August 01, 2016

Celebrate the Good Life—Together

By Kenneth Latimer

The busier life gets, the more important it is to carve out that special family time in a memorable place. What could be better than doing something you love with people you love?

Travel has always been a very important part of my and my wife Carole’s life. We’ve been fortunate to have taken many wonderful trips both here in the United States and abroad, and we recently decided that nothing would be better than celebrating my 70th birthday with a family trip.

Family vacations are as diverse as today’s families, and the possibilities are virtually unlimited, depending of course on such factors as your budget, the nature of your family, and your family members’ availability. Carole and I have three children and eight grandchildren who, at the time of our trip, ranged in age from two-and-a-half to 11. There were 16 of us in all, and we had to address many logistical issues.

Here are some of the issues we faced, along with my suggestions for addressing them in a way most of your group will be comfortable with.

1. Choose the best time frame and budget for your group. That’s actually easier said than done. With my suggestions, I’m assuming everyone in your group is in good health and has no serious disabilities, which could affect your decisions.

Obviously, the smaller the group, the easier it is to plan. The larger the group, the more complex the issues. At a family dinner, we all decided the Columbus Day weekend in early October worked best for everyone. My wife and I had previously decided on a budget, so we were able to let everyone know the trip was on us, including airfare, hotel, and meals.

If you’re not in a position to do that, I suggest looking for an inexpensive site nearby that doesn’t require air travel. I’d also suggest talking to each of the families participating separately to determine their budget. Consider using the lowest amount any one family can pay as your maximum to avoid embarrassing the family with the least disposable income.

2. Find a good travel advisor. Once you have your dates and an approximate budget (plan on exceeding your budget), you need to find a good travel advisor to recommend locations good for family trips. Once we advised our travel agent of those factors, we received several suggestions.

We chose The Cloister in Sea Island, Ga. We’d never been there but selected it for a number of reasons. First, it was only a two-hour flight from Chicago to Jacksonville, Fla., and the airfare was reasonable, although we had to multiply that airfare by 16.

Second, it appeared there was something for everyone to do during the four days of our stay. There was a beach offering various activities (depending on the weather, of course), golfing, biking, horseback riding, rifling, fishing, and sailing, just to name a few. There was also a kids’ camp at the location to allow some “free time” for the adults.

3. Nail down the trip logistics. Each airline is different, but generally if you purchase more than 10 airline tickets, you can get a group fare by working directly through the airline’s group reservations division. Air fare for our family trip totaled $5,800. We weren’t able to negotiate a discount, but I was able to pay only $1,000 when I reserved the tickets and got our seat assignments; I paid the rest closer to the time of our trip.

The next hurdle was to get everyone from Jacksonville to Sea Island, which was about a one-hour trip. It made no sense to rent cars since once we were at The Cloister, we wouldn’t need them. Because we chose a family-oriented resort, it had 18-passenger vehicles available to pick us up and return us to the airport. Be sure you ask about costs for extras like that; best not to be frustrated at unexpected expenses.

4. Make smart decisions on rooms and meals. With the help of our travel advisor, we decided each family should be in its own room. The Cloister has at its beach club suites that sleep six, so we got one suite for each family. This worked out very well because everyone had their own space.

It also allowed the family with the youngest grandchild to make sure she could catch her nap.

Remember that when you’re dealing with married children, spouses of your children may not feel as comfortable with close-quarters family time. Before you rent a large home with multiple bedrooms, consider what would make all your family members most comfortable. There’s no right answer; there’s just a right answer for your particular family members.

Meals are also a challenge. I believe breakfast is important because it gets each day off to the right start. We had a breakfast room reserved from 7:30–9 a.m. daily so everyone didn’t have to arrive all at once, though generally everyone was there at about the same time each day.

We had four nights of dinners, and we decided to arrange for babysitters through the hotel for our grandchildren on Saturday evening so the adults could have an evening out together. We purchased pizza and let the children have a pizza party together in one of the suites; then they each returned to their own suites with their specific babysitter.

5. Use your purchasing power. If you have a large group, don’t be afraid to negotiate. At The Cloisters, I was able to negotiate the free breakfast in that private room for our group so we didn’t disturb others in the dining room. On a second family trip to Colorado, I was able to negotiate room rates at a high-end hotel that included a free daily buffet breakfast, as well as group prices on horseback riding, whitewater rafting, and zip lining. Discounts ranged from 10–15 percent.

6. Agree on activities before you go, or agree to be flexible. We didn’t plan any specific activities except to sign all the children (except for the two-and-a-half-year-old) up for the kids’ camp for one day. We were very lucky the weather was perfect for our stay. Everyone loved the beach and the pool. Some family members went bike riding, others went on nature walks, while others went horseback riding.

When there are a large number of children in your group, it’s best not to try to “program” everybody but to let them choose their own activities. Again, check costs first so nobody is surprised by extra expenses.

7. Make memories. Arrange for a professional photographer for family photos during your trip. We paid about $200 for a family photo shoot. Then the photographer posted the photos on a website so everyone could choose which they wanted to purchase for themselves.

An intergenerational trip is a long way from piling into the family car and heading off to the beach or the mountains. The important thing is to carve out that special time in memorable places.

Kenneth Latimer

Kenneth Latimer is a partner in the Chicago office of Duane Morris LLP who specializes in commercial finance, real estate lending, and loan workouts. He’s a member of the Senior Lawyer Division’s Lifestyles and Leisure Committee.