Multigenerational Travel: The Ultimate Guide to Planning Perfect Family Trips

When grandparents, parents, and grandchildren travel together, magic happens. But let's be honest—coordinating a trip that satisfies a five-year-old, a stressed-out middle-aged parent, and mobility-conscious grandparents isn't exactly a walk in the park. Yet 58 percent of millennial and Gen Z parents plan to bring their extended families on vacation in 2025, and the trend shows no signs of slowing. Why? Because 89 percent cited "quality time" as the main reason for these trips.

In a world where families are increasingly geographically scattered and screen time dominates daily life, multigenerational travel offers something irreplaceable: undivided attention, shared discovery, and memories that become family lore. Whether you're celebrating a milestone birthday, creating new traditions, or simply craving connection across generations, this guide will transform your complex family trip from stressful coordination nightmare into the vacation everyone talks about for decades.

Ready to plan a trip where great-grandma, the teenagers, and the toddlers all have the time of their lives? Let's dive in.

Why Multigenerational Travel Is Exploding in Popularity

74% of parents embrace the idea of vacations involving extended family, and more than 55% have started opting for trips that include grandparents. This isn't just a passing trend—it's a fundamental shift in how families prioritize connection.

The Deeper Reasons Families Are Choosing Multi-Gen Travel:

Creating Living Legacy: Unlike material gifts that fade, travel creates stories that get retold at every holiday gathering. Grandparents share wisdom and family history in real-world settings, giving younger generations context they'll carry forward.

Combating Geographic Dispersion: Families are more geographically dispersed than they have been in the past, making intentional time together increasingly precious. A week in Costa Rica becomes the annual touchpoint that keeps families connected.

Relieving the Sandwich Generation: Parents juggling career demands, aging parents, and active children find multigenerational trips ease the burden. Grandparents help with childcare while creating their own memories, and everyone shares costs and planning responsibilities.

Post-Pandemic Reconnection: After years of separation and uncertainty, families are prioritizing experiences over possessions, choosing to invest in time together rather than accumulating more stuff.

Diverse Perspectives Enrich Travel: When a teenager discovers Barcelona alongside their grandmother, they see the city through multiple lenses—creating richer, more nuanced experiences than single-generation travel ever could.

"Multigenerational travel is still the biggest growth area for us, and has been consistently growing for years. In 2019 multigen experiences grew by 22% and now account for 32% of our transactions and 43% of our overall revenue," according to luxury travel advisor Jack Ezon.

The Biggest Challenges (And How to Solve Them)

Challenge 1: Coordinating Schedules Across Generations

When you're coordinating school and work schedules for multiple branches of a family, it's best to start planning at least six months in advance.

The Solution:

• Lock in dates 6-12 months ahead: Send a calendar poll immediately after holidays when next year's plans surface
• Identify school vacation windows first: These are non-negotiable anchors around which everything else flexes
• Build flexibility for working adults: Consider destinations with strong Wi-Fi where remote work is possible for a day or two
• Prioritize shoulder seasons: Late April, early September, and October offer better pricing and fewer crowds while accommodating most schedules
• Consider travel advisors: Working with a travel agent can help coordinate schedules and facilitate communication of travel plans

Challenge 2: Balancing Wildly Different Activity Levels

The experts know how to negotiate the particular challenges of a group that spans decades: varied interests and activity levels, reduced mobility for some, the logistics of a large group, and more.

