How I Pick Travel Destinations with a Toddler (Without Sacrificing Vibes)

One thing about me? I want to travel with Sydney to show her the world—but I’m not trying to suffer through it. I’ve done the trips that looked dreamy online but felt like chaos IRL. These days, when I’m planning our next escape, I have a checklist. Not just a “what sounds fun” list—but a real mom-approved, vibe-preserving checklist. Because yes, I travel with a toddler… but I still like my trips to feel like a trip.

Here’s exactly how I choose where we go—and why I no longer sacrifice style, sleep, or sanity:

1. Pedestrian-Friendly, Please

If I have to get in a car every time I want coffee, snacks, or to walk around—no thanks. I look for destinations or neighborhoods where everything is walkable or stroller-accessible. I want to be able to leave the hotel and explore without packing up like we’re heading into battle. Bonus points if there’s a beach, playground, or outdoor café just a few steps away.

2. Warm Weather or I’m Not Going

I’ve done cold-weather trips with Sydney, and let me tell you—it’s not the move. Between the layers, the gear, the wet clothes… it’s just more work. Give me sunshine, mommy and me swimsuits, and a sandy toddler any day. Warm weather = fewer meltdowns, lighter packing, and way more fun.

3. A Hotel That’s a Destination on Its Own

My dream hotel has a pool, several restaurants, cute shops, maybe a kids club—even if we don’t use it. I want everything at my fingertips, because some days… we’re not going anywhere. If the hotel has enough to keep us fed, entertained, and happy, I already feel like I won.

4. Rooms With Separate Bedrooms—Non-Negotiable

I need a 1-2 bedroom suite when we travel. Sydney needs her own space to sleep, and I need my own space to breathe once she’s out for the night. I’m not trying to hide in the dark on the floor with snacks and my phone on mute. Give me a suite with a balcony, and I’m good.

5. Nice Views + Balcony = I Don’t Feel Trapped During Nap Time

Speaking of which… if we’re in the room for nap time, I need a little escape. A balcony with a view makes all the difference. I can sip a drink, get some fresh air, take in the scenery, and not feel like I’m being held hostage while she sleeps. It’s a small luxury that makes a big impact.

6. Outdoor Activities = Burn That Energy

I cannot keep Sydney indoors all day. None of us will survive. I always look for places with outdoor space, excursions, and open-air fun: beach time, pool days, nature walks, splash pads, or anything that lets her run wild and wear herself out. If I can sit somewhere cute while she does that? Even better.

7. Short Distance from the Airport

After being in an airport, the last thing I want is to hop in a car for a two-hour drive. I look for destinations that are 30 minutes or less from the airport. If there’s a private hotel shuttle waiting for us? Chef’s kiss. We get off the plane and go straight into vacation mode—no detours, no missions.

8. Strong Wi-Fi (for Baby Monitor and Mickey Mouse)

Good Wi-Fi is a must—not for work, but for survival. I need to stream the baby monitor from my phone at night. And yes, sometimes I need to play the Disney parade on YouTube video at 6 a.m. while I try to gather myself. So if the hotel has patchy internet? It’s a no from me.

9. Grown-Up Vibes (Because I’m Still Me)

Just because I’m traveling with a toddler doesn’t mean I want to feel like I’m on a preschool field trip. I look for places with good restaurants, a cute lobby, and lounge areas that feel elevated and relaxing. That way, once Sydney’s asleep, we can sneak downstairs, enjoy a drink/snack, and still feel like adults—while watching her on the monitor, of course.

Final Thoughts

Traveling with a toddler can be amazing… if you set yourself up right. I’m not chasing aesthetic perfection—I’m chasing peace. And that starts with choosing destinations that meet our needs and still feel like a getaway.

So give me the suite, the sun, the snacks, and the stroller-friendly streets—and I’m in.