Each year, my tween son and I take at least one vacation together — a tradition born by chance when a hotel scouting trip to California happened to fall during his second-grade spring break. On impulse I booked him a plane ticket, and our five days on the West Coast turned out to be some of the sweetest we’d spent: catching the ferris wheel at the Santa Monica Pier, nibbling gelato as we strolled the winding streets of La Jolla, sharing funny stories and silly jokes. Since then, our annual getaways have become a treasured way to connect with each other, free of the homework, sports practice, dinner rush and other distractions that define our busy days at home.
As I learned on that first trip, there’s no better reminder to live in the moment during those too-short childhood years than a special vacation just for you and your son. Like all families, you’ll have your own unique idea of the perfect destination for one-on-one bonding. But for a little inspiration to get the plans started, here are 10 boy-approved trips that our CB! team has taken and loved.
On a ranch vacation, the vast menu of activities means that moms and sons can strike the perfect balance of alone time and together time. CB! founder Amie O’Shaughnessy recently experienced Colorado Trails Ranch (pictured above) with her son and adored everything about it, from the simple but comfortable accommodations to the personalized riding setup. As with most dude ranches, there are no TVs and no WIFI in the guest cabins, so everyone gets a digital detox. Plus, the inherent structure built into a ranch vacation, and the fact that there’s no car required, allows moms to relax and engage without being preoccupied by driving and directions.
We've traveled the world with boys of all ages! Our Family Travel Advisors can recommend destinations, book accommodations, arrange guides and more. Click to send us a request >
Venice seems tailor-made for a mother-son visit: It feels adventurous, yet it’s safe and you can walk anywhere day or night. And there are so many unique neighborhoods within the city to explore. Thrill your guy off the bat by splurging on a private water taxi down the Grand Canal — he’ll feel like a pint-size James Bond. Getting lost amid the labyrinthine streets and waterways is half the fun, so pocket the map and just wander a while, soaking up the dreamlike, slightly eerie atmosphere. When you’ve gotten oriented again, sample some of the only-in-Venice activities that make for an unforgettable trip. Get creative with a mask-making workshop; learn to row like a gondolier; take a walking tour through the convoluted history of the Doges’ Palace; stroll through St. Mark’s Square late in the evening, after the day-trippers have gone and live orchestra music drifts through the air. Pure magic!
Kind and helpful locals, widely spoken English, jaw-dropping scenery, easy driving and safety … what’s not to love? Norway is a dream destination for an adventure-loving mom and son duo. This action-oriented 7- to 10-day itinerary from CB!’s Kristi Marcelle can be done either as a road trip (very easy to navigate with Google Maps, though there are some logistics with ferries), or via train and ferry with a couple of bus transfers. Start the trip in Oslo, home to sights such as the Oseberg Viking Ship, then get into the countryside to cruise fjords, peek inside ancient stave churches, hike glaciers and more.
TIP: Norway is known as an expensive place to visit — in reality, hotels and activities are comparable to other European countries, but it’s the food that costs a lot. It’s challenging to find reasonably priced meals for families. Fortunately, Norwegian Airlines is making the airfare part of the equation easier, with reasonably priced nonstop flights to Oslo from various gateway cities in the U.S.
Learning an adventure sport, like surfing, together builds trust and brings moms and sons closer in a way that few other experiences can match. Immersive surf-instruction camps are plentiful throughout Central America, but the trick is to choose one geared toward families. Our top pick: Peaks n’ Swells on Costa Rica’s Nicoya Peninsula, which offers weeklong sessions just for parents and kids — there’s a maximum of three families at a time to ensure personal attention and low student-instructor ratios during each day’s lesson. When it’s time to take a break from the waves, relax with a yoga class while the boy in your life joins in a pickup soccer game or hangs out by the pool with other kids. As a bonus, all-inclusive pricing means the logistics couldn’t be simpler, and you won’t be doing mental math every time your ravenous son makes another trip to the buffet.
