How To Pack For A Summer Trip With The Family

Ok, guys… summer is almost upon us! Many of you will be taking at least one trip this summer with the family, so it’s important you know how to pack.

I don’t know about you, but gearing up for a trip with the family always jacks up my anxiety. I worry about if I packed everything I will need and that stress sometimes spills over into other aspects of my days preceding the trip.

I found that having a good handle on, and putting necessary thought into, packing greatly reduces my anxiety and helps me enjoy myself.

Now, the recommendations you read here assume your “summer trip” isn’t something weird and hyper-specific, like a trip to Antarctica or something. I’m talking about your regular, run-of-the-mill weekend or weeklong excursion to a beach town or AirBnB or visiting relatives or something like that.

Also, the recommendations will not include what you need to pack for the children. That could actually be a whole separate article. This article is just for you.

I will tackle not only WHAT to pack, but HOW to pack. First, I’ll go over some things to keep in mind, and then I will give you an example of what I like to pack.

#1 – Make a list.

This one simple task has reduced my stress when it comes to packing by about 80%.

A day or so before we leave, I write down everything I want to take with me to make sure I make the most of what I bring. I also write down everything I am going to wear while traveling.

When my family goes out of town, we usually visit my in-laws who live a few hours drive away. I need to carefully consider the outfit I am traveling in, since those clothes will be part of my vacation wardrobe once we arrive at our destination.

So, my list consists of two columns. One is titled “TO PACK” and the other is “TO WEAR”. I’ll flesh out what each includes further down this article.

As I am packing, I cross out each item as soon as I put it in the bag. That ensures that nothing gets left behind. This makes me feel so much calmer as we pull out of the driveway.

#2 – Take ONE bag.

You should only really take one bag for yourself. If you take more than that, you’re overpacking. I do have one caveat to this. I sometimes will take a separate garment bag with a sport coat.

For the most part, though, you should only need one weekender-sized bag for up to a week-long trip.

The main reason for this is that it’s a PAIN IN THE BUTT to lug all the stuff you need for the family from place to place. Keep your own stuff to just one bag so that you and your wife have less work.

#3 – Think “versatility”.

You want the pieces you select to be able to pull double and triple duty. You have limited space in your bag, so bring things you know you can wear over and over again. Things like chinos, polos, and oxford shirts can be worn anywhere (yes, even the beach). You can wear them bumming around during the day or taking the kids to museums or amusement parks, but then you can tuck in your shirt, toss on your blazer, and take the family out to dinner.

The thing to keep in mind with versatility is that you’re not going to have the “perfect” outfit for each scenario. That’s ok, and that can actually be kind of fun. Maybe you’ll be a little overdressed as you walk around with your kids at the aquarium or grab a lobster roll on the boardwalk. But stepping outside our comfort zones can increase our enjoyment of new experiences.

That brings me to…

#4 – Bring stuff you don’t normally wear.

If you’re like me, you have a handful of items you wear all the time. For me, these items are also the ones I think about first when I get dressed or need to pack for some time away.

But when you’re going on a trip, try packing items you hardly ever wear. I find it fun to force myself to wear things I don’t instinctively reach for normally. It helps me develop fond memories with more of my clothes. After the trip, I sometimes have a new item to add into my regular rotation (even if it’s an item I have had for ages).

#5 – Don’t underestimate the need for outerwear.

You guys know me… I love hats and jackets and boots and all sorts of sturdy, dependable, rough-and-ready items.

On a trip with the family, reliable outerwear is very important, even in the summer. Since we are usually driving long distances, I need to make sure my outerwear can handle the elements if I have to unexpectedly change a tire in the rain, or something like that.

Ok, now that we have all of those things in mind, here is what I like to pack when we go out of town for a while.

A leather dopp kit for all my toiletries – This includes things like Advil and Tums (stress plus vacation food can bring on heartburn!)

Leather loafers – These are the shoes for going out to dinner. Place them in your bag at the bottom and stuff them with rolled-up undies and socks to save room.

Boat shoes – These are the casual shoes you’ll wear most of the time. They squish down pretty flat so they won’t take up too much room in your bag.

Pajama pants/gym shorts and two t-shirts – These are for sleeping. You can also wear the t-shirts/shorts if you’re going on a run or to the gym or something.

