Travel, TV Appearances

Whether close to home or across the world, multigenerational travel is on the rise. This type of travel—bringing three generation together of grandparents, parents, and children—creates meaningful opportunities to connect and share experiences across generations. There’s also a growing trend of skip-generational travel, where grandparents travel with their grandchildren, creating special one-on-one memories.

But while the idea of multigenerational travel is simple, the planning is not.

Why Planning Matters: Without a clear plan, even the best intentions can lead to stress. With multiple generations comes a wide range of needs:

• Different energy levels and travel styles
• Mobility and accessibility considerations
• Dietary preferences and routines
• Varying expectations of what a “vacation” looks like

Start with Alignment. The most successful trips begin with one key question, what is the goal of the trip? From there, gather input from each family. This ensures every voice is heard before decisions are made. Include:

• Travel dates and availability
• Ages and specific needs
• Preferred travel styles (relaxed, active, cultural, etc.)
• Destination interests
• Budget range
• “Must-do” experiences

To make this process easier, I created a free Multigenerational Travel Planning Worksheet for each family to complete. From there, designate two to three people to take the lead and keep planning streamlined.

Great Destinations for Multigenerational Travel

The best destinations offer ease, variety, and flexibility for all ages. The key is choosing a destination that matches your group’s pace and preferences. Some of the most successful options include:

• All-inclusive resorts in places like Riviera Maya or Punta Cana for stress-free planning
• All-inclusive cruises through the Mediterranean or Caribbean for built-in activities and variety
• European trips to Italy or France for culture and shared experiences
• Domestic escapes like Hawaii for a mix of relaxation and adventure without needing a passport
• Private villas in places like Tuscany or Turks and Caicos for space, privacy, and connection

Plan Together Time… and Apart Time. Not everything needs to be done as a group. If needed, choose one that allow a tired grandparent or a mom with a napping child, to stay back. Remember, balance keeps everyone happy. The best trips include:

• Shared experiences (meals, excursions)
• Built-in flexibility
• Time for individuals or smaller groups to explore

Final Thought: Multigenerational travel isn’t just about where you go—it’s about how you experience it together. With thoughtful planning, it becomes more than a trip. It becomes time well spent—with the people who matter most.

Happy traveling! If you’d like help planning your next trip, I’m here for you—free of charge. Just reach out at Diane@OrganizedToTravel.com