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Dos and Don’ts of Family Vacation

25 tips for travel with kids

By Mike Shields |

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  • Dos and Don'ts of Family Vacation

    Dos and Don’ts of Family Vacation: 25 tips for travel with kids

    ’Tis the season when parents of new babies and toddlers ask themselves, Do I dare take a real vacation with little Johnny? It’s a tough call. You’re several years away from Disney World and, if it’s your first kid, you’re probably not too many years removed from a pre-baby getaway to the islands, or a once-in-a-lifetime trek through Europe. You remember fun and happiness. Can you still find that sort of fun on vacation? Hate to break to you, but no. You can, however, manage to somewhat enjoy yourself. So here are some dos and don’ts to survive vacation time with a little one in tow.

  • Dos and Don'ts of Family Vacation

    Don't expect to relax

    Don't expect to relax You know those Corona commercials where the couple sits quietly before a gentle surf enjoying a sunset beer? Your vacations will be nothing like that for at least 20 years. Right now it’s all about preventing your son from drowning or walking your daughter up and down the hotel steps 11 times in a row.

  • Dos and Don'ts of Family Vacation

    Do ship supplies ahead of time

    Do ship supplies ahead of time Especially if you fly. You don’t need half of your suitcase jammed up with wipes, diapers, snacks, and toys. Find out the address of the hotel you’re staying at and how early they recommend sending packages.

  • Dos and Don'ts of Family Vacation

    Don't fly

    Don't fly For years, you’ve hated those people who just won’t tell their kid to shut up on the plane. Now you are those people. Drive — and crank up the radio. (If you must fly, do bring snacks, toys, a loaded DVD player, your iPad, whatever it takes.)

  • Dos and Don'ts of Family Vacation

    Do stay at a nice place

    Do stay at a nice place You’re not backpacking through Europe anymore. Amenities are your friend. You need to embrace your inner snob — you know, the person who expects someone to set up their beach umbrella and bring them towels and drinks. Because you’re busy trying to keep your son from being carried out to sea.

  • Dos and Don'ts of Family Vacation

    Do spring for a suite

    Do spring for a suite It’s going to hurt your credit card, but without a separate place for junior to sleep, vacation days end when baby goes to bed. So unless you like spending your nights playing Angry Birds under the covers or drinking wine in the dark (with no hope of adult hugs whatsoever), pay for the extra room.

  • Dos and Don'ts of Family Vacation

    Do let your kid play in the hotel crib first

    Do let your kid play in the hotel crib first Seriously, this works. Babies need to feel comfortable, and comfort comes from familiarity. Just dumping your little guy in a strange crib for the first time one night might not go so well.

  • Dos and Don'ts of Family Vacation

    Don't go out to eat

    Don't go out to eat Your hotel is within walking distance of a swanky sushi place. There’s a high-end steak restaurant you’ve had your eye on since you checked in. Forget about both and order room service. Unless you want to be the one taking the filet mignon to go after little Sophie throws her fourth buttered roll on the floor while screaming bloody murder. If you must brave a restaurant, effectively scare your waiter as soon as you sit down: “We have to order NOW!”

  • Dos and Don'ts of Family Vacation

    Do overeat

    Do overeat That’s guaranteed fun. And you’re already married, so no need to worry about that beach body, right?

  • Dos and Don'ts of Family Vacation

    Do drink early

    Do drink early As a wise person once said, “Vacationing with an 18-month old is simply parenting in a different place, where it may be hot.” That’s why there’s no shame in a little rum punch at 10 a.m. to take the edge off.

  • Dos and Don'ts of Family Vacation

    Don't get drunk though

    Don't get drunk though You really are still watching your kid and protecting his wellbeing. Getting sloppy is dangerous and could inspire your partner to look into the local divorce laws. Plus, babies who get up at 5 a.m. still get up at 5 a.m. in the tropics. Just something to think about before downing that last Mai Tai.

  • Dos and Don'ts of Family Vacation

    Do locate the pharmacy before you need it

    Do-locate-the-pharmacy-before-you-need-it This way you’ll know how far a walk it is, and you’ll have the number for when you need your doctor to call in that pink-eye prescription.

  • Dos and Don'ts of Family Vacation

    Don't whine if your kid doesn't like the pool, ocean, or lake

    Don't whine if your kid doesn't like the pool, ocean, or lake You’ll have plenty of years to teach your young one to body surf, skim rocks, and build sand castles. Just be happy you don’t have to watch for constant sunburn signs like the rest of us.

  • Dos and Don'ts of Family Vacation

    Do give yourself an extra hour to go anywhere

    Do give yourself an extra hour to go anywhere Headed for the pool? Okay, so you’ll need to do a diaper change; slather sunscreen on your kid; slather sunscreen on yourself; pack the bathing suit, swim vest, water shoes, snacks, water, towels, and beach chairs; walk to the beach ...