The Solution:

• The "One Big Thing" Rule: Focus on one big group activity per day, leaving mornings or afternoons for individual preferences
• Parallel Activities: Choose destinations where grandparents can enjoy a wine tasting while parents hike and kids attend adventure camps—all within the same resort or area
• Accessibility First: The park makes it easy to tailor the visit to everyone's energy and mobility level, from short rim walks to longer hikes. Accessibility features along the South Rim ensure everyone can appreciate the canyon's magnificence
• Split Up Strategically: Not every meal or activity requires full family participation. Adults-only dinners and grandparent-grandchild special outings add variety
• Build in Downtime: Build in plenty of downtime—for varying activity preferences, naps for all ages, family bonding, or just vacation magic

Challenge 3: Managing Money Matters Without Awkwardness

Money can be a tricky topic when it comes to multigenerational travel. Safari company African Travel reported a 20% increase in safari bookings in 2022, with 40% of trips arranged by and paid for by grandparents. However, not everyone may be able to afford international destinations, first-class tickets or luxurious accommodations.

The Solution:

• Have "The Money Talk" Early: Before any bookings happen, discuss who's covering what—accommodations, flights, meals, activities
• Consider Partial Gifting: Grandparents might cover lodging while parents handle flights and activities
• Choose All-Inclusive Options: Staying at all-inclusive properties is the easiest way to make everyone happy and find peace while also guaranteeing zero stress over who's paying for what
• Create a Shared Budget Document: Use apps like Splitwise or shared spreadsheets to track expenses transparently
• Select Destinations with Free Activities: Many of its major landmarks are free to visit, which helps keep costs down when traveling with a large group (referring to Washington, D.C.)
• All-Inclusive Resorts Eliminate Surprise Costs: With a wide range of all-inclusive resorts, families can enjoy stress-free planning with packages that cover meals, lodging, and entertainment. All-inclusive amenities make it easy for families to relax without worrying about logistics or budgeting for surprise expenses

Challenge 4: Finding Accommodations That Work for Everyone

Finding Airbnbs or hotels that fit everyone's demands will be difficult when you need wheelchair accessibility, space for cribs, multiple bathrooms, and privacy.

The Solution:

• Don't Stay Together: You don't need to fly, drive or even stay together during multi-generational travel—adjacent hotel rooms or nearby vacation rentals offer the best of both worlds
• Multi-Villa Resorts: Flexible accommodations and a variety of spaces, like private villas, family-friendly resort spaces, and adults-only zones, so that family members can gather when they choose and retreat when desired
• Interconnected Hotel Suites: Request adjoining rooms with connecting doors for easy access while maintaining privacy
• Consider Cruise Ships: Many multigenerational groups gravitate toward cruises because of the streamlined logistics. There's no changing accommodations, lots to do on board and enough variety to please everyone
• Lodging with Kitchen Facilities: If your lodging has a kitchen, staying in and cooking saves money and avoids the hassle of dining out with a large group. Plus, it's often easier for families with young children

Top Destinations for Multigenerational Travel in 2025

Best U.S. Destinations

1. Yellowstone National Park, Wyoming/Montana

Yellowstone brings the wow factor to any multigenerational trip, offering jaw-dropping natural sights that are surprisingly easy to access. Despite the park's rugged reputation, many top spots are reachable with little walking.

Why it works: Geysers, wildlife viewing, and natural wonders captivate all ages. Boardwalk trails accommodate wheelchairs and strollers. Lodging ranges from cozy cabins to more modern stays, with options that match different comfort levels and travel styles.

Don't miss: Old Faithful (predictable timing perfect for planning around naps), Mammoth Hot Springs boardwalks, and junior ranger programs for kids.

2. San Diego, California

San Diego's sunny weather and laid-back pace make it an easy choice for multigenerational travel. The city brings together stunning coastlines, walkable neighborhoods, and attractions that work for every age group and activity level.

Why it works: Year-round perfect weather, world-class zoo with stroller and wheelchair accessibility, beach towns with varying energy levels from peaceful La Jolla to lively Mission Beach.

Don't miss: Balboa Park's museums, Old Town for history, and Coronado Island for beach relaxation without the party scene.

3. Washington, D.C.

Washington, D.C., is an outstanding destination for multigenerational trips, offering educational and cultural experiences suitable for all. Iconic landmarks like the National Mall and Smithsonian museums provide enriching environments for learning and exploration.

