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*The latest ruminations from LUPEC Boston, which appear, greatly abbreviated, in this week’s issue of The Dig.

By PINK LADY, PINK GIN, PINKY GONZALES, BARBARA WEST AND BOURBON BELLE

Lucky you, staying at the Charles Hotel [One Bennett St., Harvard Sq., Cambridge. 617.864.1200. charleshotel.com]; there’s a great night of drinking ahead of you, and you don’t even need to leave the property. Start at Rialto [617.661.5050. rialto-restaurant.com] and treat yourself to some fried olives ($4) and a Laila made with brandy, rose cognac liqueur, a dash of bitters and fresh orange juice.

Want to hear some jazz without exiting the hotel? Head to Regattabar [617.661.5000. regattabarjazz.com], where world-class performers are regularly showcased. Order a Manhattan ($9).

Some Ken Oringer restaurants

Hankering for a hunk of steak? That won’t be a problem if you’re shacking up in the Nine Zero Hotel [90 Tremont St., Boston. 617.772.5800. ninezero.com], which houses Ken Oringer’s modern steakhouse, KO Prime [617.772.0202. koprimeboston.com]. We’ve never managed to dine here for less than $100/person, so unless you’re on an expense account (some companies still have those, right?), opt for cocktails and bar fare, a far more affordable option. The view of the historic Granary Burying Ground covered in a dreamy blanket of snow will cost you nothing and makes for a serene backdrop as you sip an Old Vermont ($10) made with Plymouth gin, angostura bitters, maple syrup, orange and lemon juice (also featured in our Little Black Book of Cocktails).

When looking for a well-made classic to whet the whistle, cocktail nerds often saunter a little further down Comm. Ave. to The Commonwealth Hotel‘s [500 Comm. Ave.,
Boston. 617.933.5000. hotelcommonwealth.com] bastion of tippling excellence, Eastern Standard [528 Comm. Ave., Boston. 617.532.9100. easternstandardboston.com], making Clio [370 Comm. Ave., Boston. 617.536.7200. cliorestaurant.com] something of a hidden gem. Also owned by Oringer and situated in a boutique hotel (The Eliot [617.267.1607. eliothotel.com]) in a historic Boston neighborhood (the Back Bay), the bar at Clio is an elegant place to enjoy craft cocktails on a quieter, more intimate scale. Bartender Todd Maul has turned out a delightful list to complement Oringer’s exquisite gastronomic cuisine, and if he’s working, your drink should be a “bartender’s choice.” Prices are on par with those at KO Prime, making the Clio bar or Uni [370 Comm. Ave., Boston. 617.536.7200. cliorestaurant.com], the venue’s sushi bar, a great place to snack and sample.

After elegantly sipping at Clio, you can finish up your march down Commonwealth at Eastern Standard, and get elegantly wasted. Ask for LUPEC’s newest member, Nicole (drinking moniker TBD). The epic drink list could keep you busy from their breakfast opening hour (7am) till last call at 1:45am. Try the El Capitan ($10), our new favorite, or whatever Nicole suggests.

Historic Boston

The Oak Bar [138 Saint James Ave., Boston. 617.267.5300. theoakroom.com] is usually the first stop on our old-man pub crawl, and should be yours too, especially if you’re into historic buildings. It’s housed in the Fairmont Copley Plaza hotel [617.267.5300. fairmont.com], which was built in 1912 on the site of the former Museum of Fine Arts, and feels very Boston Brahmin. Their “martini list” is award winning, but as regular readers of this column know, there’s only one way to make a martini—with gin and vermouth. Order one in a 3-to-1 ratio, sink into a comfy armchair, and relax surrounded by dark wood and marble. Before you go, take note: Drinks aren’t cheap ($20!) and the website lists a dress code: “No Shorts, Hats, Cut-Out/Tank-Top T-Shirts, or Sport Sandals.” So, ditch the Cut-Out/Tank-Top T-Shirt for once, wouldja?

Ever slept, dined or imbibed in a jail? Umm … OK, maybe we shouldn’t have asked. You sure do shine up nice, though—why not treat yourself to drinks at The Liberty Hotel [215 Charles St., Boston. 617.224.4000. libertyhotel.com]? The venue housed some of Boston’s most notorious criminals before being shut down in 1991 and reopening as a hotel in 2007. There are five places to guzzle at The Liberty: Clink [617.224.4004 libertyhotel.com], where you actually dine in former jail cells; Alibi [857.241.1144. alibiboston.com], set in the old “drunk tank”; award-winning chef Lydia Shire’s Scampo [617.536.2100. scampoboston.com]; The Liberty Bar [617.224.4000. libertyhotel.com] in the lobby and its outdoor patio extension, The Yard. We suggest hitting them all in one night, then immortalizing it in your own 5- (or six-) drink minimum.

Bottoms up, readers. You’ve got some hotel bar drinking to do!

CIN-CIN!

FOR MORE RECOMMENDATIONS ABOUT WHERE TO DRINK, VISIT LUPECBOSTON.COM.

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