How to Plan a Multi Family Vacation

Getting together has also never been harder given people’s increasingly busier lives and the rising cost of nearly every form of travel. Making sure that you make the most of your family get together is important. It all starts with just a little bit of upfront planning.


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    Put someone in charge of the vacation. When planning a multi-family vacations, put someone in charge of the vacation. While everyone is responsible for their own itineraries (like plane flights) and special needs, someone is orchestrating the master schedule so that everyone can be on the same page. In this way, decisions can be made quickly, there’s a central point of contact for most everything and it reduces confusion and malaise.
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    Decide on the dates, location and the venue and start committing early. Usually everyone has a few places they’d really like to go to. Others have certain places that they absolutely don’t want to or can’t go to. Everyone has some level of budget restriction. The person in charge of the vacation should solicit all this information from everybody and even delegate some of the research to family members. Early decision making is really important if you want to get your first choice at a reasonable price.
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    Choose the type of housing. Some sample ideas for get together venues are:
    • Villa / Vacation Rental – getting one big house with one big kitchen/living room is a great way to spend quality time with the family. There’s nothing like being able to stroll into the living room to watch a late night movie with whoever is staying up. Conversations need not be interrupted prematurely and plus there’s always a central base that is the hub of activity.
    • Cruise – the ultimate in convenience. You don’t have to worry about food and you unpack only once. Make sure you get rooms reasonably near each other or else you risk spreading the hub of activity.
    • Tours – Some tour companies can customize a tour for your family if you have a minimum number of people in your group. Many view tours as a the great way to learn more about a place while others may view tours as being too restrictive.
    • Hotels / Resorts – suites are a great way to pack more people together and to save on costs by cooking. For large get-togethers though it can be somewhat impersonal because hotel rooms are too small to accommodate everybody for a chat or to play a game and so you end up with dispersed mini-groups within the get together. If you have to book multiple hotel rooms, try to get them all in one wing or even suites that connect if possible. Look for the group discount too -- depending upon the size of your group you may qualify.
    • Family member's house – choosing one family member’s house to congregate is definitely the cheapest option. You never have to worry about picking the right restaurant and stocking up is easy to do. There are certainly many other wonderful options, like working ranches, Disney World, RV, houseboat, camping, renting that castle in Scotland, taking that trip around America on Amtrak but the key is to get the commitment first. As soon as you agree, start booking. Once people are committed, meaningful planning goes a lot faster and easier.
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    Organize the basics online. You could do this via email, but you will be inundated with a myriad of emails that will add even greater confusion. One source that we have found to be great is to use a group website like PBWiki, where family members can add their own information
    • Have everyone put their flights in the group calendar - this makes it easier to coordinate airport pickups and car rental configurations.
    • Put local resources and maps in the group site so that everyone will have the latest and greatest information
    • Place everyone’s cell phone number, pager, instant messenger handles, etc. for quick communication online. Add any other important information such as visa’s, shots, temperature and weather patterns and provide that information to all family members.
    • Consider booking a few restaurant reservations before your trip. If you have a large group, trying to find a decent restaurant last minute that can accommodate a large party may be impossible.
    • Make an online shopping list - have all family members add things that they would like to eat, snack, beach toys etc. Think about setting up a WalMart or Costco run as your first order of business when you get there so you can stock up on the things you need early.
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    Don’t be a control freak. Nothing can sap the fun out of a vacation than somebody who can’t roll with the punches – and especially for the person who is organizing or helping to organize the vacation. No vacation works out exactly as you plan. Remember that you are having a vacation and that means having fun, not making sure everything on the planned itinerary is checked off. Also I usually only plan at most 2 things in a day. Getting so many people coordinated is difficult already and any transitions between activities takes more time than you think. Somebody always wants to visit that gift shop for a little bit extra time or to take that side diversion and you have to be able to accommodate for that.
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    But do plan activities. The purpose of a family vacation is to have family spend time with each other and especially to engage with each other in conversation. A couple of ideas to make sure you include everybody and increase those memorable moments…
    • Cooking meals together – it’s certainly cheaper to eat inside but the bigger benefit is that you get people working together in the kitchen talking. And there’s nothing like being able to share your food repertoire with your family members. (have an online sign-up sheet where families can sign-up for dinner duty)
    • Slide show – family slide shows are only boring to those who aren’t in the family. Seeing baby pictures, embarrassing photos and swapping stories are a great way to get the family laughing together. PowerPoint and a projector are the best way but bringing a DVD with all of the goods is another great way to get some great laughs.
    • Video Games? -- well it depends. For most families, banning video games are essential to prevent the children from spending their entire vacation in front of the television. However there are many group participation games that are a blast for groups. On the Wii for instance, there’s Rock Band, Karaoke type games and a multitude of brain teaser and puzzler games that are fun for everybody.
    • Exercise – the Kennedy’s aren’t the only ones who play football when they get together. Get people out on the court, get some exercise and have some fun.
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    Deal with the money early. It’s good to work out a system with regards to shared costs early so there is no misunderstanding. Some families prefer to spend everything separate by family while others pay up front and say “pay me later.” For the latter, it’s important to work out a good way to distribute the costs fairly. Some families keep track of every dish that is ordered and while that is clearly the fairest way, it’s also requires the most effort. In my last vacation we had 4 families. For shared costs like meals, we split it up by number of adults and number of kids (we counted each kid as half an adult) so that we could simplify the calculation. It’s never perfect, but why worry about nickel and dime among family. Everyone should keep their receipts and ideally, you spend the last day putting stuff into a spreadsheet so that you can settle up that day or at least soon after the vacation.
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    Start talking about the next vacation – you can’t beat face-to-face communication. Spend a little time on the last day talking about what you want to do for the next vacation. You can get a lot done talking about it in person in a group versus over email or over the phone and plus you’ll be fresh with the knowledge of what worked well and what didn’t.
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    Keep the vacation spirit alive. - make sure everyone gets back fine by sending an email or making a phone call. Do some photo sharing and if you are enterprising, put together a photo book using services like and so that you can always remember the good times.


  • Use online group sites to help organize, inform and coordinate family vacation information and tasks. Family members can check the latest information and sign-up for tasks at their own time.

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Categories: Family Vacations