F4 EZ EE THE WASHINGTON POST.SUNDAY, MAY 15 , 2022
together. Others figure it out on
the fly. My husband, Jeff, grew up
in a family of travelers, while my
own rarely took vacations when I
was a child. As a result, family
travel has always made me
slightly uneasy. Although I trav-
eled extensively as a young adult,
until I married Jeff, my trips
were mainly solo or with a friend
who shared my tight budget and
lowbrow approach to exploring.
Back then, we were nimble and
cheap. We did free activities,
stretched the youth hostel break-
fast into lunch, clutched our
Lonely Planet guidebooks and
were bound by bus schedules.
Traveling with a little more
comfort and significantly more
people, to whom I’m related by
marriage, was something else
entirely. More people meant
more opinions and logistics, and
the fact that we were family had
the potential to add complica-
tions.
When multiple generations of
a family travel together, there is
much to consider, including the
budget, itineraries and meals. It’s
helpful to know how you willBY RACHEL WALKERAbout half an hour into the
boat ride into Cape Cod Bay, one
of my nieces began to look nau-
seous; my brother-in-law, an avid
nature lover who disdains
crowds, seemed annoyed with
the other tourists on our whale-
watching boat; my 4-year-old son
crawled into my lap and fell
asleep; and my 6-year-old de-
clared that he was bored. I fret-
ted. I had dragged my husband’s
extended family — his mother
and her partner, and his sister
and her family — with my own
brood onto this boat, insisting
that whale watching was exactly
what our summer family vaca-
tion needed.
Cassandra, my mother-in-law,
had rented us all a house in
Plymouth, Mass., near the beach,
and I wanted to make the most of
our trip, although I would have
been hard-pressed to explain ex-
actly what “making the most of
it” meant. Creating memories?
Having fun? Sharing meals? Re-
laxing?
Yes, and ... after several days of
paddleboarding and playing on
the beach, our reunion had be-
gun to feel a little sleepy. It
seemed imperative to find a
uniquely New England experi-
ence that went beyond building
sand castles and looking for seals
in the surf. I landed on whale
watching, found an operator at
nearby Plymouth Harbor, and
soon all 10 of us were standing in
a long line to buy tickets for a
four-hour whale-watching expe-
dition.
As the sun beat down while we
waited to board, my anxiety be-
gan to set in. I worried that we
might not see whales and that
the trip would be a bust. I
questioned whether the cost of
the trip would be worth the
experience. (Although not exces-
sive, whale watching was a
splurge.) I feared that the boat
ride would be hot. Or cold. Or
uncomfortable. Or boring. These
worries followed me onboard,
and as the boat motored away
from the dock and into the
beautiful, watery horizon, I was
preoccupied with nerves and my
own high expectations.
Such can be the dynamic on a
multigenerational family vaca-
tion. Put 10 related individuals
into a rental house, and you’ll get
10 different opinions about what
to eat, where to go, how to spend
the day and how to spend money.
Some families have estab-
lished approaches to traveling
divide expenses before starting
the trip, as well as what everyone
hopes to do or see. As for food,
will you be eating out or cooking
in? If the latter, who will plan the
menu? Who will do the shop-
ping?
There’s also the question of
how to best spend time together.
On one hand, the very fact that
everyone is in the same place is
unique and should be savored.
On the other hand, people who
spend uninterrupted days to-
gether tend to get on each other’s
nerves. Add in different person-
alities, energy levels, ages and
attention spans, and there’s sud-
denly a raft of things to negoti-
ate, all in the name of the
common goal that everyone have
fun.
It can be a tall order. It can also
take a lot of mental energy, which
is why, for some time, I con-
vinced myself that visits with
family did not qualify as vaca-
tions. One was an important
effort to maintain bonds be-
tween relatives, and the other
offered a respite from daily life,
either in the form of adventure or
relaxation. Vacations, I thought,
were for chosen family — my
husband, my best friends — and,
after I became a parent, my kids.
But that logic simply didn’t
hold with Jeff’s extended family,
a hardy group of adventurers and
epicureans. For one, we rarely
gathered at our respective
homes. Instead, our visits took us
to the mountains of Colorado
and Vermont, to French wineries
and Parisian cafes, and to the
coast of Massachusetts. For an-
other, when we travel together,
we are almost always on an
adventure. We have biked, hiked,
swam and boated alongside one
another. Along the way, our col-
lective sharing of ourselves and
experiences have built lovely
friendships and left us rejuven-
ated, as vacations do.
