Last updated: March 2026.
Planning your first holiday with a baby can feel like a daunting task. Presuming you’ve got their passport sorted (if not, here’s our step-by-step guide), you’re probably wondering: when should you even start planning? Where should you go? What type of accommodation works best? How do you make feeding, sleeping, and travelling easier with a baby in tow?
The good news: with the right planning, your first family trip can be smooth and enjoyable. Here’s everything we’ve learned, in the order you’ll actually need it.
1. When to start planning
You don’t need a long runway for a first trip. Our first getaway as a family, a UK weekend in Norfolk, came together with R at just three months old, and Bergen followed a few weeks later at four and a half months, built around a friend’s wedding rather than months of advance planning. Waiting for the ‘right’ moment can hold you back more than it helps.
I’m a natural planner and tend to book early, and if that’s you too, it’s still worth pausing to research what will actually matter for your baby’s stage before you commit, rather than just booking based on what mattered last time. I booked a villa in Greece for R at 21 months, before he was walking, and it wasn’t until he was properly on his feet that I started noticing things in that villa I’d never registered when booking, like an unfenced pool edge and a set of open stairs. What matters at four months looks completely different to what matters once they’re mobile, so plan around the baby or toddler you’ll actually be travelling with, not the one you’ve got right now.
Beyond that, a few things are worth locking in early: direct flights if you’re going further afield, and any accommodation extras that get booked up fast in peak season, like a crib, high chair, ground floor room or garden. Everything else, packing, the finer flight-day logistics, even final transfer decisions, can wait until closer to the date, since your baby’s routine can shift a lot in a few weeks.
2. Choosing where to go for your first trip
Before you even think about flights, consider starting closer to home. Our first trip away as a family was a long weekend in Norfolk with R at three months old, staying at a cottage with an enclosed garden ten minutes from the beach. No flights, no time zone changes, just a chance to test how travelling with a baby actually felt. We spent our days on quiet beaches, seal-spotting at Horsey, and eating seafood in Brancaster, and it gave us the confidence to book Norway a few weeks later.
If you’ve never flown with your baby before, begin with short-haul trips before tackling long-haul. Our first flight was an under-two-hour hop to Norway with our 4.5-month-old. We then tried Mallorca and Île de Ré, before venturing further afield to Boston. By the end of the year, we were building up to a 9-hour flight to Miami, but only after gradually gaining confidence.
A few things worth weighing up for your first destination:
- Flight length. Direct flights are obviously easiest for a first trip.
- Climate. Babies generally cope best in milder climates, so avoid destinations during their peak heat or cold. On our Mallorca trip, a heatwave pushed temperatures above 30°C, which was uncomfortable for all of us, especially R. Chasing the hot sun isn’t much fun if you’re spending the whole time trying to keep your baby cool. If you are heading somewhere warm, here’s what actually keeps baby cool in summer heat.
- Healthcare access. Some parents feel fine venturing into the wilderness, while others prefer destinations with excellent healthcare systems. It’s a personal choice. We’ve avoided the Caribbean for now, instead opting for the US and Europe, but met our desire for an interesting beach holiday with Cape Cod (south of Boston) and the Florida Keys (south of Miami). There’s somewhere for everyone, whatever your criteria.
- Getting around. Is your destination pram-friendly? Consider cobblestones, narrow lanes and steep hills if you rely on a pram, and check public transport access before booking. Don’t forget to look at how you’ll get from the airport to your accommodation with a baby, if you aren’t taking a car seat. We always assess ‘pramability’ in our destination guides, since it can make or break a trip.
For short-haul, Greece is one of the easiest destinations from the UK: most islands are around 4 hours away and the choice of family resorts is excellent. Once you’ve got your first trip or two under your belt and want to explore your options properly, our guide to the best types of holiday with a baby breaks down beach holidays, city breaks and everything in between, and our Greek islands guide covers all the main island options.
3. What to book, and in what order
Flights first. If you do need a stopover, make it intentional. Don’t risk the chaos of unexpected overnight layovers (I once ended up stranded in Doha after a delayed London departure, which was bad enough pre-baby, let alone with one in tow).
Then accommodation. Baby-friendly accommodation isn’t just about a comfy bed. Use Airbnb and hotel booking filters to find places with:
- Cribs and high chairs
- Washing machines
- Parking
- Budget-friendly options
If there’s a must-have you can’t confirm from the listing, ask the question. Blackout curtains, stair gates, noise levels and nearby shops all matter more than you think. I forgot to ask about (or bring along) blackout blinds in Norway and ended up battling long summer evenings with a wide-awake baby.
