The Very Best Photos of Dads on Vacation

As any will tell you, the world of dad-dom is no place for the weak. Whether he’s attempting to reason with crying kids, mastering the art of diaper changing, or exhibiting the skill involved in looking fresh while driving a mini-van, a dad’s life is full of constant struggles and challenges. Not to fear however, for even the hardest working dads are able to occasionally let lose during the most sacred of all times of the year – the vacation. That’s why we’ve assembled this historic gallery of the very best dads on vacation photos for your enjoyment. 

The epic collection you’ll enjoy below goes out to vacationing dads everywhere, as well as those still hard at work. That’s right – we’ve got you covered the next time you or the dad in your life need a reminder that no matter how rough life gets, there’s always a beach and a beer out there waiting. So prepare yourself for this funny collection of dads on vacation letting loose in these delightful family vacation photos. Whether they’re clad in a completely unnecessary amount of floatation devices or so tipsy they may or may not realize they’re riding a bull instead of a horse, these dads are off the clock and doing what they want.


This Dad Busts out His Old College Dress-Up Shirt

We’re Not Sure How This Photo Was Orchestrated, but It’s an American Masterpiece

This Dad Was Told There’d Be Horseback Riding

Owning It = Winning

This Dad May Well Be the King of Vacationing Dads Everywhere

This Son Struggles to Find the Words To Suggest His Dad Schedule an Eye Exam

This Dad Enjoys Taking in the Local Art Scene

Disneyland/Jamaica Compromise = Nailing It

This Dad Attempts to Make His New Orleans Trip Appear Much More Eventful Than it Actually May Have Been

This Dad Learns Fist Bumping in a Safe Environment

This Dad Declares His Happy Shall Be Spoiled by No Man… or Child

This Dad Prepares to Mount a Stunning Comeback

This Dad Realizes What a Truly Horrible Decision He’s Made All Too Late

This Dad’s on Vacation, He Wears What He Wants

Lounging: This Dad’s Doin’ it Wrong

This Dad Finds Not So Subtle Ways to Hint That He’s up for a More Exciting Locale Next Year

This Dad Makes Friends with the Locals

This Dad Finds This a Much Thriftier Option Than Surf School

This Frog Proves a Much Better Listerner Than This Dad’s Wife

This Dad Enjoyed a Few Too Many at the Bar and Auditions to Be Featured on “Dads Gone Wild”

This Vacationing Dad Poses for Another in a Series of Remarkably Similar Photos That Line the Family Scrapbooks

This Dad Insists He Can Explain

These Dads Find New and Exciting Ways to Bond During This Year’s Men’s Retreat

Where’s Waldo: Vacationing Dad Edition

This Dad Steps out in the Latest Style

This Dad Expresses His Gratitude for Finally Vacationing Any-Damn-Where but Disneyland

This Dad Feels Vacation Is No Place for Manners

This Dad May Have Hit the Margarita Bar a Little Too Hard

This Dad Finally Reveals the True Reason Behind His Civil War Obsession

This Dad’s “Castaway” Impression Ends Here

Hollywood: This Dad Assures You It’s Not as Impressive as You Think it Is

This Dad May or May Not Have an Unsettling Confession for Wifey

This Dad Insists it Was the Horse’s Fault

This Dad Feels Vacation Is No Excuse for Recklessness

This Dad Demonstrates the Dangers of Beach Sleeps

This Dad Relives His Glory Days

This Dad Has Visions of Vegas Dancing in His Head

They See This Dad Rollin’, They Hatin’

Vacation Is a Time To Enjoy What You Enjoy Doing at Home without Interuption