Why it works: Free museums and monuments keep costs manageable. The city's core attractions are clustered around the National Mall, reducing the need for long walks and keeping everyone close.

Budget tip: Nearly all major attractions are free, allowing families to splurge on memorable restaurants and comfortable hotels.

4. Orlando, Florida

Orlando, Florida – Theme parks, golf courses, and shopping ensure activities for all ages.

Why it works: Multiple theme park options mean you can match intensity to energy levels. Universal Studios and Disney World offer varying thrill levels. Grandparents will feel nostalgic, as they take the grandkids on the rides they took you on when you were little.

Insider tip: Stay off-property for more space and kitchen facilities, using park days strategically. Kennedy Space Center makes an excellent non-park day option.

5. Glacier National Park, Montana

"Our multi-generational family of eleven people (ages 6 – 67) had one of the best family trips. Melissa made getting into Glacier National Park a breeze and arranged the best activities and guides. We did the Red Bus Tour, a boat trip on Lake McDonald, and had a private guide from the Glacier Institute for an all-day hike. We all hiked eight miles that day!"

Why it works: Iconic Red Bus Tours accommodate mobility limitations while showcasing spectacular scenery. Activities scale from gentle boat rides to challenging hikes.

Best International Destinations

1. Costa Rica

Costa Rica is a place with incredible ecological diversity where families can take nocturnal amphibian hikes at a property like Hacienda AltaGracia.

Why it works: Costa Rica has surged in popularity for its natural beauty and adventure activities. Zip-lining, wildlife viewing, and beach relaxation all in one country. Multiple resorts offer multigenerational programs.

Activity range: Sloth sanctuaries and coffee plantation tours for slower-paced mornings; volcano hikes and surfing lessons for the adventurous; beach clubs and spa treatments for those seeking relaxation.

2. Italy (Rome, Tuscany)

Year after year, Italy remains our most popular destination to send families. Multigenerational or multi-family groups love it for immersive cultural experiences like cooking classes and museum tours, plus kid-friendly accommodation options.

Why it works: It is completely possible when you choose to take your multigenerational vacation in Rome, Italy. Plus, this best family friendly vacation destination promises enhanced guided tours and family friendly museums for 2025.

Multi-generational magic: Grandparents share Italian heritage stories; parents enjoy world-class food and wine; teens get excited about gladiator history; younger kids love gelato hunts and pizza-making classes.

Pro tip: Have your advisor secure your spot for a Colosseum tour while planning your multigenerational vacation. This will ensure you can skip the line when you arrive.

3. Portugal (Lisbon)

One of the best destinations for multigenerational travel in 2025. I recommend starting with a ride on Tram 28 to check out the city's neighborhoods.

Why it works: Affordable compared to other Western European destinations, walkable neighborhoods, rich history that engages all ages, and stunning coastal areas nearby.

Don't miss: The whole family will love spending time at Oceanário de Lisboa. This is one of the largest aquariums in Europe.

4. Hawaii

There's something so universally appealing about Hawaii that it's easy to convince everyone from toddlers to teens to grandparents to get on board. Leisurely relaxation on the beach or around a family-friendly resort pairs perfectly with cultural experiences like pineapple farm tours, a visit to Pearl Harbor or a luau dinner.

Why it works: Multi-island options allow you to customize intensity—Maui for families seeking adventure, Kauai for natural beauty and slower pace, Oahu for history and culture.

Budget consideration: Hawaii – Stunning beaches, hiking and exploring waterfalls, luaus, and volcano tours cater to various interests.

5. Dominican Republic

Dominican Republic is a top destination for multigenerational travel for those that like the tropical destinations. Beautiful beaches, a variety of activities from water sports like snorkeling and scuba diving to golf for the adults and water parks for the kids.

Why it works: All-inclusive resorts dominate, making budgeting transparent and easy. Shorter flight times from the East Coast than Hawaii. Activities for every generation without leaving the resort.

