Multigenerational Travel: POV Grandparents & 7 Planning Tips

Multigenerational travel has emerged as a riding trend, bringing families together for unforgettable adventures and creating lasting memories across generations. As a travel advisor, understanding the unique dynamics and needs of multigenerational groups is essential to crafting exceptional travel experiences. After a recent multi-generational trip for my family, ages 6 months to 60, I thought it would be fun to share not just my point of view, but also my parents.  

POV: The Grandparents

We’ve been on more than one multi-generational trip now. We’ve traveled to Europe, the Caribbean more than once, and Hawaii with our kids and grandkids. It’s such a great way to travel, If you are compatible travelers! I really think this is key. 

Traveling well together can mean different things to different parties; for our family it means:

•       that we travel at the same speed, our pace is similar

•       we like to move from one resort to another 

•       we enjoy experiencing all types of exceptional food 

•       we like the same type of weather

•       we love 4 and 5 star hotels 

•       we like excursions on land and sea

•       we like to experience the culture of the area we visit

I have to say our trips and traveling over the past few years have gotten a lot more interesting. I mean after all, having a daughter as a luxury travel advisor has really upped our game! Kate is going to visit, experience, have a drink, taste an appetizer and meet with resort staff as much as she possibly can with any and all that is located around her. When we are along for the ride, we love to experience the same. 

When I first started traveling either for work or for just a trip with my husband, we would select a hotel, visit the surrounding area and experience the resort. We would rent a car for the week from the airport, go to a nearby restaurant for dinner (probably a tourist trap or two) , go shopping and drive around a bit. I couldn’t imagine moving hotels at all, isn’t that the benefit of vacation?

What I’ve discovered is actually quite different. Travel is much different for us now and so much more exciting. We now thoroughly enjoy experiencing moving to explore the next island or town. It started in Ireland where we stayed in Dublin and then went across the country to Killarney. We enjoyed two completely different experiences in Ireland, one in the city and one in the country.  And, the journey between the two can be just as fun. We’ve rented a car, taken a fast train, booked a private driver and rode on a ferry from one destination to another and they have all been great experiences. 

Favorite Multigenerational Trip

Our most recent visit to Hawaii was truly a wonderful experience. Everyone in our party experienced four different resorts in two weeks and enjoyed each and every minute of it. That’s quite an accomplishment for two grandparents, two millennials, a baby and 3 year old toddler, if you ask me. Kate personally visited 11 resorts for hands-on experiences to share with her clients and prospective customers. Now, the key here is that all members of our party like to be on the move, enjoy being active and didn’t prefer to stay in one place at one resort on the beach.

The kids stayed at the Ritz Carlton, Kapalua, while we wanted to experience the Montage Kapalua Bay, which was a great idea because we enjoyed both hotels with a free shuttle back and forth. Even better, the front desk staff drove us to our dinner reservations one night on their golf cart!

The Ritz is located on Maui’s picturesque northwest coast, The Ritz-Carlton, Kapalua exudes timeless Hawaiian charm and refined luxury. As opposed to the Montage where there really isn’t a designated lobby, the Ritz has a lively lobby with a bar located to the right, cafe on the left and oftentimes live music and cultural experiences in the middle. Couches and chairs are located throughout the lobby to relax and enjoy a drink and appetizer and the area allows for a lot of community and conversation with others. 

The kids thoroughly enjoyed the club lounge- included food, snacks and the outdoor patio is a plus for a club lounge with Hawaiian entertainment as well. There are beach activities, snorkeling and coastal hikes. The hike that leads to the nearby park is so unique. We really enjoyed watching the kids jumping off rocks and cliffs which is both exhilarating and petrifying to watch at the same time. 

The Montage is located atop picturesque Kapalua Bay and offers a luxurious retreat with breathtaking ocean views from any point on the resort. The view from the front of the resort and the spa are absolutely breathtaking. Walking down the path at the entrance to the Montage is an experience all in its own, a perfectly framed view of the ocean. At check-in, drinks and hand towels were provided as were two chairs to face the framed ocean view while the check-in experience was conducted by Montage employees. We both were thrilled with the free upgrade provided by booking with Melted&Moved. We booked a garden view room for two, and stayed in a 3-bedroom ocean view residence! The pineapple filled with fruit and champagne didn’t hurt too much either.

We are so grateful we are able to experience travel together and look forward to our next multi-generational journey together in Italy!

More on Maui? Click here for our Maui Travel Guide

POV: Travel Advisor 

As you can see Multigenerational travel provides an extraordinary opportunity for families to bond, share experiences, and create lifelong memories. Here’s a behind-the-scenes look at what, in my opinion, is most crucial when planning a memorable trip for families of all ages.

Embracing Diversity

Traveling with multiple generations includes a variety of family dynamics, from grandparents spending time with their grandchildren to extended families taking family holidays. Recognize each family member’s distinct interests and preferences so you can adjust your plan. You may design a vacation that meets everyone’s needs by celebrating togetherness as the common goal of the trip.

Communication is Key

Encourage open dialogue among family members, allowing them to express their desires, concerns, and expectations for the trip. Encourage compromise and find common ground to create an itinerary that balances different interests, ages, and physical abilities. Regular updates and clear communication channels help minimize misunderstandings and ensure a smooth journey.

Accessibility and Flexibility

Think about how the various generations within the group differ in terms of their physical capacities and levels of mobility. Ensure that the lodging, transportation, and activities are all age-appropriate and accessible. Planning multigenerational vacations requires flexibility because the interests and energy levels of the various generations may vary. The whole experience can be improved by including downtime, including a variety of activities, and providing alternate options.

Engaging Activities for All

Craft an itinerary that strikes a balance between age-appropriate activities and experiences that appeal to the whole family. From cultural tours and outdoor adventures to interactive workshops and relaxation, offer a variety of options to cater to different interests. Engage the younger generation with hands-on experiences, while providing opportunities for the older generation to share their wisdom and knowledge.

Create Meaningful Connections

Multigenerational travel provides a unique opportunity for family members to bond and create lasting connections. Encourage shared experiences, such as cooking classes, local community visits, or volunteer opportunities, to foster deeper connections among family members. Group activities that promote teamwork and cooperation can strengthen family ties and create cherished memories.

Expert Local Insight

Tap into local knowledge by working with local experts to enhance the multigenerational travel experience. Local guides can offer unique insights into the destination’s history, culture, and hidden gems. They can also adapt the tours to accommodate the diverse interests and needs of the group, ensuring an enriching and immersive experience for everyone.

Plan Ahead

Multigenerational travel requires meticulous planning, especially when it comes to accommodation, transportation, and dining arrangements. Booking well in advance ensures that you secure suitable accommodations with interconnected rooms or villas, arrange transportation that can accommodate the group, and make reservations at family-friendly restaurants. Proper planning minimizes potential logistical challenges and ensures a stress-free journey.