1. Alibi
Located in a former jailhouse, this unique nightlife spot serves a small shareable plates menu as well as plenty of tasty cocktails, beers and wines to enjoy among the framed mugshots. Savor the trendy atmosphere and upbeat music late into the night. 215 Charles St., 857.241.1144, $$$
2. Drink
The unique design of this spot puts cocktails at the forefront of the guests’ experience—unsurprisingly. The bar weaves throughout the space, leaving six corners for guests to gather, place their drinks and, of course, drink. But don’t overlook their food menu, which features plenty of delicious accompaniments. 348 Congress St., 617.695.1806, $$$
3. Haley.Henry
Oenophiles: Discover this unique wine bar that sources natural vinos from around the globe. The menu is constantly changing, so there will always be new flavors to explore. While you’re there, enjoy their food menu, which specializes in tin fish but also includes meat dishes and charcuterie. 45 Province St., 617.208.6000, $$$
4. Orfano
Specializing in homemade garlic bread, handcrafted martinis and refreshing modern ambiance, Orfano in Fenway is unsurprisingly popular. Diners enjoy a high-end menu featuring items like lobster bucatini, pig Parmesan and ribeye, along with plenty of cocktails, vinos, beers and digestifs. Sit among the chandeliers and portraits of female icons for a night of whimsical elegance. 1391 Boylston St., 617.916.9600, $$$$
5. Yvonne’s
Not only does this popular downtown restaurant boast an extensive wine list, but it also offers an assortment of Mediterranean-, Middle Eastern- and European-style food in an intimate and beautifully designed dining space. 2 Winter Place, 617.267.0047, $$$$
Photography by: JM Leach
