by Gary Bennett
Special to the News-Post
Let’s say you’d like to put together a boy’s weekend. You’ve got the boys (sort of), an understanding partner (sure you do), and the time and money (pretty much) to pull it off. What else do you need? Plenty, I say.
As a devotee and primary organizer of an annual boy’s weekend, I can tell you that a lot can go wrong — unless you plan carefully.
Before we get started, you may be wondering: why not just take your wife or girlfriend on a nice trip? My friend, if you’re asking this question, then a boy’s weekend may not be for you. The point is to take time away from your dearly beloved to enjoy some manly pursuits — without worrying about boring her or boring yourself by doing things she wants to do. The focus should be on strengthening friendships with your guy pals through shared experiences. Along the way, you’ll create lasting memories that contribute to personal growth and make you a more well-rounded person.
And don’t downplay the cost savings of just one of you going on a trip. That may sound obvious, but if you’re the type of person who gets genuine pleasure from seeing someone else have fun, then you know exactly what I mean.
SELLING THE IDEA
The first thing you must do is get buy-in. If this idea comes out of the blue to your wife, girlfriend or partner, you’ll face an uphill battle — especially if you’re planning to go somewhere she has never been.
I was smart enough to insist my wife visit her sister in Florida right after the holidays — without me. “Yes,” I said, “you can enjoy undivided time with her without worrying about me.” A few years later, I even OK’d a trip to Europe for my wife and a girlfriend who had never been. I know — brilliant, right? Now I can plan my boy’s trips with impunity.
PLANNING THE TRIP
It’s never too soon to begin planning your guy trip. These days, even retired guys have busy schedules, so I recommend giving yourself at least six months of lead time. You’ll often need that much time to secure good deals on transportation, accommodations and entertainment.
First, decide who to invite. I recommend keeping the group small — no more than four — and inviting close friends only. It may be tempting to invite that new guy you’re kind of smitten with, but resist the urge. You’ll be setting yourself up for failure. You not only need close friends on the trip, but the kind you’d be comfortable traveling and sleeping in the same room with. That’s harder than it sounds. Longtime friends who have known you at your worst — preferably since those awkward teenage years — are ideal. (This is an excellent reason to maintain friendships with high school and college chums.)
Another good tip is to choose friends your wife knows — and it’s even better if she knows their wives. This isn’t to say she’ll disapprove of people she doesn’t know, but why take a chance?
It also helps if everyone involved is a longtime, happily married husband. You never want to invite a friend who has recently married, divorced, or whose marriage is on shaky ground. (Believe me, everyone knows.) And this probably goes without saying, but you can never — I repeat, never — invite a single friend on a boy’s trip with married friends. That’s an unforced error and a recipe for disaster.
WHERE TO GO
Next, you’ll need to decide where to go and what to do. These two decisions go hand in hand. You wouldn’t head to the mountains if everyone loves the beach, but you’ll need to refine your thinking even further. Choose your destination wisely. Nothing says “boy’s holiday” like the right balance of adrenaline-fueled activities and downtime.
Plan collaboratively. Talk with your friends to find an approach everyone agrees on regarding budget and activities. Don’t over-schedule. Balance planned events with downtime, and leave room for spontaneity — some of the best moments come from it.
To drive or to fly? That depends largely on your destination and how much time you have. From the Frederick area, places like New York, New England, Florida, and even New Orleans could go either way. Choose carefully. Turning your boy’s getaway into a car trip introduces additional challenges: who drives and for how long, when to stop, where to eat, and whether the car ride is for music or conversation. My preference is to go far enough that flying is the only option. Flying offers the best combination of shared experience and personal space — and it can be just as cost-effective as driving.
Next, decide on accommodations. One big advantage of a boy’s weekend is the ability to rent a large suite — one you normally couldn’t afford — and split the cost three or four ways. But this needs to be discussed upfront. How many rooms will you need? Some friends may prefer their own modest room, while others are fine sharing. If three of you go, a large suite may be perfect. If four, two rooms might make more sense. Budget and comfort levels matter here, so don’t gloss over this decision.
WHAT TO DO
Now comes the fun part: deciding on activities. For a three- or four-day weekend, I recommend scheduling at least two structured activities. The best guy trips strike a balance between high-energy experiences and time to relax. Naturally, whatever you choose must appeal to everyone so no one feels left out.
Classic boys’ weekend ideas include outdoor adventures like camping, hiking, fishing, rafting, or golf; attending a live sporting event or concert; or exploring a city with a focus on food, drink, nightlife, or gaming. Most of my boy’s weekends have centered around sporting events and concerts. Add some beach or pool time, good meals, and maybe a short bus or river tour, and you’ve got all the ingredients for a great getaway.
OTHER SENSIBILITIES TO WATCH OUT FOR
Be mindful of sleeping and bathroom arrangements. You don’t live with these guys, so you may not know their habits. Some shower at night, others in the morning. Some wake early; others sleep in. Some eat breakfast; some don’t. These details matter — talk about them ahead of time.
You probably already know which friends are easygoing and which are a bit more uptight. Some prefer a regimented schedule; others thrive on spontaneity. Be aware of these quirks, try to accommodate them when possible, and focus on the fun. After all, you’ll be back home before you know it.
MY WEEKEND TRIPS
I didn’t start organizing boy’s weekends until I retired a few years ago, but they’ve since become an annual rite of passage. We’re not golfers or thrill-seekers, but we know what we like. True to my own advice, we plan just a few activities and leave plenty of room to relax and be spontaneous.
To date, my two (and sometimes three) pals and I have taken these boy’s weekends over three or four days, and we’ve always had a great time:
2020 — Detroit: Two Orioles baseball games and a river walk.
2021 — Arlington, Texas: Two Orioles baseball games and a Texas Hill County tour.
2022 — New Orleans: Paul McCartney concert, Bourbon Street bar hopping and a bus tour.
2023 — Denver: Pittsburgh Pirates baseball game and a Red Rocks concert.
2024 — Tampa: Two Orioles baseball games and a Siesta Key Beach outing.
2025 — Las Vegas: Eagles concert at the Sphere, Area 51 tour, light gambling.
Gary Bennett is a longtime Frederick resident who spends his time hiking, biking, volunteering and providing childcare for grandchildren. He is married and retired from his career as a nonprofit marketing executive.