Two oxford-cloth button-down shirts – You can wear these anywhere. I wear them during the day when I am still working remotely, but I also wear them on outings with the family, and as an overshirt while at the beach (the long sleeves and big collar are great for sun protection!). You can also use one of them for your “date-night” shirt.

Two polo shirts (or short-sleeved sport shirts in cotton or linen) – These will be your every day knockaround shirts. These are the shirts you wear when you’re not quite sure what the day will bring.

Khaki chinos – Your do-it-all pants. They look great but they also never look out of place. You can wear these casually, but also more formally if needed.

Wool overshirt – I wrote about this a little while ago. A wool overshirt is indispensable, even if you are taking a trip in the summer. It’s a perfect over-layer for chilly nights by the fire pit or breezy mornings drinking coffee on the front porch. Also, even though I LOVE strong air-conditioning, sometimes I do like to be a little more covered up.

Light sweater – I call it my “travel sweater” (and I wrote about it a long time ago). Temperatures can fluctuate a great deal. It’s never a bad idea to have a good sweater in your bag.

Sport coat or blazer – This one isn’t as crucial, since a lot of guys don’t feel the need to get super dressed up on vacation. But I always travel with a nice jacket. My wife and I like to go out to dinner and being on vacation isn’t an excuse to look sloppy. Sure, a simple collared, linen shirt could do just fine, but where’s the fun in that?!

Tie and pocket square – See above. If you have the chance to dress up, you should take it. Your wife will love it. Also, ties and pocket squares don’t take up ANY space in your bag. Choose a tie that’s a little outside your comfort zone. If you plan on going out a few times during your vacation, just take a few different ties. You can wear the same shirt/pants/jacket and just switch up your tie and you’ll look like you’re wearing a whole new outfit.

Panama hat – Ok, this one might be cheating since you won’t be able to put it in your bag, but it’s important to have a hat that provides adequate shade while on vacation. Some guys do fine with just a baseball cap, but I have very fair skin and I find that I need the coverage on my ears and the back of my neck, especially during the peak of summer. This is the hat you’ll wear to the beach and while sipping a martini on the patio of a restaurant while the children ignore their $25 cheeseburgers.

Bathing suit – Duh.

Ok, now that we went over what to pack in your bag, here is what you should wear while traveling to your destination (if you’re driving)…

Jeans – You need a tough pair of pants to handle anything that comes your way while on the road that can also transport all your EDC like your wallet and pocketknife. The darker fabric also hides the inevitable stains from the food your wife messily feeds you from the passenger seat while you’re driving.

Polo or sport shirt – This is a chance to get another collared shirt into your vacation wardrobe rotation. A polo shirt or sport shirt is more versatile and useful on vacation than another t-shirt.

Harrington or barbour jacket – Again, outerwear is important while you’re traveling. You don’t have to wear the jacket while driving (although I like to have a light layer on since I like to crank the AC, much to my wife’s chagrin). A light jacket is also great for keeping your phone and other essentials on your person as you navigate rest stops and gas-station bathroom breaks with the kids.

Felt hat or newsboy/flat cap – This is your “travel hat”. And yes, that means that, along with the Panama hat mentioned above, you will be taking multiple hats on vacation. This hat is the one that needs to be a little more rugged. This is the hat you’ll wear if it rains during your trip.

Boots – Sturdy footwear is imperative for any time away from home. Your vacation adventures could take you from walking around a historical village to hiking through marshes. When you have a week in which the children need to be almost constantly entertained, you never really know WHAT you’re going to be doing. You want to be able to go “Oh, we should check out such-and-such” without having to worry if you have adequate footwear.

Sunglasses – Over the past few years I have become a sunglasses convert. Surprisingly, though, it was NOT when I had expensive, prescription sunglasses. When I had those, I was nervous and precious about them. And I always had to carry my regular glasses around with me. No, I really jumped on the sunglasses bandwagon when I bought a $13 pair from the local drugstore. Man, I LOVE those things! I don’t worry about them at all and they look great! What a buy! Having a good, CHEAP pair of sunglasses is awesome for places like the beach that would otherwise damage the lenses of my regular glasses with the salt and sand.

A good watch – Indispensable. You NEED to keep track of the time. Make sure it has some water resistance so you can wear it while swimming AND sweating!

Alright, now you have a well-rounded checklist for the next time you and the family are taking a trip. Just remember to take pictures and stay hydrated!