I don't claim to be an expert on traveling with a child, but I have enough experience at this point to share which activities have entertained Blythe on the 15 flights we've taken in the past 6 months, 4 of which were long-haul flights (plus numerous train rides and extended travel time in cars). In addition to the obvious recommendation that you pack plenty of snacks, particularly those that take a while to eat and will thus keep your child occupied, these are the toys and games that have served us well.
I should add that we also always bring about 10 paperback books with us for each flight as Blythe loves to read. Yes, books are bulky and heavy (even paperbacks) but they work wonders for calming B down and keeping her busy. We also travel with an iPad and we occasionally let B watch her favorite shows and movies (Room on the Broom, Toot & Puddle (these are travel-themed, which ties in nicely), Winnie the Pooh), but try to use it as a last resort (with these headphones). Sticky notes and washi tape are two other items that I have at home but that B enjoys playing with. Also, if you live near a Flying Tiger, its a fantastic place to stock up on inexpensive, entertaining toys for travel - we particularly love the sticker book of funny faces (unfortunately, they don't have an online shop and the only US stores are in NY).
I'd love to know what you all recommend, particularly if you have little boys because perhaps they enjoy a few different things? You can never be too prepared for travel with littles!
#1 - Play-Doh can keep a child occupied for hours. Seriously, B will create all sorts of things with her Play-Doh and it is a pretty easy thing to use on airplane tray tables. Sure, it can get stuck to things and some of it will inevitably roll onto the floor, but the positives outweigh the negatives on this guaranteed crowd pleaser. If you want to travel light and still have an assortment of colors, I recommend the Play-Doh Party Pack.
#2 - Highlights Magazine immediately reminds me of childhood trips to the doctor and dentist. My parents sent B a subscription and she LOVES it. We have read each of the issues we have at least 30 times and B will read them to herself, particularly in the car. Plus, these are lightweight. I can't recommend a subscription enough.
#3 - Melissa & Doug Water Wow! books have a small brush that you fill with water. When you paint with the water, colors appear on the images. These books take up relatively little space and can be used over and over, plus there isn't clean up. Melissa & Doug ColorBlast! books are awesome and use a marker instead of a water-filled brush. Side note - NPR's How I Built This podcast did an episode about Melissa & Doug on December 19, 2016 that was fun to listen to now that I know and love their toys.
#4 - Crayola Pip-squeaks Markers are the best we've found. For travel, I stuck them all in a Ziploc bag to save space and B used these until they all eventually dried up. As an added bonus, the markers will snap together end on end so you can create towers with them, which B loves doing. These are truly washable as tested by someone (ahem) who used them to color on a white sofa in Hawaii.
#5 - What kid doesn't love Legos? We had a few Duplo blocks for awhile, but once B discovered "real" Legos in Amsterdam, there was no looking book. We have a small Ziploc bag full of miscellaneous pieces (truly random - we picked them up a flea market in Stockholm) and we build all sorts of random things with them, mostly for her other animal "friends" traveling with us (Bunny, Char, NUP, and Kiwi). Yes, you'll certainly lose some pieces in your travels so don't bring any favorites. My parents saved my Legos and we've been talking up the Lego collection awaiting Blythe in Colorado for the past few weeks.
#6 - Stickers! B loves peeling stickers and putting them most anywhere - in her coloring book, on the tray table, in the airplane magazine, on her stuff animals, etc. I don't think it actually matters what is on the stickers (she's been as entertained by Olivia stickers as she is by colorful round dots), but this is a fun item to surprise a kid with mid-flight.
#7 - A coloring book is indispensable, plus a good place to put all the stickers you brought. B colored all of her Olivia coloring book early in our trip and still asks for it, so choose one starting your child's favorite character or animals. One thing I'll add is that you can always find something to color on while traveling. B has colored on travel brochures, boarding passes, old magazines of ours, and really any piece of paper she comes across.
#8 - Maileg Mice are the perfect tiny companions for travel. They come in their own small matchbox with a pillow and blanket. They take up almost no room and playing with them seems to inspire all sorts of imaginative scenarios. Char (B's mouse) was a constant companion of ours until she disappeared off the bike in Stockholm (a very sad day). B only travels with one stuffed animal so having a few smaller "friends" helps.
#10 - Bunny! Bunny is like the 4th member of our family on this trip. He is B's constant companion and has been on many of our outings and adventures. I can't say enough about how well he has held up and thus highly recommend Jelllycat stuffed animals in general. This guy has been washed countless times, dragged all over the streets of various cities, colored on, stepped on, etc. He's still soft and in one piece and I hope B will have him for many years to come.
#11 - Thomas the Train Mini Trains are another toy B loves to play with on tray tables. These can be hooked together and the names of each train are written on the bottom so we now talk about each train as if we know it (Millie, Samson, gold Thomas, Porter, and Henry travel with us). When I purchased these, they were individually wrapped, so there was the added bonus of unwrapping something new on the plane.
#12 - Melissa & Doug Puffy Sticker Pad Sets were recommended to me by a traveling mom and her toddler daughter who we met in New Zealand. Her daughter and B played with a set for quite some time one day and I immediately tracked some down on Amazon. It's nice to have stickers that are actually reusable and these come with a few different "scenes" on which you can use the stickers. I highly recommend these for travel.