Planning the Perfect Multigenerational Vacation
Planning the Perfect Multigenerational Vacation
From safaris to Alaska: adventures that work for everyone, ages 7 to 78
The African savannah: one of those rare places where age becomes irrelevant and everyone arrives at the experience as an equal.
Right now, I'm in the middle of planning three very different trips, each one for a different kind of group, each with its own beautiful logistical puzzle.
The first: a family extending a hiking adventure through the dramatic peaks of the Dolomites in northern Italy. The second: a sister/friend group embarking on a 100-mile walking tour through the rolling villages of the Cotswolds. And the third: an epic Alaska cruise for a family spanning the full range, ages 7 to 78, with grandparents, parents, and grandchildren all making the journey together.
Each of these trips is a study in what multigenerational travel actually requires. Not just a good destination, but the right destination, chosen with intentionality, planned with flexibility, and designed so that everyone gets to be fully present for it.
Multigenerational travel is having a moment. Research shows 85% of families now plan at least one multigenerational trip per year, with the desire for deeper connection as the primary driver. Families are choosing shared experiences over shared stuff, and travel has become the most powerful vehicle for that.
"A well-planned multigenerational trip creates memories that outlast any gift. But getting it right takes more than choosing a pretty destination."
The best multigenerational trips are designed so that every generation has their own moment, and plenty of shared ones.
Why Multigenerational Travel Is Different, and Worth It
Let's start with the honest truth: multigenerational travel is harder to plan than almost any other kind of trip. More people means more preferences, more physical considerations, more budget conversations, and more potential for someone to feel like the itinerary wasn't designed for them.
And yet, families who do it well describe these trips as transformational. A seven-year-old watching her first elephant cross a dusty savannah road while her 78-year-old grandfather sits beside her, both of them speechless, that's not something you can manufacture. That shared wonder is what multigenerational travel is actually about.
The key insight that changes everything: multigenerational travel doesn't mean everyone does everything together. It means everyone feels considered. The best trips weave moments of full-group togetherness with genuine options for each generation to follow their own interests, and that design requires intention from the very beginning.
Five Foundations of a Great Multigenerational Trip
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01
Start With a Shared Wish List, Not a Destination
Ask everyone: adults, teens, and yes, the kids, what they want to feel or experience on this trip. Rest? Adventure? Wildlife? You'll find more common ground than you expect, and the destination that rises to the top will already be pre-filtered for compatibility.
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02
Choose the Right Space
How a family sleeps matters as much as where they're going. Villas, connecting suites, and lodge family configurations each offer a different balance of togetherness and privacy. Shared kitchens and common living areas are also underrated. When a family can ease into a morning at their own pace, the whole atmosphere of the trip shifts.
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03
Anchor the Day, Then Leave the Rest Open
One or two anchor experiences per day with the rest genuinely open. Structured mornings paired with loose afternoons is a rhythm that consistently works across generations, and a trip with three extraordinary experiences and real breathing room will be remembered more vividly than one where every hour was accounted for.
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04
Think Through Mobility Early
What works for a 35-year-old doesn't work for an 8-year-old or a 78-year-old. Are there elevators? How far is the walk between accommodation and activities? Are there gentler alternatives on the same day? Getting clear answers to these questions before booking is far more valuable than the aesthetics of any destination.
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05
Outsource the Logistics to Someone Who Knows This
Multigenerational trips have more moving parts than almost any other kind of travel. A travel advisor who specializes in family travel can anticipate problems before they happen, negotiate better room configurations and group rates, and build contingency into the itinerary so a change in weather or energy level doesn't unravel everything.
The Safari: Where Every Generation Becomes a Child Again
If there is one travel experience that consistently stops every generation in its tracks, simultaneously, it's a well-planned African safari. Age doesn't determine who gets the most from it. A seven-year-old and a seventy-year-old sitting side by side during a predator sighting are having exactly the same experience, and the shared wonder of that moment is what makes safari memories so deeply bonding.
Botswana's Okavango Delta: peaceful enough for grandparents, magical enough for children.
"The magic of a safari is that it doesn't sort by age. Everyone arrives at that first game drive as an equal, and leaves with the same story."
