12 steps to plan your multi-generation family vacation

A great extended family vacation obviously takes more planning than just a week-long getaway for two.  But the payoff can be so much greater.   If your family has never done an extended family holiday,  it can be daunting to figure out how to get started.  Here are the 12 steps I recommend to plan a great family getaway:


  1. Budget   Vacations take money and everyone has differing amounts of it, views on how to spend it, and issues with it.  That can make the budget issue of an extended family vacation very tricky.    Even in the easiest situations, it is important to address finances up front as it will dictate the type of family holiday you should be considering.For some family getaways, one party may be paying for almost everything.     My husband and I usually “host” an annual villa vacation for our extended family where we pay for the villa.   Each party is responsible for booking and paying for his own transportation and any excursions taken. We pay all the staff tips, food, and alcohol, but often another party will volunteer to pay for one of those items.  Even in this situation, it is still important to consider the costs that each party will incur and whether this is financially comfortable for them.     A villa in Thailand or Turkey might seem affordable until you factor in airfare.    Borrowing the home of a family friend on Mustique or Virgin Gorda could seem ideal until you factor in the costs of private charter planes to get there.      If you are going to a golf location,  is golfing included?  How much is a round?  Is that cost feasible for all the golfers in the family?If you are splitting the cost of a villa rental among the parties, it is important to consider additional aspects.  The cost of renting a vacation property varies greatly from location to location and week to week.   A 6-bedroom rental in Jamaica will cost much less than a comparable property in Barbados.    Going during peak season, such as Christmas or Easter, will mean much higher prices than during other times of the year.    Are the bedrooms of the villa all roughly “equal”?  It is not uncommon for villas to have extremely opulent master suites and  some rooms that may originally have been created for nannies or children.   In such situations, just dividing the villa price by the number of rooms may not create an equitable arrangement if everyone is paying for his own accommodation.Even if this vacation is going to be a once-in-a-lifetime, we’ve sold the family business, and grandma and grandpa are paying for everything,  it is important to lay out who is responsible for what.  Making sure that everyone is truly comfortable with the financial arrangements before the trip is the first step toward making sure that you have a great family getaway.


  1. Dates Picking a time that works for everyone can be even trickier than dealing with finances.   I don’t think it can ever be too early to begin discussing dates that might work for people.  Eighteen to 24 months out is definitely not too long when thinking about blocking a week off for an extended family holiday.  And you certainly want to have an open discussion before you get too far along into the planning process.Things to consider when selecting dates:
  • School holidays — if you have school-aged kids in your group, there will likely be a critical set of dates to work around.  If you don’t have to consider school holidays,  you are lucky, as there are many more deals to be had during “off” times.
  • Work schedules — Some jobs have very predictable crunch times and slow times. An early April getaway could be a nightmare for a US accountant.   Similarly, September is probably a no-go if anyone is a teacher.
  • Is anyone planning to get pregnant (or is pregnant)? —  I have traveled while heavily pregnant and with a newborn.  Both can be great.  However, most airlines won’t let pregnant mothers fly after a certain point (37 weeks? It can vary by airline) or with infants less than 2-weeks old.It probably isn’t possible to find the optimum week for everyone,  but planning ahead can certainly minimize scheduling problems and help narrow your destination choices.


