If you ask me, the key to survival with a toddler is being prepared. Here are some of my very favorite toddler items that have made my life with a toddler that much more doable and fun.
RuffleButts Rash Guard Swimsuits

We live near the beach and visit the beach often during the summer months so naturally, I am already preparing for summer. For a baby or toddler who will be spending any time in the sun on the beach or by the pool I definitely prefer a long-sleeve rash guard swimsuit, especially the ones from RuffleButts with UPF 50+ sun protection.
If you are thinking your little one will be too hot in the heat of summer with a long sleeve rash guard, remember that on days warm enough to swim your little one will likely end up getting wet. The wet rash guard will keep them nice and cool for longer as they dry and if they get warm again they can go for another dip. The only problem with rash guards is that they are not always super cute. With Rufflebutts this problem is solved, take a look for yourself at the selection, oh and make sure you go and check out the ruffling detail on all of the butts too since this image only shows you the front of the suits that we chose. Also when you refer a friend to View Rufflebutts UPF 50+ Swimwear
Pop-up Travel Bed

We travel around often with our daughter and people often ask us where she sleeps. Before we started travelling with her I did a lot of research on my options and decided was she would be best off with a space of her own that she was familiar with so I wanted to buy something lightweight. Honestly, nothing compared to the lightweight packability (yes it will fit in your suitcase or rolling carry on) and ease-of-use of this travel bed. When you arrive to your destination and need a bed for your little one, simply pull it out of the bag, remove the strap holding it in place and it pops open. That is all. AND putting it away is a breeze too (I swear).
At first you may feel bad zipping your little one in there (you could leave it open) and just walking away but in my case, my daughter was just fine in no time and slept all night long! We have used this more than 20 times and I will continue to use it until I cannot fit her in there anymore… but it is pretty spacious so we still have some time. It is recommended for ages 1-3. 2022 Update: My daughter slept in this pod on vacations until she turned 4, by choice!
Travel Place Mat

This place mat is a must have for a baby eating solids through the toddler years. It rolls right up so you can keep it in your diaper bag, and allows your baby a safe, clean, and stable surface to eat from. I have forgot it a couple of times when we went out to eat and the alternatives are simply not comparable at all- we are so lost without it. I personally have never seen another baby out and about with one like it but I do get stopped by parents all the time asking us where we got it, so that says something! Amazon folks!
Water Wipes

If you are like me and you need a wipe that does it all, this is the wipe that you need. It doesn’t have a scent to it, it is safe to use on any part of your baby, and it is even safe enough to use to wipe down a surface that your baby is going to have to eat off of (like the place mat I talked about above) when you are on the run. No need to carry boogie wipes, pacifier wipes, etc. and it is the BEST option you will find if your baby has sensitive skin! I SWEAR by these- 100%. You won’t find them in every store so I do recommend stocking up on Amazon. 2023 Update: Admittedly, I have another baby now, but we still have Waterwipes on us at all times!
Lucky Bum Training Skis

If you live in Maine too, or anywhere with some snow, you may want to pick up some of these training skis for toddlers. My daughter started using hers at about 20 months old. They are great for playing around in the yard, and they strap right on to their regular boots. You will be surprised how fast they catch on to skiing if you start them young.
Potty

I like this potty because it is affordable, works for boys and girls, and resembles a real toilet. It makes real flushing sounds which your toddler will love and holds wipes on the top, which in theory sounds great, but my toddler likes to just pull them all out as soon as they go in. It’s the cutest little potty that I have ever seen though.
TIP- If you buy the potty, you may want to buy these liner bags to keep things as sanitary as possible. It also helps if you think you might be the person who will throw the potty in the car for a road trip.
Potty Training Watch

I found that my daughter was always trying to wear my watch so to try to be cute I was looking into buying her a cheap watch of her own. We were also trying to potty train on and off. When I find out that there was such a thing as a potty training watch I thought “this is perfect… even if it doesn’t work for potty training”. This is the one that I chose and while cute enough, admittedly it wasn’t the one that I thought looked the coolest or high-tech as I did my research, but it had the best reviews and was cheap so I bought it.
It’s actually pretty adorable in person and does everything that we need it to and more. It fits my daughter’s tiny wrists just fine but with loads of room to grow so I am confident that it would fit any kid of potty training age and will be a great watch beyond potty training. You set the musical alarm to go off in your preferred increment of time (every 30, 60, 90, 120 minutes etc.) and it plays a tune when it’s potty time. Then we shout “potty time” (optional) and hustle to the potty. We are just a couple days into this routine and it has worked every single time! We take it off at night but in the off chance you forget the alarm will not sound during the nighttime hours of 9 PM – 7 AM.
Car Window Sun Shades

Once your baby is out of the infant car seat with the convenient canopy that blocks most of the sun in the car, you will likely find the sun is in their eyes in their rear-facing convertible car seat. So, throw these mesh sun shades over your rear doors when you need them, and take them off when you don’t. They pack super light in the car when you are not using them (or for when you are travelling and will be renting a car) and are a quick fix to the sun in your toddlers eyes offering full window coverage, while maintaining the ability to open your window. 2023 Update: We upgraded to a Honda Pilot that has build in screens so we no longer need these, but I still use them on the pickup truck.
Silicone Feeding Set

This feeding set was a great buy. The bibs are excellent for “second chance” eating, if it drops and catches, offer it again. Less waste and less mess. My daughter loves to use the plate and the bowl as well like a big girl. They stay put reasonably well, and overall this is an excellent set. It comes with some spoons too. We find that we rotate through the bibs, bowl and plate pretty continuously. 2023 Update: These have held up and work well with baby # 2 too!