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25 Hilarious and Totally Awkward Travel Photos

The memories of a trip can last a lifetime, just as the photos can too. With a collection of travel photos ranging from stunning sunsets to majestic monuments, there’s bound to be a few that are in a word – fails. Holding Mama up in her bathing suit on the beach probably sounded like a good idea at the time. And that one time Mom and her boys (one in headgear) jumped into the spa naked together…yeah.

Get a good laugh with these 25 Hilarious and Totally Awkward Travel Photos…

  • I Think You’ve Got Something on Your Back 1 of 25
    01

    This looks like a whole lot more than just a sting.
    Spotted at Travel Freak.

  • Run! 2 of 25
    02

    So many questions to ask. Why naked? Why the hippo?
    Spotted at Travel Freak.

  • Open Wide 3 of 25
    03

    So wrong on so many levels.
    Find out more at Daily Dawdle.

  • How to Hold in a Sneeze 4 of 25
    04

    And how to force your child to smile, kind of.
    Spotted at Smarter Travel.

  • Wow… 5 of 25
    05

    Is that an elephant in your hand?!
    Spotted at The Chive.

  • Zakopane at its Finest 6 of 25
    06

    Polar bears, floral capes, two real dogs, and a totally realistic background makes for a great shot.
    Find out more at Awkward Family Photos.

  • Pucker Up 7 of 25
    07

    The fish definitely brings out your eyes.
    Find out more at Awkward Family Photos.

  • Beware of Papa Bear 8 of 25
    08

    Ya, probably a better idea to stay in the car.
    Spotted at Awkward Family Photos.

  • Don’t Think Beach Days Will Happen Often 9 of 25
    09

    Good one, Dad.
    Spotted at Bloggers for Hope.

  • 4th of July Fun 10 of 25
    10

    Nothing says patriotism like buckets on your head.
    Find out more at Hilton.

  • Ride of a Lifetime 11 of 25
    11

    And gosh darn they look happy.
    Find out more at Awkward Family Phots.

  • Washington Monu-Ouch! 12 of 25
    12

    Not exactly the angle she was going for.
    Find out more at Daily Dawdle.

  • Riding Flipper 13 of 25
    13

    "Look! No hands!" You crazy kids.
    Find out more at Heavy.

  • Move Along Now… 14 of 25
    14

    Nothing to see here.
    Spotted at Heavy.

  • Lean Back, Lean Back 15 of 25
    15

    Oooh, not that far back.
    Find out more at Heavy.

  • Tour of a Lifetime 16 of 25
    16

    I don't trust this gang one bit, especially the one on the left.
    Spotted at Things to Do.

  • Head Transplant 17 of 25
    17

    This could be a good look for you.
    Find out more at Travel Freak.

  • Gazing to the World 18 of 25
    18

    Or not.
    Spotted at Travel Freak.

  • Say Cheese! 19 of 25
    19

    She looks like she is having a grand ol' time.
    Find out more at Awkward Family Photos.

  • Pretty Much Baywatch 20 of 25
    20

    More like Babe Watch.
    Spotted at Awkward Family Photos.

  • The Tunnel of Love 21 of 25
    21

    Looks like some real magic happened inside there.
    Find out more at Awkward Family Photos.

  • Where to Begin? 22 of 25
    22

    Is it the child who looks like he had one too many drinks, the child relaxing with headgear on, or that mom's naked with her kids in a wooden barrel, that makes this photo priceless? 
    Spotted at Awkward Family Photos.

  • Happy as a Clam 23 of 25
    23

    It's so great that travel brings people together.
    Find out more at Daily Dawdle.

  • Baby in a Bucket 24 of 25
    24

    This is one kind of car seat you could consider.
    Spotted at World Super Travel.

  • Bottom Bunk 25 of 25
    25

    Traveling is hard work.  
    Find out more at Tourist Places.

Jaime Morrison Curtis is author of the bestselling book Prudent Advice: Lessons for My Baby Daughter (A Life List for Every Woman), follow up fill-in journal My Prudent Advice, and founding co-editor at Pretty Prudent, the premier design and lifestyle blog providing inspiration and instruction to help anyone create beautiful things, food, and experiences for their friends and family.

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