Search for keywords like baby, child or family when reading reviews on any platform. They’ll reveal whether a property is truly family-friendly, and sometimes it’s the smaller details, like safe outdoor space or proximity to a supermarket, that make or break a stay with a little one. Not all rental sites make it easy to filter for the things that actually matter when you’re travelling with a baby, like cots, stairgates, enclosed gardens and step-free access. I’ve compared Airbnb, Booking.com, Sykes Cottages, James Villas, Luxury Cottages and InterHome side by side in my holiday rental platform comparison, including how each one scores on family search filters, hidden fees and customer service. Worth reading before you start your search.
I also do research on TripAdvisor’s forums, or pick up a cheap copy of a physical guide book like Lonely Planet for area recommendations (check the publishing year to make sure it isn’t out of date).
Then healthcare. If you’re UK-based, sort a GHIC for your baby well ahead of travel. Here’s how.
And insurance. Make sure you’ve got proper travel insurance in place too, especially cover for sickness and cancellation, which matters more with a young child than it ever did pre-kids. I’ve compared the options in my family travel insurance guide.
4. Preparing for the flight
If you’ve got an early departure, consider an airport hotel the night before rather than an early morning transfer from home. Before flying to Bergen we stayed at a Premier Inn at Gatwick so we could take the first direct flight out, and it was the right call.
At the gate, our travel pram and car seat combo got us all the way to the door, but check your airline’s cabin sizing limits in advance. Ours was technically cabin-approved but ended up gate-checked anyway, since our airline’s allowance was smaller than we’d expected. We also booked R his own seat with his car seat rather than holding him on our laps, which made a noticeable difference to how settled he was.
Our guide on all things flying with a baby is popular with parents, and if you’re flying British Airways specifically, our dedicated BA guide covers bassinets, seat choice and luggage in more detail. It’s also worth thinking about flight timing itself, since the right departure time can make a real difference to minimising the impact of jet lag.
5. Pack smart
Packing for a baby can feel like preparing for a small expedition, but a few clever choices make all the difference. Focus on the essentials: enough nappies and wipes for the journey (you can usually stock up at your destination), a lightweight travel pram, and a baby carrier for places that aren’t stroller-friendly. Don’t forget familiar sleep items like a favourite blanket or white noise machine, since they can help settle your little one in new surroundings.
I’ve created a detailed packing list for parents, which covers everything in far more depth. For your child’s own luggage, our guide to the best kids suitcases covers everything from toddler backpacks for lighter trips through to ride-on suitcases that keep little ones entertained on the way to the gate.
Don’t feel you need to buy everything either. If it’s just a one-off item you’ll only need for this trip, like a travel cot or highchair, it’s often worth hiring baby equipment at your destination instead of packing it.
6. Plan ahead for feeding, especially once on solids
Whether you’re breastfeeding, formula-feeding or weaning, a bit of planning makes life easier. We travel with:
- Low-sugar food pouches and snacks
- A small handheld blender (fits into checked luggage)
- Reusable silicone pouches for days out
This way, we can always have a mix of items to enjoy at our accommodation or on the go.
7. What’s actually different about your first trip
Nothing quite prepares you for how different travelling with a baby feels, even with all the planning in the world. Bergen was our first trip abroad with R and it surprised us in the best way. Going in, we half expected to spend the whole four days just getting through it. Instead it felt relatively relaxing and far more welcoming to families than we’d braced for. We didn’t feel like we were missing out on much with a four-month-old strapped to us, which was a huge relief as first-time parents.
That doesn’t mean everything went smoothly. Norway’s long summer evenings meant the sun was still up well past 10pm, and our Airbnb’s blinds let in enough light around the edges that R was wide awake far later than usual, a lesson that’s shaped every trip since (blackout blinds now come with us everywhere). Taxi prices at the airport were higher than we’d budgeted for too, something we only sorted out properly on the way home.
None of that stopped it being a lovely trip. By the second or third one, you’ll know your own baby’s quirks and can plan around them properly, but the first trip is really about finding out what your family needs.
8. Upgrade your experience
If you’re tackling a long-haul leg and think business class is off the table, think again. We’ve cracked the code using Avios and strategic card perks, like the British Airways American Express Premium Plus card and Barclays Avios bank, so that while you’re technically paying an economy fare, you’re often enjoying lie-flat comfort for the same price. For smart families, that’s priceless extra space to feed, soothe or nap with your baby.
Want the full how-to on using upgrade vouchers, companion fares and off-peak reward booking? I’ve broken it all down in my post on flying business class with a baby for economy prices, definitely worth bookmarking before planning.
Remember there’s no ‘perfect’ first holiday
Every family has different priorities: flight length, climate, healthcare, stroller access, or feeding convenience. The most important thing is finding what works for your family. With these steps, planning your first holiday with a baby doesn’t have to be overwhelming. You can travel with more confidence and actually enjoy the journey. Whatever happens, you’ll make some unforgettable memories.
Allie, Jack & R x
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