The $500 Weekend: Portland, Maine

For the Pine Tree State’s gourmet metropolis, the mantra is simple: Put your money where your mouth is.

The $500 Weekend Portland, Maine

Photograph by Cara Slifka

It’s not just the rolling hills, bustling harbor, and chilled-out vibe that elicit San Francisco comparisons. Like that other City by the Bay, Portland has a dining scene to rival any in the region — Boston’s included. Spend the bulk of your budget on feeding your face, but spread the love among the town’s top-notch eating spots.

GETTING THERE: Cute cobblestone streets and a centralized layout make this an eminently walkable city. For $48 from North Station, Amtrak’s Downeaster offers traffic-free convenience.

SLEEPING: The Inn at St. John ($91 a night for a queen-size bed) has neither the cachet nor the picturesque beauty of the celebrated Inn by the Sea. But for this trip, bragging rights are measured in calories, not thread count. (Besides, with an extra $200 in your pinot fund, you’ll create your own ethereal views.) The cozy Victorian boardinghouse boasts exquisite period detail, free wireless Internet, and proximity to everything.

EATING: See “Playing,” below.

PLAYING: Unlike in the gastro-challenged likes of, say, Concord — best enjoyed on a full stomach — frolicking and fueling up become one here. By visiting in April, you’ll miss the lobstering jaunts and lighthouse tours (which gear up in May), but you’ll get your pick of prime eateries in the preseason lull. Before the trip, secure two reservations: a late lunch (around 2 p.m.) at Paciarino, which both sells and serves homemade pasta, and a late dinner (10-ish) at Five Fifty-Five, a locavore spot often praised by national food mags. (The latter reservation you’ll likely use solely as a backup, if you can’t wrangle a perch in the lounge.)

On Saturday morning, head for Duckfat, right near the Inn at St. John. Pace thyself! Forgo the gravy-slathered poutine for the terrific Belgian frites ($5.75) with sides of Thai chili mayo, duck gravy, and crazy-delicious truffle ketchup. Black-belt noshers may also indulge in the BGT ($9.50), a crispy panini with bacon, tomato, and goat cheese. The 10-minute walk to LeRoux Kitchen, a Williams Sonoma–sized version of KitchenArts with far more personality, should recharge you enough to enjoy the two aisles of olive oil and vinegar samples. To kill time before your Paciarino seating (where you’ll order plump seafood ravioli, $16.95), get Bard Coffee’s cappuccino ($3.05), arguably the best this side of Milan.

Even in the off-season, throngs line up at Fore Street by 5 p.m. Arrive early to get your name on the list and troll for bar seats. Once you snag them, order a glass of floral Rousanne ($9.50) and the signature wood oven–roasted mussels ($10) in gobs of garlic-spiked almond butter. After sampling any two midsize dishes (average price: $18) at the bar at Hugo’s, owned by the Duckfat folks, finish the evening at Five Fifty-Five with an entrée (like the amazing pepper-crusted scallops, $27.95), a bottle of Zenato Ripassa ($40), and a dessert (blood-orange pudding cake with fennel ice cream and caramel sauce, $9).

BROWSING: Portland’s clothing shops are hit-and-miss, particularly for women. (For men, institution David Wood Clothiers sells Brooks Brothers–style garments with a dandier flair.) That said, the Old Port district offers plenty for the avid window-shopper. Check out Fiachre, for unique garden accessories; Rabelais Books , for its new and vintage cookbooks; and home-furnishings gallery Utopia, if only to ogle the mind-blowing sink designs. And with the Kentucky Derby just weeks away, Queen of Hats is a pilgrimage-worthy millinery mecca.

OBSERVING THE LOCALS: Despite a name that screams tourist trap, brewpub Gritty McDuff’s is popular with both residents and visitors, and this month sees the release of the Gritty’s Vacationland Summer Ale ($7). Vignola serves a full trattoria menu, but the stellar wine list is the reason for the bustling bar scene (try a bottle of 2003 Montefalco Rosso Riserva, $66).

Getting There (and Back): $48
Sleeping: $182 Playing/Eating: $240.70 Bottom Line: $470.70