“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

Planning That Family Vacation

It seems that everybody is so busy these days that it’s often hard to get quality time with the family, especially as the grandchildren grow and get busy lives of their own. A family vacation can be the answer.

For the past 14 years, I’ve taken my family on a family vacation as part of their Christmas present. We began as my daughter and son in law and two granddaughters. We now number ten adults and a one-year old child. Planning for that many people, ages from 1 to 65, isn’t always easy—there are a lot of things to take into consideration. Here are my tips to planning for a family or group.



As always, you have to ‘know your clients.” I’m lucky—my family loves cruising, the beach, or the mountains just as much as they love touring cities with museums, art galleries, and venues to eat and drink. And we’ve pretty much done it all. I started out keeping it very simple—an all-inclusive week in Cancun. Very easy. There were activities for everyone and it was just a matter of choosing which resort (one with lots of pools and restaurants) and booking the air. Piece of cake! 

One person shouldn’t have to do all the planning or get to make all the decisions. Now when vacation time is coming up, I get input from the whole tribe. Usually we start talking in January about possibilities and I do some initial research. Once the destination is selected, I urge everyone else to do some research. Then we get together and talk about what we want to do and see. Then I finalize the trip.

We expanded our horizons as time went on and the girls got more grown up. Recently, we’ve done some much more complicated itineraries—to Tuscany and to Germany. Naturally, this involved a lot more planning. Finding lodging was not as easy and both trips involved staying in multiple cities, meaning I had to arrange transportation to all the cities. But I had learned and it all went off without a hitch. And we included more cultural activities, too.

Over the years, we’ve zip-lined in Costa Rica, enjoyed the beaches of the U.S. and Caribbean isles, climbed mountains and drunk beer in Germany, yodeled into the Grand Canyon, toured churches and learned to cook in Italy. It’s been wonderful!


Activities and Abilities

One of the best ways to keep your travel budget in control is by carefully choosing your activities. Look for the free and less expensive alternatives to fill your time and your scrapbook. Even in big European cities there are lots of places to go and things to do. One of our favorites is wandering the local markets. You also get more feeling for places and people with simple sightseeing.

Some places are just logistically crazy to take a large group, especially if there are children involved. Keep in mind that you will want to all be together for activities most of the time.

Each person’s personal needs and abilities are very important considerations in terms of activities and timing, as well as transportation. It’s very important to make sure there is something that everyone can be a part of, at least most of the time. Some may be unable to walk a long way, others too young to walk much at all. If a family member has mobility issues or depends on an oxygen supply, you want to plan with those needs in mind. Select places and activities that everyone can do enjoyably. There are lots of resources online to research what there is to do in various places. It takes a little effort but helps ensure a great vacation for all.



This is a big one!  Travel isn’t cheap and costs can sometimes determine your destination and otherwise shape your plans. There usually are ways to trim costs though.

One of the first things I usually do when I have two or three places in mind to visit, is to look at how we are getting there. Can we drive?  Do we have to fly? 

If driving, I look into the cost of renting a van or SUV that will accommodate all participants and our luggage and start figuring routes and distances to see where to book accommodations along the way.

If flying, I spend a lot of time comparing air fares and considering carrier comfort as well as special charges. It’s important to check prices and schedules for every airline. In Europe, it’s very practical to go by rail once we’ve made the transatlantic hop and are linking from city to city.

Next, where are we going to stay?  Bed and Breakfast, hotel, camp, or a rental house?  If you need more than two rooms, I would always look at a rental house. It’s usually cheaper than booking more than two hotel rooms, you can fix meals there (even if it’s just breakfast, that’s a big saving), it’s great to all be together in a living room instead of split up (or crowded) in separate hotel rooms.

I usually use VRBO.com (Vacation Rentals By Owner) to find my houses and I have never rented a house that I felt was not worth what I paid for it. We’ve stayed in houses and I’ve booked houses for clients all over the world. VRBO lets you put in filters to narrow down your choices which helps a lot because, depending on where you want to go, often there are hundreds of houses available. I have found that for more than 4 people, this is the least expensive and by far the most fun.

To get good deals on lodgings, try going during the shoulder season, the couple of weeks right before and right after tourist season. Usually the weather is pretty much like tourist season, but it’s not as crowded, and you get more for your money. Shoulder season will vary with the destination, but just google “when should I go to _____?”


Don’t overplan.

Now that I’ve told you everything to plan, I’ll add, “Don’t plan too much.” Never try to schedule every minute, you’ll make yourself and your companions crazy. You really don’t want to try to cram everything in and then feel like you’ve been on a whirlwind tour. It’s much better to see a few things thoroughly and have great memories of them than to see it all and not remember much about any of the attractions.

Do some research before you go and make a list of everyone’s “must do’s” and “maybe’s.” But many of my best adventures have been spur of the moment decisions after we got there. Build in some time for relaxing and being quiet. And make sure each person gets to do at least one of their own “must do’s.”

My family vacations have given me some of my best travel experiences of my life. I hope that’s true for the rest of my clan as well.


Want Help?

It’s a lot of effort to plan for a large group and it doesn’t get easier because they’re family. You can always take advantage of help from TravelHaven to do the heavy lifting. Just a click (http://yourtravelhaven.com/tripinfo/ ) or a phone call (407-399-7758) gets us started.