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How to plan the perfect vacation (part 1)
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How to plan the perfect vacation (part 1)

From the hotel shortlists I swear by to the resources that save me hours, this is how I plan travel that feels curated, considered, and worth every penny

Tori Simokov's avatar
Tori Simokov
Jun 04, 2025
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How to plan the perfect vacation (part 1)
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The past year has been a whirlwind, leaving my nervous system completely fried. I've reached a level of burnout I never thought possible. I haven’t had the space to truly nourish my soul. My body has been begging me to slow down, to rest, to finally take a real break.

I finally reached the point where I was ready for real change, and I did the scary thing. But now I need deep, lasting healing. And at this point, I’m convinced the only thing that can truly restore me are sun-soaked, disconnected days spent swimming in the Med. You know what that means…

It’s time to plan a trip.

The most common DM I field is how I find design-forward stays and under-the-radar destinations that still feel special. The truth is, it’s real work that I’ve turned into a real, regimented process. It’s equal parts vision board, intuition, and obsessive research.

The good news? I’ve gotten it down to a science, and I’m going to share my entire guidebook with you. Below, I’m breaking down my full travel planning system, from that first spark of inspiration to a fully planned-out trip.

Read on for:

  • The first question I ask to make every trip feel aligned

  • How I discover hidden gems before they show up in every travel roundup

  • Why I always book hotels before flights (and how to know if a stay is worth it)

  • How to use ChatGPT to save money and uncover better options

  • What to do before you book anything to avoid costly regrets

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