Trip Talk No. 2: Alyssa's Family Ski Trip
What happens when a risk-averse person goes skiing?
Friends, I am SO EXCITED about this series! It will take us all over the world and showcase a variety of trips, from a cross-country family trip in an RV to a solo walk through the Cotswolds to a business trip to Australia. Today, you’ll hear from my friend Alyssa, and I have to tell you, I teared up multiple times while reading about her time in Colorado. I met Alyssa through Exhale, an online creative community, and have not only had the pleasure of creating alongside her, but also encouraging her to try things out of her comfort zone and embrace play. Her beautiful personality shines through her responses, and what she has to say about taking risks is worth paying attention to!
About Alyssa: Alyssa is a type-A Midwesterner who cares for her people through home-cooked meals and words of affirmation. She lives in Hoover, Alabama—a born Michigander turned Washingtonian turned Southerner through her family’s journey in military medicine—with her husband, son and daughter born twenty months apart, and two cats. Alyssa loves a good spreadsheet, seasonal decorations and foods, great books, and her Peloton streak. You can connect with her online at her blog, Looking for the Light.
LOGISTICS
Where did you go? Steamboat, CO
Was this your first time traveling to this destination? Yes
How long were you there? 9 days (2 full travel days)
Who did you go with? My family (my husband, 5.5-year-old son, 4-year-old daughter)
How do you approach travel spending? My husband and I have a “vacation” category in our monthly budget. At the beginning of the year, we discuss what kind of vacations we’d like to take for the year ahead, and then pay for vacations from our set-aside vacation budget category.
PRE-TRIP
Were you solely responsible for planning the trip, or did you share the responsibility with someone? How did you approach seeking input from your travel companions? I was the one responsible for planning our trip. I put together options, and my husband and I sat down together to make final selections (condo unit, flight option, rental car option, ski days, non-ski / recreation days, restaurants).
How long did it take to plan? Planning took place over six months with spurts of a few hours every few weeks (i.e., lodging, then flights, then ski school, then restaurants, then cold winter gear).
What was the most enjoyable part about planning, and what was the least enjoyable part? The more enjoyable aspect of planning this vacation was connecting with a friend on her recommendations. Steamboat, CO, is her family’s favorite place, and she was so happy to provide me with recommendations for lodging, restaurants, and non-ski activities. She was willing to answer any and all questions I had. It felt like having a travel advisor! The least enjoyable part was guessing how much skiing my family would want to do since we had never been on a ski vacation before; it felt like a risky financial commitment!
What were you most nervous about? This ski vacation was the biggest vacation we’ve ever taken with our young kiddos—so many firsts! It was also the farthest vacation we’ve taken, and I was unsure how all the newness would go: Would my kids like skiing? Would my kids do well in ski school? Would I remember how to ski? Would we all stay safe? Would the kids sleep? Would the flight plus three-hour drive feel like too much? Would the trip feel too long?
ON THE TRIP
How did you get to your destination? Do you have travel anxiety? Did everything go smoothly? There are two main ways to get to Steamboat. You can fly directly to the local airport, HDN, or into Denver (DEN) and drive ~3 hours. Either choice felt risky—either risk a connection and have a very long day in the airport, OR a snowy drive through the mountains from Denver to Steamboat. We opted to fly into Denver and drive. Thankfully, everything went as smoothly as possible. Our drive through the mountains was beautiful. We loved watching the dramatic landscape.
What was your first impression of your destination? I was awestruck, nearly speechless. After a very full travel day, my heart thudded when I swiped the keycard in front of the lock. I opened the door, ran through the condo, and threw open the balcony door. Skiers catching their last skiing of the day glided on the green circle run below me, mountains rose in every direction around me, snow glistened below me, and trees silhouetted against the waning blue sky to my right. I called for my family to come see, I couldn’t believe we finally made it, and how beautiful it was. I believed we were in for a fabulous vacation!
Using the five senses, how would you describe your vacation?
Sight: Majestic. I felt small in the best way. At the back of the mountain, on less popular ski runs, I felt like I was skiing alone in the Rockies. Peaks jutted in every direction. Bluebird skies overhead with clouds drifting lazily. Pines quieting and surrounding the runs. All I could think about was how happy I was to be alive and in this moment.
Sound: Quiet. Out on the slopes, the only sound was my inhale/exhale and the carve of my skis in the snow.
Smell: Pine
Taste: Rich, smooth hot chocolate. Creamy queso. Salty, fresh margarita. Crunchy shrimp taco.
