Pick a good place for the whole family
The first thing is to make sure the whole family can have fun. Now is not the time to re-do fun trips you had when you were single or newly married. That will only bring disappointment for everyone. Pick places that are family-friendly, even if they are not quintessential family resorts. While perhaps not on your top list of vacation spots, a trip near grandma's house might be just the ticket so that you actually get a break during your vacation.
Plan age-appropriate activities and plan your day so that everyone is relaxed
Babies are easily over-stimulated by too many sights and sounds. They also get bored on long sight-seeing bus tours or when they are stuck in one place for too long. Limit your plans to one activity a day and plan to spend a lot of time around a wading pool, which you might find is the best activity for little kids no matter where you've traveled to.
Try to plan your trip overnight
If you have a very small baby, you may want to take a very short overnight getaway just so you know what you're getting into. In many ways, traveling with a small baby is easier than traveling with a 2-year old. This will also give you a better idea on what to pack.
Keep safety in the back of your mind
If you're planning a trip to a hotel or house with a pool, make sure you've thought of how you will monitor your child 100% of the time. A leisurely vacation can be spoiled if you're worried all the time about losing a child to a pool accident, the second largest cause of death in small children. Also, make sure to adequately plan for the sun, with lots of sunscreen, hats, and clothing that covers all the body or shades the baby. Now is a good time to double check your car seat if you're planning a long trip.
Plan for the unforeseen.
Pack at least twice as many diapers for the plane as you think you might need. If you're traveling overseas, plan to bring extra formula since most countries will not have brands you recognize or it may be very difficult to find it at all.
Plan lots of rest stops
If you plan for a lot, you won't go crazy thinking that you're stopping all the time. Try to minimize stress by keeping driving hours to a minimum.
Stay at Kid-friendly hotels
Almost all hotels allow kids to stay in rooms for free, but some also give free meals or buffet access to young children.
Pack a surprise toy bag
Kids love surprises and you can stop any tantrum by pulling out some new distractions. Look for light weight and easy to carry items, including some that might be thrown away along the way. Take lightweight paper books rather than hard backs. Little cars rather than one big item. Get an early start on this by throwing a few things into a bag a few weeks before your trip.
Bring plenty or snacks and drinks
Don't skimp when packing water, juice and, especially breast milk or formula. Bring plenty of baby food if your child is eating solid food. You can never tell when you might have a lengthy delay and won't be able to get drinks and food on the plane.
Most importantly, be flexible
Traveling with kids is a great time - they will show you the world as you've never seen it before - it's up to you be relaxed and enjoy the ride.
