Expert Advice: Ski Vacation Planning Made Easy

Written by Alexa Owen • Sep 26, 2016

Have you ever wondered what really goes into ski vacation planning?

Perhaps you've read about tricks to getting the cheapest airfare, how to buy lift tickets online, and the oh-so-tricky decision of what kind of lodging to book. But what about all the little questions that come up in the process? You know -- the small ones like what time of day to book flights, or exactly how far in advance to buy those lift tickets. Does staying in a house really off-set the cost of food, or should you just splurge on the hotel? This is the time to ask the experienced experts: the ones who have done it dozens of times before.

For our expert advice on ski vacation planning, we went to seasoned ski vacationers Will and Sara, who have adventured on couple -- and then family -- ski vacations every year since they've been married. Hailing from Connecticut, they weekend in Vermont, but have ventured to various resorts across the Rockies. They eventually settled on regular return trips to iconic Jackson Hole, Wyoming, and have since refined their ski vacation planning down to every last detail. And they agreed to share some of their well earned wisdom with you.

We asked Will and Sara to lay out the logistics of their ski vacation planning. Keep reading for their answers.

How often do you go on ski vacations? And for how many days?

We book our ski vacations for 7 days so that we can get at least 5 days of actual skiing in. On top of this we ski most weekends of the winter in Vermont.

Where do you like to go?

Jackson Hole. Before we had kids, my wife and I skied at different areas each year but when we found Jackson Hole we stopped going other places. The terrain was incredible and aggressive and we were also allowed to ski out of bounds.

How do you get around the resort town without a car?

The first year we went to Jackson Hole, we stayed at Snow King in Jackson and actually planned on taking the shuttle bus out to Teton Village. That lasted 1 day. We then rented an SUV for the remainder of the week. More importantly, we really fell in love with Teton Village and that is where we stayed from that point forward. When you stay in Teton Village there is plenty of good taxi services that can take you out of the village to one of the area restaurants or even into the town of Jackson. While we prefer to have an SUV or a truck while there, a good friend of mine that vacationed with us last year with his family used the taxi service and he said it was fine. It also saves you money for a weekly vehicle rental. If you do rent a vehicle in Jackson specifically, it should have four wheel drive because of the amount of snow that we have experienced there.

Before we starting going to Jackson Hole, we had also vacationed in Vail and Whistler Blackcomb. At those resorts, there was no need for vehicle and we never had one. In both areas we generally walked everywhere. In Vail, if we need to go from one side of town to the other we utilized the bus system which was very convenient. At Whistler I believe we used a taxi.

Do you return to the same resort/hotel/house each year, or try different areas?

Yes, we have stayed at the Snake River Lodge and Spa since our 2nd trip to Jackson Hole. The rooms are luxurious, the staff is always very friendly and helpful. The resort also has a great ski and boot check for storing your equipment and the indoor/outdoor pool and spa are incredible. The location is in the center of Teton Village and is a close walk to all lifts. There is also plenty of available parking.

What kind of lodging do you like to book?

We usually go through the exercise of looking at house rentals each year. In the end, we ultimately choose the hotel for convenience. While you have to spend more on food, the last thing we want to do on vacation is prepare meals. We also like to be on the first lifts of the morning so staying at the hotel where we can eat and get out easy works better for us. At the end of the day we are generally are pretty exhausted and enjoy relaxing in the pool and spas.

Do you bring your own equipment or find it easier to rent?

We bring our boots, helmets and clothes. We stopped bringing our east coast skis out west a long time ago. Although with the change in skis that has occurred during the last 10 years, the difference has narrowed between our regular skis and the ones we ski on out west. We like to have much wider skis out west because of the terrain, snow, and more importantly powder that we try to find.

How do you go about purchasing lift tickets -- in advance, or on-site?

We purchase our lift tickets online and in advance. It allows us to save a little money by doing this. It’s also one thing less you have to worry about once you get out there.

Have you booked package deals in the past, or do you prefer to organize travel/lodging/gear/etc. on your own?

For ski vacations, we like to book our trips ourselves. Last year we did it because we were able to use mileage and points to cover our airfare and lodging. In general, we like to do it ourselves because we always like to depart the NY airports very early in the morning to ensure that we can arrive by early afternoon.

How far in advance do you book flights? Is there a time of day/night you prefer to fly to get the most out of your vacation?

As far in advance as we can. Last year, we booked the trip 2 months in advance. We like to fly as early in the day as possible. Last year, our flight from La Guardia Airport departed at 6 am. We had a connecting flight through Dallas and this allowed us to arrive in Jackson around 1 pm. This gave us the afternoon to get settled and to get our demo skis for the week. On the return trip we usually try to fly mid morning so we do not have to get up too early...also so we can arrive back home by early evening.

What is the most stressful part of planning your ski vacations? The easiest part?

Making sure we book flights where we can ensure that we are seated together. Other than that, adding up the cost and packing (because we always bring so much). The easiest part is picking where we are going since we absolutely love Jackson Hole…we really haven’t considered anywhere else in a long time.

Do you book restaurant reservations ahead of time or decide day-by-day when you get to the resort?

We typically book restaurant reservations once we are out there (if we have to). We typically decide where we are going to eat dinner once we are done skiing and our energy level will have a lot to do with how far we want to go to eat dinner.

What activities do you like to do off the slopes?

Shopping, sightseeing and “spa’ing” – which can include massages!!

What are 3 pieces of advice you'd offer to a couple planning their first ski vacation?

Don’t bother bringing your skis.

Do not check your helmets or boots – they are difficult to replace if they don’t show up at the baggage claim. I see people dragging their skis through airports all the time and its one piece of equipment you really don't need to bother yourself with when traveling. The demo skis you can get at most mountains are excellent and the cost for the week is nominal.

Research the type of terrain at the mountain to ensure it is right for your ability. Also, make sure you have the appropriate ski clothing for varying weather.