I decided long ago, when my triplets were born, that I wasn't going to just sit home and not go anywhere simply because I had 3 kids at the same age. This is one place my stubborn streak is an asset. While the planning and energy to pull vacations off seemed monumental, I got some great advice from other multiple moms and had friends and family support that made it work. Some of my favorite suggestions that I heard from multiple moms and adopted with great success were:
1) Packing a special "trip backpack" each time we went away. For mine, it was a small red Winnie the Pooh bag. Fill it with brand new things - new stickers for their sticker books, coloring books, new crayons, markers, regular books to read, diaries for drawing and writing about what they saw, Etch a Sketch and View Finders (I'm dating myself - my kids are in college - but loved these - each trip I'd buy 1- 2 new disks for them to see). The secret and RULE was that they couldn't open the backpack until we were on the plane, or in the car. Kept them happy and busy for hours and I had fun filling it each time.
2) Traveling during nap time - when they were 18 month old, we flew for the first time. Had to take an extra adult, an uncle, with us, but.... Worked like a charm - They were enthralled with the airport and sights, getting on the plane, etc. Once we were taking off, they had bottles, and then napped most of the flight. The lady in the row in front of me, who had a HORRIFIED look on her face when she first boarded the plane and saw THREE toddlers behind her, turned around to me after the flight and said "You have the most well behaved kids I've ever seen". Still makes me smile to this day.
3) Expecting great behavior and demanding it. No excuses. We started taking our toddlers out to restaurants (diners at first) very early on, and told them this was a privilege and special treat, and they needed to behave or we wouldn't go. They loved going out and probably enjoyed all the special attention that three little adorable kids get when we showed up anywhere. BUT, you have to be prepared to carry through and walk out if their behavior isn't acceptable. I promise you will only have to do this ONCE, if ever. My kids kept behaving well because they knew we wouldn't tolerate it and the fun would stop. I only walked out of a place of business ONCE with them in tow. Not a great moment for us, but I did it. The memory stuck.
4) Have them help pack and carry their own suitcases. When they were about 4, we bought them small rolling suitcases. I packed with them but taught them how to count out how many days we'd be gone, how much underwear and socks they'd need and helped them lay out clothes and make decisions on what to bring by what would fit in the suitcase. Maybe that meant they couldn't fit all their favorite bathing suits in. Time to learn. My husband is not a pack mule, although he played that role for many years, but traveling is a lot of work and they can be responsible for pulling their own suitcase and learning some responsibility.
5) Rent/bring strollers and plan stops during the day. This was especially true at Disney where we used strollers to conserve their energy so they'd not melt down and we planned stops for pool time or resting. Don't overdo it. Resist the temptation to get it all in. You will all be miserable. I said at the beginning, I'm stubborn, but I even had to give in and compromise on exactly how much we could accomplish in one day with triplets.
It's a great experience for you to travel as a family. We've had wonderful trips and made great memories. And I do have the cutest pictures!!!!