How to Plan Your First Trip with a Baby: The Complete Parent's Research Guide
You used to book a flight, throw some clothes in a bag, and figure it out when you landed. Now you're awake at 2am, nursing your baby while Googling “can babies fly at 8 weeks” — and the idea of planning a trip feels ten times harder than it used to.
Here's the thing: it's not actually ten times harder. It's just different. The variables changed, and nobody gave you the new playbook. That's what this guide is.
Not vague advice. Not a list of 47 things to worry about. An actual step-by-step workflow to take you from “we should take a trip” to “we're booked and packed.” It's built on the same real-world research behind our 250+ city reviews — because where you're going changes everything about how you plan.
Before You Start: The Two Questions
Before you open a single booking site, answer these honestly. They shape every decision that follows.
Question 1: How old will your baby be at travel time?
- 0–2 months: Most pediatricians recommend waiting until at least 2 months and the first round of vaccinations before flying. Short road trips are usually fine earlier. Check with your pediatrician — then trust their answer and stop Googling.
- 2–5 months: The sweet spot many parents swear by. Baby is portable, sleeps a lot, and isn't mobile yet. Feeding schedule is your main logistical factor, but you're basically carrying a very cute travel accessory.
- 6–12 months: More alert and interactive — which is wonderful and exhausting. They're heavier now (carrier fatigue is real), starting solids adds food prep logistics, and crawlers want to move. What “relaxing” looks like changes significantly.
- 12–24 months: Walking. Running. Opinions about everything. Nap schedules become non-negotiable. But also genuinely more fun — they react to everything, and the memories start sticking (yours, at least).
Question 2: What kind of trip do you actually want?
This matters more than people think. Be honest with yourself:
- Beach relaxation, city sightseeing, family visit, or nature escape?
- How many hours per day do you realistically want to be “out and about”?
- Are you trying to do things, or trying to rest?
- Is this trip about exploring a new place, or about changing your scenery while maintaining routines?
Your answers determine destination, gear, and pace. A beach week in Faro requires completely different planning than a city break in Paris. Get clear on this before you start booking anything.
Step 1: Choose Your Destination Type (Not Just a Place)
Start with what your trip needs — from Question 2 — and narrow to specific destinations from there. Not the other way around. Falling in love with a place on Instagram and then trying to make it work with a baby is how you end up hauling a stroller up 400 bridges in Venice.
Before you commit, check whether your destination actually works for families with babies. That's exactly what our city database is built for — every city is scored on real-world factors like terrain, transit accessibility, and family facilities.
The differences are bigger than you'd think:
- Singapore (Stroller Score: 85) is phenomenal for first-time family travelers — clean, accessible, incredible food halls, and everything just works. If you want a confidence-building first trip, it's hard to beat.
- Venice (Score: 28) is a dream destination, but it's stairs and bridges all day. Save it for when the kids are older — or fully commit to the carrier and leave the stroller at home.
- Lisbon (Score: 62) looks flat in photos but is actually built on seven hills. Absolutely doable with planning, rugged stroller wheels, and a willingness to embrace the tram instead of walking straight uphill.
- Copenhagen (Score: 82) was practically designed for families with babies. Flat, accessible, and Danish culture treats children like welcome guests everywhere.
Browse all cities by trip type — beach holidays, city breaks, winter sun — on our city guide page.
Step 2: Check the Practical Infrastructure
This is where most generic travel articles fail. They tell you to “do your research” without telling you what to research. Here's the actual list:
🛞 Stroller & carrier friendliness
Is this a stroller city or a carrier city? The answer depends on terrain, sidewalk quality, and how old towns are laid out. Our Stroller Score covers this across 7 factors, or read our stroller vs. carrier guide for the full decision framework.
🚇 Transit accessibility
Does the metro have elevators? Can you board buses with a stroller without folding it? This varies wildly — Amsterdam's trams are tricky but the city is flat enough to walk. Paris's streets are great but the Métro is notoriously inaccessible. Know before you go.
🏥 Healthcare proximity
Locate the nearest hospital or pediatric clinic to your accommodation. Save the local emergency number in your phone. If you're traveling internationally, confirm your travel health insurance covers infants — and print the policy number. You probably won't need any of this. You'll sleep better knowing you have it.
🏠 Accommodation specifics
Call ahead — don't just check the website — and confirm: crib availability, room layout (separate sleeping space?), elevator access, stroller storage. Apartment rentals often beat hotels for families: you get a kitchen for bottle prep, a washing machine, and more space to spread out during nap time.
✈️ Flight logistics
Direct flights dramatically reduce chaos. Check your airline's stroller and car-seat gate-check policies before you get to the airport. Night flights can work magic if your baby sleeps through — but that's a gamble only you can assess.
👶 Baby gear rentals
Services like BabyQuip (or local equivalents) can save you from packing a car seat, travel crib, and high chair. Research what's available at your destination — it might completely change what you need to bring.
Step 3: Plan Your Gear Based on Your Destination
This is not a packing list — the internet has thousands of those. This is decision logic: your destination research from Steps 1 and 2 tells you what to bring.