Bonus: If traveling all the way to Hawaii as a multigenerational group seems too much of a hassle when all you really want is to relax together in a tropical paradise, consider the Dominican Republic instead.

Adventure Destinations for Active Multi-Gen Families

Alaska (Cruise or Land-Based)

One of the best destinations for multigenerational travel in 2025 is Alaska. A vacation in Alaska promises adventures filled with discovery, shared experiences, and lasting memories.

Why it works: Cruise ships offer ultimate convenience—unpack once, wake up in new ports, activities for all energy levels onboard. Land-based options in Anchorage or Juneau provide deeper immersion.

Wildlife wins: Whale watching, glacier viewing, and bear spotting create shared awe moments that transcend age differences.

Patagonia, Chile

"Our multigenerational family of eight just returned from a two-week trip to Chile over the holidays. From our first conversation, I knew that Jordan understood the challenges of traveling with both teenagers and grandparents".

Why it works: Explora has so many activities to choose from, and we planned our itinerary once we arrived: Moon Valley, Mars Valley, the geysers, Cejar Salt Lagoon, Rainbow Valley, stargazing at Explora's onsite observatory, and a hike to Explora's private hot springs! Next we traveled south to Patagonia and stayed at Cerra Guido, a ranch just outside of Torres del Paine National Park. They were super-accommodating to everyone's activity level and physical abilities.

Banff, Canada

You won't need to travel too far from the US to experience one of the best family-friendly vacation destinations in 2025. Banff, Canada offers year-round family fun. And this year, there are more family oriented outdoor activities within Banff National Park.

Why it works: Stunning mountain scenery, accessible gondola rides for those with mobility limitations, and world-class skiing or hiking depending on season.

Expert Planning Tips from Seasoned Multi-Gen Travelers

Tip 1: Print Everything (Yes, Really)

If you're traveling with the over-50 set, it might be a good idea to print everyone's boarding documents, copies of IDs and passports, itineraries, check-in confirmations, etc. ahead of time.

Why it matters: Be prepared to be called old-fashioned with your file folder of papers—until the Paris train station WiFi isn't working and you're the only one with the tickets.

Create a physical trip binder with:

• All boarding passes and confirmations
• Emergency contact information
• Hotel addresses and phone numbers
• Day-by-day itinerary summaries
• Reservation numbers for restaurants and activities
• Copies of passports and insurance cards

Tip 2: Don't Travel as a Pack

Traveling separately means Gran and Pa can fly first class and drink wine in the airline lounge without feeling awkward for not including the rest. Plus, everyone's schedules are different. The kids need a nap at noon? Hit the road at 6 a.m. so you arrive beforehand. And while it's nice to have a helping hand with kid stuff—the travel stroller, car seat, pack-n-play—it's also nice to change locations in smaller numbers.

Split travel strategy:

• Book different flights that arrive within hours of each other
• Drive separately if road-tripping, meeting for meals
• Let grandparents splurge on comfort without guilt
• Parents maintain their own schedules around nap times

Tip 3: Leverage Nature as the Great Equalizer

"Nature is calming and soothing and easy on everybody." More nature, less artificial stimulation (i.e., TVs, smartphones, computers, tablets, Nintendos) is a dependable recipe for deepening connections.

Nature-based destinations excel because:

• They naturally limit screen time
• Wildlife viewing captivates all ages equally
• Outdoor activities scale to energy levels
• Natural beauty creates shared awe moments

Jackson, Wyoming, is an amazing destination with year-round outdoor options, including sleigh rides, dogsledding, skiing, floating, hiking, fly fishing, and wildlife safaris. Fiji enables travelers of all ages to engage in a love of the ocean, with Jean-Michel Cousteau Resort taking special care with the youngest generation.

Tip 4: Use Technology for Planning, Not Just Booking

Consider using itinerary management tools like Travefy or TRES to keep everyone informed and organized.

