Tip 1: Get everyone involved

One of the keys to a successful multi-generational vacation is plenty of communication up-front. Make sure you involve everyone in the planning process. Have each person in your group, including your youngest members, offer at least one thing they really want to see or do and make sure it happens.

Not only will this ensure everyone has a good time, it takes the pressure off one person feeling responsible for everyone’s happiness.

Tip 2: Don’t do too much

Just because the size of your group has increased doesn’t mean the number of activities has to. There’s only so much time in the day after all. Don’t over-schedule yours with too many. Feeling rushed to get from one place to the next only adds stress for everyone, especially if you’re traveling with people who have limited mobility. Allow lots of downtime for relaxing, chatting, and spending time together as a family. It’s often in these moments when unscheduled, spur-of-the-moment fun happens.

Likewise, don’t try to extend your trip unnecessarily. For most families, a week or two (at the absolute max) is the sweet spot between the “trip of a lifetime” and the one that “felt like it would never end.”

Tip 3: Choose activities everyone can enjoy

You don’t want to leave anyone out of the fun. The wider the age range in your extended family, the more options you’ll want to consider. 

Be sure to plan a few activities that everyone in your family will enjoy doing together. While there’s a time and place for Adrenaline Row, it may not be everyone’s cup of tea. Instead of flyboarding, try a dolphin-tour. Instead of zip-lining through the trees, plan a visit to De Soto National Memorial, which is at a slower speed and also ADA compliant, like many of Florida’s parks.

Places you can explore at your own pace, like Cortez Fishing Village or the Bishop Museum of Science and Nature are ideal for multi-generational families. And of course, there are all our award-winning beaches — each offering a different mood, with different sorts of activities and amenities to enjoy.

But don’t be afraid to split up every so often. Give the adrenaline junkies time to get their thrills. Just be sure there’s some low-key fun for the rest of the group while it’s happening.

Tip 4: Keep everyone together

Not all accommodations are created equal. Hotel rooms are good for a single family. But booking multiple rooms is expensive and divides up larger groups. Instead, consider home rentals or villas that offer multiple bedrooms as well as communal spaces where everyone can be together and still have their privacy. They also come with kitchens, so you don’t have to eat out all the time. Ask about first-floor units, which are ideal for groups that include both young children and seniors. 

These types of rentals are especially ideal if beaches are closed or not within easy reach. Some popular ones include Anna Maria Vacations, which specializes in luxury properties on the island; AMI Locals, which has a wide range of inventory and professional cleaning service built in; and A Paradise Vacation Rentals, which offers more than 300 options across Anna Maria Island

Tip 5: Why buy when you can rent?

As anyone with infants, toddlers, and young children knows, they require a lot of equipment — equipment that is hard to pack and takes a lot of time, energy, and money to transport from one place to another.

Save yourself the trouble of bringing your own. Instead, book your baby gear online and have it delivered to your rental. Many of these companies offer free delivery of cribs, high-chairs, strollers, and more. And you don’t even need to be home to receive it. On the other end of the spectrum, you can also rent what you need for members who require special-needs access, including adult walkers, shower stools, and even beach-friendly wheelchairs. 

Likewise, spend less time shopping and more time doing by renting all your beach items, including towels, beach chairs and umbrellas, life jackets, paddleboards, snorkel gear, and more. 

Tip 6: Have food come to you

Eating out is fun once in a while. Eating out for every meal is unnecessary and expensive. And with the convenience of food delivery services, cooking dinner at home can save time and money. It’s also a great opportunity for everyone to just spend time cooking and chatting together. Who says you can have too many cooks in the kitchen!

Tip 7: Live in the moment!

Planning a successful multi-generational vacation does require more time, coordination, and communication. But at the other end are memories you’ll all cherish for the rest of your life. So, take a million pictures. Then take a million more. The laughs and adventures you’ll experience will more than make up for the headache or two you may experience in the planning process.

Besides, you never know the next time busy schedules will allow everyone to come together like this again.