Whale watching was no excep-
tion. With the first slap of a
whale tail on the water, the boat’s
onboard naturalist announced
over the loudspeaker the appear-
ance of a humpback on the port
side. The crowd swarmed over.
Then came another announce-
ment: Look to starboard for a
pod of minkes. And that was just
the beginning. It began as a slow
trickle, then suddenly whales
surrounded the boat. The natu-
ralist narrated what we were
seeing, but even she had trouble
keeping up with all the activity. It
was as if the entire whale popula-
SEE WHALES ON F5On Cape Cod Bay, whale-watching tour goes swimminglyPHOTOS BY ISTOCKFROM TOP: Minke whales (pictured), humpbacks and fins all made appearances during a family
whale-watching expedition in Massachusetts; the Duxbury Pier lighthouse in Plymouth Harbor.put all trip charges on a personal
credit card. However, if you only
have joint accounts, ask your
partner to avoid looking at the
relevant statements. Finally,
when browsing for bookings or
researching your destination,
“search on your phone instead of
a computer, and close all your
tabs afterwards,” advises Jen
Campbell Boles, founder of Ex-
plore More Family Travel, a fami-
ly-focused travel agency.
Consider everyone’s obliga-
tions. Although a vacation is
intended to be a welcome break
from normal routines and obliga-
tions, those can’t be ignored.
Before you make any nonrefund-
able reservations, ensure that
your partner can get time off
from their job and that there
aren’t any too-costly penalties for
pulling a child out of a sport,
summer camp or school. There is
nothing worse than a vacation
during which one of the parents
is stressing about a big work
project or deadline, or a child is
moping because they aren’t com-
peting in a championship gameor are missing time with the BFF
they only see at camp.
Find co-conspirators. To pull
off a surprise this big, you’re
going to need help. Relatives and
your partner’s dearest friends are
your best bets — if they can keep a
secret. They can provide intel you
lack and ask your partner the
questions you don’t want to ask,
so you don’t pique their suspi-
cions. If you feel comfortable
approaching your partner’s boss,
and you believe they can help
ease stress around work commit-
ments, bring them onboard, too.
Finally, if the whole idea of put-
ting together a vacation is freak-
ing you out for whatever reason,
consider engaging the services of
a professional trip planner.
Pick their perfect destina-
tion. “Ask yourself, ‘Where do
they want to go?’ ” says Guido
Adelfio, president of Bethesda
Travel Center, which creates cus-
tom vacations. “Bucket-list spots
always go over well.” Think about
what your partner and children
like to do, their energy levels and
their comfort zones. For a triplike this to deliver the intended
wow factor, it must be designed
with their tastes in mind. Now is
not the time to go somewhere
you’ve been aching to visit.
Craft a balanced itinerary
with a few blowouts. Creating a
schedule that pleases everyone is
a herculean feat. Exponentially
up your chances of success by
including one element every day
for each person to enjoy, even if
on some days that moment is a
small one. Always leave extra
time between activities, so you
don’t get stressed if you’re run-
ning late. Leave a few big chunks
open on your calendar, so you can
simply chillax or do something
unexpected on the fly. Take your
vacation to the next-next level by
including a few splurge-y, splashy
moments. “Think about buying
concert tickets or tickets to a
sporting event. Get a nice restau-
rant reservation. Go drive a Fer-
rari,” Adelfio recommends. “Do
something with a little panache.”
Steer clear of danger. This is
not the trip to push someone out
of their challenge zone and intoBY NEVIN MARTELLPlease don’t tell my family, but
I’m planning a surprise vacation
for us this summer. The goal is to
go somewhere warm and wel-
coming, where we can divide our
time between fun activities and
lazing by the beach.
This is the first time I’m coordi-
nating a trip without any input
from my wife or our 9-year-old
son. I’m a little concerned. Plot-
ting vacations is already a knotty
process. Although I usually take
the lead, they both, understand-
ably, have strong opinions on
where we should go and what we
should do when we get there.
However, the potential payoff — a
much-needed getaway that
spares my wife the headaches of
planning and springs a surprise
on my son while they’re still
young enough to be delighted
rather than annoyed by it —
vastly outweighs my reserva-
tions.