If you and your son are itching to tackle Asia, Japan is a terrific entry point: It’s distinctly, enticingly different yet offers the familiar conveniences kids are used to. Our favorite Japan itinerary with kids pairs a few days in Tokyo with a short stay in Kyoto for a taste of both ancient and modern. Gamers and gadget lovers will be especially mad for Tokyo’s Akihabara electronics district, 24-hour arcades, high-tech museums, driverless bullet trains and, of course, conveyor-belt sushi shops. But don’t get so caught up in the digital world that you miss out on other must-dos, like ascending Tokyo Tower, exploring the Senso-ji Temple, strolling the Ueno Zoo or sampling sea creatures at the Tsukiji Fish Market.
Denmark may be famous for Viking history and midcentury design, but kids know it for one big reason: Legos! Capture a brick-builder’s heart with a visit to Billund, home of Lego headquarters, where a very special Lego Inside Tour is offered several weekends a year (these sell out in a blink, so sign up early). Your son can meet and build alongside Lego designers, tour the factory, pick up souvenirs at the staff shop, and get a close-up look at rare building kits you won’t find anywhere else in the word. As a bonus, the original Legoland amusement park is nearby, with enough rides and hands-on activities to keep little guys busy for a whole day. And when it’s time to settle in for the night, get cozy in Legoland Holiday Village, which offers life-size replicas of cottages and cabins from popular Lego series like Ninjago. And be sure to dedicate at least two or three days at the start or end of the trip exploring Copenhagen.
New York’s high-octane energy is perfect for active boys, and the bottomless layers of history, culture, iconic sights and just plain fun make it effortless to design a trip around kids’ personal interests. My son and I spent a week in the city last summer and agreed it was one of the best vacations we’ve taken together. We admired the views from the Empire State Building and Top of the Rock; craned our necks skyward at the base of Lady Liberty; conquered the Met and the Museum of Natural History; ate pizza in the shadow of the Brooklyn Bridge; strolled amid vintage planes on the flight deck of the U.S.S. Intrepid — and that’s just for starters. From Broadway to baseball to biking along the river, both moms and boys will have a blast discovering their own slice of Big Apple bliss.
Want to wow even the most jaded teen? Take him to Iceland. With its wonderfully weird landscape and endless supply of thrills — think driving on glaciers and scuba diving between tectonic plates — this otherworldly island satisfies an older kid’s craving for new and offbeat experiences. He may be long past the cute and cuddly animals phase, but he’ll be entranced by puffins, minke whales and sturdy Icelandic horses. Plus, there’s something about this remote country that inspires boys to let their silly side out. On Amie’s recent mother-son Iceland vacation, one of the highlights was an off-road buggy ride through bumpy terrain and muddy rivers … giggles galore!
Group trips are great opportunities for mother-son getaways — as with a dude ranch or surf camp, there’s a built-in social environment and enough structure to take the pressure off Mom. Our love affair with Adventures by Disney is well documented on Ciao Bambino. It goes without saying that Disney is tuned in to what makes kids tick, but the difference makers here are twofold: the access privileges and special experiences that come with the company name, plus the joy of sampling an action-packed itinerary without having to plan every step. Destinations span the globe, from Peru to Scotland to South Africa, and at least one of them is probably on your son’s bucket list. Best of all, Adventures by Disney allows kids as young as 4 on some trips, a perfect fit for those who want to start the mother-son travel tradition sooner rather than later.
I know more than one tween (including mine) who has serious New Zealand envy after watching the Lord of the Rings movie trilogy, which was filmed there. Indeed, the rich and rugged scenery is straight out of a fantasy novel. New Zealanders have capitalized on the Tolkien craze and guided tours of “Middle Earth” pop up everywhere, but it’s not difficult to put together a self-drive pilgrimage on either the North or South Island (to do both requires at least two weeks and a ferry transfer). Gems include the movie-set village of Hobbiton; Kaitoke Regional Park, aka Rivendell; and the town of Twizel, from which you can tour the site that became home to the iconic Pelennor Fields battle scene. Just know that driving is on the left side of the road and many roadways can be steep, winding and narrow, i.e. not for the timid.
Want to save all the great intel and tips you are finding on Ciao Bambino? My Trip Planner allows you to bookmark articles, family-friendly hotel reviews, and family vacation packages. Simply click the heart icon on anything you want to save. Site registration is required to get started. Happy planning!
Please fillout the form below to create your free My Trip Planner account.