Bar crawls are great when they're done right: with one or two friends, absolutely no thematic T-shirts for the occasion and no time frame, so you can savor each stop. Also, never use the term "bar crawl." Not having to, you know, walk too much is key too. There aren't too many places in the city where you can set up a bar crawl all under one roof, which is why I find myself gravitating toward the three bars at the W Hotel when I'm in the Theater District, each of which offers a distinct drinking experience.
The bar at Descent is woefully underutilized every time I've been in. Later at night on the weekends it gets more crowded, but it's a fine option for sneaking away for an early evening cocktail. The room itself -- with the slick racing-stripe bar -- has a sense of movement, almost a gravitational pull, like it could turn on its side at any moment. Probably best to start here, then, when you've still got your legs. The drink of choice? The Tea Party, made with Benromach scotch, English Breakfast tea, barley syrup lemon and soda.
Upstairs at the lounge in the hotel lobby of the W is typically a more crowded affair, but there are plenty of plush couches where you can sip the Ginger Margarita made with Sauza Hornitos reposado, ginger and lime. Quoth famed margarita expert, my wife, "Oh my God, that is so good. I would divorce you and marry that drink." To make the garnish for the rim, they steep lime juice with fresh ginger, cook it down and strain off the ginger before dehydrating it and mixing with salt.
Inside the more refined restaurant Market by Jean- Georges, you'll find the inimitable Domingo-Martin Barreres behind the bar. If it's not too busy, ask him to run wild with an idea. For us he mixed up a cocktail called the Ishihara, named for the Japanese doctor who invented the color-blindness test, which makes sense when you see it. The drink -- made with gin, muddled orange marmalade, yuzu, lychee and chilli and basil oil -- is refreshing and wholesome, with a milky consistency from the lychee and light contrasting spice from the chilli. It's like three drinking flavor profiles all at once, like the hotel itself.