That being said, I would never
plan such a trip for people whose
preferences and peccadilloes I
didn’t know so well; the potential
for catastrophic error is too high.
Pulling off a surprise vacay suc-
cessfully requires a different
mind-set, extreme detail manage-
ment and a fair amount of stealth.
To help you navigate the unique
challenges of organizing such a
trip, I gleaned tips from a trio of
experienced travel professionals
and paired them with insights
I’ve gained along the way.
Remember: My family is in the
dark about our sunny getaway, so
please don’t mention this article
to them. Thanks for your help!
Cover your tracks. Keeping
secrets in the digital age can be
incredibly difficult, but it’s possi-
ble with some spycraft-level ef-
fort. Use an email address to
which only you have access to
receive all confirmations and cor-
respondence. Don’t request text
alerts for flights or other book-
ings, because they may pop up at
inopportune moments. Never
add your family’s frequent-flier
mile numbers to a reservation,
because they may receive an alert
with the itinerary. (Just don’t
forget to add them once everyone
is in on the surprise.) If possible,
their panic zone. “I wouldn’t in-
clude any activity with an el-
ement of danger that you’re un-
certain how they’ll respond to it,”
advises Rob Taylor, founder of the
LGBTQ family travel blog
2TravelDads. “It could lead to
anxiety, them not being able to
process it or feeling obligated to
participate because it was a sur-
prise, even though they don’t
want to. For example, if you
surprised me with a day of rock
climbing or rappelling, I would
literally break down in front of
you.”
Gather paperwork and pack
properly. Do not screw this step
up, or your entire trip will be in
jeopardy. If you’re going out of
the country, double-check that
everyone’s passports are up to
date, keeping in mind that some
countries will deny a visitor entry
if their passport is valid for less
than six months. Check whether
there are any regulations regard-
ing coronavirus safety and vacci-
nations. Speaking of the latter,
ensure that everyone has any
vaccinations required at the des-
tination. Don’t forget to pack
everyone’s medications, and
bring along any necessary medi-
cal documentation. Last but notleast, you must make sure they
bring the right wardrobe, so they
can comfortably enjoy all the
activities you have planned.
Making your grand reveal. I
advise letting partners and family
members know in advance that
you’re going somewhere, so
they’re prepared to be gone. How-
ever, how much you tell them and
when depends on your style and
what you believe will achieve the
biggest bang for your efforts.
Adelfio suggests telling them at a
momentous occasion, such as a
birthday party or family event.
You could also have your travel-
ing companions open clues to
help them figure out the destina-
tion, which Campbell Boles rec-
ommends. Another idea is to have
everyone pack two bags — one
with beach gear and one with
wintry clothing, for example —
and then tell them which to bring
just before you depart for the
airport. Or you can reveal the trip
in stages, creating fun revelations
throughout the vacation.
When Taylor and his husband
want to surprise their two sons,
they share selective slivers of
information. “We’ll say we are
going to California or Georgia,
but we’ll leave it there,” he says.
“Or we’ll say, ‘Here are some
things you should be packing.’
That leaves it a little mysterious
but sets an expectation about
what’s ahead.”
Temper your expectations. Be
honest with yourself about why
you’re planning the trip. Other-
wise, you could be in for a sur-
prise of your own. “You don’t
know how people will respond to
a surprise that clearly took a lot of
your time, effort and money to
plan,” Taylor says. If your big
“ta-da!” doesn’t get the reception
you’d hoped for, at least you’ll
have the consolation of knowing
your motives were pure. Take in
any negative feedback gracefully,
keep it in mind for future travels
and do your best to ensure that
everyone gets the most out of the
trip they’re on.Martell is a writer based in Silver
Spring. His website is
nevinmartell.com. Find him on
Twitter and Instagram:
@nevinmartell.Guess what? We’re going on vacation! A guide to surprise family getaways.ISTOCK/WASHINGTON POST ILLUSTRATION
Engineering a surprise family vacation takes a lot of planning — making sure schedules align, crafting
an itinerary that pleases everyone, gathering the right paperwork — but the payoff can be worth it.Keeping secrets inthe digital agecan be incrediblydifficult, but it’spossible with somespycraft-leveleffort. Use anemail addressto which onlyyou have accessto receive allconfirmations andcorrespondence.