We are a society on the go. Whether it’s work, school, daycare, activities, or trips, we are usually preparing to leave or regrouping upon return. Taking the baby out for the first time can be a logistical challenge. The backbone of success in my opinion is to keep things organized, and be consistent with how you prepare.
My husband and I just returned from a lovely trip with two college–aged daughters, it is potentially one of the last “family vacations” for our nuclear family. It was wonderful. We spent a week in a new city, did sightseeing, ate out, and really enjoyed the time together. I spent many hours planning the trip, down to the smallest detail. That is not to say that we had a rigid plan. On the contrary; my planning was contingency planning. It was amassing knowledge about the city we were visiting, becoming familiar with the transportation system, the restaurants, and what we would see at each site, each activity etc. This may sound nuts to you, but hear me out. 
On another trip, I was taking a mid-day break by the hotel pool, and over heard a conversation that was something like this. “So, what did you do this morning?” “Oh, it was so frustrating! We went to the museum, and it was closed! We wasted the entire morning and didn’t get to see anything.” Blah blah blah. I grimaced. Waste indeed! Like me, and countless others, these tourists had paid for airline tickets, hotel, etc. and gotten nothing in return for their investment.
My time, and yours, is valuable! Especially when you are traveling, you want to get value for your money.So investigate the opening hours of the places you want to go! See what’s offered, so your child doesn’t pitch a fit because they want to see the dolphin show, but can’t because you didn’t sign up for the free tickets weeks before. My strategy is to put my name on every list, reserve the space, just in case! (Disney World is a particularly intense destination; I’ll have a whole essay on that.) Similarly if you are planning a day of errands on main street, see when the library story hour is, and work it into your day as a break. In addition to your groceries, you’ll have books, and an accomplishment to feel good about!
So the best strategy for any excursion, near or far is to plan for the contingencies. On this most recent trip, I was prepared by knowing which sights were located close to each other (so we didn’t waste time crisscrossing the city), several restaurants in the area that we could choose (so we didn’t get so hungry and cranky we would fall into an expensive tourist trap), and a list of subway and bus lines that would easily link the places we wanted to go. Most importantly, I had grouped them according to the days and hours they were open, so we knew if we wanted to see Headliner A we had to visit on a Tuesday or Wednesday; Headliner B was a Monday visit, and so on. That gave us the flexibility to visit the headliner, and then say, “ok, what else do we feel like doing? X.Y, Z are close by, and we can grab lunch here or there, some fresh air at this park, and an ice cream at this place.”
Let’s apply this same strategic planning to a day of errands. If you have to get drug store items, groceries, a hair cut and pick up dry cleaning, then you have to arrange them in a logical way (groceries last), identify where you’ll stop for a break ( and pack the snacks ahead of time) and know what time the dry cleaner closes, so you don’t miss it and have to go back. Also keep in mind the location of hot-spots like the carnival/ toy store/ pet store, don’t choose the store where the kids will see the attractive hot-spot, go 5 minutes out of your way to the other grocery store, to avoid the tantrum and stress that would have ensued. Then when you do have the time and plan to see the “funtastic” attraction, you are the hero for giving the kids such a wonderful surprise!
As for packing for your trip, I always had my diaper bag stocked, with each item carefully tucked away in the same pocket every time. Each day I would replenish the consumable items; diapers, juice boxes, clean bib, binky etc. I kept some bigger rarely used things in a box in the car. Things like a change of clothes, first aid kit, and a couple of party favors incase all hell broke loose and I needed a new shiny distraction! I also kept my things in the exact same place all the time. My bag hung on a hook. The keys were in the zippered pocket, my sunglasses on the outside pocket, etc,etc. I never had to run around looking for these items. I was consistent, which I am sure is the key to organization and stress reduction!
So let me end where I began. This family vacation was the first vacation for which I did not need to make any parental preparations, or work while I was on vacation. My girls are adults, they knew how to pack, prep, travel and take care of themselves. We were four adults on vacation together. What a joy! I used to say of other vacations, while they were fun to varying extent, for me it was “same job, different location.” Because I was still meeting the children’s needs every day, and then some, because I had to anticipate the new needs of being away from home. I promise you, the day will come and you will sigh with relief that all the years of planning have paid off. Hopefully your example will be another gift for your child, and the organization and planning will be part of their lives too. Few of us have the benefit of being taught this at home, so whatever you can do to anticipate, plan, prepare and be consistent, you and your child will benefit! Happy travels!

Pet Peeve:
I know so many people who have stayed in posh hotels, which offer amenities they will never use. Your room rate supports the spa, the salon, the room service etc. If those things are not part of your plan, skip it, and spend the money on something you will enjoy! You can save so much money, and spare yourself the tease of temptation when you are not able to take advantage of those amenities, by staying someplace else! Try to think of it as a family trip, not a vacation! Personally, I would rather stay focused on the kid – fun on family vacations, and then spend time pampering myself when I can really be free of responsibilities. When I’m with the family, I want to be with them. That usually means doing kid stuff, not going somewhere just to leave the kids in the resort camp. If that means making your family trip a bit shorter and going away with only your significant other on another occasion for a real vacation, or just getting a babysitter and having a day to yourself in your hometown, I’d rather be focused on either the family or myself. Trying to do both sounds too frustrating to be worth it.Family tr