Italy With 11 Kids Under 10? How to Plan (and Pack for) an Extreme Family Trip
A gigantic family vacation with three sets of cousins and grandparents along for the ride is no time to wing it Anthony Bourdain style. Strategic packing and a flexible yet well-considered itinerary are key to making big multigenerational trips work, both on the road and once you make it to your destination.
To help you plan (and when you’re planning for this many people, it’s certainly best to start doing so well in advance) I asked 20 parents with extensive experience traveling with lots of kids and other relatives for their best tips. Whether you’re road-tripping to a lake house, spending a week at a Disney resort, or trekking to Machu Picchu with ten 2-year-olds, here’s how to make sure an extended family trip is the best — or at least the most memorable — you ever undertake.
Streamline your strollers and carriers
Travel agent and Adventures of a Disney Dad founder Matt Brandabur, who vacations with five kids aged 8 and under, says remaining hands-free is critical: “The baby carrier we love is the BabyBjörn Baby Carrier Free. Since we had twins, it was even more useful because both parents can carry a baby while also having free hands to help with the other kids.”
He adds that double strollers are a game changer and recommends a collapsible model like the UPPAbaby G-Link V2 Double Umbrella Stroller (which, unfortunately, is sold out everywhere): “It’s great quality, and the lightweight size makes it easier to carry through the airport when also carrying luggage, other kids, or car seats.” Magic Expeditions travel agent Alison Assner recommends the City Mini GT2 (which also collapses quickly and folds one-handed) as an alternative, and the Strategist’s resident stroller expert, Liza Corsillo, directed me to Zoe’s lightweight and compact Twin V3. For more adventurous trips, Brandabur tries to rent a double BOB Gear jogging stroller (“it has shocks and is easier to maneuver on uneven surfaces”) once he gets to his destination.
As for car rides, for kids aged 4 and older, Essner likes to bring along the BubbleBum inflatable booster seat. “It collapses flat for packing, but you can quickly blow it up if you need to hop in an Uber or taxi.”
Develop a day-hike game plan
Clearsurance travel-insurance expert Melanie Musson and her sister take their families on a joint summer vacation every year, and they always add several day hikes to the itinerary to keep everyone busy. Eight of their combined 11 kids are currently under the age of 10, so this seems ambitious. “But we have the best time,” she promises. Good gear is key, and she recommends the Kinderpack baby carrier, which remains “so comfortable, even on long hikes.”
She also likes to give each child a CamelBak Mini Mule water-bladder backpack. “They get to pack snacks and one or two small toys of their choice,” she explains. “Then they have what they need to keep themselves happy, but the adults aren’t stuck carrying it.”
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Infant Kinderpack
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Stay on your sleep schedule
“If my kids have naps or quiet time at home, I try my best to keep a similar schedule on vacation,” says Brandabur. If you’re entering different time zones with a big group of kids, there are ways to signal when it’s time to get some shut-eye, says travel agent LaDell Carter, who took 12 members of her family to Italy and Switzerland this past summer: “With younger children, I put them in their pajamas before we even leave for the airport — I want them boarding the aircraft already understanding that this is bedtime.” And when boarding a flight, “never check the lovie, blanket, or pacifier because those keep naps happening in an unfamiliar place,” says Essner. One exception: You might consider relaxing family screen-time rules on travel days. “A favorite movie can buy you an entire flight.”
If your flight gets in early and you have the budget for it, Carter suggests booking your hotel room for the night prior to arrival so you don’t have to wait around for a 2 p.m. check-in. “Otherwise, you may have an exhausted toddler still wearing pajamas, tired grandparents, teenagers who want Wi-Fi and a shower, and hours to fill,” Carter says.
Duffel bags can do it all
“Duffels over suitcases,” recommends Foley PR co-founder Jen Boersma, who travels with her six kids. “Hard suitcases are wonderful right up until you are stacking eight of them in a minivan. Duffels squash, stack, and slide into the gaps. The only hard case we bring is the one that holds anything breakable.”
