Courses

As a special introductory offer, we will give 50% off to the first 20 people registered for the live course delivered over Microsoft Teams in five 60-minute 1:1 sessions where we work through the 5 W's vacation planning framework to help you make smart travel decisions with less stress.

Vacation planning shouldn't be stressful, but you want the trip to go well. Maybe it's a family vacation, a multigenerational trip with your parents along or a getaway with friends who all have different budgets and different ideas of a good time. Instead of feeling excited, you're stuck cycling through browser tabs, half-finished spreadsheets and group texts that never quite land on a decision. You also don't know what AI recommendations are real. And it's not just your time that's going. It's your energy for the trip itself.

That stuck feeling isn't a sign you're bad at this. It's a sign you're missing a process.

A process, not a checklist

This live course walks you through the five decisions every vacation actually comes down to, the 5 W's: where you go, when you go, what type of vacation to go on, who's coming with you and what it all costs (wallet impact). This isn't the same scattered advice you've already tried from travel blogs and group chats. It's a sequence, so you always know the next decision to make instead of jumping between all of them at once.

Each step comes with pages in the workbook you can fill in as you go, so by the end you're not just holding a bunch of ideas. You have clear, actionable steps to build your vacation itinerary.

Who this is for

• You're planning a trip for a group you're responsible for, whether that's your immediate family with small or older children, extended family, or a friend group
• You're planning an extra special trip that you don't want to get wrong, like a honeymoon, family reunion or first cruise
• You've planned vacations before, but it always feels harder and more stressful than it should
• You want a repeatable process you can use for this trip and every trip after it, not a one-time fix
• You're not looking to hire a full-service travel agent; you want to build the skill yourself

What you walk away with

Picture the next time someone asks, "So what's the plan?" and you actually have one, calmly, without the spiral. By the end, you'll have a workbook that can be used on future vacations, plus the skills and a clear process to work through your own vacation decisions, ready to apply to the trip you're planning now and every trip after it. The goal isn't just this trip going smoothly. It's that you never have to feel unsure about how to plan a vacation again.

How it works

After you purchase the course, you will immediately see the Vacation Planning Help calendar where you will schedule your first of five 60-minute sessions that occur over Microsoft Teams. You will receive the online meeting link in an email once you have scheduled your first session. At the first session, you will schedule the second session and so on. The five sessions must be completed within four months of the purchase date. See our Terms of Service for our cancellation policy.