  1. Assess your groups’ interests A trip to European capitals or New York could be a great family destination if your party is comprised of teens through active seniors.   A tropical island with a private pool and nearby golf and  beach could be heaven for families with young kids.   Some families may want a ski holiday with a number of other activities available.   If you want everyone to enjoy the vacation you plan (and to want to come),  it is important to find a destination that offers something for everyone.For example, in our extended family, we have some young children who often are happiest just playing at the villa pool or beach.   Then there are older (school-age kids) and adults who definitely want some adventurous outings.   Some in our group want to be able to visit cultural spots or experience nightlife.    These preferences mean that when I am looking for villas I want a property that is luxurious and great for kids on its own.  But I also want some day-trip activities within an hour’s drive or less.   Access to a nearby town or resort with tennis courts, a kids club, and some nightlife is also a big perk.      We have found many islands in the Caribbean where all of these needs can be met simultaneously.
  2. Pick a property Once you narrow down your dates and location you can begin to see what villa and hotel options are available for your group within your budget.    If you are going the villa route, either contact a villa agent to discuss options or work directly with the owner to secure your dates and make the necessary deposits.
  3. Make the announcement I think my favorite email of the entire year is sending out the details of our villa to everyone in our family.    Make it a big deal.  In addition to all the key details (dates, airports to fly into, etc), include pictures, links to activities you are excited about, and references to family jokes.
  4. Book your travel Anyone who needs to book flights should start looking for deals and anyone planning on using points should book as soon as possible (assuming there is availability).   The urgency of booking flights varies by location and time of year, but I think it is never too early, especially if you are traveling over spring break or the winter holidays.
  5. Relax (a little) Assuming that you have planned far out in advance, you should have some time to just chill.  About 3 months ahead of your departure is probably when you need to think about it again.  (Exceptions to this would be places like New York, London, or Disney World where you probably want to be making dining reservations or book tickets to events.)
  6. Start planning the details Three to four months before your vacation is time to start doing some list making and planning.   In addition to your own packing list,  there are other things to consider at this time.    Do you need to book a driver or rental car?   What about airport transfers?  Would you like to book a photographer to do a family photo shoot?    Does anyone need a passport renewed or visas for your destination?   Now is the time to take care of all these details.Additionally, now is the time to start thinking about the details that will make your getaway “grand”.   Perhaps you want to get t-shirts or hats for everyone.   Maybe you will be on holiday over Easter and want to organize an egg hunt.   Or perhaps send young kids a “busy bag” for a long plane flight or road trip.   Matching Christmas PJs for the kids?    Even if you aren’t booking a professional photographer, if you want everyone in coordinating clothing for a group picture, don’t wait to send out those instructions until two weeks before departure.  Communicate and plan now.
  7. Plan food and activities as necessary      At least a month in advance of the trip is time to start getting into the nitty-gritty in terms of food and activity planning
    • Renting a staffed villa? You will likely need to provide the chef with  menus for  your first dinner and breakfast.  Additionally, I always survey our group (especially the parents of young kids) to ascertain if there are any must-have food items.     Depending on the villa and the location, you may also be able to pre-order alcohol and drinks, which I highly recommend doing.
    • Cooking your own meals? Plan out and/or assign people to be in charge of meals.   If possible, consolidate and streamline your grocery lists (do you really need peanut oil and vegetable oil if you are only there for a week?)   Are there any hard-to-get items that you may want to bring from home, especially for a special meal or family recipe?    Again, be sure to put on your list any foods that picky kids just have to have.
    • Eating out? Research restaurants and make reservations, especially if you have a big group.    Important to note, for some urban destinations such as major cities and Disney World, you probably need to make dining reservations way more than a month in advance to get what you want.Four to six weeks ahead is also the time to start planning and booking activities.  Contact your villa manager or hotel concierge to see if you need to book tee times, spa appointments or excursions.   While at some places and times of the year it may be fine to wait until you arrive to think about those things, it’s upsetting to find out once you are there that you needed to book something a few weeks earlier.   Remember, with a bigger group more advanced planning may be necessary to get the days or times you want.   Again, for urban destinations (think Broadway or West End tickets) or Disney World, you may need to plan your activities much further in advance.


  1. Pack & do last minute preparations I am the type of person who starts my packing list three weeks in advance and am beyond stressed if I am not mostly packed the weekend before I leave.  But I know that I am probably the exception.     In the week ahead don’t forget to make sure you have sufficient prescription medications and plenty of sunscreen.
  2. Enjoy your Grand Family Getaway! Live in the moment and enjoy.   Now is the time to benefit from all of your careful planning and spend time enjoying your family.
  3. Turn your photos into lasting keepsakes  After my family trip is complete, I love going through all of the photos that were taken and creating a photobook.   I then get a copy printed for everyone on the trip to commemorate our vacation.  If you are not into creating photo albums (digitally or otherwise),  perhaps you or someone else in your group is savvy at creating photo and video montages.     There are also many options to create photo gifts such as mugs, calendars, and coasters.   I often find that the photos we take on our family getaways appear in Christmas, birthday, and mother’s/father’s day gifts for years to come!


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