Best planning tools:

• Travefy: Creates shareable itineraries with maps, confirmations, and daily schedules everyone can access
• Google Shared Calendars: Block out activities with different colors for optional vs. required events
• WhatsApp Groups: Keep everyone in the loop without endless text chains
• Splitwise: Track shared expenses transparently
• Doodle Polls: Survey family on activity preferences before booking

Tip 5: Work with Specialized Travel Advisors

"I start by learning the interests and activity levels of each family member traveling. This helps uncover both shared passions and individual preferences, ensuring a personalized and engaging experience for everyone".

What travel advisors handle:

• More families are turning to travel advisers to help with complex itineraries, multistop trips and destination recommendations. Instead of spending hours researching, parents are outsourcing the planning to professionals who can find the best deals and experiences tailored to their family's needs
• Negotiate group discounts
• Coordinate special needs (dietary restrictions, mobility accommodations)
• Arrange skip-the-line access at popular attractions
• Build in appropriate pacing and downtime

Tip 6: Embrace All-Inclusive Resorts (Even If You Usually Don't)

If you'd asked single, childless me if I'd recommend all-inclusive resorts, my answer would have been a resounding no. But as much as we may not want to admit it, kids change things (and all-inclusives are changing, too). Your parents getting older and becoming grandparents changes the travel equation, too.

Modern all-inclusives offer:

• Multiple restaurant options accommodating picky eaters and dietary needs
• Kids clubs with age-appropriate programming
• Adults-only areas for parents and grandparents
• Included activities from water sports to cultural experiences
• Zero awkwardness about who pays for what

If a kids club is available, you can send the little ones there when there's a desire for adults-only time (and it's also a good venue for grandparents to play with them—with extra sets of hands to take the pressure off). Grand Velas's Mexico resorts and Mohonk Mountain House, a Victorian castle in the Hudson Valley, illustrate the range of what's possible.

Tip 7: Create Flexible Daily Structures

If you have very active family members and those who would prefer a slower-paced trip, you have to decide as a group what compromise best suits your family. For those who are not involved in the immediate planning, set expectations around activity level with everyone. If your family members know what to expect, they will have a much more enjoyable experience.

Ideal daily structure:

• Morning: One planned group activity (museum, boat tour, scenic drive)
• Midday: Free time for naps, pool time, or individual exploration
• Late Afternoon: Optional second activity for the energetic subset
• Evening: Group dinner (alternating casual and special)
• Post-Dinner: Flexible—game night, evening walk, or everyone retreats

Tip 8: Have Clear Financial Conversations Early

When it comes to multigenerational travel, it's important to make sure everyone is on the same page about who's paying for transportation, lodging, activities and meals—and how expensive those things will be. It's crucial to understand that not everyone may be able to afford international destinations, first-class tickets or luxurious accommodations.

Money conversation checklist:

• Who's booking and initially paying for lodging?
• Are flights individual responsibility or shared?
• Does "all-inclusive" mean truly everything, or are spa treatments and premium alcohol extra?
• Will one person cover group dinners and get reimbursed?
• Are activities opt-in (each family pays their own) or group-funded?
• How do we handle souvenirs and personal shopping?

Avoid awkward family money squabbles at all costs.

Why This Trend Isn't Slowing Down

Trips that include grandparents, grandchildren and extended family provide a way for everyone to come together in a desired location and relax—while creating traditions that will last a lifetime. Additionally, as more baby boomers reach retirement age, they're looking for new ways to spend time with their families and create meaningful experiences.

The convergence of several factors ensures multigenerational travel will only grow:

Aging Boomers with Time and Resources: Retired grandparents have both the time and often the financial means to invest in creating family memories. According to a report from Virtuoso and Globetrender, in 2025, seven generations will be traveling at the same time for the first time in history. The youngest of these, known as "Beta Babies," will be born to Gen Z parents.