  • Dos and Don'ts of Family Vacation

    Don't be ashamed to spend an afternoon at the mall ... or Wendy's

    Don't be ashamed to spend an afternoon at the mall ... or Wendy's Because all that prep to go to more tourist-y places will get old. And you can only order in surf and turf so many times. And you don’t need sunscreen. And your kid can eat Frosties and throw them on the floor.

  • Dos and Don'ts of Family Vacation

    Do blow some of your son's 529 fund money at the casino

    Do blow some of your son's 529 fund money at the casino You deserve it. (And he’ll never know.)

  • Dos and Don'ts of Family Vacation

    Don't change a swimmy diaper alone

    Don't change a swimmy diaper alone Whoever invented the swimmy diaper should be beaten or jailed. While it’s a lovely concept, that fact that the diaper doesn’t open or close on the sides but must be slid off a wet, sandy, shivering, angry body while possibly loaded up with number 2 — well, that just creates a dangerous slingshot effect that no one should be subjected to without assistance.

  • Dos and Don'ts of Family Vacation

    Do tip housekeeping well

    Do tip housekeeping well Because with the constant wet clothing, diaper leakage, sunscreen spills, and food dumped on every inch of the floor, junior will end up treating the room slightly better than The Rolling Stones did on tours in the ’70s. And you’ll always, always need more towels.

  • Dos and Don'ts of Family Vacation

    Don't dress up

    Don't dress up You’re not going out to eat — or anywhere nice at least. Those nice clothes are just going to sit in your bag torturing you. And if you do put them on, your kid will need his swimmy diaper changed immediately. Embrace that Myrtle Beach t-shirt you bought for $9.99 at the gift shop.

  • Dos and Don'ts of Family Vacation

    Do dress your kid up

    Do dress your kid up It will make you feel good, and more importantly, make her more tolerable to others when she tries to break things in the hotel.

  • Dos and Don'ts of Family Vacation

    Don't bring a book you've always wanted to read

    Don't bring a book you've always wanted to read You’ll never even break the binding. But do bring Big Red Barn.

  • Dos and Don'ts of Family Vacation

    Do let your kid run around the hotel lobby

    Do let your kid run around the hotel lobby The staff will love her, and you’ll have 30 seconds of free babysitting to read USA Today.

  • Dos and Don'ts of Family Vacation

    Don't bother with the sights

    Don't bother with the sights Baby Joshua doesn’t want to see where the British, the French, and the Indians signed some treaty or built some wall in the woods. And really, neither do you.

  • Dos and Don'ts of Family Vacation

    Do take turns having fun

    Do take turns having fun When you are all together on vacation as a family, at most you can have moderate amounts of fun, with a constant sense of life’s limitations. But if you separate occasionally — daddy takes the baby for a walk while mommy sunbathes — then at least someone is having real, relaxing fun. For at least 10 minutes. Dysfunctional, yes, but effective.

  • Dos and Don'ts of Family Vacation

    Don't separate too long

    Dont-separate-too-long How was your 90-minute massage honey? Or your hour at the casino? Well, the baby wouldn’t nap for me, had a dirty diaper, and hit her head on the side of the pool. Take her now! Relaxation, meet resentment.

  • Dos and Don'ts of Family Vacation

    Don't go

    Dont-go Have you been paying attention at all? Does this sound worth it to you? A vacation with a toddler that’s equal parts joy and hell for thousands of dollars? Skip it. Resign yourself to the fact that good vacations won’t exist for a few years. Instead take a week off and stay local. Hang out with your family in your house. Drive over to your in-laws’ place. What? Are you insane? What the hell kind of vacation is that? One where you’ll sleep, possibly even get drunk, or go out — and know that somebody reliable is watching your little angel.

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About Mike Shields


Mike Shields

Mike Shields is a senior editor at Digiday, where he covers the business side of the Internet and digital media. A former Manhattanite, Shields now lives in exile in Queens with his wife, Nicole, and their son, Christopher. He enjoys chicken and the Economist, which he read once.

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28 thoughts on “Dos and Don’ts of Family Vacation

  1. beach says:

    There were a handful of things on this entire list that were even worth reading. The rest was crap. i.e. Don’t eat out? But gamble the 529? Maybe you didn’t think about that “last Mai Tai” before you read the article. ha

  2. Agnieszka Mscichowska says:

    Wow, maybe my son is different, but I didn’t have half of these problems when on vacation with him. It’s true you have to watch over the babies constantly and with running (and talking like ALL THE TIME toddler it’s maybe not that relaxing, but if your vacation is to be drinking, massaging and sunbathing, maybe really it’s better if you leave the baby at your parents’? (I couldn’t, I would have missed them too much)

  3. Melinda Bogue says:

    I really hope this was a joke, either that or you obviously shouldn’t be parenting. Don’t bring your kid out to eat? Excuse me but how do you think they learn to behave in a restaurant if you don’t bring them anywhere? How about spending their 529? Yeah your a really mature parent! Vacationing in my house has always been fun for everyone and we didn’t just sit in our room or the mall all day we actually went out in public and didn’t expect the hotel staff to watch our kids. Maybe if you learned to parent then you could also take a vacation.

