7 Rules to Survive the Modern Multi-Gen Vacation

Once upon a time, family vacations meant cramming parents and kids into a station wagon, arguing over the radio, and hoping to make it to the nearest national park without bloodshed.

Today, family travel has evolved. Americans are increasingly choosing vacations that include not only parents and children seeking quality time together, but also grandparents, great-grandparents, cousins, in-laws… you name it.

And these multi-generational trips can be an incredibly rewarding experience.

Really.

My family took its first multi-generational trip to Disney World 28 years ago. (We like to be ahead of the curve.) And we’ve been lucky enough to take many shared trips since… traveling en masse to Italy, Spain, Portugal, Turks and Caicos, and more.

Over the years, we’ve learned that planning a multi-gen trip comes with its own set of challenges. Honed by two decades of experience—and a recent trip to Athens, Paros, and Antiparos with family members aged 28 to 71—here are seven rules to follow to make your family adventure a success.

Rule #1: Plan Ahead for Multi-Gen

Take individual preferences into consideration while you plan, whether that’s budget, dietary restrictions, or mobility issues (for example, wheelchair accessibility for Grandpa).

Months before arriving in Greece, my brother-in-law Mark did yeoman’s research to arrange a great boating experience around the islands of Paros and Antiparos that would accommodate everyone’s needs. Included in the day were swimming, snorkeling, fishing, some history, and a delicious seafood lunch.

We had the boat to ourselves. Our own music. Our own itinerary. A delightful captain and first mate. Shade from the sun. All in all, a perfect day.

Could we have arranged a boat once we arrived? Maybe, depending on what was available at the time. Most likely it would have been either a "party boat" or a "sunset cruise," where you’re crammed with 40 strangers and served stale crackers and cheap champagne. (Not ideal for Grandpa.)

Instead, thanks to Mark’s planning, we had a private boat for an entire day where we simply showed up, cast off, and had a blast. Cost for the day: under $200 per person.

Rule #2: Opt for a House, Not a Hotel

A house beats traditional hotel rooms in every way. More breathing space to unplug, unwind, and relax… common areas for coming together or spreading out… a full-sized kitchen and a table to share meals around.

Granted, a house isn’t cheap, but it can be a bargain compared to separate hotel rooms. In Paros, hotels can run from $50 a night for basic accommodation… up to $650 a night for a high-end stay. Times that by the six rooms we needed for the week, and that’s a whopping $2,300 per person.

On Le Collectionist, we found a six-bedroom luxury villa for nearly half the cost ($1,350 per person) that included an infinity pool, gym, outdoor theater, gourmet kitchen, fire pit, two-person staff, and private chef.

Admittedly, it was a splurge. You can find more economic deals, albeit missing the outdoor theater and private chef. But with a house, you get so much more for your money.

And the cost can be more equitably dispersed across the whole group. Someone’s on a budget? Have them take the smaller bedroom.

Rule #3: Get Multiple Cars

Multiple cars mean maximum flexibility. One group can hike the Kolymbithres Trail while another goes shopping in Naoussa. Some can meditate on the beach at dawn while others take selfies at Pirate’s Cave on Cape Fanos.

Plus, it makes airport transfers and moving luggage easier… especially if you’re flying in separately.

Our rule of thumb: one car for every four people. For Paros, we used Surprice Car Rental.

Rule #4: Hire Guides

Rule #4: Hire a guide, whether your family is touring the Pyramids or the Parthenon. |©iStock/mit4711

What’s the difference between "Hmmm, I wonder what this is," and "Wow… that’s amazing"?

A guide.

Whether you’re visiting the Parthenon, the Pyramids, or the beaches of Normandy, a good guide makes history come to life. They can pick up a nondescript rock and turn it into a mesmerizing tale you’re still talking about hours later. They fill in the missing pieces. Add drama. Intrigue. Perspective. Meaning. And connect us to another time and place in the human journey.

Here’s a snippet from our Acropolis guide, Evan:

"It took 400 years to build Chichén Itzá and nearly 200 years to build Notre Dame Cathedral. The Parthenon took only nine years. In 440 BC. Without machines. Or modern technology. That shows how advanced their engineering, mechanical, and architectural skills were.

"Athenians like to joke that it took nine years to build the Parthenon and 45 years to renovate it— and we’re still not done."

Sounds like the Connecticut turnpike.

Rule #5: Build in Shared Experiences

Whether it’s hiking, biking, kayaking, a cooking class, or game nights, shared activities create cherished memories. When we sit at Thanksgiving dinner and reminisce about prior vacations, what do we talk about? It’s not the places, it’s the experiences. The time Mom got bounced out of the whitewater raft. Or when Grandpa and his wheelchair got trapped in Villa d’Este outside Rome. Or the time Dad tried to swallow a flaming sword in St. Lucia.

Having our day on the Aegean Sea together gave us snorkeling in the Blue Lagoon… sea caves in Antiparos… the Sanctuary of Apollo on uninhabited Despotiko… and cliff diving.

We’ll also remember a charming Cocoon moment on our Paros-to-Antiparos cruise. As we were overtaking a boatload of older French tourists, the passengers suddenly transformed into giddy teenagers, ripping off clothes and lustily leaping overboard to frolic in the sea.

As we were chuckling and trying to figure out what sparked the paroxysm of euphoria, the first mate approached. "Can I get you a drink?" she asked.

"I’ll have what they’re having," I said.

Unhurried time together also provides opportunities to pass on family stories and history. In Greece, we learned how my brother-in-law lashed himself to a mast to ride out a hurricane… and how an Egyptian tribe once offered to buy my wife for eight camels.

Rule #6: Leave Room for Serendipity

Sometimes the best memories come from unexpected detours.

Our chef, Nakos, kindly invited us to his family farm in Paros. There, we got to tour the vegetable garden; count chickens; play with dogs; admire the family’s lemon, lime, and mandarin orange trees; and marvel at a 3,000-year-old olive tree. (It didn’t look a day over 2,600.)

On a trip to Sicily, serendipity struck again when our Agrigento guide revealed he was friends with the mayor of Cammarata… the hometown of my mother-in-law’s ancestors.

The guide sent word of our impending visit. When we arrived, we were met by a welcoming committee including the mayor, his assistant, and the local town newspaper. The mayor gave us a tour of city hall, walked us through town, arranged a lavish welcome lunch, and feted us like VIPs.

So leave some room in your schedule for the unexpected.

Rule #7: Embrace Idiosyncrasies

My bride is obsessive about driving directions and has appointed herself trip navigator. Excellent.

She’s also a curious person. She’s curious about Athena and her victory over Poseidon. She has questions about The Iliad, The Odyssey and Herschel Bernardi. Also excellent.

What’s not so excellent is when her curious mind engages. Usually, it’s when I’m negotiating an impossibly narrow road while arm-wrestling a stick shift. This can lead to news flashes such as, "Oh, I think we were supposed to take that right turn two miles back."

Leave room in your schedule for the unexpected.

Another peculiarity: Have you heard of the five stages of grief? My travel companions have three stages of readiness.

Stage 1: Agreeing to go on a hike at 8 a.m. means sitting and having coffee at 8 a.m. and talking about the hike.

Stage 2: Around 8:20 a.m., there’s a general movement to start preparing to go on the hike.

Stage 3: At 9 a.m., we’re ready to walk out the door and finally go on the hike.

Every family has its quirks and habits. It’s best to embrace these idiosyncrasies rather than trying to fight them. After all, they’re what make a multi-generational trip unique… and often amusing.

That’s the most important rule of all. The heart of a trip is not the destination, but the shared moments.