By Matt Villano, on March 21, 2014

Vegas, with the boys

If you’re a guy, there’s nothing quite like vacationing with a bunch of your male friends. The stupid jokes. The silly games. The stories about wives and kids. We men don’t talk about this camaraderie that often, but we crave it, and when we manage to capture it for a few days, the feeling is glorious.

One of my favorite dudes-only vacations every year is an all-guys weekend in Las Vegas. I and about eight of my closest friends make this pilgrimage every year to celebrate the first full weekend of the National Collegiate Athletic Association men’s basketball tournament—a.k.a., March Madness. We book a big suite (the hotels vary from time to time, but we usually head to Red Rock Casino Resort and Spa) and use it like a frat house. We reserve a VIP booth in the sports book. We gamble. We drink. We smoke. We play poker. We share a nice meal or two. And we just let loose.

Planning—and executing—these kinds of trips takes skill. Here, then, in no particular order, are six tips for engineering a mancation you’ll never forget.

Build the visit around an event. The best Vegas trips—the best all-dude adventures, really—revolve around a big event, something that keeps everyone excited and interested for the duration of the trip. For the group that goes every march, that event is March Madness. The first weekend of the tournament always is the most exciting, with 48 games spread out over four days. In the sports book, where multiple televisions enable us to watch up to four games at once, this means we’re like parrots on speed, monitoring (and often cheering on) bets as they play out in real-time. Because there’s so much action, we spend the bulk of our time in a booth in the sports book. For a long weekend, the place becomes our living room. Against the backdrop of these games, we enjoy time away from our day-to-day responsibilities and (drink and smoke and) catch up on old times.

Schedule off-sites. We don’t spend all of our time in the sports book. To spice up the itinerary every year, we usually indulge in a couple of excursions to mix things up. For a few years last decade, we spent a night driving go-karts at the Las Vegas Mini Gran Prix. Two years ago, a handful of us staged a Pop-A-Shot contest at Circus Circus. Last year, we spent a few hours at the Casa Fuente cigar bar inside the Forum Shops At Caesars Palace. This year, the plan was to take a limo to Brooklyn Bowl, a bowling alley in the brand-new Linq, a shopping and entertainment destination on the Center Strip. Some guys I know even schedule a group outing to one of the local courses for a round of golf. (In case you are wondering, our group is NOT into the strip-club scene. But if you *are* into that, you can do that, too.)

Indulge in the good stuff. Guy time means it’s high time to splurge on the things that make us happy. Like good booze. And good smokes. And man-pampering. In recent years we’ve stocked the bar in our suite with the likes of Tullamore Dew (whiskey), Hendrick’s (gin), and Sailor Jerry (rum). I’m a huge fan of brandy, and I always ship myself a few bottles of good stuff from Germain-Robin, a boutique distillery in Mendocino County, California, near my home. I mentioned the cigars from Casa Fuente—those are a must. Many of us also treat ourselves to spa excursions; in the past, I and some of the group have gotten flat-razor shaves from Sal Jeppi, the master barber at Qua Baths & Spa inside Caesars Palace. Last year, two of the guys in our group sprang for massages from the spa at Red Rock.

Allow for free time. As much as we dudes try to stick together as a group, we also value and encourage alone time. This serves three valuable purposes: 1) It allows those of us who really like to play craps and blackjack—that’d be me—to have time to do that without feeling guilty, 2) It guarantees we won’t get sick of each other by the end of the weekend, and 3) It creates an environment where each of us can call home to talk to the wives and kids—something about which some of us otherwise might feel sheepish. There usually are at least a few guys in our group who try to maintain their fitness regimens during our Vegas trip, as well. This free time gives them the opportunity to do that. (Personally, though I’m an avid runner, I throw my routine out the window during these guy trips. It’s just easier that way.)

Commit to paying your share. Nobody likes that uncomfortable moment when a group of people are deciding how to split a bill. The best way to avoid it: Publicize the plan for splitting costs from the very beginning. When we go away as a group, we take the total expected amount on the bill and divide it by the number of nights we’ve stayed. From there, we divide each night by the number of guys who plan to stay in the suite. This way each dude knows exactly what he owes for each night. I usually play point on this matter and inform the guys via email what the per-night, per-dude price will be. Once I send out this breakdown, I back off and trust that, because we’re all grown-ups, everyone will pay his share. If dudes have questions about what they owe, they ask.

Viewfinder Tip: Bet a few dollars on each horse race in the sports book and you can spend the day drinking for free.

Break bread together, at least once. Despite the inevitability of disparate budgets, regardless of different dietary restrictions, we make it a priority to go out for at least one nice meal—together. Without question, this is the most “formal” of the interactions we guys have over the course of our March Madness weekend. It’s also one of the most enjoyable. There, around a big table, we have the opportunity to focus on each other—not the ballgames or the card games or the dice games or the booze. The meals usually last anywhere from 3-5 hours. Sometimes they go even longer than that. Most years we have the meal at a steakhouse—after all, the vast majority of guys like meat. And some years, I admit, we’re sloppy. The bottom line, however, is that this tradition of breaking bread is a great touchstone, almost like our own take on Christmas dinner. It’s a fitting way to celebrate friendships that have come to feel like family.

What are some of your annual travel rituals?