  4. Carol Jean says:

    We always traveled with kids..3 kids in fact and yes it was difficult. We didn’t drink or go to fancy restaurants but we had children to be with them. We did go around and look at buildings, museums..there are many children’s museums. A ride in a stroller is always good and babies don’t care what mom and dad are looking at as long as they are riding. We would rent a suite type room with a kitchenette as the kids got older..breakfast and lunch were at the hotel. Kids had their own rooms..we had a balcony to enjoy evening alone. Now we are traveling with grandchildren. One 5 one 4 months..we have a blast. One kids are in the picture life is not the same…but do vacation. There are many places to take kids…dont just stay home.

  5. Carrie says:

    While there may be some good points here, I don’t apprecaite the tone of this list. A bit too sarcastic and snarky, there’s plenty of good advice to be made to make the most fun of vacations.

  6. Snakecharmer says:

    Honestly it depends on the age of your kids, their temperaments and where you decide to go. You do need to be realistic about your expectations on what you can and can’t do. We went to Italy with our then 9 month old and it was fabulous..we didn’t go out dancing all night mind you but we went pretty much everywhere and she happily sat in her backpack carrier and went with the flow. We recently went to a resort in Mexico when she was 16 months and it took much more work/planning but we made it work. Did we go out for dinner..yes, but made sure it was family friendly and at a reasonable time. I’m looking forward to close-at-home vacations too of camping…not every vacay needs to be overseas!

  7. Erin says:

    While some of these were actually good suggestions, the tone did suck. If you’re looking for tips for traveling with a toddler, this is obviously disappointing, particularly with the moral being “don’t go.” And don’t fly with toddlers?? Are they really going to enjoy being strapped in their carseat for hours any more than they’ll enjoy being seated on an airplane? And everyone knows you rip swimmy dipes off, you don’t pull them soaking wet down the kid’s legs, sheesh. Those sides are easily tearable. Bam. Problem solved.

  8. Anne says:

    Gah, what a terrible article/slideshow. There are tips to be had, and I was looking for some (more).
    Here are some good ones I’ve heard/developed: (1) do your research. There are even guidebooks for traveling with kids. I always look up city parks on the Internet.
    (2) don’t stay in a regular hotel. Condos/vacation rentals/extended stay hotels are great for families. (3) Traveling is a great time to break out new toys or snacks that your kids aren’t bored of yet.
    Anyone else have anything helpful??

  9. Stoich91 says:

    Haha, the moral of this story, kids, is that it takes guts to travel with toddlers. While many wonder how to remedy this bane of life with toddlers, the better question may be: What else is new?

  10. Donna says:

    Oh people, come on. Of course this was tongue in cheek. I chuckled out loud on a few of them. Vacationing with our toddler is certainly not vacationing pre-baby-we all know that. I agree with some of the things: not going out to eat-my son will not tolerate being tired down in a booster seat. We had sushi in Hawaii, cost $70 and we were there for all of 20 minutes because my son grab anything in sight and flung a piece of raw fish hitting another diner on the leg. I also agree about the suite. Much better than getting a single room hotel!

  11. SMT says:

    Going to have to agree with the rest of these comments. We travel every 3-4 weeks with our 19 month old (and have been since he was 4 weeks old) and have enjoyed it greatly. Sure we’ve got to take turns when we go surfing and we don’t get to watch as many movies on flights, but this list is ridiculous.

  12. Stacy says:

    Swim diapers are meant to be torn off on the sides. Don’t slide them off your baby. Same with pull ups.

  13. Nicole says:

    Who wrote this article? Do you have kids? Do you like kids? What is the deal? Having children is not the end of life and fun. Vacations are different. But, it’s not a prison sentence when traveling with a small child (children.)

  14. Ellie says:

    I feel sorry for this guy, he definitely hasn’t experienced the joy of exploring a new place with children. We have traveled all over with our 5 and 7 year old boys and we make a point to always go out to eat. It’s good for them to experience different foods and if you can’t control them in a restaurant, then you most likely can’t control them anywhere. I disagree also with shipping your items there. This guy obviously hasn’t done his research because shipping costs are outrageous now and the likelihood of it arriving there is slim. There are several baby equipment rental companies now all over the world and they deliver right to your destination. Can’t beat that.