Viktor Marohnić, founder and CEO of 57hours, essentially only takes his family on extreme trips in terms of destinations — his youngest daughter spent a week camping in Yosemite when she was just 4 weeks old. So he only invests in the most durable, family-friendly adventure gear, such as Patagonia’s Black Hole duffel, which comes with backpack straps. It “survives being thrown into a van, a boat, or onto a mule, or anywhere a roller bag doesn’t,” he says.
If you just can’t do without roller bags or are contending with mobility issues, duffels with wheels offer “the perfect mix of space, usability, and utility,” says the Luminaire founder Adam Sebba.
Or consider non-clamshell suitcases
Strategist senior editor Jen Trolio went on an 11-person (including five kids ages 3 to 10) family trip to Disney World Orlando last year that required packing skills of steel. A big takeaway was that non-clamshell suitcases take up a lot less valuable hotel-room space when everyone’s competing for it. She likes Away’s flexible Softside Carry-on, which has one deep packing compartment rather than two and can be rummaged around in with ease.
Whichever luggage you use, try to reduce its size and choose accommodations with laundry facilities instead of bringing lots of spare clean clothing. “For these trips, if everybody has massive suitcases, then it really limits what you can do, and makes every transfer a pain,” says Richard Campbell, founder of 10Adventures.
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Everyone gets their own bag …
On the subject of luggage, “one thing I have learned about traveling with children is that they love feeling involved,” says Carter. “They want to help pack. They want to carry something. They want to feel as though they have an important role in the adventure.” So let them have their own (appropriately sized) bag, especially as it means you won’t have to carry it yourself once they’re past a certain age.
Boersma also says “one bag per child” is the way to go. “The moment you start packing by category instead of by person, you own every outfit decision for the entire trip. If it is their bag, they know what is in it, and a 9-year-old can get themselves dressed.”
It’s still a good idea to bring one additional family “float” bag where the shared stuff lives, says CityMoms founder Jeanine Bobenmoyer: “Extra chargers, a mini-first-aid kit, sunscreen, the stuff that’s shared between everyone.” Her other nonnegotiable is a dedicated dirty-laundry bag. “Book an Airbnb with laundry or schedule a laundromat stop near the end of the trip — coming home with clean clothes is a gift to your future self.”
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And their own snacks
Mom of eight Linda Perillo, whose mom runs Perillo Tours, has eight kids and a lifetime of travel experience. She says that doing a dollar-store run before the trip and letting everybody pack their own snack bag “eliminates the ‘Mom, do you have’ routine and gives them some sense of control while giving me some peace.”
Ziplocs work great as snack bags, and Carter also recommends Stasher’s silicone bags, which she’ll often fill up at the hotel breakfast buffet with fruit for later: “They are reusable, easy to rinse, and useful for everything from snacks to small travel accessories.”
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But not their own passport
Keeping one parent in charge of all the travel documents “helps reduce airport chaos,” says Sebba. The risk of one family member leaving their passport in their plane seat pocket just isn’t worth taking.
Bring some exciting new toys
When it comes to kids’ toys, alongside everyone’s favorite stuffed animals, “I always save a few surprises specifically for travel,” says Carter. “Something they have not played with every day at home tends to hold their attention a little longer.” She likes suction toys for young children who might need to be entertained while waiting in lines and at airport lounges and also recommends packs of temporary tattoos to mark the trip. “My biggest rule is to avoid games with dozens of tiny pieces,” she adds. “There is nothing enjoyable about crawling underneath an airplane seat searching for a miniature game piece while the person behind you is trying to sleep.”
Don’t be afraid to separate the group …
“If you’re traveling with eight or more people, I wouldn’t plan every activity for everyone together,” says Andrés Serra, head of operations at Optimise Travel. “I suggest having one group activity in the morning, giving two options in the afternoon, and meeting up for dinner. Before splitting up, make sure everyone knows when and where to meet, how they’ll get around, and which adults will be with each group.”
