The Ultimate Double Stroller Guide for Travel: Tandem vs. Side-by-Side

Allison Hass
Jan 13
5 min read

Updated: 3 days ago

Traveling with two little ones comes with enough decisions—choosing the right double stroller shouldn’t add stress. To find out what works best, two travel advisors recently hit the road together: one traveling with a side-by-side stroller (Zoe Twin²) and the other with a tandem stroller (UPPAbaby Vista). We tested them through airports, Walt Disney World parks and transportation, and a cruise ship, giving firsthand insights on what really works for family travel.

Here’s what we discovered:

Side-by-side strollers excel in airports and Disney parks
Tandem strollers shine for naps and certain Disney transportation
Cruise ships require something compact—like an umbrella stroller

Traveling Through the Airport

Side-by-Side Stroller Experience

Our side-by-side traveler found navigating TSA lines, airport trams, and long terminals a breeze. The stroller fit through security easily, and gate-checking was simple using its travel bag. Boarding the plane was straightforward—just fold, check, or carry as needed. At our destination, loading the kids back into the stroller was effortless.

Tandem Stroller Experience

The tandem stroller was smooth through TSA and terminals but folding and gate-checking proved trickier. Unlike the single-piece side-by-side, the tandem required removing a seat and securing parts together, which was cumbersome and time-consuming all while wrangling two toddlers (thank you to all who lended a helping hand during this transportation).

Airport Winner: Side-by-Side

Cruising With a Double Stroller

Double stroller waiting to get onboard cruise ship

The side-by-side stroller did not go on the cruise voyage, meanwhile the tandem stroller and an umbrella stroller did make the cut. Between the two, it was so much easier to navigate the hallways, ports, and elevators with the umbrella stroller. The tandem stroller, although it was nice when taking both toddlers down to get breakfast–its downfall was how much room it took up in the stateroom. There was no easy way to fold the two pieces and store them without taking up valuable closet space. While it was doable, in a smaller room the process of breaking it down just to bring it inside—and then having to maneuver around it once in the room—didn’t feel worth the effort. It also caused some issues when strolling down the hall midday with the laundry and room attendant carts throughout the hall. We found that taking the umbrella stroller meant less time detangling from laundry bags, dodging food trays, or the larger attendant carts.

Navigating Walt Disney World Parks

Moving through those Disney crowds can be difficult without adding in a stroller–especially a double stroller into the mix. The turning radius is larger on the tandem stroller making the ease of turning through the parks a little more difficult. The doorways were wide enough for the Zoe Twin to fit through, causing no issues there. When navigating through the parks and ease of talking with the toddlers, catering to their needs–water, snacks, and conversation–the side-by-side took the win here, as with the tandem it is hard to hear the kiddo up front or easily pass them things. The side-by-side kept the kids closer for redirection, meanwhile the toddler sitting at the front of the tandem stroller was loving trying to kick people as they walked by.

A benefit of the tandem stroller was naps, if one child is sleeping, the other could not bother them being up top or under them. Since we were traveling together, many times we chose to put the infant in the top of the tandem stroller for naps and more peace of mind for mom knowing she was safe, cool and content there.

Another advantage of the tandem stroller was its storage. While both undercarriages offered a decent amount of space, the side-by-side stroller couldn’t accommodate heavier items and was limited by the shallow depth of its basket. We often found ourselves transferring items from the side-by-side stroller to the tandem because the tandem made it much easier to access what we needed—whether in stroller parking, at a restaurant, or during a stop at a baby care center.

Disney Transportation & Ride Parking

Here’s the biggest comparison we noticed–transportation ease. For the buses, the side-by-side stroller was the easier option as there wasn’t an extra piece to keep track of getting onto the bus. If you are using a tandem stroller–or any stroller for that matter–we recommend a big bag that holds everything that you have in the stroller to lighten the load that you’re carrying.

Bus Winner: Side-by-Side

The monorail seemed easy for both the tandem stroller and side-by-side stroller. There is no collapsing, just drive it right on–we even fit both strollers in one car of the monorail. I could see that a wider side-by-side stroller may have a few more complications.

Monorail Winner: Tie

On the older boats, guests are generally asked to break down strollers when possible. As with other forms of transportation, the side-by-side stroller was easier to collapse. On the newer boats, however, the wider walkways are designed to accommodate strollers, allowing you to keep them in use. We found that on the older boats, if you have a sleeping child, you can keep the stroller open, but the side-by-side stroller is slightly wider and more difficult to maneuver when getting on and off the boat.

Boat Winner: Tandem

When approaching the Skyliner, we initially thought we could keep the side-by-side stroller open but quickly remembered that the narrow doors only allow tandem strollers and single strollers to roll straight on. Side-by-side strollers must be collapsed. We did learn that you can ask Cast Members to slow the line or request the accessible Skyliner if you need extra time to board. In our case, we were loading with two sleeping kids, an awake toddler, a double stroller, and all of our belongings spread out in the undercarriage (key tip: keep a bag handy to quickly gather everything). It was hectic trying to condense our items, break down the stroller, and get everyone onboard. Knowing this in advance makes a big difference, but overall, the tandem stroller is the clear winner for Skyliner transportation.

Overall, when deciding which stroller, understand the transportation options at the resorts and for the parks to select which resort is best for you and your stroller option!

Ultimate Double Stroller Guide for Travel Final Thoughts: Which Stroller Wins?

Choosing between a tandem and a side-by-side stroller ultimately comes down to where you’re going and how you’re traveling. Airports, cruise ships, and Walt Disney World all come with tight spaces, transportation rules, and long days–making ease of folding, maneuverability, and size just as important as comfort.

Planning a trip with little ones doesn’t have to be overwhelming–that’s where Touring and Cruises comes in. With many advisors experienced with traveling with littles, we are here to help parents plan vacations that are smooth, stress-free and truly magical–from stroller-friendly resorts to transportation tips and packing strategies.