Touch: Crisp and cool—snow, mountain air, ice
Tell us about a challenging moment. How did you handle it? I grew up skiing on small hills in Michigan and have skied four times as an adult over the last 15 years (twice in Colorado and twice in Utah), but I am no expert. I started the week as a fairly cautious skier—skiing blue squares (intermediate terrain)—but continued to feel more confident as the week progressed. I took a ski lesson, and the instructor really encouraged me. I skied with two friends (met up with both in Steamboat, more on that below) who made me believe in my abilities as well. By the end of the week, I was surprised to push myself on black diamond runs (expert) and some easier bump runs. My very last day of skiing, I didn’t even come in for lunch because I wanted to ski the entire day. It was an experience that reminded me to trust myself and my abilities, and that taking the risk can be worth it!
Was there a time on the trip that you felt fully relaxed? In my real life, I am a pretty serious person with an organized To Do list. But on this trip, I was Vacation Alyssa. Skiing made me feel like a kid again in all the best ways. I was totally present on each ski run, I didn’t wish I was anywhere else. The only things on my mind were the beauty of my surroundings and making the next turn. It felt like playing again. I was euphoric at the end of each day, I compared it to going to the Taylor Swift Eras tour. Present, joyous, pure fun, and thankful.
What surprised you? I was surprised by how amazing my kiddos traveled on such a big trip. They slept well in a new place. They did amazing with all the gear and cold weather (we live in the South). They walked around downtown Steamboat and did wonderful going out to eat. They were so brave in learning how to ski and going to ski school. They showed me how resilient they are, and it makes me excited to continue traveling with them.
Did the thing you were nervous about happen? No! My kids did amazing! They loved being on the mountain and at ski school so much that we signed them up for an additional day!

What do you think you’ll remember most about the trip 20-30 years from now? I will remember People and Presence. The trip was special because of the people. It was the biggest trip my family had ever done together, and we got to meet up with some special people, too. My long-distance BFF, Sara, drove from her small mountain town to ski with us. And I got to meet one of my internet writing friends, Lauren, in real life. We met for a morning at a coffee shop and then skied together. Fun fact: Lauren was the friend who helped me plan our trip! I will also remember feeling totally present in a way that is hard to find in real life—whether it was pushing my body skiing, sipping hot chocolate with my family after skiing, or soaking in the hot tub at the end of the day, I didn’t wish I was anywhere else.
Fill in the blanks:
This trip is for people who like: adventure!
Insider tips? Book your accommodations early. If you’re skiing with littles and can budget for it, ski-in/ski-out is the way to go! We stayed at Storm Meadows Condominiums. Reservations open 10 months in advance, and most rentals were reserved six months in advance. Make dinner reservations in advance. Restaurants book up! Our favorite family-friendly restaurants were Salt & Lime and Mazzola’s. Backdoor Burger was also a hit (they don’t take reservations, so arrive around 5 pm to minimize wait times). Don’t forget to book ski lift tickets and ski school early. We booked three months before our trip. You get the best deals!
Whatever you do, make sure you: plan rest days from skiing. We skied 5 out of 7 days. On our off days, we did ice bumper cars, went snow tubing, walked around downtown Steamboat, and went swimming at our condo’s pool.
POST-TRIP
What was the hardest thing for you to face when you got home? The hardest part was returning to normal life after being so relaxed and on such a high.
Do you have any routines in place for easing back into “normal life”? Before leaving for a trip, we clean the house (i.e., run + empty the dishwasher, clean counters and floors, take out the trash). I also make a meal plan for our first week back and make a grocery list in advance; on the way home from the trip, I’ll add the food items for a grocery pickup and will usually splurge for the order to be delivered so we have food as soon as we get home.
Did you bring home any souvenirs? My husband and I collect Christmas ornaments from vacations, so we brought home one with wooden skis and “Steamboat” on it. The kids picked out Steamboat t-shirts, my husband picked out a hat, and I came home with a vintage feeling sweatshirt. I celebrated my birthday a few weeks after we came home from our trip, and my husband surprised me with a print I fell in love with during the trip, done by a local artist. “Last Run” by Mark McMahon is a watercolor capturing the view from our condo. The print is framed in our living room. It makes me smile every time I look at it.
What did you learn about yourself during this trip? The importance of play, people, and nature. It was exhilarating coming back to a sport I enjoyed as a kid, meeting up with a writing friend (I wrote all the time as a kid and came back to it as a mother), and losing myself in the majesty of the mountains. I learned how vital it is to trust myself, even in risks, and that being brave in front of and with my kids will serve my family well.
Thank you, Alyssa! I love that Alyssa’s husband surprised her with a piece of art from their trip. What a thoughtful gift!
Potential things to discuss in the comments: Have you ever skied with your kids? Have you ever met up with a friend while on vacation? Are you surprised Alyssa made it through the Denver airport without any issues? (IYKYK.)
Would you like to share about one of your trips for this series? Comment below, DM, or email me!
Thank you for sharing my story!
I love this series, Laura! Nitty gritty travel details are my fave!