Aim for one big group event or meal per day — and because restaurant reservations for groups of ten people can be tricky to get, book well ahead of time or cook together at your accommodation.
Or rent more than one car
On road trips with big groups, “having multiple cars is easier,” says family-travel expert Emilie Brillon, who recently road-tripped to San Diego with two families. “We rented a seven-person car and all traveled together, but it would have been nice to have two cars so my sister could have gone back to the house to put the little baby down for a nap when it was getting to be too much.”
Games will bring everyone together
Compass realtor Stephanie Moon recently spent a ten-day Alaskan cruise with 39 extended family members and friends. While it was important for everybody to have their own space and downtime, card games united the group when needed. “Piles! was the biggest hit for this year,” she says. “At first, it was my nuclear family playing, then the cousins, and one night, all the kids, young adults, and aunties.” Similarly, “some of our funniest family travel memories happen when everyone gathers in one room to play a card game,” says Carter. “We recently returned from Lancaster, Pennsylvania, and everyone was playing Taco Cat Goat Cheese Pizza until midnight.”
Let teens take charge
When traveling with a large group that includes a bunch of teenagers, Serra recommends putting “more of the budget toward good accommodation and less toward booking lots of paid activities” because teens prefer to choose how to spend their time and are less inclined to stick to regimented schedules. A centrally located hotel within walking distance of local attractions is ideal for these scenarios.
He suggests giving each teen “a small cross-body bag for their room card, portable charger, and emergency contacts” before letting them roam free. “Also,” he says, “save an offline copy of the itinerary on everyone’s phone with two meeting spots and a contact number in case someone can’t get online.”
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Set up a buddy system
“My big kids help with the little ones,” says Fun Park Go travel agent Alan Eskelsen, who’s a single dad of six. “When you’re the only parent, you need a team. I pair each older kid with a younger one for the day. The younger one has a buddy, and the older one feels trusted.” For park trips, he also suggests getting everybody the same brightly colored T-shirt so they can be spotted from a distance.
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AirTag everything
“Because keeping track of 12 people is enough,” Carter advises putting AirTags (or similar Android-compatible Bluetooth trackers, such as Tiles or Samsung SmartTags) in “checked luggage, carry-ons, backpacks, and sometimes smaller bags that have a habit of being left behind.” (Apple’s FindMy app allows you to label AirTags and other trackers so you know which items they are tracking.) She adds that if lots of people are using the same brand of suitcase or duffel, it’s worth purchasing custom luggage tags for each person to visually differentiate the bags at a glance. For similar reasons, “I recommend getting packing cubes in different colors for each family member,” says Voyagers Travel Company adviser Maria Emilia.
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Leave fluffy towels at home
While not as plush as regular cotton towels, microfiber alternatives are essential when you’re heading to the beach for the day with 11 kids, says Musson. “They’re much easier for parents to carry in a beach bag.” They’re also easier to wash in the hotel sink or beach shower and will dry much more quickly.
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Let the tripod be your photographer
You’ll definitely want to chronicle your big family trip, but who takes the multigenerational group photo? “One of our best travel purchases is a collapsible phone tripod,” says Sund. “We set a ten-second timer and get photos with the whole family, even somewhere remote where nobody is around to help.”
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Relinquish control to a local guide
Marohnić always hires a local guide on his family trips, even if he understands the destination well. This way, he says, you’ve got one person who knows the area, makes the safety calls, and (“this is the part parents underrate”) can be the voice of authority. “Kids will listen to a guide when they’ve long stopped listening to their parents,” he says. Guides are also pretty good at taking group shots if you forgot to take along a tripod.
Bring offline activities
For kids who are digitally detoxing and need to be kept busy, Whitt likes bringing offline games and art supplies. She also recommends packing a pair of compact, kid-size binoculars, plus an old-fashioned compass that they can learn how to use on the trip.
