Cigar Aficionado

The Pen-Top Bar & Lounge, New York City

Smoking up high on the roof of the Peninsula Hotel in midtown Manhattan.

Rooftop-smoking enclaves can be elusive and exclusive. Right smack in the middle of midtown New York City, down the street from the Ferrari and Mercedes-Benz dealerships on Park Avenue, you'll easily find the Peninsula Hotel. What you may not know as the average walker-by is that here resides a rooftop terrace with a soft spot for the cigar smoker.

Enter the ornate mable lobby festooned with flowers. Hang a quick right and then a left down the wood-paneled hallway to the elevator that leads to the roof. When the elevator doors open 23 floors up, you've reached The Pen-Top Bar & Terrace. The first stretch of patio my smoking partner and I encountered was dotted with your basic patio-style furniture. We sat down at one of the tables and a waitress hurried over just as the caps were snipped off our Romeo y Julieta Short Churchills.

"I am sorry, sir" she said. I immediately jumped to the conclusion that my intel on this being a smoke-friendly spot was misguided, but I was wrong. "But," she continued, "smoking is only permitted…on the other side of the bar." I stopped in mid-grimace as she uttered the latter half of her statement and experienced a glimmer of hope.

I have come to expect the short end of the stick in terms of accommodations, so I was still a bit doubtful on my way to the other side. In light of the minimalist surroundings that constituted the nonsmoking section, I was expecting little more than a perch placed possibly on the outer recesses of an overhang. We walked back past the elevator and continued in the other direction. We came to a glass door and entered to find a packed glass-enclosed bar populated by the suit-and-sunglasses crowd. We continued through the room and turned the corner to find a large terrace far superior to the nonsmoking side. This is a rarity in the current climate where those who enjoy the leaf are usually punished for it with some outpost of a section, subpar to where the nonsmokers get to hang their hats. Not the case here.

The smokers' side of the deck is situated with metal and glass tables and chairs all outfitted with umbrellas. The rim of the space is lined with bushes, and just beyond tower the geometric shapes of the midtown skyline. The scenery is spectacular during the day and only improves the darker it gets, with the night sparking a surrounding patchwork of window lights that bring out the embers of your smoke. The bar seemingly caters to cigar smokers with its cigar ashtrays at the ready and many aficionados lighting up left and right. You'll feel at home sparking a premium cigar and won't bump elbows with the person next to you as the seating is nicely spaced out. If you have a large party, though, you may find yourself jockeying for chairs with the bustling wait staff.

The bar is not stocked in the connoisseur's vein, but does have little something for everyone in the premium brown spirits category. Cocktails and Martinis dominate the libations list, with prices reaching up to the $22 per glass neighborhood, while most everything else is $10-plus. No one said the sky terraces of New York City were cheap.

It gets busy quickly around happy hour, so get there early. We came in around 5 p.m. and already were faced with a waiting list. If you can manage it, the optimal arrival time is 4 p.m. when the place opens. If you do find there's no room on the terrace, the glass-enclosed bar that stands sentinel to the roof-deck entrance is a fine place to wait with a cocktail -- you just have to hold off on lighting up until you get fully outdoors.

If you're looking for something to nosh on, a pricey bar menu includes a cheese platter, a shrimp cocktail, wraps, and a sushi and sashimi platter in ample portions for two, but like most everything else at the Pen-Top, food and drink is all fringe to the locale and the view it affords.

The Pen-Top Bar & Terrace
The Peninsula New York
700 Fifth Avenue at 55th Street, Roof deck
New York, NY 10019
Tel: 212-903-3097
Monday to Thursday, 4 p.m. to midnight
Friday and Saturday, 4 p.m. to 1 a.m.
Sunday, 3 p.m. to 10 p.m.