From Chaos to Calm: Navigating the 20-Month Milestone with Your Toddler

During our most recent trip, we had to lower our dining out expectations and focus on family-friendly settings rather than fine dining. Traveling with a toddler? We discovered it was far more challenging than we ever anticipated. What started as a complete shift in our expectations turned into an adventure in adapting to our new frontier of parenthood. But here’s the beautiful thing about toddlers—just when you think you’ve figured them out, they surprise you with a developmental leap that changes everything.

From Restaurant Disasters to Dining Success: The 20-Month Breakthrough

I’ll be honest—eating out with a busy toddler took some serious adjusting on our part. From 12 to 15 months, we found a workaround: I’d put her to sleep in her Doona stroller and we’d go to dinner while she slept peacefully beside our table. It felt like we’d cracked the code on maintaining our social life while parenting.

But then something shifted. Around 15 months, this reliable system became less dependable, and we had to pivot again. The 15-18 month window truly felt like the hardest phase for restaurant dining. The fidgeting, the outbursts, the constant need for redirection—it was exhausting for everyone involved.

But something magical happened around the 20-month marker. We’ve hit a new stride, and it’s exciting to witness. Our daughter now shows:

  • A sudden deeper interest in coloring
  • Sustained attention for staying at the table
  • Overall fewer outbursts
  • Longer stamina both at home dinner time and in restaurants

Our motto became simple: if she’s happy and behaving well for the setting, just let her be. We only think of new redirection strategies when absolutely necessary. It’s amazing how this shift in our approach coincided with her natural development—and suddenly, family dining became enjoyable again.

Audio Magic: How Tonie Box Became Our Independence Builder

As a parent, I constantly worry about whether my daughter is getting enough language exposure. I also found myself thinking ahead—what activities could she do independently to support her language development while I tackle other tasks around the house?

After seeing two mom friends’ children enjoy their Tonie boxes, I decided to invest in one. Yes, they’re technically rated 3+, but they worked beautifully even for our younger toddler. I researched competitors but ultimately decided the authentic Tonie figures were worth the extra cost—they definitely stood up to the roughness that comes with baby handling.

We bought the box during a Prime sale before our trip, and while she enjoyed it somewhat during travel, the real magic happened after we returned home. Within just a few days, it became her natural wake-up and wind-down routine—something I hadn’t planned but was delighted to discover.

Initially, she loved the songs, but she’s recently started gravitating toward stories. I also bought the Creative Tonies, and she often listens to the one where I sing to her. My husband created another one with a sweet personal message just for her—it’s become one of her favorites.

Now some mornings when she’s up early after our travels, she calmly listens while the rest of us wake up gradually. During the day, she’s still more interested in running around and active play, but when bedtime approaches, she sits and listens, naturally unwinding before our official bedtime routine begins.

I’m excited to see how this develops into more independence around waking up and going to bed. We’ll absolutely still prioritize sweet family time, but having this foundation gives us something wonderful to build new routines upon.

Why Your Toddler Wants to Floss Too (And That’s Actually Great)

We were genuinely surprised when we mentioned to our pediatrician that our daughter was brushing her teeth, and they suggested we try flossing too. Apparently there’s always room for improvement in the dental hygiene department!

Funny enough, our toddler absolutely loved it. Looking back, it makes perfect sense—kids want to do whatever you’re doing. The key was that my husband has always been great with routines and regularly flosses and brushes, so she was naturally interested early on.

Now she’ll actually ask for “baby floss” (which is just regular floss that’s become hers) and pretend to floss before one of us helps her properly and disposes of it safely. With teeth brushing, she starts on her own and we help her finish, making sure all teeth get properly cleaned.

An unexpected bonus? Our new solid family routine has me brushing and flossing more consistently too. Turns out, the family that brushes and flosses together really does have very clean teeth together.

The Real Talk: We’re Still Figuring It Out

Each phase of toddlerhood brings its own unique challenges and victories. We’ve successfully navigated the trickiest restaurant phase, discovered tools that support language development and independence, and stumbled into dental hygiene habits that benefit the whole family.

We’ve definitely hit the terrible twos territory—there’s been a lot more protesting and unexpected behavior that keeps me on my toes. I constantly find myself thinking, “Okay, what do I need to do so this doesn’t get reinforced?” And honestly, I’m still figuring some of it out. But we are figuring it out like any parent does—through trial and error, patience, and hopefully growth on all fronts.

The key lesson? Sometimes our biggest parenting wins come not from rigid planning, but from staying flexible, following our child’s natural interests, and remembering that they’re always watching and wanting to participate in whatever we’re doing.

What new challenges lie ahead? I’m sure there are plenty. But with each milestone we cross together, I’m learning to trust both my daughter’s development and our family’s ability to adapt and thrive.

I’m most grateful that when it seems like I’ve given up hope, suddenly we hit a milestone and discover new strengths alongside new challenges. It keeps parenting interesting, for sure—but it also helps me feel successful as a parent, knowing that growth and progress are always just around the corner.


Stay tuned for our next blog where we dive into our travels in Italy. Some of my favorite trip memories happened on a family-friendly beach in the Mediterranean!

For more travel adventures, check out our travel page. For other parenting adventures, check out our blog.

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