1:00 PM: Arrive in the city and head over to Duck Fat for a bit of lunch. Have lots of trouble deciding what should accompany your duck fat fries. Curry mayo? Raye's mustard? Roasted garlic aioli? Curse life for being so hard. Then enjoy your fries and locally brewed Maine root beer to the utmost.
3:00 PM: Hop in the car with two locals for an excellent driving tour. See South Portland, the up-and-coming East End, that gorgeous rugged coastline and even swing by the most photographed lighthouse in America. (One that this blogger failed to photograph. Are you really surprised?!)
5:00 PM: Go to Grace for a drink. Try not to be weirded out that you are drinking a gin martini in the upper deck of a beautiful former church.
7:00 PM: Let's have another drink, shall we? It's vacation after all. This time, head to Hugo's. Sit at the bar, and nibble on some chorizo dusted pig ears and their delicious butcher's block of charcuterie. When the sweet bartender asks if you are walking to your next destination, it is so cold, can she call you a taxi? Try to look stoic and strong when your fiance insists that you will be fine. You are New Yorkers who walk everywhere!
Street and Company. Sip on gin and tonic, eat some local oysters, and share some buttery scallops. Everyone else at the bar works at another restaurant in Portland. Does everyone in Portland work at a restaurant?
11:00 PM: End the night with a beer at Gritty McDuff's. Feel old, but tell yourselves that Portland must be a very young city to have so many fresh-faced 21 year-olds around.
11:30 AM: Head over to Hot Suppa! for brunch. Eat that famous corned beef hash -- it will live up to the hype. Any place that has the enthusiasm to include an exclamation point in their name must be great.
1:00 PM: Drop your shopping-adverse fiance off at Sebago Brewery while you visit a few stores. At Sebago, ask for the special one-batch seasonal beers -- delicious, apparently. See lots of lovely things at this fun place, but ultimately just purchase some gummy bears and Swedish fish from the bulk bin at a fancy candy shop.
3:00 PM: Head a little bit out of town to go the Allagash Brewery for a free tour and tasting. Learn all kinds of things about making beer, and promptly forget them all.
8:00 PM: Reservations at Fore Street. Think that sweetbreads and roasted oysters have never, ever tasted so good. Think that the hanger steak is perfectly cooked, perfectly beefy (if you can imagine that?), and that the halibut is light as a cloud.
10:00 AM: Breakfast sandwiches at 158 Pickett Street Cafe. Get in the car and feel very sad that you are leaving Portland, but take comfort in the fact that you may be there on a permanent basis in the not-so-distant future.