Top Destinations for Multigenerational Safari
Kenya: Masai Mara
The classic safari destination. Consistent, dramatic wildlife viewing, including the Great Migration from July through October, with lodges offering strong children's programs, hot air balloon experiences for older travelers, and Maasai cultural visits that engage every age.
Botswana: Okavango Delta
For families seeking something quieter and more intimate. Mokoro (dugout canoe) rides through the Delta channels are peaceful enough for grandparents and magical for children. Private concessions offer near-complete solitude and a sense of genuine wilderness.
South Africa: Sabi Sands and Madikwe
South Africa's malaria-free regions make it the most practical choice for families with very young children or older adults with health considerations. Excellent infrastructure, world-class game viewing, and combining Cape Town with safari is one of the most satisfying trip structures in all of travel.
Tanzania: Serengeti and Ngorongoro
For the full East African experience. Vast open plains, the extraordinary Ngorongoro Crater, and the opportunity to pair safari with cultural visits that give everyone, especially children, a more textured understanding of the continent.
Expedition Travel: The Multigenerational Experience in a Category of Its Own
There is a style of travel that sits entirely apart from the typical vacation, and for multigenerational families willing to venture a little further off the beaten path, it produces some of the most profound experiences any group can share together. Expedition travel, at its core, means going somewhere genuinely wild, with a team of experts who help you understand what you're seeing and why it matters.
Unlike a resort or a city itinerary, expedition travel doesn't require participants to be physically extraordinary or especially adventurous. What it requires is curiosity. Small expedition ships, remote wildlife lodges, and guided wilderness journeys are all built around the idea that the destination itself is the experience, and that everyone on board, regardless of age or ability, deserves full access to it.
Alaska's Inside Passage, where glaciers calve into the sea and humpback whales surface beside the ship.
What Makes Expedition Travel So Well-Suited to Multigenerational Groups
The Expedition Advantage
- Small ships and intimate group sizes mean access to places larger vessels and tour groups simply cannot reach: remote bays, wildlife-rich coastlines, glacier fjords
- On-board naturalists, scientists, photographers, and cultural specialists turn every outing into something genuinely educational, engaging for all ages without feeling like a classroom
- Daily activity menus offer options at varying intensity levels: kayaking, hiking, Zodiac cruising, naturalist talks, photography walks, so each generation follows what calls to them
- You unpack once. The ship or lodge is home base. No packing and unpacking between destinations.
- The pace is deliberate. There is always the option to stay aboard, rest, observe from the deck, or join a gentler activity while others push further
Operators like Lindblad Expeditions in partnership with National Geographic have been pioneering this kind of travel for decades, and they remain one of the gold standards for multigenerational expedition cruising. Their National Geographic Explorers-in-Training program gives children and teens a hands-on, field-educator-led curriculum available in Alaska, the Galápagos, Baja California, Iceland, and Antarctica. But the expedition travel landscape has grown considerably, with excellent operators now offering immersive small-ship and land-based journeys across every continent.
Alaska: A Perfect Expedition Destination for Every Generation
I'm currently planning an Alaska expedition cruise for a family with members ranging from a seven-year-old to a great-grandparent in her late seventies, and Alaska was the clear choice the moment I understood the group.
Alaska rewards presence more than almost any destination on earth. The landscape is so vast, the wildlife so immediate, and the wilderness so unfiltered that it creates something rare: a genuine shared experience across every age. The youngest traveler earns a Zodiac "driver's license" through an on-board youth program. The oldest finds a naturalist talk in the ship's lounge, a warm deck chair, and a humpback whale surfacing fifty yards off the bow. Neither is a lesser version of the trip. Both are the trip.
The Inside Passage between Juneau and Sitka winds through Tracy Arm, Glacier Bay National Park, Icy Strait, and Chichagof Island. Each morning brings a wake-up call from the expedition team when something worth seeing has appeared: bald eagles, orcas, breaching humpbacks, calving glaciers. Naturalists are on hand to put it all in context, which transforms a beautiful wildlife sighting into something you actually understand and carry with you.
"Alaska doesn't ask you to be athletic to be astonished. It just asks you to show up and pay attention."