  15. Adriana Phillips says:

    I have traveled with all of my children. We have 4. We started early. My oldest was on her first flight before she was even 2 weeks old. I have never had a problem with traveling with any of my kids. Keep them busy and entertained during a long drive or flight it is easy to do. I don’t know about the guy who wrote this article, but all of my family vacations have been fun. The key is planing ahead.

  16. mommy2boys says:

    I agree with most of the previous posters! I really clicked on this article looking for some good advice- but didn’t find any. We traveled with our then 16 month old, and had a nice time. And we plan on traveling soon with our now 3 and 1 year olds.

  17. Stupid suggestion Dont eat out w says:

    I think the “Don’t eat out with Children” is stupid. My 2.5 year old daughter eat out at a restaurant once a week. It’s a really special mummy daughter time. Not every child screams and acts crazy outside. And Recommending that you “over eat?” it doesn’t matter whether you are married, single or divorced. Over eating isn’t healthy for anybody.

  18. Imthaprincess says:

    Ok people its just a funny blog post lets all relax. But a helpful tip is that all the swim diapers are easy to rip down the sides for diaper changes. They are like waterproof pull ups which also tear easily top to bottom on both sides so its just like a real diaper.

  19. mikeshields001 says:

    Hi everyone – sorry I’m late in responding here. I did want to address a couple of things. For one, I do hear some of your frustration that this list was a mix of humor and serious advice, and you were looking for just advice. But as I was having alot of fun with this topic – and maybe being a bit extreme in my suggestions, as Snakecharmer mention, alot of this really comes down to the temperament of you kid. Mine is a maniac you likes to run fearless at ocean waves or dive headfirst into the pool and must be watched like a hawk. He also likes to throw food and scream at the top of his lungs at a restaurant. It’s not for lack of trying on our part that dining out isn’t fun right now, and if we just did it more he’ just “learn to eat out.” it’s just alot more trouble than it’s worth.
    I think this also comes down to a philosophical question regarding parenting – are you the type that must rigidly stick to the script that toddlers are an ever magical blessing, constant source of joy and always easy to deal with, or can you admit that sometimes they are a pain in the ass and make certain activities less fun than they used to be? I think you know where I stand – I suppose that does make me an awful father. Thanks Nicole!
    And yes Melinda, I was completely serious. You should gamble away all of your child’s savings, because hey, it’s really your money anyway. You’ve proven to have a great sense of humor. You must be a ton of fun at parties!

  20. kk2323 says:

    I’m sorry, I thought this was hilarious! Good work, Mike. Thanks, readers, for the tip about the swimmy removal. I wish I had known about ripping the sides this past weekend! Happy vacationing all!

  21. Kalea says:

    Stay inofmrative, San Diego, yeah boy!

  22. Kevrel says:

    Keep these articles coming as they’ve oepned many new doors for me.

  23. ChoCho says:

    I kow I’ve driven–a lot–since we’ve had our little one, and with an iPad each that my hubby and I have that not only have movies we like, but the kiddie stuff our son likes, as well. one of my hubby’s cousins asked don’t we think we’re spoiling him, I said no, whatever it takes to keeps the peace, and on a 12-hr. drive from VA to MI, it certainly does!

  24. bcca518 says:

    People have taken this too seriously. Most of babbles articles are sarcastic in some way, why be surprised that this one was too? I thought it was hilarious. He found everything thing that could go wrong to highlight. Not saying it is what always happens, but what could happen. He is just making light of situations many of us have found ourselves in at one time or another. Plus he is giving dads point of you, not moms. Of course most dads would see vacations to be more hectic then what its worth. And moms are usually easier to adjust to situations as they arrive. Just take your time to plan and be prepared if things do go down hill. But surely vacation to the best of your means.

  25. Sarah Yamaguchi says:

    This is just nasty!! I just got back from a backpacking trip to Bhutan with my baby and husband and it was the best trip ever!!! But if you need to keep more new parents at home and scared to travel – I guess you did a great job!!! Bur for real I laughed at most of these- what a crappy article!!!

  26. Anonymous says:

    The onlyhelpful thing on here was to send supplies in advance. so thanks for that.

  27. Marissa says:

    Last year I took my 4 and 1 1/2 year old to Smuggler’s Notch. Obviously, my 1 1/2 year old couldn’t ski, but she could go to the wonderful kid’s program and spend time with us. My 4 year old loved learning to ski with mom and dad and participating in the kid’s activities. The best part was that my husband and I did get to go to nice dinners and have some romantic time alone. We now have a 4 month old daughter, so this year’s vacation is going to be postponed but when she turns 1 or 1 1/2 we plan on going on a cruise where we can do the same thing.

  28. Anonymous says:

    there are some parents who already feel entitled to leave a mess wherever they go simply because they have young kids. the staff at places like Wendy’s do not get tipped for cleaning up our messes, so to write that kids can “throw [frosties] on the floor” is just as bad as parents who let their kids do so without cleaning up or apologizing.

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