Stroller Score 65+? → Compact travel stroller is your best friend
Cities like Copenhagen (82) and Amsterdam (78) are built for wheels. A lightweight, compact stroller handles the terrain and doubles as a nap station. Read our full stroller vs. carrier guide for specific recommendations.
Score under 50? → Carrier is primary
In cities like Venice (28), a stroller is genuinely more trouble than it's worth. Make the carrier your main mode and maybe keep a lightweight stroller at the hotel for evening walks on flat stretches.
Beyond the stroller-or-carrier decision, a few things parents consistently wish they'd researched earlier:
- Portable blackout shades — hotel curtains are never dark enough. Suction-cup blackout covers are lightweight and transformative for naps.
- White noise machine or app — masks unfamiliar sounds in a new environment. Your phone works in a pinch.
- Lightweight travel crib — only if your accommodation doesn't provide one. Call ahead first (Step 2) to avoid packing one unnecessarily.
Step 4: Build a Flexible Itinerary (Not a Packed Schedule)
The number one mistake first-time traveling parents make: planning like they used to. You are not doing four museums and a food tour in one day anymore. That version of travel will return — just not yet.
The one-activity rule
Plan one main activity per day — morning or afternoon — with downtime built around it. If you get to do two things, great, that's a bonus. But designing for one means you won't feel like the day was ruined when a nap ran long or a diaper situation required a full retreat.
Nap logistics
Will your baby nap in the stroller? If yes, you can keep moving and you've got range. If they need a quiet room, your radius shrinks to however far you can get and come back in time. Plan for your baby, not the internet's.
Feeding logistics
Breastfeeding? Research nursing-friendly spots and cafés with comfortable seating. Formula feeding? Check what brands are available locally or pack enough. Starting solids? An accommodation with a kitchen makes this dramatically easier.
Build in “zero days”
Days with no plans. Walk to a park. Find a café. Let the trip breathe. These often end up being the best days — and they're your safety valve when the previous day was chaotic.
Step 5: Prepare for the Travel Day Itself
We're not going to tell you to pack extra diapers — you already know that. Here are the decisions that actually matter:
Airport strategy
Use the carrier through security — the stroller gets scanned or gate-checked. Arrive earlier than you think you need to. Everything takes twice as long now, and “running to the gate” is not an option with a baby and a car seat.
Flight timing
Red-eye, nap-time, or morning departure — each has real tradeoffs. Pick based on your baby's sleep patterns. A baby who reliably sleeps 7pm–7am might be perfect for a night flight. A baby who fights sleep in new environments? Morning departure, no question.
Documents
Yes, babies need their own passport for international travel — and it can take weeks to process, so start early. Also bring: insurance cards, pediatrician's number saved in your phone, and any medication with the prescription label visible.
One underrated tip
Take a photo of your stroller before you gate-check it. If it comes back damaged, you'll need evidence for the airline claim. Takes three seconds, potentially saves hundreds.
Step 6: Embrace the Imperfect Trip
Something will go wrong. A diaper explosion in the taxi. A missed nap that leads to a meltdown at dinner. A rainy day that wrecks your one outdoor plan.
That's not a failed trip. That's parenthood on the road.
The bar for success is lower than you think: if you changed scenery, ate something good, and made a memory — you won. That café in Barcelona where the baby charmed the waiter? The sunset walk along the canal in Amsterdam when everything finally felt calm? Those are the moments.
The first trip is the hardest. Every trip after gets easier — not because the logistics get simpler, but because you learn your family's travel style. And that's something no article can teach you. You just have to go.
Quick-Reference Planning Checklist
Screenshot this, bookmark it, or print it out. Grouped by when you need to do each thing.
📅 8+ Weeks Before
- ☐ Check baby's age at travel time — confirm with pediatrician if under 3 months
- ☐ Decide trip type: beach, city, nature, or family visit
- ☐ Research destinations using Stroller Score city guides
- ☐ Determine stroller vs. carrier needs for your destination
- ☐ Book accommodation — confirm crib, kitchen, elevator access
- ☐ Book flights — prefer direct routes, check stroller gate-check policy
- ☐ Arrange travel health insurance that covers your infant
- ☐ Apply for baby's passport if traveling internationally
📅 2–4 Weeks Before
- ☐ Research baby gear rentals at your destination
- ☐ Build flexible itinerary — one main activity per day
- ☐ Check transit accessibility: elevator access, bus boarding with stroller
- ☐ Locate nearest hospital or pediatric clinic to your accommodation
- ☐ Save local emergency number in your phone
- ☐ Confirm passport and all documents are current
- ☐ Order any gear you still need: travel stroller, carrier, blackout shades
📅 Week of Travel
- ☐ Pack based on destination type and score (see Step 3)
- ☐ Download offline maps and save key addresses
- ☐ Charge devices, download entertainment and white noise app
- ☐ Confirm accommodation check-in details and crib request
- ☐ Photo your stroller before gate-checking
- ☐ Breathe. You've done the research. You're ready.
You're More Ready Than You Think
The fact that you just read a planning guide — a long one — means you're already the kind of parent who's going to make this work. Most families wing it and have a great time. You're going in prepared.
StrollerFriendly exists to take the guesswork out of the hardest part: figuring out whether your destination actually works for your family. We've done the research for 250+ cities so you don't have to piece it together from forum posts at 2am.