Owned by married couple Michelle and Steve Corry, Five Fifty-Five has been among Portland, Maine's top fine-dining destinations for over a decade. The Wine Spectator Best of Award of Excellence–winning wine list of 350 selections reflects chef Steve’s Mediterranean-influenced American menu. California is the program’s strongest region, featuring benchmark Napa producers like Cakebread, Caymus and Stag’s Leap, plus some interesting sparklers and blends. The program also excels in Burgundy and Bordeaux, with verticals from Château Calon-Ségur, Château Pichon-Longueville Lalande and more. Though Five Fifty-Five is an upscale restaurant, the wines are moderately priced, with a designated page of staff picks that includes several bottles under $100. There are also more than 20 wines available in half- or full-glass pours and another 20 available in half-bottles. The two-story dining room is cozy and romantic, but for guests seeking a more casual setting, the adjacent Point Five Lounge offers the same impressive wine list with bar bites and cocktails.