One Baby Now, Maybe Two Later? These Strollers Have You Covered!

Stroller shopping is one of those new-parent milestones that feels… important. Like choosing a stroller is somehow symbolic of who you’ll be as a parent (spoiler: it’s not). But let’s be real—if you're planning to grow your family or just want flexibility from the start, choosing a convertible stroller—one that goes from a single to a double—can be a smart move.

At Galt Baby, we love helping new parents find their perfect stroller match. If you’re looking for the best stroller that grows with your family, this guide’s for you.

Let’s dive into top strollers we carry that are built for first-time parents and future siblings.

UPPAbaby Vista V3

The crowd favorite just got even better.

This stroller has been the family go-to for years, and the new Vista V3 is better than ever. It’s smooth, sturdy, and includes the toddler seat and has the option of their bassinet (sold separately)—perfect for newborn snuggles and afternoon walks.

When baby #2 comes along? Just add the RumbleSeat + adapters, and boom: instant double. The ride is still buttery smooth thanks to upgraded suspension, and the massive storage basket means you’ll always have room for snacks, a diaper bag, your coffee, and a half-eaten banana.

Bugaboo Donkey 5

Double the kiddos, double the fun.

Thinking of back-to-back babies? Twins? Just like the idea of both kids getting equal views of the world? The Bugaboo Donkey 5 is your side-by-side soulmate. It converts from a single to a double in a snap—no wobbly attachments or crazy stacking.

In mono mode, you’ll love the handy side basket for easy access to your purse, diaper bag or a small bag of groceries. In duo mode, both kiddos ride comfortably side-by-side without playing footsie. Plus, the fabrics are dreamy, the ride is ultra-smooth, and the fold (considering it’s a double) is surprisingly compact.

🚨 Tip: The Bugaboo Donkey 5 fits through modern, standard doorways. However, if you live in a more historic building in Chicago, we recommend measuring your doorway.

Bugaboo Kangaroo

Sleek. Smart. Super adaptable.

If the Donkey is the social butterfly of the Bugaboo fam, the Kangaroo is the minimalist with a clever twist. It’s lightweight, modern, and designed to quietly keep up with real life. Its suspension is top-notch, the push is whisper-smooth, and it converts to a double when your family’s ready.

The Kangaroo’s charm is in its simplicity. No flash, just function—and the kind of good design that makes parenting feel a little bit easier (and cooler).

💡 Ideal for city parents and neat freaks. We see you.

Silver Cross Wave 3

Timeless luxury + toddler-proof toughness.

Want something that says refined but ready for real life? The Silver Cross Wave 3 is your match. It includes a toddler seat, bassinet AND the tandem seat—right out of the box. Even better, it has built-in tandem adapters so you're not chasing down extra parts once you add baby #2.

It’s beautifully made (British vibes included), sturdy enough to handle rough sidewalks, and loaded with versatility—over 30 configurations in total! Whether you're pushing a newborn and a toddler or coordinating twins, the Wave 3 can flex with your family.

✨ Bonus: The tailored fabrics and chrome accents are chef’s kiss.

Cybex Gazelle S

Your everyday-everything stroller.

The Gazelle S is like that friend who always has snacks, a spare charger, and exactly what you need. It’s not just flexible—it’s intuitive. It seamlessly converts from a single to a double without adapters, and it even includes a removable shopping basket that you’ll wonder how you lived without.

Whether you’re managing daycare drop-offs, errands, or weekend outings, the Gazelle S keeps up without complaint. It’s compact enough for city life but sturdy enough for big days. And it grows with you and your babies with 20+ configurations, including car seat combos and forward- or parent-facing options.

🙌 Best for families who like options, need storage, and love when things just work.

Nuna Demi Next

Premium feel with a parenting brain.

The Demi Next is what happens when Nuna decides to level up an already-loved stroller. With its sleek lines, compact frame, and built-in flexibility, it’s a top pick for parents who want function and form.

It converts to a double by adding a second seat below (stair-step style), comes with a rider board and adapters included, and offers a magnetic harness that makes buckling in a squirmy baby actually manageable. The ride is smooth, the build is solid, and—let’s be honest—it looks really, really good.

📷 It’s giving “cool parent” energy.

Try Them Out IRL — We’re Here to Help

You can read stroller specs ‘til 2 a.m. (we get it, we’ve been there), but nothing beats actually pushing one around, folding it up, and seeing what clicks. Come visit Galt Baby in Northbrook or Chicago and get hands-on help from our stroller experts. Whether you're team Vista V3 or curious about the Cybex Gazelle S, we’ll help you figure out what works for your life.

🛍️ Shop online anytime at galtbaby.com
🧸 Stroller demos, assembly, and local delivery? Yep, we do that.
💬 Got questions? We’re real parents and real gear nerds—ask away.