How to Plan for a Trip

Europe has turned me into a travel animal. I currently have all the freedom (thanks, entrepreneurship), and all the places (thanks, Europe tininess). I’ve been doing a lot of trips. As a creative person, this is wonderful. As a perfectionist, this has the grand opportunity to be stressful. But I have Evernote. This is how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported).

1. Maintain a Travel notebook stack in Evernote

How to plan for a trip - how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported)

I have four Evernote notebooks related to  traveling.

  • Upcoming Trips – titled with an underscore to make sure it’s at the top. In this notebook is only trips that will be happening within a month.
  • Archived Trips – trips that have been planned for and passed (saved as reference for when we visit the place again)
  • Future Travel – plans for travel happening within the year, or that have a few things already booked
  • Travel Ideas – any ideas for travel that can be acted upon (included in there are notes on UNESCO sites in Europe, places with their distance from where we are, opportunities for day trips, a list of castles in Germany, and interesting AirBNB places)

2. Start an Evernote note

How to plan for a trip - how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported)

I always start my trip labels with the starting date, it’s the easiest way for me to refer to or quickly find them. Usually it just gets the name, but since I was meeting someone pretty fantastic, I included her name in there.

3. Decide on details

My trip booking process is usually:

  1. decide on the place and any travel partners (if applicable)
  2. decide on dates
  3. brainstorming for possible itineraries and which makes the most sense if we’re doing more than one place (this involves staring at Google Maps and figuring out the most efficient route)
  4. transport (I use SkyScanner to find the cheapest options for flying, Rome2Rio if I’m unsure of the best method of transport, and Deutsche Bahn online for train tickets)
  5. accommodation (with AirBNB, almost exclusively)

4. Add Basic Details to the Note

As I make decisions, they are added to the note with as much detail as possible (but not overwhelmingly so).

How to plan for a trip - how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported)

A Thin Image at the Top

At the top of the note to make it fancy, I include the panorama image from Wikivoyage. Since I had already been to Paris and used that image before, I found a lovely sketchbook image of Paris and used that.

Overview

Accomodation. Transport. Anything important (in this case, V’s cellphone number).

I put the exact details for the train or flight because that’s the most important to me.

Itinerary

Overview for the itinerary with one line per day, and then a bit more in depth after that.

Ideas

Any ideas that I have for the visit. Duh.

5. Save Booking Emails or PDFs

How to plan for a trip - how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported)

Use Evernote’s Clipper for this and save it directly as a note. Then delete the email cause you don’t need that anymore.

6. Do a Bit of Research

When I travel, I like to get the “feel” for a place, rather than check off all the big touristy places. I like drinking coffee, sketching, and people watching. I like to wander the small streets. I also really like planning. I have never been to most of the places I put down in my ideas, but googling a place and exploring it that way is almost as fun as the trip itself.

My favourite places to figure out what to do (in order):

7. Download Apps

CityMapper

If I’m in a big city that has public transport (Paris, Berlin, London, Brussels, Rome, Barcelona), I will download CityMapper. That app helps you decide which is quicker – walking, metro, or catapult.

Google Maps

For walking around and getting a feel of the place

Spotted by Locals

If Spotted by Locals has a guide for the city, it’s going to be coming with me. The guides are written by local people only, and include the BEST travel tips I’ve ever read. It’s how I found out about the best view in Paris.

How to plan for a trip - how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported)

PS: I was alone when I took this shot.

8. Screenshot Important Bits

I’m not always guaranteed cellphone reception, and even though my Evernote notebooks are available offline, I can’t take the risk. If I don’t think I’m going to have cellphone battery, I’ll put the very important bits in my travel journal too.

GO ON HOLIDAY AND ENJOY EVERY SECOND OF IT

How to plan for a trip - how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported)

See how happy I am? That’s cause I’m not stressed about the details. Visit tiny shops, spend time in cafes, wander, get lost, and know that when you forget where you’re staying, or you’re not sure of the platform your train arrives at… you have it all in Evernote.

Don’t forget to Archive once you get back

How to plan for a trip - how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported)

To save your sanity, put your trip note into the Archived notebook. If you’d like to keep your tickets as reference, add them to the bottom of the note. I liked seeing how much more I paid for my Paris train ticket that I booked three days before the time compared to the one I booked last year in advance.