Experience Economy Over Material Goods: Multigenerational travel is on the rise because families are seeking ways to connect and make lasting memories across different age groups with experiences taking precedence over gifts.

Remote Work Flexibility: Parents can extend trips by working remotely for a few days, making longer multigenerational vacations feasible.

Industry Adaptation: The demand for multigenerational travel and wellness is expected to continue rising, especially among luxury travelers who prioritize connection, privacy, and exclusive experiences. These trends are reshaping the industry, encouraging hotels and tour operators to focus more on creating shared yet personalized experiences.

Your Multigenerational Travel Checklist

6-12 Months Before:

• Send calendar poll to all family members
• Identify must-attend family members vs. optional
• Have initial budget conversation
• Decide on destination type (beach, adventure, cultural, all-inclusive)
• Consider hiring travel advisor for complex trips
• Book flights and accommodations

3-6 Months Before:

• Survey family on activity preferences
• Book any skip-the-line tours or special experiences
• Arrange mobility accommodations if needed
• Confirm dietary restrictions and special needs
• Purchase travel insurance
• Start shared itinerary document

1-3 Months Before:

• Finalize daily schedule with built-in flexibility
• Make restaurant reservations
• Create emergency contact sheet
• Set up family WhatsApp group
• Confirm who's bringing shared items (first aid kit, sunscreen, games)
• Print all confirmations and create trip binders

1-2 Weeks Before:

• Final group video call to review itinerary
• Share packing lists tailored to each generation
• Confirm all reservations
• Set expectations about together time vs. separate time
• Remind everyone about flexibility and patience

During the Trip:

• Stay flexible—plans change and that's okay
• Take group photos daily
• Allow for spontaneous moments
• Respect when people need alone time
• Don't force togetherness every single moment
• Celebrate the privilege of time together

The Lasting Impact of Multigenerational Travel

When we step out of our daily routines and disconnect from all the distractions, we can focus on bonding with our loved ones and creating lasting memories.

Years from now, nobody will remember the stress of coordinating eight people's schedules or the minor hiccup when the restaurant reservation got mixed up. They'll remember:

• Grandpa pointing out constellations on a Costa Rican beach
• Three generations laughing until they cried during a family game night in the rental house
• Grandma's face when she saw the Grand Canyon for the first time alongside her grandchildren
• The teenager who finally put down their phone to help a younger cousin build sandcastles
• Parents getting a child-free dinner while grandparents proudly supervised bedtime

Some of the most treasured memories are made when families come together, stepping away from the daily grind to share new experiences. The best multigenerational travel ideas create rare and invaluable opportunities for families to reconnect, celebrate milestones, and build stories that will be told for generations.

Multigenerational travel isn't about creating the perfect Instagram moment or checking destinations off a bucket list. It's about building a living legacy—showing younger generations that family matters, creating touchstone memories that strengthen bonds, and giving older generations the joy of watching their legacy unfold in real-time.

Multigenerational travel continues to grow, with extended families pooling resources for trips that cater to every age group. The trend reflects something deeper than vacation preferences—it signals a cultural shift toward prioritizing connection, shared experience, and intentional time together in an increasingly distracted world.

So yes, coordinating that multigenerational trip will take effort. You'll need patience, flexibility, and probably a few extra phone calls. But when you're sitting around a table in Tuscany or watching a sunset over Yellowstone with four generations present, you'll understand why 89 percent cited "quality time" as the main reason families choose multigenerational travel.

Because some investments pay dividends for decades—and the best ones aren't financial. They're the stories your grandchildren will tell their grandchildren about the time the whole family traveled together.

Ready to start planning your multigenerational adventure? Begin with the calendar poll today, because the memories you're about to create won't make themselves. And when your teenager inevitably complains about the family trip, remind them: someday they'll be planning these trips for their own families—and they'll understand why you insisted on going.