Traveling with an infant is a great challenge, and it can be manageable and even fun if preparation is done well. We just came back from Maui. It was Calvin's first flight and it was really fun. Here are a few big lessons we learned:
1)
Day time flights are better. In general, people have more energy during day time and are crankier at night. So when you fly with an infant (or <4 year old kids), aim for day time flight because infants are unpredictable and require more attention when you're traveling, and you will have more energy to deal with them during day time. Let's look at a few scenarios. Suppose the infant is active during day time: he can walk around the isle (or you can walk him around) and people in general will not mind. And if he sleeps, great! On the other hand, when you have a redeye flight, you are gambling-- if he sleeps, great. If he doesn't sleep, no one on the plane sleeps! Here are some key questions to ask yourself before you decide to fly redeye flights: will my baby sleep through heavy turbulence, constant intercom from the pilot and stewardess (even at night), stewardesses asking if you want a drink, people walking back and forth on the plane, so on so forth?
2)
Rent a condo/house (or go to a resort if you have +2 year old), and on day 1 buy lots of water/bread/etc so that you can spend more time with kids. Chances are, you're not going to go to the same activities before you had kids (cycling down Haleakala Volcano, snorkeling with your spouse, romantic dinner for 2, rough boat trip to Molokini, etc). Chances are, you will spend more time with the kids because they demand your attention. What that means is that with kids, it is much easier to stay close to where you live and just relax by the pool or the ocean. Renting a condo/house is great because chances are, it is a lot easier to eat breakfast at home (than to drive out to the restaurant, having to buckle the infant, pack up stroller, prepare milk/water, toys, so on so forth). Also, condos/houses have washer and dryer (absolutely essential with kids), as well as dishwashers so it makes your hectic parenting life a lot easier.
3)
Leave all the baby stuff at home and rent them. This will save you a lot of trouble in the airport. We rented a bunch of baby stuff, including an umbrella stroller, high chair, bath toys, bathtub, and plastic potty, and toys. For a whole week, it was only ~$80, delivered to your condo/hotel of your choice. There are many great rental places in Maui (just Google for it). We used
http://easytravelhi.com/ and they gave us a BUNCH of toys and books that Calvin loved. Some condos/hotels will provide a complementary crib as well, or you can rent them as well.
4)
Call the activity sites to see if they are stroller friendly. We went to Feast at Lele Luau and it was right on the beach, so we had to hand carry the car seat, stroller, and a bunch of stuff to the sand (pain). The Luau turned out great anyways, but keep in mind not all activities are baby friendly.
5) Similar to 4,
there are actually many great baby friendly places if you do some research ahead of time. For example, Baby Beach (north-west of Lahaina) is a really really great shallow beach for kids, but it is not well documented even on the web so you may have to do some research to know how to get in.
Road to Hana is really Road to Hell for infants and children, because the drive is long, rough, and restroom access is very limited.
6)
Aim for high number of adults/kids ratio. The more adults there are, the less daycare work for each person and more fun you'll have. We had 3 adults and 1 infant, so each person only needed to spend 1/3 the [full-time] energy on daycare and the rest on fun. On the other hand, imagine 2 adults/2 infants-- the adults will spend the entire vacation taking care of kids!
7) Internet != WIFI. Many hotels/condos that say they have internet-- but many will still use ethernet (no WIFI). This means if you bring a Macbook Air or a tablet, you're screwed.
That's it for now, I hope this helps other parents!
