The best places in the world to smoke a cigar

Smoking a cigar the correct way demands a critical mix of solitude, contemplation, and most important, awareness of surroundings. All other things become subservient to the act of observing and evaluating. With this game plan in play, the smoker’s post-ignition environs take on as much importance as the flavor, taste, and draw of the tobacco. Here is one man’s list of the top ten places in the world to smoke a cigar.

10. Right before the Ironman Triathlon World Championships in Kona, Hawaii.
Kailua Kona is usually a sleepy tourist town on the western side of the Big Island of Hawaii. But once a year, in late October, the best athletes in the world gather for the Ironman Triathlon World Championship. The 2.4 mile swim, 112 mile bike ride, and 26.2 mile marathon takes most competitors most of the day, so the gun goes off at 7 a.m. sharp as upwards of 2,000 swimmers turn “Dig Me” Beach into a feeding-frenzy of arms, legs, and splashes. Light up early, puff and marvel; let your cigar tell the crowd, “I’d rather die young that try something like this.”

9. Seated in the square before the Piazza Duomo in Florence, Italy.
Brunelleschi’s Duomo (1296) in so beautiful, so massive, so spiritual, that a visitor has to sit and puff and wonder: Could this masterwork actually have been created by man? Have a demitasse from one of the square’s little bistros, enjoy the soundtrack provided by the voices of passing Italians, and let your cigar smoke rise up and mix with the angels flying above the Dome.
8. Atop the Smoking Platform in Colchester, Vermont.
In the dooryard of an old farmhouse in northern Vermont stands a twenty foot granite cliff. Atop that cliff sits a chair and a small table holding an ashtray, a pack of wood matches, and bug spray. The owner of the house climbs the cliff once a week to enjoy a solitary smoke. “You’re such a child,” the smoker’s wife tells him, “You’ve built a fort up there, just like a little kid would.” “Rather,” he informs her, “it is a Gentleman’s Smoking Platform.”

7. At the gaming tables in Las Vegas, Nevada.
It might be changing, but the casinos have remained one of the few public places in America where cigar smoking is not only permitted, but encouraged. Try apologizing for your smoke as you lean over the Caribbean Stud table, and the lovely lady at your right might actually tell you she’s been enjoying the aroma. Plus: Cigar smokers always look like winners, even when they’re not.

6. On the French Quarter in New Orleans.
Katrina delivered a near-deadly body blow to the city, but its soul survived and is reinvigorated. Smell the Cajun cooking and listen to the muted jazz lifting up from the street. The still air and pressing humidity combine to make blowing smoke rings as effortless as breathing.

5. At the rail of Saratoga Racetrack, Saratoga, New York.
The oldest continually operating track in the country, and still one of the stateliest. Faux southern belles mix with true-life losers. Dixieland bands and picnic tables. Three bucks to get in. Everyone has a system and everyone has just won big. Continue the tradition started by Red Aurebach of the Boston Celtics-after one of your “wins,” light up a victory cigar to celebrate, and to let the crowd know that you know how to pick ‘em.

4. Halfway up Pioneer Peek, outside of Anchorage, Alaska.
The city is closeted by the Chugach Mountains, with so many massive peaks that some don’t even have names. Drive just a few miles up the highway towards Fairbanks, pull off and park, and start hiking/climbing up a peak that maybe nobody has ever climbed before. Before too long eagles will be flying by at eye level; airplanes will actually be lower than you. Sit. Marvel. Ignite.

3. After sundown in the early springtime of Phoenix, Arizona.
How many tourist destinations can list March as one of its best months to visit? The dessert really does cool down after dark. Step out among the Saguaro Cactus and light up. Pretend you’re a daredevil and the flame at the end of your cigar is warding off the coyotes and the rattlers.

2. On the street of Duck Alley, New York (or in whatever town you grew up).
There, you can use the cigar as your time machine, transporting you back to your first smoke, your oldest pal, your first love.

1. In the middle of the Brooklyn Bridge, Brooklyn/Manhattan, New York.
The verdict is in: The Brooklyn Bridge is the most beautiful edifice ever created by man. When the Roeblings, father and son, designed and built the bridge in the 1870’s and 80’s, it was roughly equivalent to someone building a bridge to the moon. The Bridge’s combination of engineering and artistry has never been equaled. Walk the foot path halfway across the East River, sit on a bench and gaze at the cathedral-like towers. Iron cables will cut squares and trapezoids above your head in the sky. Smoke there, and think about what man has wrought. Look over your shoulder at the Twin Towers site only if you want to be reminded that the work of man isn’t always this magnificent.

Jim DeFilippi is a crime novelist and cigar maker living in northern Vermont. His recent novels include The Family Farm and Duck Alley. Read his blog on Red Room.

[Photos: Flickr | alexbrn; Monica Arellano-Ongpin; bobistraveling; valentinapowers]