A Look Into Archived Trips (and some extra planning tips)

The archived trips become a sort of memory keeping form. I wish I had have started this process in 2013, but I only found a need for it for my first trip to Paris since I was going alone. Here are some tips from other trips:

For a bigger trip, create a calendar

How to plan for a trip - how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported)

For a road trip, link to the Google Maps directions

How to plan for a trip - how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported)

Include Costs for a budget holiday

How to plan for a trip - how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported)

Link for more information

How to plan for a trip - how I manage to go on spontaneous weekend vacations, or month long adventures and still manage to be in the moment and not go crazy (or be deported)

Do you have any tips for planning trips? I’d love to hear them!

  • Holy crap this is amazing, Caylee, but it seems like a lot of work? I don’t get to travel much, so I’m not really versed in having to really plan the details of a trip (I’ve only taken one “real” trip in my life, to the Bahamas last summer, which required very little planning aside from booking the ticket and hotel). We do “staycations” more than anything, and I guess since for staycations we end up staying in the city in which we already live, we already know what there is to do and how to get around, so planning at this level is kind of a moot point.

    I think this approach is so thorough and fantastic, but I think for me personally, I’d get overwhelmed planning a trip like this. I’m more the type that likes to check out things to do online before visiting a new place (which rarely happens), and then winging it when I get there. Though if I had the ability to travel more frequently and stay for more than 36-48 hours, a thorough and centralized approach like this would absolutely be ideal.

    And in general, I still want to explore Evernote. I tried using it once before when it first came out and was more overwhelmed by it than without it. Off the search your archives for Evernote-related posts!

    • Agree with Kelsey! I’m so curious about Evernote. It seems like a really robust program, but I’m kind of overwhelmed by it. And I’m a paper-and-pen girl, so I’m wondering if it’ll work for me. I’ve been making lots of use of Google Docs lately, which I love. It’s not pretty, but it’s simple and functional. I’d def read more on Evernote, Caylee! xo

      • I love Google Drive too. You could scan in your papers if you felt like it. I use it as a reference system, not really for planning. Nothing beats a good pen and paper brainstorm / brain vomit. It’s like filing away important thoughts in my brain.

        Evernote is also not pretty, which is why it works so well for me. It helps me get directly to the content.

        IF you’re overwhelmed, I would just start with putting any important reference documents in there (rental agreements, contracts, etc), then add a few travel ideas (like Pinterest with the idea for action). It’s also great to keep any processes for work or the blog. It’s just great all round.

    • Oh yeah, it’s totally personality dependent. I personally adore this shit. Planning is as fun as the trip itself. Once I get to the place, I usually throw my planning out the window. The bare minimum for me is to have all my documents in one place because that’s really important. As a South African, we have to get a visa for every place we go to and if we’re not careful, we can get kicked out. We’re not German (yet) or American where we can just flash a passport and people trust us. I also go places where I don’t speak the language and don’t want any issues that I can’t show with pointing.

      Maybe my planning is a bit of learning on my part. I prefer to learn about a place before I get there and then feel the vibe of the place once I’m there. I’m not often reading the plaques at memorial sites, etc. It’s also become a bit of a memory documenting, which I love.

      But you’re right! Not for everyone :)

      Evernote is fantastic. It’s an external hard drive for your brain.

  • This is very cool. Sadly I’m not really an Evernote fan – I prefer Trello, which would totally also work, though without your pretty panorama headers! (Boo… love those.)

    For booking flights I find Hipmunk better than Skyscanner – it ranks flights by “agony” as well as cost, making it easy to see just how horrible your layover might be.

    • Ah yes, Trello. Also cool.

      OOH! Hipmunk’s Agony ranking sounds brilliant, exactly what SkyScanner is missing. Thanks for sharing!

  • I’ve never used Evernote but I’m going to check it out. Just curious, do you still use a paper planning journal as well?

  • Do you want to makeover my life? You’re just ON IT, girl. I basically make a million lists on paper, keep a running list on my phone, and hope I didn’t forget anything critical for the kids. There isn’t a Target in every city here, know what I’m sayin?? Ha! We need to put a Catherine & Caylee trip in there…

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