Marking Milestones: How, and Why, More Families Are Celebrating Special Occasions With Travel

A recent AAA survey reports that 76% of Americans planning to travel this year are centering their trips around life milestones. The study also notes that two in five respondents say traveling for important events helps them reconnect, and nearly half say they rely on travel advisors to help plan their trips.

"As families spread out, travel has become an essential way to stay connected," said Stacey Barber, vice president of AAA Travel. "It’s inspiring to see travelers thoughtfully planning trips around life’s most meaningful celebrations.”

It’s a trend advisors are noticing, as well.

“Clients tell me experiences feel more meaningful than things — and everyone has too much ‘stuff,’” said Erin Smith, founder of Cultivating Connections Travel Planners. “Travel is becoming their way of marking their milestones. They want to create memories they’ll carry for years.”

Experiences feel more meaningful than things — and everyone has too much ‘stuff.’

According to Smith, the wide-ranging destinations and types of celebration trips she's planned include Turks and Caicos to mark a milestone birthday; anniversary celebrations in Italy, France, Greece, the Dominican Republic and Japan; and trips to Hawaii, Cancun and a Danube River cruise to commemorate high school and college graduations.

But families are not limited to marking only one milestone at a time. Steve and Abby Smith from San Diego, California, are planning a tailor-made Smithsonian Journeys itinerary with Audley Travel for their family of five to celebrate a 60th birthday, their 30th anniversary and three graduations.

“We were willing to splurge on one big trip rather than celebrating everything separately,” Abby Smith said. “We’re also looking forward to bucket-list experiences we wouldn’t have done otherwise.”

Multi-Gen Milestones

The 2025 U.S. Family Travel Survey conducted by the Family Travel Association found that multigenerational trips of three generations or more are a major trend, with 71% of grandparents having taken one and another 57% planning one in the future. There’s also an uptick of parents, aunts, uncles and grandparents gifting one-on-one trips to younger family members, signaling the expanded potential of multi-gen bookings.

Jeffrey Roy, vice president of marketing and sales at Eurobound, says the company is seeing a rise in dual-generation trips, including an aunt planning a graduation trip to Norway and Sweden with her nephew.

“The nephew wanted outdoor activities, so they’re doing a self-drive [trip] for two weeks to Oslo, Alesund, Vaga, Mora and Stockholm,” Roy said. “The same aunt has several nephews and previous trips included Greece and Italy.”

Eurobound is also working with parents who are taking their son to Paris for a cultural-immersion trip. And last year, Roy says, a set of grandparents and their grandchild planned an Italy itinerary centered around sports cars, visiting producers Ferrari, Lamborghini and Maserati.

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Lauren Quirk, founder of Travel With Character, is seeing growth in one-on-one milestone travel, as well, including one client who is taking her nephew to Spain during this summer’s solar eclipse.

“The priority for her is designing the entire experience around his interests,” she said. “Their itinerary includes private food tours in Barcelona, boating in Mallorca and guided museum visits in Madrid.”

How Are Families Celebrating Milestones?

Cultivating Connections’ Smith says many celebration trips are tailor-made, and several tour operators specialize in curating private, personalized itineraries for families, including Kensington Tours.

“Every family is different in what they want to do and see, but a really common request is going ‘off the beaten path’,” said Karolina Stringer, a Kensington destination expert for Italy, during a family travel webinar.

Stringer explains that this can mean visiting lesser-known destinations, or can serve as a request for unique experiences, such as Rome's Gladiator School, where kids can learn about gladiators and then dress up for a fun battle, or the operator's one-of-a-kind opportunity to go truffle hunting with an Italian princess in the Tuscan countryside.

“She has bloodline from Mona Lisa, so that’s pretty amazing,” Stringer said.

For clients who'd rather mingle with other travelers, Trafalgar, Adventures by Disney, Tauck and Backroads all offer family-focused small-group tours.

“Milestone travel aligns naturally with what Adventures by Disney does best — bringing families together in meaningful ways while they explore the world,” said Kyle Raser, senior manager of Adventures by Disney Trip Operations. “What we see time and again is that families aren’t just celebrating a moment — they’re creating a shared memory that becomes part of their family story.”

And of course, Sarah Kruger of Travel With Character notes that cruising continues to be popular with families, particularly multi-gen groups that include a wide range of ages and interests.

“Cruises remain a standout favorite,” she says. “Itineraries offer something for every generation, from kids’ clubs and family-friendly entertainment to gourmet dining and relaxing spas. Add breathtaking scenery and cultural in-port experiences and cruising is the perfect choice for families wanting to celebrate collectively without sacrificing anyone’s interests.”

Ellen Bettridge, president & CEO of Uniworld Boutique River Cruises, says the increase in families choosing to celebrate milestones through travel encouraged the line to offer a product specifically tailored to such trips. 

“[Families] are trading traditional gatherings for shared experiences they’ll remember for years to come,” she said. “That’s exactly why we introduced Generations Collection sailings designed for families and timed around school breaks, so it’s easier to bring everyone together. These sailings turn a special occasion into something even more meaningful — an opportunity to experience the world side by side.”

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The More the Merrier

While some families splurge on one big adventure to mark a significant life event, planning several smaller celebrations throughout the year may be better aligned with a client’s budget — and many resorts are jumping on that bandwagon, including Sensira Resort & Spa in Mexico’s Riviera Maya and Beaches Turks and Caicos, which are seeing a rise in families choosing resort vacations to mark important moments in a meaningful way.

“We’re seeing more families choose travel as the way they celebrate moments they want to experience together,” said Antonio Mendez, CMO at Arriva Hospitality Group, parent company of Sensira. “It reflects a broader shift we’re seeing: Families are redefining celebrations as time together, shared experiences and memories that feel personal. That’s what makes these trips feel meaningful.”

Deryk Meany, general manager of Beaches Turks and Caicos, notes that families also appreciate the opportunity to step away from their everyday routines and share uninterrupted time.

"Many of the most memorable moments we see aren’t the big celebrations themselves, but the in-between ones: families reconnecting over dinner or learning something new together," he said.

Gathering to mark special occasions is nothing new, but traveling together to mark them makes family celebrations even more special.

“I'm seeing more and more clients investing their time and resources in exploring new places and sharing experiences, rather than acquiring more things,” Kruger said. “Clients return from these vacations saying the memories will last far longer than any material gift ever could.”