Other Exceptional Expedition Destinations for Families
Galápagos Islands: The ultimate nature immersion, where wildlife evolved without natural predators and has no fear of humans. Children walk beside blue-footed boobies and marine iguanas at close range. Grandparents sit on ancient lava fields and watch sea lions sleep in the afternoon sun. Everyone leaves changed. Year-round access makes scheduling flexible, and the remote setting ensures the experience feels genuinely rare.
Baja California (Gray Whale Season): A shorter, more accessible expedition into the lagoons where Pacific gray whales come to breed each winter. This is a bucket-list wildlife encounter that works beautifully for families traveling with older adults who want something profound and unhurried rather than physically demanding. Whales approach the boats willingly, sometimes close enough to touch.
Iceland: For families drawn to dramatic, otherworldly landscapes rather than wildlife alone. Expedition journeys in Iceland offer hiking past waterfalls, Zodiac cruising through glacier-carved fjords, puffin colonies along the Westfjords coast, and humpback whale watching in the north. The activity range is wide enough to suit every fitness level, and Iceland's long summer days mean more time to be out in it.
Antarctica: The most remote and arguably most awe-inspiring destination on earth. Expedition travel is the only way to experience it properly, and for families with older children and grandparents who have truly seen the world, it is often described as the journey nothing else quite prepares you for. The scale, the silence, and the sheer improbability of being there tends to bring even the most widely traveled families to a standstill.
Adventures Beyond the Typical: Three Trips I'm Building Right Now
Every family is different. And sometimes the most meaningful multigenerational trips aren't safaris or expedition cruises. Sometimes the most meaningful are something quieter,, more personally tailored to who the family actually is. Here are three I'm currently designing.
🇮🇹 The Dolomites Extension: Where the Mountains Do the Work
The Dolomites of northern Italy are among the most dramatic mountain landscapes in the world: sheer limestone towers, bright green meadows, stone villages that haven't changed in centuries, and a network of trails ranging from gentle valley strolls to serious alpine ascents.
For a family extending their Italy trip into this landscape, the Dolomites offer something crucial: optionality. More active travelers can take on the famous Alta Via routes or multi-day hut-to-hut treks. Others can follow the wide, accessible valley paths through Alpe di Siusi, Europe's largest high-altitude meadow, or take cable cars up for the views without the climb.
The key is choosing the right base: a property with enough character to feel distinctly Italian, positioned so that everyone can set out in different directions and reconvene over dinner with a different story to tell.
🏴 The Cotswolds Walking Tour: 100 Miles of Sisters, Friends & English Villages
The Cotswolds Way is a 100-mile National Trail winding through some of England's most quintessentially beautiful countryside: honey-colored stone villages, ancient beech woodlands, rolling hills, and pubs that have been serving walkers for centuries.
What makes this kind of trip so special is what it strips away. There's no agenda beyond the next village, no decisions beyond which path to take, no distractions from the extraordinary simplicity of walking through a landscape that has barely changed in three hundred years.
Planning a multi-day walk requires careful logistics: luggage transfers between each night's accommodation, a mix of village inns and country houses that balance character with comfort, and enough flexibility to account for weather, blisters, and the irresistible temptation to linger over a cream tea in a garden that feels too perfect to rush.
🇺🇸 The Alaska Family Cruise: Ages 7 to 78, and Everyone Gets Their Moment
A family spanning four generations is, in essence, four or five different travelers with a shared love for each other. The expedition cruise format serves exactly that reality: it offers genuine adventure and genuine accessibility in equal measure, without anyone having to choose between the two.
Grandchildren can kayak through a sea otter habitat in the morning while grandparents settle into a naturalist talk on deck, binoculars trained on a bald eagle in a nearby spruce. Come dinner, every seat at the table has a story attached to it. Those stories tend to get retold for years.
Alaska also does something quietly profound for multigenerational groups. The landscapes are so vast and the wilderness so genuinely untouched that it humbles everyone equally. Nobody has been here before in quite this way. And arriving somewhere new together, without hierarchy, is one of the most connecting things a family can do.
Ready to Start Planning?
Whether you're dreaming of a safari, an expedition through Alaska, a walking tour of the Cotswolds, or something entirely your own, I'd love to help you design it.
Begin Planning Your Trip →