As many people know, I’m a travel freak and I happen to think the kids should come along most of the time. I’m also obsessed with the details and have often said that planning is half the fun.

Here’s how I do it.

1. Booking flights

It’s not a real trip to me unless flying is involved. There’s something magical about having the privilege to fly. I’m not sure my kids, having been on dozens and dozens of planes, think this way but I think I always will. I used to love going to the airport as a kid and still consider it a huge privilege to fly. It’s a real trip if I get to fly there.

(Having said that, Crazy Casey does road trips like nobody’s business. Her trips are real, too, but just not something I’m interested in.)

Fly direct if at all possible

One of the best things about moving back to the DFW area is the availability of direct flights. Unfortunately, I’ve vowed not to fly American Airlines ever again which greatly reduces my options.

If you have direct available, book those. The stress from layovers and possible delays and missed flights is intensified with kids. Missed naps, running out of supplies to keep them happy and boredom are not things you want to add to your itinerary.

Pick your seats

Many airlines have gone to an unassigned seat system and you have to pay more for an assigned seat. Splurge on the extra to make sure you can sit by your child.

When picking seats, pick things that work for you. Kids often love window seats. If you have a flight during your child’s typical nap time, think about booking seats in the back where the drone of the engine will knock anybody out.

Also, consult SeatGuru.com for the specifics of the seats on flights.

Other tools I use:

• ITA Software – this site is great purely for researching flights. You can then book them directly with the airline or on my favorite site for booking airfare, Orbitz.com. The ITA Software site does NOT include lower fare airlines such as Southwest Airlines so you’ll need to research those separately.
• Fare Compare graphs – for some reason, these graphs are kind of buried on FareCompare.com but they are super helpful to see historically what prices tickets have been.
• Checkinsooner.com – allows you to check-in online ahead of time using this site which is especially handy if you won’t have access to a computer right before your flight.

2. Booking the hotel

Picking a hotel based strictly on price isn’t smart when traveling with little ones. I’m not saying you can’t book something affordable but you’ll have to do a bit of research first.

My favorite, will-not-book-a-hotel-without-it source is TripAdvisor.com. The reviews there are fantastic and give a really accurate picture of what a hotel is like. I’ve picked hotels a couple of times for Andy’s family (and there are a LOT of us, including kids) and I’ve always ended up looking like a genius because the hotels have worked out well. Trip Advisor lets you narrow it down by trip type, including the “Family” option. Use that.

If you want or need a bit more space than a standard hotel, look at suites or hotels that have connecting rooms (adjoining is not the same as connecting. Adjoining just means next to each other, not necessarily accessible with a door between the rooms). Having the extra beds and bathroom can often be worth the extra dollars.

3. Plan a loose itinerary

I’ve heard people say they like to be spontaneous and others plan every detail of their vacation. I’m in the middle of those two. I research everything to death so I don’t have to spend time on vacation trying to think about what to do but then I pick a couple of things each day to try to do. Pick the things you think you’ll want to do and then re-arrange them like puzzle pieces to fit into your days. For research, I would look for websites and books specific for your destination and TripAdvisor.com is also a great site for researching what to do. Many destination-specific sites also have forums where you can ask questions about your vacation.

Allow for breaks

This is something I’m very passionate about. Running kids until they are exhausted is no way to have fun. We try to build in mid-day breaks every day for some down time. The morning is spent doing something, afternoon is for resting and then the evening is for doing something else. If you’re somewhere hot, the afternoon is often the hottest part of the day anyway so it’s a nice chance to get away from the heat.

Breaks can mean different things to different people. Naps, swimming, quiet time in a hotel room. Whatever you want it to be. Just try to prevent exhaustion and sensory overload by allowing for some downtime.

Now, if you have to be gone all day for some reason, I highly recommend your next day be a very easy day. Do not wear everybody out. Vacations are marathons, not sprints.

Involve the kids in the planning

Get books about where you’re going, look at websites for the area, get free materials by mail (brochures, DVDs, etc.) about your destination. When we went on our cruise and I was trying to pick excursions, I watched videos on YouTube with the kids to show them what it would be like. It made it easier to choose our activities knowing what they thought looked fun.

Schedule a child-free night

Although I love bringing the kids on trips, there are just some things kids can’t do. We try to schedule a night where we can do something without the kids – a nice restaurant, a comedy club or the same things you did with the kids but do it KID FREE – one time during a vacation. You can use local childcare, swap date nights with other adults you’re traveling with or, if you’re like us, you can have your older child babysit.

Give your kids the itinerary

One of the issues with kids on vacation is often that they just don’t know WTF is going on. They know their home routine but away from home, they don’t know what to expect.

Prepare itineraries for your kids so they can follow along but make it kid-friendly so they’ll get it. Non-readers can have an itinerary with pictures and older kids can have a text-based itinerary with a brief overview of what’s planned on each day. I don’t know if everybody’s kids like knowing this kind of stuff but mine absolutely do.

Consider leaving the last day of your vacation completely unplanned. Tell the kids all week that they get to pick the last day so if you have trouble leaving somewhere, you can remind them that they can pick what to do on the last day. Won’t work in all scenarios but consider it if it makes sense on your trip.

4. Add some magic

There are lots of ways that you can add magic to a trip but my way is typically via the Vacation Fairy. I’m going to go ahead and trademark the concept of the Vacation Fairy because I sort of invented it, I think. I’ve used this in various forms but the basic idea is that every morning, a fairy has left something overnight. You can tie this to rules (if you follow certain rules, the fairy will come!) or just have the fairy bring things applicable to that day (attending a parade that night? Fairy can leave glow sticks to wear to the parade.). This can also replace souvenir shopping because you can get souvenir-style gifts ahead of time for cheaper (The Dollar Store is my favorite place to buy things) and give it to them as gifts. I like to bring all the gifts along except for the last day and then make the last day a souvenir they’ve been eying during our trip.

