When I was 11 years old, my dad won a trip to New York City as part of a recognition package from his boss. All expenses paid, and no expense spared. We flew on an airplane, stayed at the St. Moritz Hotel (now the Ritz-Carlton, New York, Central Park), and went to my first-ever Broadway show, Annie.

But the best part of the trip?

Was it Bloomingdale’s?

Nope.

Was it eating a hot dog in Central Park?

Nope.

How about room-service sundaes from the famous, but now closed, Rumplemeyer’s?

No way.

It was Courtney, our babysitter.

Since my folks weren’t footing the bill, they decided to spring for a plane ticket for the teenage girl who watched us from time to time when my parents went out for date night (which is, frankly, something I choose not to contemplate even at my ripe old age).

Courtney went with us on all of our expeditions that weekend, lending that extra-special touch of teenage glamour to the events. I copied her hairstyle and her nonchalant attitude as we cavorted through the city, eyeing sights like the Empire State Building with my oh-so-jaded fifth-grade eyes.

Then, on our last evening, my folks went out for a fancy dinner on their own and we three kids hung out in the lavish suite with Courtney, eating room service hamburgers and the aforementioned Rumplemeyer’s sundaes, dished up in enormous, elegant glass cups.

It was heaven.

Looking back, I can see what a luxury it was for my parents to not only take this trip, but also bring along an extra pair of hands. Three kids under the age of 12 in New York City for the first time? With two young parents in New York City for the first time?

Dude, you couldn’t pay me enough. Unless, of course, you paid for my babysitter to go with me.

Dual Incomes, Added Expenses
It’s no secret that these days, most families are bringing in two incomes from two very busy careers. The price of childcare is so high that more and more parents are opting for in-home care provided by a professional nanny.

Suzanne Royer McCone, president of Annie’s Nannies Household Staffing, says that her Seattle-based agency is placing or referring about 400 nannies at any given time.

While the nanny business may be booming, it’s still an expensive proposition to bring your caregiver along with you on vacation, especially a trip that includes air travel and hotel rooms.

“It is a luxury for you,” McCone says. “It will be very expensive. You’ll have to pay for all of her lodging and her incidentals.”

Those “incidentals” can run you anywhere from $50 to $200 a day, depending on how many meals your nanny will eat with your family, and how often she will be with you and your children during the trip.

Think about it how would you like to be stranded on a business trip without an expense account? Because that’s what it is for your nanny it’s not a vacation. She or he is simply doing their regular job in an exotic location.

Setting Expectations
I know that changing diapers, no matter if it is in my living room or Hawaii, is not my idea of a good time. So you should always be upfront with your nanny when discussing what her duties may be after she gets off that plane.

“The nanny may be expected to be available more than she is at home,” said Judi Merlin, president of A Friend Of The Family Home Services in Athens, Ga. “The children are in a different environment, rules are relaxed, schedules are disrupted. All of this can create havoc for the children and, therefore, for the nanny.”

Both parties, Merlin adds, need to sit down well before the trip and discuss their expectations. She suggests laying out very specific guidelines, such as:

How much time will the nanny be expected to spend with the children each day and each night?

Will the nanny sleep in the same room as the children?

Is the nanny going to be paid her regular salary, or should she expect to be paid more for more time with the children?

Will the nanny have specific time off duty each day?

Are the parents going to pay for all of the expenses of the nanny, including transportation, hotel or rental accommodation, all eating and entertainment expenses?

“Does this sound like fun?” Merlin asks. “Well, it can be if all parties agree on the ground rules and then honor their commitment to each other.”

These details should be worked out before you ever apply for that passport, says McCone, and put it in writing. Most nannies these days demand professional contracts, she says, with all of their duties laid out in black-and-white at the beginning. That way, there can be no misunderstandings when it comes time to travel – or not.

McCone also points out that you should be prepared to pay even if you decide to leave your personal Mary Poppins behind. Most nannies will expect to receive their regular, weekly salary while you and your kids are away.

The Best Of Both Worlds
McCone adds that bringing your nanny with you on a big family vacation can result in a memorable time for all involved.

“It really is the best of both worlds,” she says. “You get to have a great time with your kids, and still go out and have that special dinner or alone time as a couple.”

Now, if only I can convince my babysitter to tag along when we make our next trip to Cleveland. A 12-hour road trip to the Rust Belt? Shouldn’t be too hard a sell, eh?