How to Pick Your Anchor Trip: A Visionary Travel Planning Technique

“Someday I’ll go to Paris.”

“I’ll visit New Zealand in a few years, when my life looks more stable.”

“I would go to South Africa, but my partner doesn’t like to travel.”

Whether it’s time, expenses, companions, anxiety, or random “what if” scenarios, there are no shortage of reasons NOT to travel. Yet a majority of Americans still find a way to go — with 61% of Americans taking at least one trip in the past 12 months.

As a travel writer, I come across people all the time who gush how I must have the perfect job, and wish they could travel more frequently or at all. I often want to tell them you can! Travel doesn’t have to be expensive, it doesn’t have to take you far to be transformative, and you can trust your instincts to travel how you want.

That’s part of the reason I started Travel Pretty, to help guide would-be travellers actually go. Here we’re not about bucket lists, or X number of countries/continents visited, or the perfect Instagram pose (though we have fun with those too!). Rather, my aim is to tap into your own knowing and intuition to help you plan the single trip (or trips) where you’re looking to understand the why on top of the where.

My philosophy is rooted in that the before/after of a trip is just as important as the during. And integrating all of them together makes travel more meaningful and more joyful. The quality of the experiences matters so much more than the quantity.

With that in mind, I’m starting the year off with my “Before” series. As a seasonal driven person, I believe the winter and Capricorn season is the best time to dream into the year ahead. To write down visions and start clarifying them. While I understand that in our modern world we’re travelling all the time, a seasonal approach to travel and travel planning has always served me well. Understanding which season you want to experience a place is also an important question to answer!

The Anchor Trip Technique

Here’s my technique for starting to dream into the year ahead, and some of the “Before” work necessary before getting into the nitty gritty:

Step 1: Light a candle, brew some tea, take a few deep breaths — whatever it is you usually do to shake off the day and come into focus. Grab a pencil and paper (handwriting is always ideal, but I too have used the computer/phone — don’t beat yourself up).

Step 2: Without thinking too hard, write down 10 places you’ve always wanted to travel or travel experiences you want to have (a solo cozy retreat in the woods, for example). Don’t explain, just write.

Step 3: Review what you just wrote, and circle the 5 that have the most resonance for you.

Step 4: On a new page, rewrite the five places/experiences with space between each. Sit with each place, and write down all the words that come to mind when you think about what draws you there. Emotions, attractions, the food?

Step 5: Take a second again to close your eyes, and imagine the year ahead of you. Spring. Summer. Autumn. Winter. Understanding the energetics of the year, look back at the list. Circle the one you feel is the one right for this year — don’t focus on budget or logistics yet, just energy.

Step 6: Just sit with the place or experience you picked for a bit. How does it make you feel? Write those feelings down. How do you hope the place makes you feel or transforms you? Circle or underline the one feeling that feels most bone-deep.

Step 7: On a new, blank sheet of paper, write this sentence: “In 2026, I want to experience [Place] in order to feel [Emotion].”

This is your anchor experience for the year! Print it out, keep it on a Post-It. Keep it conscious. The budget, timing, and planning all come later.

If you’re interested in diving in deeper with this technique, or need more support in reaching your travel dreams, check out my Before You Book 1:1 coaching session. In 60 minutes, we’ll go deeper into your anchor trip intention, pull a tarot spread for your journey, and you’ll leave with a personalized Departure Card and the clarity to actually book.