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How to Plan Your Best Vacation Yet: Part 2
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How to Plan Your Best Vacation Yet: Part 2

What are we doing? A virgo's guide to trip-planning and packing

Jun 14, 2024
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How to Plan Your Best Vacation Yet: Part 2
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Hello,

Last week we covered where we’re going with part 1 of this travel planning series. Today let’s chat about what we’re doing once we get there.

As a proud virgo/type 3 enneagram, planning is my middle name. In fact, the planning and research that goes into a trip is equally pleasurable for me as the trip itself. And over the years, I’ve developed quite a few tips and tricks to plan a perfect itinerary, so my actual vacation is as enjoyable and stress-free as possible.

Why plan?

Honestly, do you. If you love flying by the seat of your pants, more power to you. Alison Roman made a great case for going off the beaten path and the power of discovery in a recent newsletter, and I agree… in theory.

But, personally, one of my worst traveler traits is that if I don’t have a plan, I start to panic. I’ve spent all this money on flights and hotels. I may never come back. I don’t want to “squander” the experience. Especially a meal.

So, my travel-planning philosophy is to have a dinner reservation each night of a trip (if something better comes along or I get a rec from a local, I’m happy to cancel and diverge from the plan). I also like to have 1 – 2 anchor activities for each day (unless it’s a beach vacation, in which case I like to have 1 – 2 books to read… but that’s for next week’s beach reading guide).

Planned spontaneity

Sounds like an oxymoron, right?1 My biggest tip is to make a Google Map with recs saved to a list. This way, you can open the map at any time and see what’s nearby that came recommended. For extra virgo points, use the notes section to save additional details about the rec (who it came from, if there was any context. i.e. for a restaurant if they mentioned favorite dishes to order.)

OK, that’s all well and good, but how do we figure out what goes on the map?

Here’s how I form the basis of my itineraries:

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