How to plan a skiing trip
with kids.
The part of a family ski trip that goes wrong is rarely the skiing. It is the lesson that was sold out, the rental line that ate the first hour, or the mountain that was too big for a kid on their third day on snow. Our girls learned to ski at Gunstock, in New Hampshire's Lakes Region, and this is how to plan a skiing trip in the order that avoids those problems.
The family ski trip plan,
in booking order.
Choose the mountain, pick the dates, then book in this order: lessons, lodging, rentals, lift tickets. Pack last.
| Step | What to decide or book | Why this order |
|---|---|---|
| 1. Mountain | A small or mid-sized mountain within a comfortable drive | Beginners need gentle terrain more than a famous name |
| 2. Dates | Midweek or an ordinary weekend if you can; holiday weeks only if you must | Every later booking depends on the dates |
| 3. Lessons | Kids' ski school, booked online | On busy weeks, lessons sell out before lodging does |
| 4. Lodging | Only if the drive is over about two hours | A day trip needs none |
| 5. Rentals | Skis, boots, poles and helmets, reserved online | Skips most of the morning rental line |
| 6. Lift tickets | Bought online ahead of the day | At many resorts, cheaper than the ticket window |
| 7. Packing | Layers, mittens, helmet, goggles, a day bag | See our ski packing list for kids |
The booking order is how we would plan a ski trip with our girls. Lesson ages, ticket prices and online booking rules are set by each resort and change every season, so this page doesn't quote prices. Check the resort's own site before you book. Researched November 5, 2026.
How do you plan a family ski trip?
Lessons first, lodging second.
Most travel planning starts with the place to sleep. A family ski trip should start with ski school. A mountain has only so many instructors and only so many spots in each kids' group, and on a holiday weekend or school vacation week those spots go before the rentals in town do. Book the lesson, then book the bed around it.
Rentals and lift tickets come next, and both are worth doing online. A reserved rental usually means a shorter line and a fitting that's already half done. Many resorts also price lift tickets lower online and in advance than at the window on the day, sometimes by a lot on a busy Saturday.
Book the lesson for the morning. Kids are freshest early and the snow is usually best then too. An afternoon lesson after a long drive is the one most likely to end in tears.
Pick the mountain for the kids,
not for the trail map.
For a first season, a smaller mountain beats a famous one. Gunstock, in Gilford, is where we ski as a family. It is about 2 hours from Boston, it never felt like too much mountain for the girls, and it has a ski school, a children's center for kids too young for lessons, night skiing on some evenings and a tubing hill for a sibling who isn't skiing yet.
Kyle grew up in Wallingford, Vermont, and skied Killington, Pico and Okemo many times growing up. They are great mountains, and Okemo is the Vermont one we would point a family to first. But they are about 3 hours from Boston, and Killington in particular is big. Save the bigger Vermont mountains for when the kids can ski a full day.
What to look for, whichever mountain you choose: a separate beginner area away from fast traffic, a carpet lift or a slow chairlift for first days, one base lodge where everyone can find each other, and a kids' program that fits your youngest child's age.
Our family ski resorts from Boston guide compares Gunstock, Cranmore, Waterville Valley, Bretton Woods, Okemo, Killington and Smugglers' Notch side by side.
When to go:
timing the season.
The New England ski season usually runs from December into early April, and the busy weeks are predictable: the stretch between Christmas and New Year's, the Martin Luther King Jr. Day and Presidents' Day weekends, and February school vacation week, which is the busiest of all. Those weeks are fine if school leaves you no choice. Just plan them early, starting in the fall.
If you have a choice, January weekends away from the holiday ones are quieter, and March is the friendliest month for small kids: longer days, warmer afternoons and softer snow that's kinder when they fall. A midweek day on any week of the season is the quietest of all.
Our school vacation week dates page has the February and April vacation dates by state.
Ski lessons for kids:
what to book.
Ski schools sort kids by age and by ability, and many start group lessons somewhere around age 3 to 5. Younger than that, some resorts run a children's center or a snow play program instead. The age cutoffs differ by mountain, so read the ski school's own page before you book anything else.
For a child's first time, a lesson is worth more than a parent's best intentions. Kids listen to an instructor in a way they won't listen to us, and it frees the adults to ski, or to drink a coffee in the lodge, for a couple of hours. Multi-day lesson packages are often cheaper per day than single lessons if you are staying the weekend.
Lodging, rentals
and lift tickets.
Lodging: Gunstock, about 2 hours from Boston, works as a day trip, which is how we would do a first ski day with small kids. Leave early, ski the morning, eat lunch in the lodge, and drive home in dry clothes. Okemo, about 3 hours from Boston, is a weekend. If you stay over, look for a rental with a mudroom or a washer and somewhere warm to dry boots, mittens and socks overnight. That matters more than being slopeside.
Rentals: rent skis, boots, poles and helmets at the mountain for a first trip or a first season, and reserve them online ahead of a busy weekend. Kids outgrow boots in a season or two. Once they ski most weekends, a junior season lease from a local ski shop is usually the better deal.
Lift tickets: buy online, ahead of the day, from the resort's own site. Ask about beginner-area-only tickets for a child's first day, since some mountains sell them for less, and check what age kids ski free or at a reduced rate, which varies by resort.
Search Vrbo rentals, already set to Gilford. Look for two bedrooms and a full kitchen. Where we would stay. Affiliate link, our disclosure.
What families ask us.
How do you plan a skiing trip with kids?
Pick a mountain that fits your kids' level and your drive, then choose dates. Book kids' lessons first, because ski school spots sell out before lodging does on busy weeks. Then book lodging, reserve rental skis, boots and helmets online, and buy lift tickets online ahead of time, which at many resorts is cheaper than the ticket window. Pack last.
How far ahead should you plan a family ski trip?
For a school vacation week or the Christmas to New Year stretch, start in early fall: lessons, lodging and rentals fill first on those weeks. For an ordinary weekend in January or March, a few weeks ahead is usually enough, and a midweek day can often be booked the week before.
What age can kids start ski lessons?
It depends on the mountain. Many ski schools start group lessons somewhere around age 3 to 5, and some resorts run a children's center or a snow play program for kids too young for lessons. Check the ski school's own age rules before you book, since they differ from resort to resort and change by season.
When is the best time to take kids skiing?
For a first trip, a midweek day or an ordinary weekend in January or March. Lift lines and lesson groups are shorter than on holiday weeks, and March usually brings softer snow and warmer afternoons. February vacation week has good snow but is the busiest week of the season.
Is a ski day trip or a ski weekend better with young kids?
For a first season, a day trip keeps it simple: Gunstock is about 2 hours from Boston, and if it is too cold or the kids are done by lunch, you go home. Once the kids are skiing a full day, a weekend at Okemo or Killington, about 3 hours from Boston, makes sense, because that drive is too long to do twice in one day.
Should you rent ski gear or buy it for kids?
Rent skis, boots and poles for a first trip or a first season, and reserve them online before a busy weekend. Kids outgrow boots fast. Once they ski most weekends, a junior season lease from a ski shop is usually the better deal. Own the clothing, goggles and mittens.
Keep planning.
Gunstock, where our girls ski, and the Vermont mountains Kyle grew up on.
February and April vacation weeks, the busiest ski weeks of the year.
Ice Castles, the Cog Railway and where Gunstock fits.
Planning something further afield?
The Boston-to-Europe family flight guide: which routes run year-round, the order we book things in, and how far ahead to buy for a school vacation week.
Plus our 12-page field guide, free: where we stay, what we pack, and the eSIM, VPN and insurance we set up before every trip.
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