For travelers, a milestone celebration can serve as the perfect occasion to gather friends or get the whole family together for the multigenerational trip of a lifetime. After all, what could make a birthday, anniversary, or family reunion more memorable than staging it in a location nobody, most importantly the guest(s) of honor, will ever forget?
According to luxury tour operator, Zicasso, inquiries for summer 2026 travel arrangements are seeing an acceleration in trip requests for multigenerational groups. And many of those trips involve milestone celebrations of one type or another, says Marci-Beth Maple, senior manager of the Zicasso advisory team.
“Especially in the post-pandemic years, we are seeing more multigenerational families treat the trip itself as the milestone celebration. Rather than gathering for a single dinner or event, they are investing in an experience that gives several generations meaningful time together,” Maple says.
Adult children are increasingly bringing their aging parents along on trips, and grandparents are increasingly initiating trips centered on their grandchildren, she added.
Families are combining several occasions into one extraordinary journey. There is a strong sense of ‘If not now, when?’ And a desire to create the kind of shared memory that will remain part of the family story long after the trip ends.
The company recently planned a trip that involved grandparents who wanted to design a vacation to engage their grandsons in the history, culture, and wildlife of New Zealand, while keeping the adults invested at the same time.
“Our specialist built the itinerary around that mission. Dolphin watching in Queen Charlotte Sound, glowworm caves, nighttime tree walking in Rotorua, [and] luge runs in Queenstown. The family spent Christmas in a house in Nelson, where the kids swam in the pool while the adults grilled steaks,” says Maple.
Another trip planned by Zicasso for an extended family was centered around a Kenyan safari that brought together milestone birthdays and several grandchildren’s high school graduations, she says.
“In many cases, families are combining several occasions into one extraordinary journey. There is a strong sense of ‘If not now, when?’ And a desire to create the kind of shared memory that will remain part of the family story long after the trip ends,” says Maple.
When planning your own travels, she says, keep in mind that often it’s the simplest moments during a celebration-focused or multigenerational trip that end up becoming the most memorable since that is often when connections are made among travelers.
If you are planning a group gathering that spans a large range of ages, be aware of the “pacing gap,” says Joanna Rigby-Jones, an Africa Specialist with Timbuktu Travel who has planned such trips to places like Tanzania and Egypt.
“Young kids often lose interest in activities and experiences quickly and prefer to move around at a faster pace, while the older generation moves at a slower speed and likes to really soak up each spot,” she says.
In order to work around that, Rigby-Jones builds itineraries that cover key touring spots in the mornings—when everyone is rested, energized, and more patient—and leave afternoons for downtime.
For inspiration for your own birthday, anniversary, or multi-gen family reunion, we talked to tour operators and travel advisors about some of the most epic and rewarding celebratory trips and destination gatherings they’ve planned for their clients in recent memory.
Conversations have been condensed for brevity and clarity.
An unforgettable milestone birthday set on a yacht in Antarctica
Gather your closest friends and family for a polar adventure on the 12-person expedition yacht Octopus.
Courtesy of Mosaic Studios/EYOS Expeditions
As told and organized by Ben Lyons from EYOS Expeditions.
Yachting vacations create a natural ebb and flow. You can have the whole, multigenerational group together, and then they can disperse for different activities according to their own activity levels. Later, they come back around the table together for a celebratory meal. It’s a rhythm that creates a natural camaraderie between generations, instantly.
One of our clients was planning a young milestone birthday shortly after the pandemic. He invited his friends as well as his parents and other family members in their early 20s through 70s to come along for a yachting adventure in Antarctica aboard the 413-foot-long expedition superyacht Octopus.
They flew to Antarctica to meet the yacht. And on his actual birthday, the skies turned baby blue and our client wanted to go heli-skiing. We were able to get him up on a peak that had never been skied before to ski down. The experience evolved to include his friends and family, too. We set up a lounge area on the top of this mountain with views probably for 100 miles down the Antarctic Peninsula. You could see whales blowing in the distance, the peaks on the other side of the peninsula stretching to the horizon, and the yacht, far below. Everybody was up there toasting to him, his parents gave a very heartfelt toast. It was just a wonderful memory that is going to last forever for them.
A meaningful family and friends reunion trip to Mongolia
Does it get any more epic than a group getaway to the Three Camel Lodge in Mongolia’s South Gobi province?
Courtesy of Nomadic Expeditions
As told and organized by Undraa Buyannemekh of Nomadic Expeditions.
Our clients wanted to recreate a trip they’d taken with their daughters decades ago to Mongolia, when the girls were just teenagers. Now, they’re grandparents to six grandchildren. The group includes other families, with 14 people in total ranging from age 8 into their 70s, and they’re traveling for 12 days [in August 2026].
