These unforgettable intergenerational trips create strong bonds, shared experiences and cherished memories to last a lifetime
By Nancy Schretter, Contributing Editor
Dorothy Marsh owns a treasure trove of magical memories made while traveling individually with her grandchildren. Between 2007 and 2025, the avid Road Scholar traveler has taken seven grandchildren on 22 intergenerational trips.
“The experiences have been life-changing for me and my grandchildren,” Marsh says.
To express their appreciation, each of Dorothy’s grandchildren wrote a thank-you note to her for Christmas last year, sharing their favorite experiences and the heartfelt joy of traveling together.
This well-traveled grandmother is not alone. Increasingly, families are leveraging the benefits of grandparents traveling exclusively with their grandchildren on skip-generation vacations. Often referred to as “skip-gen trips,” these meaningful getaways involve just two generations – grandparents and grandchildren traveling together without the parents.
“Skip-generational trips have been on the rise in recent years and show no signs of slowing down,” says Jessica Griscavage, founder and CEO of Runway Travel. “With fewer time and budget constraints, grandparents are often well-positioned to plan these trips – giving parents peace of mind and a meaningful shared experience for the family.”
Grandparents and grandchildren bond and enjoy time together on memorable skip-generation trips. Photo courtesy of The Walt Disney Company
WHY GRANDPARENTS AND GRANDKIDS ARE TAKING TRIPS TOGETHER
Grandparents traveling with grandchildren is a popular part of today’s family travel patterns, according to the 2025 U.S. Family Travel Survey, conducted by the Family Travel Association (FTA), the NYU School of Professional Studies, and Good Housekeeping. The survey found that 73% of grandparents typically take at least one multi-day skip-gen trip each year. About three-quarters of today’s grandparents plan and organize their skip-generation getaways, and the vast majority pay for the entire experience.
Parents and grandparents believe skip-generation vacations are an excellent way for grandparents and grandchildren to forge closer bonds, spend extended time together and make lasting memories. Since many grandparents live farther away from their grandchildren than ever before, distance can make it difficult to spend as much time together as they desire. Skip-generation trips can help close that gap, allowing grandparents and grandchildren to enjoy extensive one-on-one time together and share unforgettable experiences.
The advantages of these trips are substantial. “One of the biggest benefits is the memories made, but beyond that, it’s the opportunity for uninterrupted time together,” says Dr. Kerry Byrne, founder of The Long Distance Grandparent. “Through travel, you experience new things together, experience challenges together and build trust,” Byrne added. Skip-gen trips can also help children build resilience and confidence.
According to multiple surveys, over 70% of grandparents consider their role as grandparents their most significant function at this stage of life. Skip-gen trips allow grandparents to get to know their grandchildren better. The FTA study revealed that grandparents feel skip-generational travel has positive impacts on their grandkids, helping them to become more adventurous, flexible and confident. Grandparents value the educational value of skip-gen getaways, enabling their grandchildren to develop their interests and become more engaged learners and better communicators.
Since experiences are now valued more than gifts, many grandparents view skip-gen trips as an opportunity to instill a love of travel and give their grandchildren a special treat. These getaways are also perfect for celebrating birthdays, graduations and other milestone events. Parents often welcome skip-gen trips, as they can eliminate the need to take time off work during school holidays and provide a break from childcare demands.
Top skip-gen travel options promote bringing generations together. Photo courtesy of Woodloch Resort
GREAT TRAVEL IDEAS FOR GRANDPARENTS AND GRANDCHILDREN
Many travel industry segments are reporting skip-generation bookings, including family-friendly tour companies, cruise lines, beach destinations and resorts. Major cities, national parks, museums and theme parks are also benefiting from the skip-gen trend.
Disney Parks are great for family bonding, featuring a wide array of activities, amenities and immersive experiences for grandparents and grandchildren of all ages. Some grandparents seamlessly extend the magic by adding a Disney Cruise Line sailing to their trip. Additionally, attraction-rich cities such as New York City, Orlando, San Diego and Washington, D.C. are also popular with skip-gen travelers.
If you’re thinking about planning a memorable skip-generation trip, here are some great vacation ideas to consider.
Grandparents and grandchildren make treasured memories and share new experiences on Road Scholar’s Grandparent Programs. Photo courtesy of Road Scholar
Enriching Group Tours for Intergenerational Travel
Family-focused tours and curated educational programs can be excellent choices for skip-gen travel, since all planning decisions and logistical details are handled by experts. Road Scholar has decades of experience leading enriching trips specifically designed for grandparents and grandchildren. The leading not-for-profit organization features 50 engaging domestic and international Grandparent Programs, as well as Family Programs for three generations.
Road Scholar’s learning-oriented trips for grandparents and grandchildren ages five to 18 offer worry-free itineraries, allowing both generations to relax while sharing new experiences and making lifelong memories together.
“Choosing a group travel option like a Road Scholar skip-gen trip is a great option, because you can rely on our experts to take care of all the planning and details, so you can just focus on bonding with your grandchild,” says Kelsey Knoedler Perri, Road Scholar’s director of public relations.
Other top tour operators offer group trips for families, including G Adventures, Intrepid Travel and Tauck Bridges.
Uniworld’s Generation Collection sailings feature exceptional experiences and well-curated activities for children. Photo courtesy of Uniworld Boutique River Cruises
Great Cruises for Skip-Generation Trips
Cruise Lines International Association (CLIA)’s recent industry research highlights the popularity of intergenerational travel, reporting that 28% of today’s cruise passengers sail with multiple generations.
