Preparing for my first ski trip: Choosing the ideal mountain and renting winter gear

As I reach my thirties, I'm finding that there are fewer experiences left for me to try for the first time.

Yet, skiing is one adventure I've always dreamed of but never had the chance to pursue while growing up in Missouri.

When the chance arose for me to learn skiing this month with two colleagues, funded by TPG, I couldn’t pass it up.

However, I'm quickly realizing that there's a lot to think about when planning your inaugural ski trip.

Choosing the right mountain

Though my colleagues and I had ambitious plans to ski at various destinations across the U.S. — including Utah, Wyoming, and Vermont — we soon realized that booking a trip in late January for February meant many popular spots had limited openings at this time of year.

We were also advised by TPG staff, who considered themselves experienced skiers, to evaluate the accessibility of each mountain we were considering. It became clear that starting at a less challenging mountain would be wiser than tackling the heights of Peak 8 at Breckenridge, which boasts a 9,950-foot elevation (whatever that entails).

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

Taking into account availability, budget, and recommendations from the aforementioned TPG skiing experts, we ultimately chose Jiminy Peak for its emphasis on beginner-friendly skiing and snowboarding lessons.

The Jiminy Peak website states: "With our innovative Terrain Based Learning, beginner ski and snowboard lessons focus on teaching skills through experience and instinct rather than just words or visual cues." It further explains: "Our methods utilize tailored activities on snow in specially designed terrain parks to manage speed, change direction, and introduce the concepts of vertical motion (weight shifting)."

Here's to experiential learning.

Essentials to purchase: Lift tickets, lessons, and ski attire.

Jiminy Peak was attractive to our group of novice skiers for many reasons, particularly because it provides beginner-specific ski sessions that come with all necessary rental gear (including a helmet for safety), a 90-minute group lesson, and a lift ticket.

We chose to take two days of beginner lessons, which cost $318 per person. This streamlined the booking process and left us with little to purchase aside from clothing.

"I honestly thought that arranging gear rentals, getting lift tickets, and scheduling classes would be much more complicated than it turned out to be," said TPG editor Madison Blancaflor, who is skiing for the first time alongside me. "Selecting a resort that offered a beginner ski package that included lift tickets, lessons, and equipment made everything significantly simpler than trying to coordinate those elements separately."

If you're just looking to try skiing (or snowboarding), we suggest renting some of the clothing instead of buying everything, as it can get quite expensive; ski socks alone can cost about $50.

My two colleagues and I (you'll hear about their skiing experiences shortly) opted to rent a Complete Outerwear Kit from Kit Lender, which ranges from $37 to $75 per day with a minimum rental of three days.

The kit I rented includes a ski jacket, ski pants, goggles, and gloves. There are various brands and styles available, featuring well-known names like North Face and Patagonia, along with some retro onesies if that suits your taste better.

You can have the clothing shipped anywhere in the United States, including to hotels. That’s where we plan to collect our gear upon arriving later this month.

Along with the outerwear rental, I also purchased two pairs of socks, a vest, two turtlenecks, and two sets of thermal underwear. Additionally, I'll be bringing a neck gaiter that I already own.

When it comes to ski clothing, a Stowe Mountain employee I spoke with advised that synthetic layers are the best choice and to steer clear of cotton. They also suggested getting disposable hand and boot warmers, opting for mittens instead of gloves, and using a balaclava ski mask.

Finally, we are renting goggles as part of our clothing package, with Kit Lender assuring us that their goggles are thoroughly sanitized for each use. However, if you're concerned due to COVID-19, it might be a good idea to bring your own pair.

Many mountains provide beginner packages, but be sure to check what is not included so you can arrange those elements separately. At a minimum, you'll need a ticket for lift and mountain access, as well as equipment and clothing.

Additional factors to think about: transportation and accommodation.

Jiminy Peak features a resort with ski-in/ski-out access, which is particularly beneficial for novice skiers, especially those who prefer not to haul their gear back and forth from their hotel to the mountain. Just thinking about it tires me out! (Keep in mind, if you're staying off the mountain, having a car is absolutely essential.)

"Even at mountains that provide ski-in/ski-out access, hotel rates can be significantly higher than nearby accommodations that don’t offer the same convenience. However, for many people, saving hundreds of dollars is worth the short drive, which is precisely what we’ll be doing," said TPG reporter Chris Dong, who will also join in this winter adventure.

As former TPG credit cards editor Juan Ruiz wisely noted during his family's first ski trip last winter, having a rental car is quite beneficial for getting around most ski towns:

Hauling ski gear from your hotel room to your rental car and then back to the ski resort is no fun at all. While many resorts in Keystone, Vail, and Beaver Creek provide red wagons to assist families in transporting equipment from the parking lot to the mountain base, the most convenient and stress-free option is undoubtedly staying at a resort with ski-in/ski-out access.

As you might expect, lodging options were very limited when we booked last month, and the nearest hotel with availability is in Lenox, about a 30-minute drive from the mountain. This won’t be a problem for us since we’re renting a car.

The bottom line

As three adults in their late 20s to early 30s trying skiing or snowboarding for the first time, it was essential for us to find a mountain where we felt at ease and that provided both beginner ski lessons and easily accessible rental equipment.

We've chosen a destination in the Northeast that's conveniently located for those traveling from New York City and offers an affordable package for first-timers that includes both lessons and gear. Plus, as a bonus, we can explore the nearby Berkshires during our downtime from skiing.

This is the first in a series of stories about our trip, so stay tuned for more updates.