The Planning Nightmare
Let’s be real. Planning a vacation, especially with multiple families involved, is a nightmare. Clashing expectations and competing planning styles are enough to make any well-meaning planner throw in the towel and just stay home. Add ski gear and snowy flights into the mix and you’re going to want a vacation from your vacation planning.
So, instead of going on the defensive and waiting for the planning drama to crop up, may I recommend an offensive planning strategy for your next ski trip? You read that right. You’re going to make a plan for your vacation planning.
4 Months Out: Pick the Group and Play Some Hardball
It’s 2020 and we are DONE with bad communication. As you set about picking who you want to come along on your ski vacation, keep in mind who is going to communicate their wants and needs the best, and who you can feasibly travel with for any sort of extended period of time.
As much as we love our flakey friends, ski trips can be pricey, and now is not the time to have people back out last minute, leaving you stuck alone with the bill.
While you discuss with your group what you’d like to do and where you’d like to go establish a budget that each party is willing to spend. Setting this expectation up from the get-go will eliminate potential money drama down the line.
Want to take it an extra step further? Break the budget down by accommodations, food, activities, and travel. One of the biggest pain points on combined trips like these are the moments when one family wants to stick to a set price point and the other is ready to spend whatever they need to to have the best time possible. Communicating these financial expectations months before you actually arrive will save unnecessary stress and establish set boundaries that keep everyone comfortable.
Once you’ve picked the group, stick to it. Another couple and their kids decide they want to tag along a month before you’re set to go? Great, but they can plan their trip themselves. Stick to your original group’s needs first, then accommodate newbies (if you have to).
3 Months Out: Reserve Accommodations & Establish Sleeping Arrangements
Is it childish to call dibs on the biggest bedroom in the Airbnb? Maybe, but after a full day of sending it down the mountain and teaching kids to ski, having a place to escape to for a quiet night of sleep is essential. If you’re going to spend big on anything on a shared vacation, make it the accommodations.
With the boom of the vacation rental industry, finding a house big enough for a few families isn’t too hard in a tourist town. A good rule of thumb, especially in a group full of couples, is making sure that there are enough “real” beds (no pull-outs or bunk beds here) for every couple coming. Concerned about space? Give the rental manager a call and get the real scoop on how many people can comfortably live in the home for a handful of days.
Scheduling accommodations early into the planning phase allows you to build the foundation for your trip’s itinerary based on location. What ski resort you go to, what restaurants you eat at, and what activities besides skiing you do can all be directly determined by your home’s location. This is especially useful if you’re not planning on having a car and you need to walk or shuttle everywhere.
Is this your first ski trip? Learn a little bit more about what you’ll need to prepare for here.
1.5 Months/1 Month Out: Flights & Supplies
It’s fairly common knowledge that about 8-6 weeks out is the best time to schedule flights for the best rate. Figure out your travel timeline following flight and car rental bookings. Will you need to request an early check-in? Do you want to try and get a day of skiing on the day you arrive? Is your whole group going to travel together or do separate arrangements need to be made from the airport to your rental?
Next, figure out what supplies you’re going to need. If you have your own ski gear, that’s great, but is it worth the cost to travel with it? Look into shipping it beforehand, or compare the price of rentals to the cost of flying with ski/snowboarding gear. A lot of vacation rental companies in ski towns will have ski rental partnerships that make renting a lot cheaper through sponsored links.
Finally, based on your arrival times, determine if you’d like grocery delivery or similar services. One of the hardest last-minute requests to accommodate as a rental company is grocery delivery and we love when guests are on top of these types of planning items.
Planning activities that may need reservations (ski passes, high-end dinners, specialty skiing, kid’s camps, spa retreats, etc.)? Book your reservations in the same session you book your flights. Travel to vacation is the worst part. Planning the fun parts of the vacation after planning the worst part alleviates some of the stress of coordinating everyone and helps you really get excited about your trip.
1 Week Out: The Final Touches
A week out, follow up on your travel plans. Ensure everyone in the group is on the same page about when flights leave, how you are getting from the airport to the rental, and what food plans are that first day.
Chat with the rental company about any last-minute accommodation questions you may have and if there is anything local going on that might affect your vacation or that you might want to check out.
Finally, make yourself a rough draft of what the trip’s itinerary is going to look like based on your reservations. You don’t want to be too beholden to this, you are on vacation after all and schedules are for the office. But, if you’ve made dinner reservations or once in a lifetime heli-skiing plans, you’ll want to keep track of when everything is happening.
Day of Arrival: Let it all Fall into Place
Let your accommodation manager know when you’re arriving, and save their contact information for potential emergencies. Read through the check-in instructions fully so you know what to expect when you arrive at the home and where the home information is going to be.
Then, just follow through with your plan. You’ve spent 3 months prepping for this moment, and the time has come to see your hard work play out. While you can only plan for so much and emergencies are going to happen, you’ll sleep tight knowing you’ve prevented a lot of them.
You’re the trip planning hero. Pat yourself on the back.