“Cruises continue to be especially popular for skip-generational travel, as they offer a relaxed itinerary along with activities designed to appeal to all ages,” says Jessica Griscavage. The Caribbean and Alaska are sought-after cruise destinations.
“Alaska offers experiences that are accessible and engaging for a wide range of activity levels and ages, making it an ideal choice for grandparents and grandchildren traveling together,” Griscavage noted.
Holland America Line’s voyages are well-suited for grandparents and grandchildren traveling together. The cruise line’s midsize ships provide a wide variety of room configurations, outstanding restaurants, attractions, and programming for all ages, and Kids Club activities for young guests ages three to 17. For skip-gen vacationers seeking ships with massive water parks and thrilling attractions, cruise lines such as Royal Caribbean and Norwegian Cruise Line can be a good fit.
Cruises on smaller ships are also gaining in popularity. Expedition-style voyages with companies such as National Geographic-Lindblad Expeditions offer family-friendly opportunities for enrichment and nature-oriented experiences. River cruises are an excellent option as well.
Uniworld Boutique River Cruises’ Generations Collection cruises are a great fit for grandparents and grandchildren who want to explore different cultures together. These voyages offer a variety of exceptional experiences and dedicated family hosts to oversee kid-focused programming.
“Our Generation Collection sailings are designed to make skip-generation travel effortless and meaningful, with thoughtfully curated activities for young travelers, expert supervision from our family hosts, and itineraries timed around school breaks,” says Ellen Bettridge, president and CEO of Uniworld Boutique River Cruises.
Beaches Resorts are filled with popular attractions and amenities for every generation. Photo courtesy of Beaches Resorts
Family-Friendly Resorts for Grandparents and Grandchildren
Some amenity-filled destination resorts promote bringing generations together, making them ideal for skip-gen getaways. A Beaches Resorts survey found that most families want generations to vacation together, and 71% of Gen Alpha children want to travel with their grandparents. Beaches Resorts’ all-inclusive properties in Turks and Caicos and Jamaica make skip-gen travel easy and fun.
“Each resort is uniquely designed so that families experience the perfect balance of independence and togetherness, creating memories that grandparents and grandchildren will cherish long after they return home,” says Deryk Meany, general manager of Beaches Turks and Caicos.
Hawaii’s tropical paradise is also filled with opportunities for rich shared experiences. OUTRIGGER Resorts & Hotels caters to grandparents and grandparents traveling together at its portfolio of properties in Hawaii. The brand offers a Grandparent Guarantee designed explicitly for skip-gen vacationers, promising that guests will leave with deeper connections and shared memories.
Families can also find outstanding destination resorts nearby. Located within an easy drive of major Northeast cities, all-inclusive Woodloch Resort offers easy-to-plan vacations designed to foster strong bonds and unforgettable memories. The family resort includes meals and a full schedule of over 30 daily activities and entertainment for all ages, so grandparents and grandchildren can relax and have fun together.
Involving grandchildren in skip-generation travel planning makes these trips more meaningful and special. Photo courtesy of Kampus Production
TIPS FOR PLANNING SKIP-GENERATION VACATIONS
Organizing a memorable trip for grandparents and grandchildren involves time and advanced preparation. Here are a few expert tips to help you plan the perfect skip-gen getaway.
Discuss Travel Goals and Expectations
Begin by speaking with the parents to ensure they are comfortable with a grandparent-grandchild getaway, and have meaningful conversations about the journey.
“Write down what’s important to them,” says Dr. Kerry Byrne. “They might have thoughts and preferences for screen time, routines, food, or their own fears.”
To plan the best trip possible, generations should share their perspectives.
“For grandparents, this means understanding their main goals – whether they’re looking for bonding time, celebrating a milestone, or incorporating educational or cultural elements into the trip,” says Jessica Griscavage. These can be used to design the itinerary. In addition, it’s key to outline travel rules and expectations before the trip.
Include Grandchildren in Travel Planning
Involving grandkids in vacation planning from the outset helps align the trip with their desired activities and interests and makes the journey more meaningful and enjoyable.
Kelsey Knoedler Perri suggests researching destinations together, collaboratively making packing lists, asking grandchildren to help you identify smartphone apps to download, and having them assist with navigating through the airport. “The more you can help them become confident travelers, the more likely they’ll continue to explore the world in the future,” Perri says.
Plan Itineraries with Activity Levels, Mobility and Relaxation in Mind
Craft skip-generation vacation itineraries that offer opportunities for special moments and memorable activities, while incorporating mobility considerations, physical activity levels and downtime.
“Ultimately, the goal is to strike the right balance between structure, flexibility and free time – allowing the trip to focus on meaningful experiences rather than a packed schedule,” says Griscavage. While the point of a skip-gen vacation is to bond while spending extended time together, it’s essential to set a relaxing pace.
Start Creating Vacation Excitement
Making special memories together can take place even during trip planning, notes Dr. Kerry Byrne.
“I think it starts before the trip by building anticipation – using countdown calendars, learning fun or quirky facts about the destination,” says Byrne. “Making a trip playlist together or choosing airplane or car snacks can be part of the fun, too.”
Parents and grandparents know that life moves quickly and that generational bridges are strengthened through precious time spent together. Skip-generation vacations provide extensive opportunities for shared experiences and one-on-one bonding with those you love. As renowned author Alex Haley wrote, “In every conceivable manner, the family is the link to our past, bridge to our future.”
The treasured memories and meaningful connections forged on skip-gen trips are priceless possessions, creating new traditions and a lasting family legacy to be cherished.
Header photo courtesy of Road Scholar