“Give each kid a project: a disposable or camp camera to shoot on the trip or a scavenger hunt you set up the first morning,” says Elena Rodriguez, founder of Studio Roam Travel. “It gives them something to do that isn’t asking you what’s next.” Instant cameras are also a hit, says Julie Day of multigenerational travel agency Gatherwell Travel. “Kids can use it themselves — some of our favorite photos from family vacations were taken by our kids on a Fuji Instax Mini.”
Plan around the youngest or slowest family member
Everyone I spoke with advised forming travel plans around the youngest or slowest member of your family group. Still, you should also trust they can do more than you think. “We always treated our kids like they were capable, and when you go in with that mind-set, it surprises you how much more they can do,” says Marohnić.
Outdoorsy destinations are ideal for mixed-age groups …
There are lots of adventurous destinations that hold up for big groups of mixed ages, says GearJunkie founder Stephen Regenold, who has five kids. Hut-to-hut hiking in the Dolomites or the Alps is a wonderful option because you can eat at restaurants on the trail and “there’s enough infrastructure that you’re not lugging too much gear.” (To avoid the Instagram crowds, he says Slovenia’s Julian Alps are “the quieter, cheaper version of the Dolomites.”) He also recommends Iceland for an outdoorsy group trip because it’s a place where “everyone is outside and you’ll see grandparents and toddlers on the same trail.”
… But resorts and cruises are still the safest bet
Host of the Family Travel Unpacked podcast Melissa Conn plans a wintertime family trip with over a dozen family members each year, including seven kids ranging from 5 to 20 years old. And while they’ve experimented with all types of trips, the easiest “has definitely been a cruise,” she says. That’s because there’s always something going on for everyone, from sports to karaoke to pool time. And “the all you can eat at all hours is perfect for teens’ weird sleep schedules and hollow legs,” she adds.
Choose a cruise line with an onboard nursery for babies and toddlers if you’ve got young kids with you (“Disney Cruise Line and Royal Caribbean are good choices,” says Essner), so the adults get to enjoy at least one grown-up dinner. If you’ve got teenagers, consider a smaller expedition-style cruise. “The Galápagos Islands are perfect for this because the destination does much of the entertaining for you,” says Emilia. “Instead of parents constantly having to convince people to put their phones down, the days are filled with snorkeling alongside sea lions, kayaking, spotting giant tortoises, and discovering extraordinary wildlife.”
For trips on dry land, Disney resorts work well, although not all Disney accommodations are made equal. “We love the family suites at Disney’s Art of Animation Resort,” says Eskelsen. “You get a separate bedroom, a pull-out couch, and a table that folds down into a bed. The best part is the two full bathrooms. There’s also a mini-fridge and microwave, so we do breakfast in the room and save a lot of money.”
Our experts
• Alison Essner, travel agent, Magic Expeditions
• Jeanine Bobenmoyer, founder, theCityMoms
• Matt Brandabur, founder, Adventures of a Disney Dad
• Emilie Brillon, family-travel expert
• Richard Campbell, founder, 10Adventures
• LaDell Carter, travel agent, Royal Expression Travels
• Melissa Conn, host, Family Travel Unpacked
• Julie Day, travel agent, Gatherwell Travel
• Maria Emilia, adviser, Voyagers Travel Company
• Alan Eskelsen, travel agent, Fun Park Go
• Viktor Marohnić, founder and CEO, 57hours
• Melanie Musson, travel-insurance expert, Clearsurance
• Stephanie Moon, Realtor, Compass
• Linda Perillo, travel agent, Perillo Tours
• Elena Rodriguez, founder, Studio Roam Travel
• Stephen Regenold, founder, GearJunkie
• Adam Sebba, founder, the Luminaire
• Andrés Serra, head of operations, Optimise Travel
• Jen Trolio, senior editor at the Strategist
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