Summer sleepaway can foster a kid's sense of freedom and give him a confidence boost. Here's how to get him ready.  
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Every summer, my daughter Lena goes to day camp, where she meets new friends, improves her swim stroke, and pursues her passion for musical theater. Now that she's 8, I'm wondering whether she's ready for another kind of adventure (even if I'm not sure I am): overnight camp. "Sleepaway camp is a great place for kids to learn to navigate situations without you," says psychologist Jerry Weichman, Ph.D., a parenting expert at the Hoag Neurosciences Institute, in Newport Beach, California. "These experiences build autonomy and foster a sense of self-esteem." Find out whether your child is ready for sleepaway, and make the separation a success.

Lay the foundation. For some families, overnight camp is a beloved tradition and it's only a matter of time before their child bunks up, usually starting between ages 8 and 12. "I had good sleepaway- camp experiences as a kid, so I felt strongly that my boys should go," says Sarah Worth, of Greenville, South Carolina, whose 9-year-old twins, William and Charles Price, were happy to try a week of overnight camp for the first time last summer. "It taught them all kinds of awesome skills, like eating what they're served, cleaning up after themselves, getting along with other kids, and being outside their comfort zone." If you're not confident that your kid is ready to pack his bags yet, Parents advisor Michael Thompson, Ph.D., author of Homesick and Happy, suggests simply talking to him about overnight camp and seeing how he reacts, particularly if he has friends who will be going away. "When a child expresses some interest in sleepaway camp too, that's the indication that he or she is becoming ready," says Dr. Thompson. Many camps offer springtime programs where kids can spend a full day or a weekend with other kids, which can be a great introduction to camp life. If your child is cool to the idea, though, stick with day camp and work up to sleepaway by asking him to try an overnight at a friend's.

Assess what matters most. First, think about what kind of camp might appeal to your child—there's no shortage of options. "There are traditional camps, religious camps, special-needs camps, and camps dedicated to performing arts, sports, science, dance, special dietary needs, and more," says Melanie Singer, a consultant with Arlene Streisand's Camp Specialists, a free referral service that matches families with camps nationwide. "It's such an individual decision, and what's good for someone else's child might not be good for yours." Singer recommends taking into account location, budget, and your child's personality. If she's on the shy side, she might enjoy a small camp close to home; an adventurer might love a camp that offers field trips; a sporty kid may love a camp with lots of team options. That's just what Chicago parents Robin and Peter Gruen did when they set out to pick a four-week camp for their 9-year-old daughter, Charlotte, last summer. "We had specific criteria," says Robin. "We wanted an all-girls camp that was within driving distance and attracted kids from all over so Charlotte would make friends from around the country." That winnowed their list to four before they chose a favorite.

Decide together. To get a more complete sense of your top contenders, reach out to the camps to visit their open houses, schedule a meeting with the directors (some make house calls and do sessions over Skype throughout the year), and view camp videos, which give you a feel for a camp's personality, culture, and facilities. "While it's helpful to visit a camp in full swing, you can find out a lot just by talking with the director," says Lauren Kasnett Nearpass, cofounder of Summer 365, a free service that vets camps across the country and helps families pick the best fit. She recommends asking questions such as: Can you describe the bunks and meals? What is the camper-counselor ratio? What is the daily schedule? What percentage of campers returns each year? How do you handle homesickness? The camp directors should be prepared to answer all these and more. "Although it's a great idea to include your child in the process, you should be the driving force in the decision," explains Kasnett Nearpass.

Do the emotional prep. No matter how excited your kid may be to go to camp, it's natural for him to feel some anxiety. "Many parents avoid talking about homesickness because they're afraid it will increase their child's fear," says Dr. Thompson. "However, nothing reduces homesickness like empathizing with it and acknowledging that it might be a bit tough to overcome but that most children do." Then talk about what your child may be looking forward to at camp. Dr. Thompson notes that it's one of the few places kids can go these days to be in a no-gadgets zone where time slows down, be part of a multigenerational community, and participate in meaningful daily rituals like group meals and campfire sing-alongs. Character-building experiences like these can allow kids to do some of the greatest maturing of their lives, says Dr. Thompson. It's what Leigh Flusser Gourvitz, of Livingston, New Jersey, found the first time she visited her daughter, Avery, 10, at overnight camp two years ago. "There was a maturity about her, an independence I saw as she grabbed my younger daughter by the hand and guided us all around the grounds," she says. "She grew up more, in a good way."

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