From picking the perfect mountain to renting winter clothes: How I'm prepping for my 1st ski trip

As a 30-something, there are fewer and fewer things in life that I am doing for the first time.

But there's one thing I've always wanted to do and never got the opportunity to try growing up in Missouri — ski.

So when the opportunity presented itself for me to learn how to ski later this month along with two colleagues on TPG's dime, I couldn't say no.

However, as I'm quickly discovering, there's a ton to consider in planning your first ski trip.

How to pick a mountain

Although my colleagues and I initially had lofty aspirations to ski in various places across the U.S. -- including Utah, Wyoming and Vermont -- we quickly realized that booking a ski trip in late January for February meant most of the desirable locations had limited availability this late in the season.

We were also advised by TPG staffers who considered themselves proficient at skiing to consider the barriers to entry at each mountain we were discussing. It then seemed prudent to start at a lower-level mountain versus a Peak 8 and 9,950-foot elevation at Breckenridge (whatever that means).

Because we would be driving from New York City, we narrowed down our options to three mountains — Butternut in Great Barrington, Massachusetts; Jiminy Peak in Hancock, Massachusetts; and Camelback Mountain in the Poconos in Pennsylvania.

Factoring in availability, budget constraints and a recommendation from those aforementioned TPG skiing staffers, we ultimately landed on Jiminy Peak for its focus on beginner terrain-based skiing and snowboarding lessons.

According to the Jiminy Peak website: "With Jiminy's revolutionary Terrain Based Learning our beginner ski / snowboard lessons are able to teach skills by feel and intuition rather than verbal commands or visual demonstrations." It continues on to say: "Our Terrain Based Learning methods use adaptive activities on snow in our specially designed terrain parks to control speed, change directions and introduce vertical motion (weighting and unweighting)."

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Here's to learning by doing.

Things to buy: Lift tickets, lessons and clothing

Jiminy Peak appealed to our group of first-time skiers for many reasons, one of which is that it offers beginner-specific ski sessions that include all rental equipment (including a helmet, because safety first), a 90-minute group lesson and a lift ticket.

We opted for two days of beginner lessons, costing $318 per person. This made booking easy and left very little other than clothing in terms of additional gear for us to buy.

"I was actually expecting the planning and logistics of renting gear, acquiring lift tickets and scheduling classes to be much more difficult than it was," said TPG editor Madison Blancaflor, who will be skiing for the first time with me. "Choosing a resort with a beginner ski package that included lift tickets, lessons and skiing equipment made everything so much easier than having to organize all of those trip elements separately."

Related: Believe it or not: How booking a private ski lesson saved us money

If you are planning on just trying skiing (or snowboarding) out, we would recommend renting some of the clothing versus buying all of it yourself, which can be very pricey considering ski socks alone cost roughly $50.

My two colleagues and I (you'll be reading about their ski experiences soon) decided to rent a Complete Outerwear Kit from Kit Lender, which runs anywhere between $37 and $75 per day with a three-day minimum.

The kit I rented includes a ski jacket, ski pants, goggles and gloves. There is a variety of brands and styles to choose from, including the usual suspects like North Face and Patagonia, but also some vintage onesies if that's more your style.

You can ship the clothing anywhere you'd like within the United States, including hotels. The latter is where we will pick up our gear upon our arrival later this month.

In addition to the outerwear rental, I also bought two pairs of socks, a vest, two turtlenecks and two pairs of thermal underwear. I'll also be bringing a neck gaiter that I already own.

Regarding ski clothing in general, synthetic layers are best and you should avoid cotton, according to a Stowe Mountain employee I talked to when first researching various mountains we were considering. They also recommended purchasing disposable hand and boot warmers; mittens, not gloves; and a balaclava ski mask.

Lastly, we are renting goggles as part of our clothing package, with assurance from Kit Lender that its goggles are thoroughly sanitized and cleaned for each use. If you are concerned though, because of COVID-19, you might want to consider bringing your own.

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(Photo by Caroline Tanner/The Points Guy)

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While a lot of mountains offer beginner packages, take note of anything that is not included so you can book that separately. At the very least, you'll need a ticket to access both the lift and mountain, equipment and clothing.

Other things to consider: Transportation and lodging

Jiminy Peak offers a resort on the mountain with ski-in/ski-out access, which is something for new skiers in particular to consider, especially those who don't want to lug their equipment back and forth from hotel to mountain. I am tired just thinking about it. (Note that if you're staying off-mountain, a car of some sort is 100% necessary.)

"Even at mountains that do offer ski-in/ski-out access, hotel pricing can be much, much higher than nearby properties that don't offer quite the level of convenience. But for many folks, paying hundreds of dollars less is worth the short drive, which is what we'll exactly be doing," said TPG reporter Chris Dong, who will also be partaking in this winter adventure.

As former TPG credit cards editor Juan Ruiz aptly observed when he skied with his family for the first time last winter, a rental car is helpful to get around most ski towns:

Lugging around ski equipment from the hotel room to your rental car and back to the ski resort is no fun — at all. While most of the resorts in Keystone, Vail and Beaver Creek offer red wagons to help families schlep equipment from the parking lot to the base of the mountain, undoubtedly the most convenient and stress-free way to ski is to stay at a resort with ski-in/ski-out access."

As you might suspect, lodging options were extremely limited when we booked last month and the closest hotel we could find with rooms is in Lenox, about a 30-minute drive from the mountain, which will not be an issue for us since we are renting a car.

Bottom line

As three adults in their late 20s to early 30s attempting to ski or snowboard for the first time, it was important for us to find a mountain where we felt comfortable and that offered both beginner ski lessons and easy-to-rent equipment.

We've landed on a destination in the Northeast that's easy to reach from New York City and offers an affordable first-timers package combining lessons and gear. (And as an extra bonus, during our time off of the mountain we can explore the nearby Berkshires.)

This is the first in a series of stories to come about this trip, so stay tuned for more.

Read more: 8 tips for planning a fun-filled family ski trip