Man Management: How to (Painlessly!) Plan the Annual Guys Trip

It’s the best weekend of the year. But someone has to plan it.

November 30, 2018 9:00 am

According to a recent study done by Oxford University, while women are able to maintain close friendships via non-face-to-face communication (phone calls, email, etc), men tend to require in-person contact and physical bonding to prevent growing apart. A second unrelated study, this one conducted by Harvard University, concluded that the health of interpersonal relationships (for both sexes) has a direct correlation with long-term physical health.

Put these together, and the nerds have spoken: quality time with your buds is good for your well-being. Hooray, science!

The problem? As we grow older, various responsibilities have a pesky way of forestalling such get-togethers. Such is life, unfortunately.

The solution? What we’re colloquially referring to around InsideHook HQ as the “Lads Jaunt,” a term that essentially encompasses any group trip of several fellas with the express purpose of, you know, camaraderie.

Below you’ll find your comprehensive guide, from who to invite (and who to leave out) to the apps that make splitting the bill a breeze to a few recommendations on locations we consider LJC (Lad Jaunt Conducive).

Now all that’s left is to round up the lads. And please, resist your urge to say, “Dilly, dilly.”

Step One: The Guest List

  • The ideal group size for a Lads Jaunt is between 6 and 12 — any less and you risk losing the sense of occasion, any more and you’re getting into cat-herding territory.
  • It’s ok if not everyone knows each other — this is prime friendship-forging territory. However, everyone should know at least two other guys on the trip to avoid awkward, periphery-guy scenarios.
  • People to leave out: anyone who is a drinking liability, has diva tendencies, insists on discussing politics, is annoyingly frugal or will use the whole trip as an excuse to chase tail.

Step Two: Getting the Ball Rolling

  • For choosing a date, look no further than Doodle — this handy app syncs with everyone’s calendars to make finding the ideal date a snap. Congrats, you just saved endless email back-and-forth.
  • Next, choose a captain — without one, this sort of enterprise can go off the rails REAL quick, so either take the reins yourself or coerce your most organized friend. This person will be the keeper of…
  • …a central Google spreadsheet with flight info, bookings, etc. This will save countless questions like “what time does Dave get in again?” or “Did we make a dinner rez for Thursday?”
  • To navigate the traditional paying-for-stuff clustercuss, download Splitwise. You’ll create a “trip” with all your party members, and each guy can enter expenses as he incurs them. The app does the math and then syncs with PayPal and Venmo for easy settling up.

Step Three: Choosing Your Destination

Obviously there are groups whose interests run more specific, but a good jumping off point for a Lads Jaunt is a locale with a healthy mix of good food, solid bars, outdoor activities and other people having a good time. For those in need of a little inspiration, our recommendations based on season:

Spring: Nashville, TN

A legendary live music scene, close proximity to some of the best whiskey distilleries in America and, of course, hot chicken sandwiches. Pro tip: cool folks can always be found hanging out at Urban Cowboy, who offer the handsomest of digs (plus a top-shelf bar/restaurant) and are the friendliest of hosts. 

Summer: Cape Cod, MA

Affordable accommodations abound, the beach scene is killer, and you can’t throw a rock without hitting amazing seafood. Pro tip: Provincetown is the liveliest hamlet on the Cape (see: Drag Karaoke at The Governor Bradford).

Fall: Austin, TX

In early fall, Austin’s scorching summer temps dip into the 80’s, allowing you to take advantage of the area’s aquatic offerings (Barton Springs, river tubing, Lake Travis) comfortably without the summer crowds. Add some of the country’s best Tex-Mex, BBQ and bars and you’ve got a guaranteed winner. Pro tip: a BBQ pilgrimage to The Salt Lick in nearby Driftwood is well worth the drive.

Winter: Vail, CO

Plenty of wintertime diversions even for non-skiers, cosmopolitan dining options (Matsuhisa, Sweet Basil) without the Aspen pretense, and one of the best damn apres scenes in the country. Pro tip: skiers should finish their day on the Minturn Mile, an approachable backcountry jaunt winding down to the neighboring town of (you guessed it) Minturn, where the eponymous saloon is the perfect setting for margaritas and post-slopes braggadocio.

Step Four: Accommodations

Having everyone under the same roof is a must — hotels are where true camaraderie goes to die. Thus, Airbnb is the name of the game. When choosing, let the following criteria be your guide:


      • A bed for everyone. Nothing sadder than the one guy on the couch.
      • 1 bathroom for every four people, max. Think about the typical male bathroom. Now multiply that.
      • Some kind of patio or outdoor space. The ideal congregation venue. Preferably one with games or a firepit.
      • A large refrigerator with an ice maker. Beer takes up a lot of space. You’re gonna run out of ice.


      • Laundry
      • Grill
      • Pool or hot tub
      • Late check-out
      • Chill neighbors (or at the very least distant neighbors)


      • A big TV set up. If you turn it on, people will veg out in front of it. Fine at home, but not why you’re here.
      • A gym or exercise equipment. Let’s be realistic — no one is going to use it, and anyone who does is just going to make everyone else feel guilty.

Step Five: Sustenance

Unless cooking is a big part of your plan (in which case you’re on your own to sort that out), stocking up is relatively simple. Your essentials:

      • Coffee
      • Milk + non-dairy option
      • Cereal
      • Chips + according dip(s)
      • One case of beer per guy
      • Hooch of choice + mixers
      • Gatorade or similar electrolyte-replenishing hangover killer
      • Bottled water
      • Advil
      • Ice

Your actual eating should be eating out — exploring a city’s eats is half the fun after all. Things to remember:

      • Make reservations: Attempting to wing it with a large party is a recipe for disaster, so sort yourself out in advance accordingly to avoid hungry pissed off dudes who eventually wind up eating something terrible because it’s the “quickest option.”
      • Inquire about a private dining room: Many places have them, they allow you to be as loud as you want, and usually there’s a set menu option that reduces ordering hassle.
      • Let one guy pick up the check: The staff will love you, he’ll get crazy points on his card and the aforementioned Splitwise app will take care of the rest.

Step Six: Transportation

  • If you can swing it, a Lads Jaunt is the perfect opportunity to splurge on some sort of party bus — it keeps the squad together and getting from A to B becomes a fun hang in its own right.
  • When ridesharing is the name of the game, give Bellhop a spin — it aggregates Uber, Lyft, etc to make finding the quickest and cheapest ride a no brainer.

Last thing: never hurts to have a local lawyer’s number in your phone.


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