The grandfather’s goal in recreating the trip he remembers is to make sure the group doesn’t only stay in established camps but gets to see remote wilderness areas, too, to appreciate the vastness of Mongolia. We’ve arranged a drive from Ulaanbaatar to reach the Eastern Grasslands, which is home to the largest herd of gazelles in Mongolia. They’ll travel with biologists to spot the wildlife, enjoy nature hikes and drives, and spend two nights camping in the wilderness at a remote camp we are organizing in an area with no accommodations.
After that, they’ll return to Ulaanbaatar and fly to Three Camel Lodge in South Gobi province for more activities, including seeing dinosaur fossils the kids have learned about in museums back home.
One evening at the lodge, we’re planning an outdoor dinner under Mongolian tents and inviting young kids similar in age to the kids in the client’s group to perform a concert and traditional dance. Children love seeing kids their own age, so that’s always so meaningful.
We’ll always make sure there are activities for everyone to enjoy. While someone is riding a bike outside or doing archery, someone else can be doing an artisan workshop, for example.
The kids have been hearing about Mongolia all their lives, and now they’re reaching an age where they can really appreciate it. And that’s what the client wants for this trip.
A villa in Tuscany for a birthday to remember
Villa Tramonti in Tuscany is the ideal place for groups to slow down between sightseeing adventures.
Courtesy of Villa Tramonti
As told and organized by Jessica Russell of Red Savannah.
Our client was celebrating a 60th birthday [in May 2025] to include three generations of the family as well as close family friends. We landed on Tramonti villa, in Tuscany’s Chianti region, as the perfect setting. The hosting party stayed in the main house while friends joined them in a guesthouse next to the pool.
The main challenge was encouraging the family not to overpack their itinerary, and to make sure they could spend time enjoying their villa, which came with two swimming pools, a media room with private cinema, Technogym, and lots of outdoor space. The family was very active, wanting to fill every minute exploring the area, and we had to encourage them to scale back their initial list of activities to something more realistic and less exhausting. We also wanted them to allow time to enjoy being together by the pool, dining alfresco with a lovely view over the Chianti hills, and just to let serendipity intervene. In the end, we found a happy balance that accomplished activities every day yet had time to unwind, too.
Among the activities we planned for the group were a guided hike in Fonterutoli, following the Etruscan and Black Rooster route, concluding at the Wine Bar Società Orchestrale for lunch.
Another day, the group enjoyed a truffle-hunting experience with a professional guide and his dog, followed by lunch made with fresh truffles. There was a wine tour, tasting, and private cookery class; as well as a private tour of Florence, visiting the Accademia (to see Michelangelo’s statue of David), the Uffizi, and Vasari Corridor; and climbing the bell tower in the Duomo.
On another day, the gentlemen spent an afternoon golfing, while the ladies took a trip into Florence to visit the Accademia gallery, the Duomo (to climb the famous bell tower), and the Farmacia Santa Maria Novella. In this location midway between Florence and Siena, there was always plenty for the party to see and do.
A Japanese American grandmother hosts a reunion in Japan with her family
Bring the family together for a fun-filled road trip through Japan’s Hokkaido region with stops in places like Noboribetsu.
Photo by Aestelle/Unsplash
As told and organized by Jessica Klauzenberg of Timbuktu Travel.
Our client, a grandmother, 76, who is originally from Shikoku, Japan, wanted to take her two children (in their early 40s) and two grandchildren (ages six and 12) back to the country for something new. They’d all traveled to Japan before to visit family in Shikoku. But this time, the grandmother wanted to take everyone to someplace that none of them had visited before.
Opting for a wild itinerary through Hokkaido meant the trip became a shared discovery for everyone, including the grandmother, since it reframed what traveling to one’s home country can look like.
The family had told me they didn’t know whether they’d travel together again, emphasizing the importance of this trip, and it was something very powerful to consider and shaped the itinerary. We wrapped in more downtime and more room for the family to simply be in each other’s company and enjoy all the places they visited.
Since I speak Japanese and lived in Japan, I was able to design the itinerary directly with the grandmother, in her language, with cultural nuance and trust built in from the first conversation. We landed on a self-drive loop through Hokkaido so they could travel at their own pace—the majority of the trip was self-guided and self-drive as they wanted the flexibility to explore smaller hidden places along the way; they had one guided tour in Sapporo.
With a six-year-old and a 12-year-old in the car alongside three adults and grandma, flexibility mattered far more than the ground covered. The 10-day trip started in Hakodate and finished in Sapporo, taking in highlights like visiting a traditional onsen resort, Dai-ichi Takimotokan, in Noboribetsu, which the client says she particularly enjoyed since it had activities for all ages, and sampling lavender ice cream and enjoying the colorful flower fields in Furano that were in prime bloom during their summer trip.