This was a set of rules that I created before a Disney trip that Tinkerbell left. The kids (Blake and Reaghan) decorated the gift bags with stickers and stamps and stuff and left them out every morning. As long as they followed the rules, Tinkerbell would come each day with gifts.

On a trip to Virginia with all of our nieces and nephews on Andy’s side, I made these bags ahead of time for each child and had them leave them on their hotel doorknob each night. When they woke up in the morning, it was filled with something new. This involved taking a whole extra suitcase to accommodate all of the gifts. In today’s pay-per-bag airline policies, I’m not sure if I’d still be able to do this.

We have a week-long trip with Andy’s family again this summer so I’m debating what to do. We have even more kids now. Hmm.

Also, I don’t do the fairy thing with my kids anymore because just like belief in Santa Claus ends, so does the Vacation Fairy. Sad.

Another way to add magic would be to have gifts waiting in the hotel room when you get there. A nice gift basket with snacks and items applicable to your trip is a nice surprise when arriving to your hotel room.

5. Packing

Luggage

I’m not a fan of light packing with little ones. I think you should bring enough stuff to make your trip easier. To keep from forgetting things for your trip, I like to use this Ultimate Packing List because it includes anything and everything you might want to bring. Although it was designed for Disney trips, I use it for all trips. I also try to include fruit alongside the packaged snacks that I pack which some people find strange for some reason (I guess the idea of packing fresh fruit on a flight seems like it wouldn’t be allowed but it is). Things like grapes, packaged in individual bags, are a nice break from the junkie snacks that often happen on vacation.

When packing, I like to put outfits in Ziploc bags to not only make more space in the luggage but because it’s also easier (especially for kids) to know what goes with what. I would also recommend not assigning a piece of luggage to each person because if it gets lost, that person will have nothing. Spread everybody’s things out evenly amongst the luggage you are taking.

Bonus points: Make your own luggage tags and laminate them. You can design them in a fun way specific for your trip and use this self-laminating set to laminate them.

Bonus bonus points: I throw one of those over-the-door shoe organizers in our luggage and then hang it over the hotel room door. Keeps a messy hotel room fairly organized. You can throw anything in it – gadgets, snacks, toiletries, whatever. Better than having them piling up all over the room.

En route

Aside from packing your luggage for your trip, you’ll need to pack your carry-ons that should include entertainment and snacks for the kids. I’ve always told the kids that they’ll get their backpacks once we get to the airport gate and then it’s filled with snacks and activities and has their version of the itinerary and anything else I can think of. They really look forward to this and it keeps them busy while we travel.

During your trip

If your trip involves going out and doing things each day (as opposed to staying at a beach house and hanging out), you’ll probably want to pack a bag each day to have while you’re gone. I’ve actually created lists ahead of time that detail the items I want to bring in my day bag. Little ones require so much sometimes. I’ve never regretted packing so much stuff because it’s always come in handy.

Backpack tip: throw in a towel from your hotel room. We’ve used ours to dry off, to save a spot, to provide shade on a stroller. It always comes in handy.

Random and awesome bonus tips

• When you’re boarding the airplane and they say that people with small children can go first, don’t go unless you really need the overhead space or some other good reason. Extra time sitting on the plane will only make it worse. Waiting to board until the end will prevent the kids from having to sit any longer than they have to.
• 

  They all look the same. Make yours stand out with something bright tied onto the handle.

  If you’re going somewhere like an amusement park and plan to rent a stroller that will look like everyone else’s, throw something brightly colored into your luggage that you can tie on the handle of the stroller. This will save a lot of time locating your stroller in the sea of strollers.

• If it’s possible, arrange for a postcard to be sent to your child ahead of time from the destination you are going to. “Excited to see you in two weeks!” or something like that can be written on it to help get the kids excited for the trip. If you’ve been participating in a forum on a website for where you’re going, the locals are often willing to do this for you.
• Before leaving for your trip, you might want to have your mail held while you’re gone. Did you know you can do it very easily online?
• When you return from your trip, it’s often a flurry of activity with unpacking and laundry and settling back in. Reduce your amount of work by making sure your house is clean and have some frozen food in the freezer that you can pop in until you can get to the grocery store.
• If your kid has trouble sleeping away from home, consider getting some Chewable Dramamine. Kids 2+ can take it. I used to carry it in my purse for Blake and give him half a tablet at his typical nap times and bedtimes because he needed the extra push to get to sleep.
• Tips! You should leave them daily for housekeeping. I like to have Blake help me make envelopes ahead of time that say “housekeeping” and then he decorates them and we pre-fill it with money.
• Every night of your trip, jot down a list of things you did that day and want to remember for later. It’s one of my favorite ways to end the day and helps when trying to recall after you get home.
• Consider getting a scent ahead of time that is new for your vacation. One time, Payton and I went to one of those stores where you can mix up your own bottle of lotion and took that on a vacation. Now, every time I smell something like it, I’m immediately taken back to that trip.
• If parts of your trip will involve a lot of waiting, bring things along to help with that. Ideas can include the party-sized bottles of bubbles to blow while waiting (and kids around you will enjoy catching them too), a deck of cards and notepad/pen for easy games like tic-tac-toe or hangman.

As you can tell from many of my examples, going to Disney happens to be a particular passion (and I could do a whole other blog post or many posts just on that topic) but the ideas apply to any trip that I plan with the kids. We’ve traveled with other people and they’ve told me that they want me to plan all of their trips so I’m confident that these tactics work not just for us but for other people as well. I hope you will find them useful.

What other tips can you add to my list?

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