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Traveling with Grandkids: Tips for a Successful Three-Generation Trip

by Susan Crandell | November 21, 2023

A friend of mine took each of her grandchildren on a trip of their choice when they turned 13. One kid opted for an African safari; another wanted a posh spa week in Hawaii. While I love to travel with my grandson, Zeke, I have no desire to whisk him away, leaving his parents at home. For me, there is no better time to be had than exploring a wonderful new place with all three generations on hand. Seeing my daughter, Brook (’s Executive Editor), and her husband, Ryan, parent Zeke is a privilege (not so fun, I suppose, if you aren’t in tune with your child’s parenting style).

The key to a great family trip is finding the sweet spot where everybody’s aspirations overlap. For us that means physical activity, glorious scenery and geology, and coming away with a new understanding of a foreign place.

And so on our latest trip together, we chose Iceland. All four of us crave outdoor experiences, which were on offer in abundance. We soaked in hot springs, summited a volcano, transited a glacier cave, and even eyeballed one of the youngest islands on Earth, born in a fiery eruption just 60 years ago. I am older than that island.

Susan and her family inside an ice cave in the Myrdalsjökull glacier, Iceland.
Zeke crosses a bridge inside an ice cave in the Myrdalsjökull glacier, Iceland.
Zeke crosses a bridge inside the cave. Photo: Ryan Damm
A little teamwork gets Brook across a stream near Hverager∂i, Iceland. Photo: Ryan Damm
Susan and Brook hike the path from Hellnar to Arnarstapi on the Snæfellsness Peninsula. Photo: Ryan Damm
Three generations hiking near Budir, on Iceland’s Snæfellsness Peninsula. Photo: Ryan Damm
To go off-road in Iceland, you need a specialized “super-jeep,” like this. Photo: Ryan Damm


On any trip, each family member must find their role. In Iceland, Brook, our resident travel expert, was our driver and trip leader. Ryan and Zeke roamed beaches, mountains and glaciers with cameras slung around their necks, trading lenses and composition tips; call them our staff photographers. Me, I pay the bills.

Zeke lines up a shot from atop the Eldfell volcano on Heimaey island, Iceland. Photo: Ryan Damm
Zeke photographing Kirkjufell, on the Snæfellsness Peninsula. Photo: Ryan Damm


Grandchildren are a joy to watch as their personalities and capabilities grow. Nowhere is this more evident than on a trip. Travel provides a backdrop that makes us ponder, even reconsider, our own customs and behavior. There is nothing more thrilling than seeing a grandchild connect with a new place, delving into life there and asking smart questions. (On a zodiac ride through a lagoon full of icebergs that had just calved off a glacier, it was Zeke who picked up on the particularly glassy sheen of some bits; those spots, our private guide explained, had recently been underwater and surfaced when the chunk’s center of gravity shifted.)

Susan and her family on a private zodiac in the Jökulsárlón glacial lagoon, Iceland.

We spent 10 days in Iceland. We like to travel independently, so a self-drive trip was right up our alley. Perhaps our family is a little too type-A. In the early days of the trip, we were putting in 12-hour days, often hiking more than six miles. There was so much to see, and we are a no-stone-unturned group. I have to say, nobody complained. We made a return trip to the magnificent Seljalandsfoss and Gljufrabui waterfalls first thing in the morning to avoid the crowds that had thronged these cataracts in late afternoon the previous day. On the island of Heimaey, we weren’t satisfied with just viewing the world’s largest colony of puffins at the recommended hour of six a.m. when the birds take flight to spend the day fishing. That afternoon, we took a RIB boat around the Westman Islands to watch the plucky little birds dive for their lunch, then capped our puffin experience with a visit to the Beluga Whale Sanctuary, which provides a haven where injured puffins can live out their lives. I would love to revisit Heimaey in August, when the baby puffins, called pufflets, fledge. Thousands each year, diverted by artificial lighting, end up in town rather than at sea. The residents, and any tourists lucky enough to visit Heimaey at that time, race around with boxes, scooping up lost pufflets and releasing them at the ocean’s edge.

A path takes you behind the Seljalandsfoss waterfall on Iceland's southern coast. Photo: Ryan Damm
A puffin on Heimaey island, Iceland. Photo: Zeke Damm


A good three-generation trip involves compromise too. A horse lover from childhood, I couldn’t wait to ride an Icelandic horse, a breed so protected that no one is allowed to bring any horse in (or even return a horse that had previously left the country). Not everyone in our party shared my enthusiasm, but we all signed up for a trail ride at the Skálakot Manor Hotel (our favorite lodging of the entire trip). The Icelandic breed is compact and muscular, and five-gaited rather than the typical three. Farrah Fawcett would envy their flowing mane and tail. I was in heaven trying one of the extra gaits, a fast-walk/slow-trot called tolt.

Susan and family ride Icelandic horses through purple lupin. Photo: Ryan Damm
Skálakot Manor Hotel, a friendly farmhouse-turned-hotel in Iceland. Photo: Ryan Damm


In return, I agreed to an ear-splitting, bone-crunching ATV ride to a black-sand beach where we viewed the wreckage of a DC-3 that crash-landed in 1973. An ATV will never be my ride of choice, but the beach scene and the remote river gorge we traveled to afterward was worth every bump.

Some of Iceland’s most beautiful spots are best accessed via ATV. Photo: Ryan Damm

Any trip, however many generations you have on board, needs a good laugh. Another Icelandic black beach delivered. The Djúpalónssandur Beach of shiny ebony pebbles lies on an outcropping of land we referred to as the Snuffleupagus Peninsula (Icelandic is beautiful to listen to but impossible to pronounce; can you say Snæfellsness?). I don’t know whose idea it was to bury Brook in pebbles, but once that had been accomplished and photographed, of course Zeke had to be buried too.

Brook got buried in black pebbles on Djúpalónssandur Beach. Photo: Ryan Damm
Zeke got buried next. Photo: Ryan Damm


Witnessing a grandkid’s first is always worth the price of admission; sharing that first with your grandchild’s parents multiplies the thrill. Iceland’s classic tourist route, The Golden Circle, served up a tall one for Zeke. Generally, the sights were paler imitations of the mountains, canyons, and waterfalls we had seen on our far-flung driving itinerary. But this day became remarkable when Zeke spotted his first geyser. (Iceland is a country of hot springs, with enough geothermal energy to power the entire island with kilowatts to spare; the very word geyser is derived from Icelandic.) Luckily our geyser was a busy one, spouting every few minutes, because Zeke wasn’t satisfied that he’d gotten the right shot until it had erupted more than half a dozen times. Watching him check a photo, then reposition himself for the next one, was more memorable to me than the steamy water spurting into the air.

Zeke lines up his fourth shot of the Strokkur geyser in Iceland. Photo: Ryan Damm

Iceland was such a success that another cluster of volcanic islands is our number-one candidate for next year’s three-generation trip. The Azores seem on the brink of popularity, which fits our family motto: “Get there before the crowds.” That’s an important factor in our formula for success. For another family, exploring a vibrant city or seeing the artifacts of an ancient civilization might be the best choice. Here, as in all other family matters, communication is key—making sure everybody is enthusiastic before you book the trip.

Find more ideas and advice for multi-generational trips here. Want to make lifelong memories with your family in Iceland or elsewhere? Click the black button below to get our advice.



Susan Crandell is a former Executive Editor of Travel + Leisure magazine. These days, when she’s not traveling with her grandson, you can usually find her building houses with her local chapter of Habitat for Humanity.


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