The Ultimate Guide to Family Travel with Robin DeGracia
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The Ultimate Guide to Family Travel: How to Explore the World With Your Kids (Without Losing Your Mind)
Think family travel sounds impossible, especially once your kids hit the teenage years and have their own schedules, opinions, and social lives? Robin, founder of Around the World with Kids and mom to a 13- and 15-year-old, is proof that it’s not only possible, it’s one of the most rewarding things you can do for your family. With four continents, roughly 12 countries, and most of the United States under their belts, all while holding down regular jobs and keeping her kids enrolled in public school, Robin has cracked the code on how to make family travel work in the real world.
Here’s your ultimate guide to family travel, packed with her best tips for every stage of the journey.
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Start Small — But Start Now
The single most important piece of advice Robin offers: don’t wait for the “perfect” moment. Start small if you’re nervous. A full day trip to a local park or city gives you a chance to practice packing, managing kids on the go, and rolling with unexpected hiccups, all without the pressure of a flight or hotel reservation hanging over you. Graduate to a weekend trip, then a longer one.
And start young. Babies at three months old are surprisingly easy travel companions — they’re immobile, easy to soothe, and don’t yet have the mobility or the opinions that make toddlerhood so challenging. Robin learned this the hard way, first attempting India with a nine-month-old (who was crawling, in the stranger-danger phase, and eating solids — a recipe for travel chaos), and then returning a year later with a three-month-old, which she describes as a completely different, and far easier, experience.
The key insight? The earlier you start, the more your kids grow up seeing travel as normal. They don’t know any other way of being, and that makes everything smoother over time.
Work With the School Calendar — Not Against It
One of the biggest obstacles families face is the school schedule, but Robin has found that with communication and creativity, it’s much more manageable than people expect. She and her family focus travel on school breaks, but when a truly meaningful trip comes up (like a week in Washington, D.C. tied to a family wedding) she has found teachers to be remarkably accommodating.
In fact, Robin’s daughter’s teachers leaned into a D.C. trip by making it part of the curriculum: her daughter had to visit the Supreme Court and take photos for a presentation on the three branches of government. Travel became homework, and everyone won.
The lesson: communicate with teachers early, keep students accountable for what they miss, and know that most educators understand the irreplaceable value of experiential learning. As Rachel, a high school teacher on the podcast, put it — she actively encourages her students to travel because peak-season prices are brutal and no trip is worth missing if the alternative is just sitting in class.
Get Your Kids Involved in the Planning
One of Robin’s most effective strategies for traveling with teens and tweens is including them in the planning process from the start. When kids have a say in where the family goes and what they do, they have buy-in — and that buy-in is the difference between an enthusiastic travel companion and a miserable teenager sulking through every museum.
On a recent trip to Hawaii, Robin let her oldest choose snorkeling with manta rays over her preferred Captain Cook Memorial snorkel site. Was it exactly what she had planned? No. Was everyone happy? Absolutely. For their Europe trip, which included Warsaw, Auschwitz, Prague, and Berlin, she had the kids help research memorials and immerse themselves in the history through an audiobook, We Were the Lucky Ones, during a pre-trip road trip. By the time they arrived, they were engaged, curious, and emotionally prepared.
As kids get older, you can hand over even more responsibility. Robin’s daughter helped plan an entire Disneyland trip for her Girl Scout troop, complete with a shower schedule, while her oldest served as navigator and DJ on their California road trip. These aren’t just fun roles; they’re life skills in disguise.
Use Points, Miles, and Smart Budgeting to Make It Affordable
Family travel is expensive, but it doesn’t have to be prohibitive. Robin is a devoted points-and-miles strategist. Her family is loyal to United Airlines and stacks credit card points alongside airline miles to offset the cost of flights. On their Europe trip, she used points to cover two of the four tickets — saving somewhere in the range of $3,000 to $4,000 on flights alone.
Food is where budgets tend to spiral, and Robin has a system for that too. She Instacarts breakfast supplies directly to the hotel room or Airbnb before the family arrives, cereal, waffles, fruit, granola bars, coffee, so mornings don’t turn into expensive restaurant bills. She also packs snacks in her day bag to avoid the $20 theme park popcorn trap. For meals out, the family aims for one or two memorable splurge dinners per trip and keeps the rest to moderate restaurants and street food.
She’s also started teaching her kids to budget during trip: giving them a set amount of money at Disneyland to cover food and souvenirs over three days. Watching her daughter weigh whether she really needed the full meal or could survive on a Mickey pretzel was, Robin says, one of the best financial lessons she could have given her.
The Best Destinations for Families
When it comes to choosing where to go, Robin’s recommendations vary by age. For younger kids, she suggests beach resorts — the Caribbean, Hawaii, Mexico — where there are kids’ clubs, calm waters, and built-in ease. Amusement parks are always a win, and camping is an underrated, budget-friendly option for local exploration.
Her most surprising international recommendation? Buenos Aires, Argentina. She took her kids there when they were three years old and 18 months old, and it was one of the easiest international trips she’s ever taken. Every neighborhood had bright, well-maintained playgrounds where families congregated after school. Every restaurant had a high chair. Waitstaff played with her toddler. A street singer spontaneously held her daughter through the rest of his set when she toddled up to him. The city was warm, welcoming, and genuinely family-oriented in a way that surprised her.
For older kids, she’s a strong advocate for culturally rich destinations — Europe for history and context, Bali for perspective on how others live, India for a complete immersion in a world very different from their own.
Travel Builds the Humans You Want Your Kids to Become
Perhaps the most compelling argument in Robin’s ultimate guide to family travel is the least logistical: the way travel shapes kids’ characters. Her children have learned to navigate public transportation, exchange currency, communicate across language barriers, and adapt when plans change. In Bali, they played soccer with local school kids and came home with a genuine understanding of how different (and how similar) lives can be around the world. In India, they had hard conversations about poverty and inequality that no classroom lesson could replicate.
Travel teaches empathy. It builds confidence. It creates shared memories that families carry for a lifetime.
And if you’re still on the fence? Robin’s closing advice is simple: just take the trip. Start local, start small, start wherever you are. The more you go, the more natural it becomes — for you and for your kids. You’ll make mistakes (a forgotten swimsuit, a forgotten formula, a terrible timing decision), and it will all be okay. Because the memories you build along the way are worth every single moment of the chaos.
Robin shares family travel tips, destination guides, and money-saving strategies at AroundTheWorldWithKids.net and on Instagram, Facebook, and TikTok at @AroundTheWorldWithKidsBlog.
