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The Guys’ Guy’s Guide to Weekend Road Trips

There’s nothing like getting out of town for a long weekend. And it’s even better when you travel to another city.

Guy’s Guys maintain wanderlust for travel and adventure. And although I’ve had the good fortune to visit exotic locales like Kuala Lumpur, Taipei, and Hong Kong for business, I still look forward to a stateside weekend getaway in the company of a Guy’s Guys crew. In fact, I recently returned from a quick jaunt to Pittsburgh where I met up with three old friends and one of my college roommates who hails from the Steel City. Why Pittsburgh? First of all, Pittsburgh is only an hour and change flight from NYC. It’s also an overlooked little city with a great layout, rocking bars, and wonderfully real people who work hard and show authentic pride in their hometown.

The focus of this past weekend was a Rolling Stones concert at Heinz Field, the home of the Pittsburgh Steelers. I’ve been doing the daddy thing with my young son 24/7 for the past two years, so when the invitation hit my email, my wife urged me to get out of town. She knew how restless I’d been, and I’m thankful for having someone as thoughtful as her. It also gave my son a break for a few days as he wondered why his “Da-Da” had disappeared. The weekend went by in a flash, and like any worthwhile road trip with your buds, it left me with what are now memories of a good time with old friends and a classic, riveting performance by the ageless Stones under threatening gray skies. The weekend prompted the notion of what makes a good road trip and how to make the most of a few precious days off from our ultra-busy lives. So, here is my Guys’ Guy’s Guide to Weekend Road Trips, with a nod to the Rolling Stones for their rocking’ vibe.

1. START ME UP – Book your flight and lodging accommodations early, especially if you are attending a big event. To a certain extent, dealing with airlines and hotels is a crapshoot. That said, it’s always advisable to set up your trip as far in advance as possible. Since this last minute road trip was built around a rare Stones appearance in the Steel City, finding non-stop flights and a room within proximity of the concert venue was tricky. I tracked flights and prices for a few days using the usual digital apps, but ultimately found the fastest, cheapest and most accessible methodology by simply booking directly with an airline. The hotel was a different story. Even three weeks prior to the show, almost every room in town was booked. Fortunately, my friend who hatched the road trip plan and bought tickets on Stub Hub at retail prices, managed to use his elite status with a leading hotel chain to score us the last room within walking distance of the venue. Two of us needed to share a room, but we scored two queen beds so it was kind of fun to bunk up with an old buddy for two nights. Beyond sleeping, we didn’t spend any time in the room, so it turned out fine, even with some snoring involved. That said, from Friday to Saturday night, the room rate was jacked up fifty percent due to the concert.

During my career in business, I’ve made it a goal to get my packing down to a perfect science. Now I travel almost anywhere with the minimum amount of clothes and sundry items in tow. I have little tricks for saving space by wear running shoes on the plane (which I can use for walking around or working out) and packing a second pair of lightweight shoes, sneakers or sandals in my overnight bag, which I carry on. I pack sparsely with a minimum of clothes. You can always buy a shirt or pants if you need them when traveling anywhere in the US and most overseas destinations. And, I always leave room in my bag for a keepsake t-shirt, hat, or whatever.

2. WAITING ON A FRIEND – Make a flexible plan for your time during your short trip. I’m not suggesting you become a slave to a schedule, but it’s always nice to have a blueprint to work from.In this case, one of my college roommates hails from Pittsburgh, so of course I made sure I connected with him in advance of our arrival. He met us on Friday night and acted as our tour guide. We hit a few bars near our hotel and eventually had dinner and drinks at the Jerome Bettis Bar 36 (his number as a Steeler).The food was good and the drinks were cheaper than NYC, which was no surprise. And, being a gracious host, my old roomie paid the check without our knowing before heading home for the evening. That’s class. During our dinner, my roomie gave us the names of other restaurants, bars and cultural things to consider for Saturday. The next day we walked from our hotel to the Strip District, which is known for its farmer’s market, seafood shops, team merchandise kiosks, and bars. It was off the beaten path and an area most visitors would never know existed. The walk was great for getting our bearings and a feel for the city. We eventually found a bar that served the best Bloody Mary and lobster nachos that I’ve ever tasted.

3. SALT OF THE EARTH – Make friends with the locals. One of the best things about Pittsburgh is the people. I first met folks from Pittsburgh during my years at Villanova University, on the Main Line near Philadelphia. For some reason, a lot of kids from Pittsburgh attended the school and I became friends with a lot of them. To a person, well almost, they are down to earth, straight-talking, real folks and a lot of fun. I immediately noticed the similarities even during the cab ride from the airport. Our driver was friendly and proud of his city. He pointed out where many NFL quarterback legends from the Pittsburgh area lived and he even offered to give us a ride back to the airport on Sunday. I took his number because my roomie told me that unlike NYC, cabs are hard to find in downtown Pittsburgh. There was a shortage of cabs so we ended up using his service again on Sunday.

During our stay, the locals at the bars, concert, and even the people working in the shops and restaurants were friendly and real. We got tips for where to go and what to eat, where the Stones were staying, etc. It was a pleasure interacting with everyone.

4. GIMME SHELTER – Checking out the weather forecast in advance can be helpful. With the risk of sounding like grandma, I suggest checking a weather app before packing for your trip. In this case, the forecast called for intermittent rain for three days. I wisely packed a water-resistant windbreaker and bought a Pittsburgh Pirates cap at one of the many team merchandise shops. A few hours before the concert it was raining heavily and all the bars along the river walk were jammed. Fortunately, the people were cool and super-friendly. One guy even bought us a round of beers for simple letting him get to the bar to order drinks. It was that kind of crowd. Coming from Manhattan, this was a nice reminder of how chill people can be given the right circumstances. About thirty minutes before show time, the rain stopped. The skies cleared as the Rolling Stones took the stage. We had stopped by Heinz Field that afternoon to pick up our souvenirs, so we did not have to deal with a crowd that was fifty deep waiting to buy $40 t-shirts, so we had time to enjoy a cold brew while watching the crowd pour in.

5. SATISFACTION – There’s nothing like a quick road trip getaway to reinvigorate your spirits and remind you of the importance of good friends.

The four of us (my buddy from Pittsburgh did not attend the show) took our seats a few minutes before show time and with beers in hand stood together for the next two and one half hours of razor-sharp rock n’ roll. The show was electric, sensational, riveting. We had perfect seats at the end of the catwalk. And unlike most of his rock band brethren of the same age, Mick Jagger can bring it. His voice still fills up a venue, and in this case a stadium with 55,000 seats. The guitars were loud, almost to the point of distortion. The beers were cheap (Yuengling 24 oz cans for $12) and unlike the stadiums and arenas in NYC, you could cruise around holding toting the can.

After the show, the four of us had a few final drinks at a nearby steak house before calling it a night and saying our goodbyes. The next morning our cab showed up on time and we were back in NYC a few short hours later.

Every road trip is different and each one has its own special flavor and surprises. That’s one of the joys of getting out of Dodge for a long weekend.

Safe travels and happy trials to you, amigos.

This week’s Guy’s Guys of the Week are the Rolling Stones.Twenty-five years ago they seemed old for the rock n’ roll game, and we all had a few laughs at their expense. Today, it feels like they’ve stopped aging. Could it be that they are now in better shape than most of their boomer audience? Rock on, Mick, Keith, Charlie and Ronnie. You are all Guy’s Guys.