooklyn's Sixpoint Craft Ales, where owner Shane Welch recently introduced the "Spice of Life" series featuring a unique hop strain for every month of the year.
  • A visit to New York wouldn't be complete without a night at the theater, but leave the singing superheroes for the tourist hordes. You'll be sitting front row for "Magic Bird," the story of the great basketball rivals premiering in March at the Longacre Theater. Produced by Kirmser Ponturo Group, the same folks behind the recent hit "Lombardi," "Magic Bird" finally gives Boston sports fans the chance to see the Great White Hope on the Great White Way.
  • There is no better way to see the lights of the city than an evening stroll across the Brooklyn Bridge. The 1.1-mile walk from Brooklyn to Manhattan will build up an appetite, which we'll take care of at the Bridge Cafe. It's housed in a 1794 wood frame building that's been a brothel, a speakeasy, a pirate bar, and the rough saloon where Ms. Gallus Mag, a 6-ft. Irish bouncer, would bite the ears off of rapscallions and pickle them for posterity. They aren't on the menu, but the city's best soft-shell crabs are.
  • New Yorkers will fight to the death over who makes the best pizza, so why not sample the top contenders and decide for yourself? Your guide on this crusty crawl will be Famous Fat Dave, proprietor of the Five Borough Eating Tour.
  • Everyone loves cartoons, but few make the connection between Batman and fine art. POW! At the Museum of Comic and Cartoon Art, you'll learn why cartoons are to be respected and laugh out loud while doing so. You might even run into New York native son Stan Lee. Afterward, get to doodling on napkins over beers at nearby Fanelli's Cafe, which goes back to the days when SoHo was actually filled with artists.
  • No matter how much money flows through New York, it will always be a draw for the weird and eccentric. That's why we're offering a gift certificate to The Evolution Store. Pick up a little something for the mantle back home like a head puzzle, a pigeon skeleton, or the ever-popular freeze dried bat.
  • Grandmaster Flash, Run-DMC, Beastie Boys, Biggie Smalls, Jay-Z ... New York City is the hip-hop capital of the world and what better way to experience the dope beats and fresh rhymes the city made famous than on a personally curated Hush Tour? Founded in 2000, by hip-hop guru Deborah Harris, the Hush Tours take you to the street corners, housing projects, stoops, 'hoods and music clubs from which rap evolved. As a bonus, stories are often told by old-school stars of the game like DJ Red Alert, members of the Cold Crush Bros. and Kurtis Blow. You feelin' it?
  • Yankees games are overpriced and Mets games involve the Mets, so we'll wrap up your sporting weekend with a trip to Coney Island to take in a Brooklyn Cyclones game. Even if you don't love baseball, it's hard not to be swept away looking out past the neon center field lights to the Atlantic Ocean. After the last out, head to Luna Park to ride the actual Cyclone, the 85-foot wooden roller coaster that reaches 60 mph, and then dig into the fried clams at Ruby's, the oldest bar and grill on the Boardwalk. We highly recommend riding the Cyclone first.