55 days until 2027?!


Hi Reader!

WOW, what a week! Normally I'd be feeling a little SAD this time of year (that's a little Seattle joke for you), but nothing can get me down after the midterm elections. 🌊

I have spent way too much time this week watching results roll in, and enjoying a little bit of that Obama-era hope and change in the air.

But a quick look at my calendar says I need to quit checking the news, and get to work on finalizing 2027 plans, because there are less than 60 days left in the year.

Wild! Can you believe it?

So instead of refreshing election results, I'm going to sit down and plot out my plans - including my own travel - for 2027. It's really important to think through this, because otherwise we won't travel at all.

And while we can't do everything, every year, we can get closer to having done everything we wanted to in this lifetime. And isn't that what it's all about?

So how about it Reader - do you need to think about your 2027 travel plans, too?

Here is how I tend to think about it. Maybe these tips will help:

  • What are the big, immovable objects on my calendar in 2027? Is there a conference I have to attend, a kid's school breaks, a family member's wedding? Are there times I absolutely want or need to be at home?
  • Where do I want to go? What is calling to me? Don't edit - it doesn't have to make sense yet. But actually write down the name of each place.
  • Why do I want to go there? Why does it sound fun or worthwhile? Don't overthink this, either. "Because it sounds cool" or "because I've wanted to go since I was a kid" are totally valid reasons!
  • How much time would I need to FULLY enjoy this destination the way I want to, without compromise? If your answer is many months or years, break it down by region.
  • When can I make it work on my calendar, and/or, will this be a pleasant time to go? Think about weather, crowds, and local holidays.
  • What is holding me back from going next year? There are lots of good reasons not to travel somewhere - big life events, money, PTO, not having a great petsitter, etc. - but fear of the unknown is not one of them.
  • Is there a way to do it anyway? ⬅️ This is where I can help.

It's only after thinking about these things that we can get into the nuts and bolts of planning a trip.

Hit reply and let me know you'll be planning your 2027 travel, too. Let's cheer each other on! It'll be fun.

Here’s to a happy end-of-year!

-Carolyn

PS - Need someone to come speak at your group/work/etc. about this, as well as how to make a 5 or 10+ year plan? Reply and let me know. I'd love to.

Windward Path - Luxury Travel Advisor

Hi, I'm Carolyn! I believe your vacation should actually feel like one - not another project to manage. As a luxury travel advisor based in Seattle, WA, I'm here to ensure every journey delivers exactly what you desired, completely effortlessly. Think of me as your personal curator, your cultural interpreter, and your detail-obsessed advocate, all in one. I email weekly to the Windward Circle, a group of thoughtful explorers who receive insider insights and cultural travel inspiration. Join us!

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