You’ll get instant “Great” Grandparent status by booking a trip with your grandkids…with or without their parents.

Booking.com’s annual Travel Predictions research* reveals that “travellers are ‘rewriting their playbook’ in 2025, defying the norms of age, gender, or simply what society thinks travel should look like for them.”

According to their research, Boomers (those who are parents and grandparents) are favouring  multigenerational megatrips, dipping into the inheritance fund they had set aside for their children. 42% of them would rather spend money on the “trip of a lifetime” with their kids and/or grandkids in 2025 than leave it behind after they’re gone. Booking has labelled this S.K.I. vacations, but it’s not referring to the slopes, but rather Spending the Kids Inheritance vacations.

Grandparents are looking to help their kids pay for vacations they might not normally be able to afford. 51% of Canadian travellers admit their parents have contributed to their vacation funds since becoming an adult. 79% of grandparents surveyed say they would be happy to pay for their grandchildren.

But what kind of trip would you like to take your grandkids on? A good way to start is by taking a road trip, but it doesn’t have to be a road trip that starts from your home driveway.

Introducing kids to an airplane ride with a short hop to somewhere new can be a terrific way to acclimatize them to air travel and negotiating a busy airport, with a comfortable ride at the end. I recently did this trip like this, with one of my kids.

Flights from Toronto Airport to Dulles in Washington, D.C. are under two hours in length. And once there, the beautiful state of Virginia is at your fingertips to explore. We rented a car to make our way across the state. Here’s our itinerary:

Start your journey by stopping at the charming town of Winchester, Virginia. A pedestrian mall makes for an easy shopping excursion with the kids, and you can take in some history for the older ones.  The Shenandoah Valley Civil War Museum is located in town, and there are various restaurants to choose from, including Violino Ristorante, serving up authentic Italian food everyone will love. The George Washington Hotel is the perfect place to stay, with an indoor pool for the kids, a pizza restaurant on-site, and a gorgeous lobby bar in this historic and stately hotel.

Just over an hour’s drive south are the mesmerizing Luray Caverns, a U.S. Registered Natural Landmark. These are the largest caverns in Eastern America, plus the most visited in the U.S. This natural wonder was discovered in 1878 as a sinkhole, and after excavation now covers over a mile in these four hundred and fifty million years old caves. It’s an easy self-guided tour that’s accessible for all. Also on the site there’s a Car and Carriage Caravan Museum, a toy museum, and the Shenandoah Heritage Village and Luray Valley Museum. Grandkids will also love the Garden Maze and trying their hand at gem mining.

Get back in the car and drive just 90 minutes to Lexington, a significant city in the history of the Civil War. Take the kids on a horse drawn wagon sightseeing tour to take in the history in an easy and fun way. The main street has a variety of local artisan shops, outdoor retailers, and restaurants and cafes to please every age palate. The Gin Hotel is centrally located and includes a continental breakfast for hungry travellers, plus a fitness room for active grandparents.

From Lexington you are just 20 minutes from the Natural Bridge State Park. This state park is home to the largest limestone arch in North America. It is simply breathtaking. At 200 feet tall, the bridge is one of the oldest geologic features on the east coast.  There are a number of hikes to choose from, at various difficulty levels, including an easy one that leads to a natural waterfall

Leaving the park, take a drive up the Blue Ridge Parkway through the mountains, to the Peaks of Otter Lodge (open again in Spring, 2025) to take in lunch while looking out at Abbott Lake. A popular and crowded lunch spot.

In under an hour, you can get to the city of Roanoke, Virginia, the “Star City of the South”, so named for the world’s largest freestanding illuminated man-made star, at the top of Mill Mountain. Roanoke is a mixture of the old and new, with a walkable downtown, easily accessed by a pedestrian bridge (over the rail tracks) from the iconic Hotel Roanoke and Conference Centre . A “railway hotel”, this historic and well-maintained flagship hotel is home to conferences, family holidays, romantic getaways and gourmet dining experiences. The hotel has just completed a $14million makeover, incorporating new technology, design and furniture to each of the 327 guest rooms, including a new Health & Wellness floor.

Just over an hour down the road, the kid in you, and maybe your older kids, won’t want to miss visiting the Mountain Lake Lodge, where most of the iconic movie, Dirty Dancing, was filmed. Even without knowing this pedigree, the lodge is a terrific family holiday spot, with swimming pools, games, activities, and hikes. But with the knowledge of the Dirty Dancing weekend, you might want to check out their special weekends to take advantage of the look-alike contests, trivia games and scavenger hunts around the property, including sneaking a visit to Baby’s cottage porch and standing on the cinder blocks Patrick Swayze stood on to do the famous lift. And yes, to confirm the rumours, that lake is dried up now, but the greenery and the fall foliage surrounding the lodge more than makes up for that.

This is a full agenda you can easily do in six days. But maybe you’re looking for something a little more chill…in the heat.

If you’re itching to take the grandkids to sun and sand, a destination that more and more Canadians are flocking to is Punta Cana in the Dominican Republic. It’s a direct four-hour plane ride from Toronto, making it an easy hop for kids of any age. The recently converted Sunscape Coco Punta Cana resort (a part of the Hyatt family) is only 20 minutes from the airport, located on beautiful Bavaro Beach, and once there, it’s basically a kids’ (and kids-at-heart) paradise.

From trying out the fantastical Le Petit Chef (for an additional cost), to joining in on the fun at the Kids’ Clubs, this 1,059 room resort has something for the whole multi-generational family.

Families will love the  two-bedroom and three-bedroom suites which offer spacious accommodations, including connecting rooms and amenities with kids in mind.

The Sun Club offers upgraded suites offer a range of additional services, including the Sun Club Lounge (where kids are welcome), as well as room service for those nights when the kids are tired and everyone wants to relax.  A dedicated beach area is also available in the family friendly and adults-only sections of the resort. And of course, don’t forget about the spa, to smooth out some of those sore grandkid-carrying shoulders.

Foodwise, Sunscape Coco Punta Cana has 12 restaurants, including à la carte, buffet, grab-and-go, and a café. Italian, Asian, and authentic Amazonian cuisine are on offer, as well as Chopsticks, a popular and fun teppanyaki experience everyone will enjoy. Leave the kids with their parents and head to the Wine Cellar for a private and unique dining experience. And, there’s even an on-site food truck for snacks.

Kids’ Clubs are age appropriate with an Explorer’s Club for Kids ages 3-12,as well as a Core Zone for tweens and teens . Water sports, daytime and nighttime entertainment, this resort is perfect for family time together, or private time apart.

Whatever type of holiday suits you and your kids and grandkids, 2025 is the year to do it.

“Canadians, like most of the world, are feeling the stresses of accelerating change across multiple fronts. Global elections, rapid AI advancements, and increased costs of living, to name a few, have us feeling fatigued, needing to withdraw, pick a side, or simply disconnect.” said Arjan Dijk, Senior Vice President and CMO at Booking.com. “We continue to see travel as a force for good that can uplift local economies, nourish personal growth, shatter misconceptions, and strengthen relationships.”

And relationships are what we as grandparents care about the most.

Let’s get out there and SKI.

*Booking.com commissioned research among more than 27,000 travellers across 33 countries and territories to present nine travel predictions that foresee 2025 ushering in new ways of experiencing the world.