I’ve been really lucky in my life. I have amazing friends and a wife that has taken them on as her own. I’m sure you have great friends too. On the surface it seems there is no better way to enjoy a vacation than with the friends you love. But is it?

No really… Is it?

I always loved the stories of Don Rickles and Bob Newheart and their wives vacationing together for the last 50 years. But here is the truth we all know deep inside us but we aren’t allowed to talk about:

Not all friends are meant to vacation together.

You know what I mean? You have to be honest about the trip you are planning and match the right friends to the experience you want to take. And this isn’t bad thing. It’s just being realistic. You’re not going to take your Vegan friend to your road trip to the 10 best BBQ shacks in Texas. Or that One Friend (you know the one) that likes Jesus a little too much to the Vegas bachelor party.

In the last year we took “friend trips” to New Orleans, camping on California’s Central Coast and a 5 family beach house rental. And none of those trips had the same friends twice. So how do you pick the right friends for the right trip?

Be Honest

We take lots of vacations with friends. The key to picking the right friends for the trip is being honest about the experience you want to have.

Case in point: Megan and I recently celebrated 10 years of marriage (I know how lucky is she, right?) And we knew we wanted to have a no holds barred super trip to New Orleans. I’m talking no kids and no kidneys. The kind of trip you can only do every couple years. So we had to be honest about the trip we wanted to have.

• No Plan: This trip needed to be more improv than itinerary. If you’re going to a spot like New Orleans we felt you gotta go wherever the city takes you. Not every person in your life likes to just float down the river of life. And there are times we don’t either. But this trip wasn’t one.
• No Fixed budget: That’s a bit of a lie, because obviously we don’t have infinite money, but we were comfortable spending whatever made sense to take full advantage of the city we were visiting. That meant sometimes we may have a $400-500 dinner for two if it meant having a unique experience we may never have again. And that’s OK.
• No Drama: Let’s not bullshit each other, we are gonna be half a continent away from home, in a place that is basically in the middle of a swamp in July. The people you are going with have to be able to put the experience above the comfort of the moment.
• No Bedtime: It’s fucking New Orleans.

So once you have the architecture for your trip you have to ask yourself, who fits the bill?

To use the same tool as demonstrated above here is how we profiled our other two trips we took with friends last year.

RV Adventure

Last year for spring break we knew we wanted to do a family camping trip. I say camping but it was March and after three disastrous camping trips in recent years, Megan made it clear there would be no tents. Here is how we profiled this trip.

• Veteran Leadership: As stated above we totally fucked up our last few camping trips, so having good friends that are always prepared for anything and willing to pool resources over 5 days is essential.
• Kid Management: We have a 6 and a 10 year old, so finding friends with kids in the same general range to interact with would be a plus.
• Nature Is Enough: No room service, no hair dryers, no problem.
• Sound Budget: It’s camping, it doesn’t cost much if you don’t want it to. Within reason you will have a good idea what the final costs will be barring any emergency. This can be super important between friends. Maybe most important if we are being honest.
• Structure Is Good: These days you have to have reservations to camp most places, so this allows you to have an itinerary. This gives a lot of comfort to a lot of people and allows you to take friends that this appeals to. Knowing where you will be every night can be a good thing, because it allows you to plan exactly what you need. Are there fire pits? Are there electrical hookups? Are there showers? Are there toilets? To be honest the last two don’t matter to me when I’m camping, but Megan would kill me in my sleep if I ever took her somewhere without a toilet.

Beach House Bums

This is a vacation we have taken every year with friends for the last 8 years. When I say friends I mean 5 families (11 adults, 11 kids) in two houses for 7 days. For many this sounds like a terrible idea, but for us its our favorite week of the year. It’s not for everybody and we know that so when inviting a family to join us we have to consider the following:

• Embrace The Chaos: 11 damn kids, in two houses next door to each other. And most days friends are hanging out since the beach house is only an hour from home. So 11 is just what we start the day with. But here’s the thing. The kids all just take care of themselves in a Hillary Clinton “It Takes A Village” wonderland. As long as one adult is designated as being on duty, it gives far more freedom than the normal family vacation for adulting. But you have to bring people that can relax in this environment.
• Chill Factor: You’re at the beach homie. If your friends are the type that have to fill each day with sight seeing, or excursions, this may not be the trip. You paid for a beach, use it. The vacation is at your doorstep. And sometimes that means the best activity may just be looking at it with a margarita in your hand.
• Close Quarters: You have to bring friends that are OK sleeping in the same house, sharing bathrooms and maybe yelling at your kids if they act the fool. But that’s when you know you have achieved real friendship right? When your friend feels comfortable smacking your kid upside the head… No? Just me then I guess.
• Chipping In: We rotate dinner every night and each family takes a night. You have to bring friends that are willing to do their part. When renting a house, you all have to clean it at the end. If you have a friend that doesn’t pull their weight, they may not be the right one for the trip.

Listen, I’m gonna tell you everything always works out perfectly, or that I have all the answers. This method just works for us, and as far as we can tell our friends are all happy with it as well. I guess I’ll find out for sure when they read this.

Anyone want a friend for an upcoming trip? We may need it…