I meet him and seven others outside the White Horse Tavern, a delightful English-style pub with a Tudor façade and a traditional outdoor courtyard complete with red and white umbrellas. It's a bustling Saturday night and we're about embark on a pub crawl through one of New York's most engaging districts: the West Village.
After quick introductions we head inside for a drink and Sam talks us through the pub's illustrious history. Opened in 1880, it has long been a gathering place for writers and bohemian types living in the area. Jack Kerouac mentions the pub in his best-selling book On the Road and he is commemorated by the "JACK GO HOME!" message scrawled on the bathroom wall - he was thrown out on more than one occasion.
Other famous patrons include Bob Dylan, Jim Morrison and Hunter S. Thompson. Dylan Thomas was a regular in the pub and, according to Sam, he still holds the record for the most whiskey shots consumed in one sitting. If you're tempted to try and better his effort of 18, it's worth knowing that he died in a nearby hospital the following morning.
From the White Horse Tavern we stroll along 11th St, past the Magnolia Bakery (whose cupcakes are now famous courtesy of the Sex in the City girls), and through graceful tree-lined avenues featuring rows of elegant New York brownstone houses.
Our next stop is the Kettle of Fish, a dimly lit, low-ceilinged establishment on Christopher St that doesn't look like it's changed in decades. Boasting an old-fashioned jukebox, a dartboard, an open fire and several comfortable sofas, it's a refreshing respite from some of New York's $15-a-beer, "sorry, you can't come in because you're wearing the wrong kind of shoes" type of establishments.
Bottles of spirits compete for shelf space with books and other knick-knacks and at one end of the bar a large stuffed dog stands guard. Stationed at the other end is an old guy who looks like he walked in when he was 21 and hasn't left since. It's the sort of place where you can imagine the world gets put to rights in an alcohol-fuelled haze most nights of the week.
Our final port of call is Kenny's Castaways on Bleecker St. A veritable live music institution, it has hosted to a long list of legendary acts including Aerosmith, Bruce Springsteen and The New York Dolls. The walls are plastered with memorabilia and the bar boasts some truly bizarre interior furnishings. Beer barrel tables, an antique brass till and an antler's head covered in trilbies are just some of the highlights. Imagine a lotto winner going crazy on eBay and you'll be on the right track.
At the start of the tour Sam declared that "by the second pub, I'm largely irrelevant". As I look at the seven people who started as strangers and who are now merrily laughing and chatting away, I can see what he means. This tour is as much about meeting like-minded travellers as it is about exploring one of New York's most charming neighbourhoods.
TRAVELLERS' TIPS
Getting there: V Australia flies daily from Auckland to Los Angeles via Sydney. Phone 0800 8287 82. Delta Air Lines flies direct from LA to New York.
Touring with Uncle Sam: The West Village tour runs every Saturday at 7:30pm. Cost: US$75.
Further information: See the official guide to the city.
Top 3 NY casual eats
Flight Centre's Frances Cebalo has travelled to New York and shares her top three casual eating spots:
1. Levain Bakery, 167 West 74th St
Blink and you'll miss it, this tiny bakery is in a basement and not far from Central Park. It sells amazing cookies for around US$4 each, each is the size of a muffin - about an inch thick, crisp on the outside but soft and gooey on the inside. I recommend the double chocolate chip and the chocolate with peanut butter.
2. The Stanton Social, 99 Stanton St
A great tapas bar that has a New York vibe to accompany the delicious food. I recommend the French onion soup dumplings with a glass of wine - a great way to end a busy New York day.
3. Grand Central Station
A tourist destination in itself, with a big food hall where you can munch on classic NY deli sandwiches while watching the hustle and bustle. For more information on New York, contact Frances Cebalo at Flight Centre on 0800 427 555.
Rob McFarland was a guest of V Australia, Delta Air Lines and Uncle Sam's Tours.