3-genearation family trip to Bermuda

10 Tips for “KILLER” Family Trips (so you don’t kill each other)

A long time ago, when my firstborn was a baby, a seasoned older parent told me:  “Your children will always travel with you as long as you pay.”  

I have found that to be true 🙂  But there’s more to a successful family trip than the finances.   So here are our tried-n-true strategies at Rare Finds Travel for creating a family vacation that’s unforgettable (in a good way)…

#1.  Keep it short

4 days.  That’s my rule.

For starters, those millennial “kids” have limited vacation time which they have to divide between Coachella, friend trips, and love lives.   Don’t make them choose. Keep family time in an easy-to-fit-in block.  4 days/3 nights seems ideal.

And truthfully, when you are feeding (and housing, and entertaining, and …) an entire group of children, plus their new spouses and then young offspring, it can get expensive.   4 days contains your costs.

And finally, family gatherings can be intense.  Short stays seem to keep everyone on their best behavior – just enough time to really reconnect without sinking in the quagmire of birth order, politics, and pettiness.

#2. Commit far in advance

Schedules are often the biggest hurdle to getting a family trip off the ground.

I usually pick a holiday (which we tend to subconsciously delegate as family time, and when most people will have time off from work) and I book at least 7-8 months out.  I set the intention and extend the invite.   And our family trip is  off to the races…

#3.  Pick a sexy destination

Face it – Kansas reunions might not generate the buzz that a Hawaii trip does.   But really, it’s more about what you do than where you go.

We sent Clara’s family to Key West where college nephews could walk into town for late-night music, and where young grandchildren could play on placid beaches like Fort Zach. There was one remarkable venue on a beach for their grand finale dinner but they otherwise bought groceries and cooked at their conch cottages. There was something for everybody!

On the other hand, don’t offer too much distraction. Remember that you are underwriting a trip to bring the family together, so a resort where your family separates in different directions all day long is not going to create the bonding that you want.

#4.  Choose spot near major hub or airport.

This is super important because it’s inevitable that someone in your family will have a work commitment or life situation that forces them to arrive late, or leave early.  It will make everyone’s life so much easier if it’s rather seamless to get them to and from their flight without disrupting everyone else’s schedule.

Good locations could be in Old Havana (a 15-minute taxi from the airport) or Normandy (a 2-hour TGV fast train ride from Paris) or Key West (multiple flights a day go in and out, and it’s easy to drive from Miami area too).

#5.  Balance structured and free time

Busy hands are happy hands – ever heard that?  So I tend to create a plan that flows each day with meals, pre-booked activities, and a little rest.

I consider the schedule compulsory, but usually make a morning activity optional (I remember a Yoga With the Dolphins class at 7am in Vegas that my college kid almost opted out of)

I like to create scavenger hunts like a Gelato A Day in Rome or a Cafe A Day in Paris – or a hunt for small ornaments (handmade or natural or commercial) to decorate a  Christmas tree.

And I always keep a few tricks up my sleeve – surprise them with a dance class in our Casa after supper, or reserve a secret spot for special sundowners.

#6:  Decide on your guest list.

Do you include son- and daughter-in-laws?  Surely.

What about significant others?  At what point are relationships worthy of the family invite?  And do you want to be the policeman of this?

I don’t pretend to have the answer for this question.   I am only saying:  think about this and have a plan.

#7:  Prepare for last-minute changes.

My daughter-in-law changed jobs, 3 weeks before our Cuba trip. People get pregnant, or sick.  The unmarried ones find a girlfriend – then break up.   There are 3 words for this:

BUY TRAVEL INSURANCE (for your flights).

#8:  Cover all costs.

You want, if possible, to remove money as an obstacle for family travel.  What we may think of as an incidental, like taxi to airport, can be a significant hurdle for a graduate student or starving artist.

So think carefully through each step of the trip, from Visas to transfers, and cover as much as possible.

In my family, I cover air, transfers, lodging, a full slate of fun, and all group meals, for the 4 days.

They want to stay longer?  Got a dog to board?  Want to party late a night in Old Havana?  Buy cigars to bring back to their officemates?  These are all THEIR costs.

I find that including the money plan along with the invitation is very important.   How can they accept an invite without knowing what’s included (or not).

#9:  Create a challenge (my favorite!)

As though family trips cannot be inherently challenging enough, I like to add a BIG one!

Challenges create a “common enemy syndrome”…. an “us against the world” bonding.  This “enemy”, of course, is whatever is unknown.   It could be a language or cultural barrier that you face together.   It could be facing a fear, from sky-diving to night snorkeling.  It could be a physical challenge like walking the 20+-mile cross-island trail on Dominica, or living ashram-style at the yoga retreat.

But often it’s teamwork.  Like my cooking competition, CHOPT!

Designed loosely on a cooking TV show, here’s how we do this:

  • I divide the family into 2-person teams (random team assignments are key to nix any favoritism – picking straws is an easy team-assigning tool)
  • I hand out pre-organized gear:  knives, cutting boards, hand towels.
  • Teams have 30 seconds to privately strategize before the picking begins.  To pick, teams take turns choosing from an assortment of ingredients  – some typical like fresh spinach or pancetta or fresh shrimp- others unusual like a whole coconut or fish paste.
  • Teams have 30 more seconds to plan their dishes, then the timer starts.
  • They have 15 minutes to plate an appetizer.

I always have a bank of shared ingredients on the side, like herbs and spices, oils and vinegars.  There are rules – like you must use every single ingredient – and, over the years, the kids have added more rules like the “force swap” where you can force one of your ingredients (usually that dread coconut that no one knows what to do with) onto the other team.

I serve prosecco during the competition, and always plan a full dinner for afterwards (just in case those plated appetizers just don’t quite work out).

Also note that you’ll need a kitchen!  This means that you’ll want to stay in an AirBnB or villa or apartment – but in a pinch, even a campfire and camp stove can work.

Other variations have included Muriel’s all-adult family who comb the Burgundy countryside each summer for the most scrumptious, artisanal ingredients that they use for truly gourmet meals, each night’s “chef” trying to out-do the one before.

And when my sons were very young, we’d draw numbers for dinner duty.  Everyone got 2 numbers – one night to be the chef and the other number to be sous-chef (chop and wash).   Even if the menu consisted of little more than melon and mac-n-cheese, each child took his turn – even the 8 year old!

#10:  Open arms, close mouth.

A good friend of mine once shared good advice from her rabbi that is perfect for family trips:  Open arms. Close mouth.

Family trips bring ALL of us together (our histories, our beliefs, our habits, our lifestyles)  so there’s an inhernet train wreck as our differences mesh over 4 days.

But, just like in visiting foreign countries, it’s the differences that make the memories so rich.

Be brave, and book it!

Want help to pull off your next family trip?  

Call us today to get started:  609 923 0304!

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