Articles & Guides

What can we help you find?

Real Story: How I Hired a Sitter for a Destination Wedding Vacation

We could take the kids to the destination, but not to the destination wedding. So, we needed to find child care when we got there — and fast.

Until recently, high on my list of parenting “Never Have I Evers” was, “Never have I ever hired a babysitter on vacation.” But when I accepted a unique and emotionally meaningful request to officiate at my husband’s cousin’s wedding in Lake Tahoe, California, I nervously realized that “never” was about to be a thing of the past for our Boston-based family.

I was intimidated by the task of finding a stranger to entrust with my 5-year-old son Ben for a 10-hour stretch of time in a place I’d never even visited. True, he’s not a helpless infant or an inarticulate toddler. But he is my baby. And the wedding was an adults-only affair.

5 tips for hiring a vacation sitter

After striking out with friends-of-friends, I signed up for and created a job post, which yielded several responses, led to a number of email exchanges and 3 phone interviews. I was impressed with the range of ages and experiences among the sitters, as well as the professionalism reflected in quick email responses and on-time phone interviews.

Before too long, I connected with Shivon, who was the perfect salve for my nerves. On paper, she was outstanding — being a babysitter and nanny is her full-time job, and she has incorporated her business, a sign of professional pride and accountability. She grew up in the area and teaches ski lessons to kids at some local resorts. She has undergone thorough background checks, including extra levels of certification to qualify as a caregiver to children in the foster care system. I felt my blood pressure falling exponentially as I learned more about her.

Our phone interview confirmed my good feelings. She sounded calm and kind, acknowledging my feelings of being outside my comfort zone. She communicated her rates and policies clearly. She provided two references — one a local family who uses her as a nanny, the other a vacationing family like us. Speaking with them added yet more layers of confidence in her demeanor, skill, and professionalism. We had found our sitter.

The wedding day arrived, and so did Shivon—right on time. She came prepared with a bag full of toy trains, books, and board games. We gave her sunscreen, a tour of our hotel suite, and our only child. Dressed in our formal outfits, we left for the wedding, feeling more confident than I would have predicted.

Throughout the evening, Shivon sent texts and photos that chronicled a boy having a great time. He was eating lunch. He was mini-golfing. He was playing in the hotel room. He was going on a nature walk. He was having dinner. And then, he was in bed and asleep, all according to the schedule we’d outlined.

I had a big responsibility at the wedding, crafting the words that would launch the happy couple’s marriage. But making sure my son was well cared for is the most important responsibility of my life. Even far from home, I was able to fulfill both.


Holly Lebowitz Rossi is a freelance writer and editor who has covered religion, health, yoga, parenting, children’s music, and more for two decades. She has also written extensively for print magazines, newspapers, and radio, in a series of commentaries for NPR’s “All Things Considered.” Freelance clients include Newsweek, The Washington Post, Slate, Tablet, Parents, Prevention, and the Boston Globe Sunday Magazine.Together with yoga teacher Liz Owen, she is the co-author of “Yoga for a Healthy Lower Back: A Practical Guide to Developing Strength and Relieving Pain.” You can find more of her work on her website.