Booking seats together. Reserving multiple hotel rooms. Coordinating around school calendars, sports team schedules, work events, and more. If you’ve ever planned a family vacation, you know how challenging finding the right time—and right destination—can be.
So we asked three expert family trip planners to weigh in with their tips to help you finally get your trip out of the family chat (and into TripIt). Here’s a quick summary:
| Tip | Why it matters |
|---|---|
| Plan 6-12 months ahead | Better flight and hotel availability |
| Use a travel itinerary app | Keep reservations organized |
| Be flexible with destinations | Helps maximize points and miles |
| Limit daily actitivies | Prevents travel burnout for kids and adults |
| Prioritize educational experiences |
Make travel more meaningful |
1. Plan family trips in advance
“Plan as far out as possible,” said Lauren Trimble of Adventuring Party of 4. “For flights, that’s about 11 months. For hotels, sometimes even earlier.”
Jenna Hansen, founder of The Traveling Hansens and full-time travel consultant, and Kamree Price, founder and creator of Our Family Passport, both agreed.
Jenna often books multi-week trips a year in advance. The same for Kamree: “I’m often planning six months, nine months, sometimes a year in advance,” she said.
Advanced planning is especially important when using points and miles—and when planning around school breaks. “The earlier you plan, the better the options,” Lauren said.
2. Count on TripIt to keep your family vacation organized
To keep their travel plans organized, all of our family travel experts use TripIt.
“I’ve been using TripIt for over a decade. It’s second nature at this point,” said Lauren. “The first thing I do when I book anything is forward the confirmation. Then, I always check Nearby Places to find a gas station close to the airport before returning a rental car. And I rely on the Notes section to add reminders for myself—like, pick up snorkel gear—while we’re on the go. Plus, I can easily share an itinerary with my husband so he knows what’s been booked.”
“When you’re planning trips that last two or three weeks, there’s a lot of moving parts,” added Jenna. “Thankfully, TripIt organizes all the details: flights, hotels, activities, tickets, and more. I often ask myself, ‘Did I book us a hotel for that city?’ And of course, the answer is always in TripIt.”
Kamree likewise leans on TripIt to keep track of her advanced plans.
“Thanks to TripIt, I’m not digging around for our December trip to Egypt that I booked back in January,” she said. “It saves me from the stress of wondering, ‘Where is that reservation number?’ Or, ‘Are we all on the same booking?’ With TripIt, everything is in one place—and I can quickly check the app for the details I need.”
3. Use points and miles to plan a family trip
“Traveling with a family of six is a lot different than as a couple—or even a family of four,” shared Jenna. “Between flights, hotels, and meals, costs really add up—but we travel more now thanks to points and miles.”
Jenna was quick to point out that there’s more to award travel than just cashing in: “First, using points and miles is for people who have healthy credit and budgeting habits.”
Once you’ve earned points, you can start thinking about how to book travel. The key? “You have to be flexible,” said Jenna. “And with points and miles, that sometimes includes being flexible with your destination.”
And while no destination is off the table, there’s a reason to stick to bigger cities.
“Anywhere children live, children can visit,” she said. “But I tend to book bigger destinations because there’s more availability and I can use our points for hotels.”
4. Unlock the best places for family vacations
Like the others, Lauren uses points and miles to offset the cost of every trip, helping her feel like no place is off-limits anymore.
So, what destination has stood out among the rest? For the Trimbles, it’s the Galápagos Islands.
“It’s a place that changes you,” Lauren said. “It doesn’t feel like real life.”
Her family snorkeled alongside sea lions and sea turtles, spotted blue-footed boobies (a must-see for her six-year-old), and even saw orcas just feet from their boat. They also learned about the importance of protecting wildlife—and understanding that, as humans, we’re just visitors to their habitats.
Want more of Lauren’s tips? Read her story here.
Kamree’s dream trip would be taking all the generations of her family on an African safari. “I want all of us to be immersed in the natural beauty of Africa; to wake up hearing and seeing the animals,” she said. “It will be educational, yes, but it will also be magical.”
And the number one on the bucket list for Jenna and her brood? “It’s so hard to choose! We want to see the Northern Lights in Iceland, and go on a safari in Africa. We’re also dreaming of staying in over-the-water bungalows in the Maldives.”
5. Book one family-friendly activity per day
Being flexible also comes in handy while traveling with kids. Jenna shared that allowing room for your travel plans to flux is important—for your kids and your peace of mind.
“I tell my clients: set your expectations so low that they’ll only go up,” she said. “Don’t book yourself solid. Delays happen; things go wrong; kids get tired—or bored. Stay positive and don’t overdo it.”
As a rule of thumb, Jenna likes to book no more than one activity per day. Then, she makes a list of the things she’d like to do, but embraces going with the flow. “So much is out of your control when you travel. You will enjoy your trip more when you let go of expectations.”
6. Turn travel into a learning experience for kids
As an art history professor, mom, and stepmom, Kamree knows the value of an education. But she also believes in the power of traveling—especially as a family.
“School is, of course, incredibly important, but so is seeing the world,” she said. “Those experiences are also an education. Traveling shows us how similar we are; that we’re all global citizens.”
Keep reading: Going Places: A Conversation with Kamree Price.
Lauren agreed, saying she sees travel as an extension of her kids’ education.
“They learn about Picasso in school, and then suddenly they’re seeing his work in a museum in Spain,” she said. “That’s an a-ha moment you can’t replicate.”
Her kids attend a Spanish immersion school, so travel also gives them a chance to use their language skills in real life—from ordering food to navigating new places.
“Travel helps them connect the dots.”
