Travel Diary: Hilton Head, South Carolina 2021

Three Generations Traveling Together

I am a seasoned and lifelong traveler, but in October of 2021, I set out for my first multi-generational family trip. My adult sons are 29 and 31 and they each have their own families with kids ages 6, 4, and 2. We intentionally chose Hilton Head Island, South Carolina as the destination as it is a nice and relaxing venue. Half of the group arrived on a Wednesday and the rest came on Friday, all staying until the following Tuesday, so 6 nights in total.

Disney's Hilton Head Resort

We stayed at Disney’s Hilton Head resort since we had taken our boys there when they were young, so it was fun to reminisce and see what they remembered. It was also nice to be somewhere familiar so we knew what to expect, especially with young children. The highlight of the trip was definitely being able to spend time as a family.

Plenty of Room for the Whole Family

We had a two-bedroom villa, which had a full kitchen, two bedrooms and two bathrooms, along with a pull-out couch and pull-out oversized chair. We quickly realized that each family having their own room or space was very important. Pullouts are tough as they can be uncomfortable and there is no space for privacy. Plus if they want to sleep in, it is incredibly difficult with the kitchen close by. We made it work, but next time I would opt for at least three bedrooms so that each family unit had their own space. And for meals,  I would recommend staying somewhere with a grocery store nearby to be able to make several trips throughout your stay. This way people can decide if they would like to eat in versus out, and have the convenience of both.

Recreation and Activities for All Ages

The resort had a lot to do, for kids and families, including a swimming pool, marina, a lot of lawn type games (bocce ball, bags, shuffleboard, etc.) as well as a playground, fishing pier, bike rentals, and more. They have a beach house on the beach side which you take a shuttle to, or you can drive yourself. At the beach house there was another pool, games and a restaurant. 

Top Multi-Generational Travel Tips

• Find a place with plenty for everyone to do. We had the luxury of beautiful weather so people were outside most of the time. 
• Cruising or all-inclusive destination would be great for multi-generational trips. Everyone will have their own room and you are waited on for meals versus someone having to take charge. And it also gives the parents time away from their kids (grandparents are always the best babysitters).
• Take time to spend quality time with your grandkids (or kids) one-on-one versus everyone always together. You will find some fabulous moments when you do this.   
• For flights and car rides, be sure you have plenty of snacks, games, etc. for the little ones. Our littles were great travelers, but you need to be prepared!