* a packing checklist (peace of mind and helps you to not forget to pack certain things like pills, chargers, etc.),
* daily outline of spots I want to hit (collected through a combination a Wikitravel and friends' recommendations)
* important phone numbers (AirBnB hosts, emergency etc.), URLs to museum ticketing sites, admission ticket discount sites, etc.
* a png of my passport.
I also have a printed copy of said document in case my phone dies or whatever.
I duplicate the doc the next trip, delete the irrelevant bits and add new relevant bits. Most other data stay the same.
It's important for me to keep things simple and dynamic. I used to have more complicated systems, but simple lets you explore but still have peace of mind. Travel is a dynamic thing, and one has to allow for serendipity.
Also if you lose your passport, you have a copy to show the embassy.
I don't have a travel blog unfortunately.
I use Kayak. But typically find that I still need to manually perform searches for each leg of the trip. Across flights, hotels, transportation, tickets, etc. And usability of these sites can be abysmal, especially on mobile.
My pro tip: book well in advance. 6+ months to ensure availability. Particularly around busy travel times.
For discovery my tool of choice: Google Maps. Helps to visualize, find local eateries, attractions, CVS shops, etc.
Humans did the searching based on your prefs and learned you over time and the same human helped the whole trip, all modes.
Concierge travel in an app. So good.
I’d heard they might be pivoting. Don’t know if that’s true. I can’t use any more since switching employers, we have in-house travel.
If you try it, tell them I sent you. :-)
For what to do and places to stay I tend to go to the Reddit sub-page for the city/region and wing it from there. Reddit can have quite a bit of noise and group-think, which just takes getting used to, but the signal can be a true gold mine. I don't post unless I've got something really specific about a place that's not been asked before.
And simply as a European in Asia for a long time, where other foreigners and internationally-minded locals tend to migrate here and there quite a lot, a network gets build over LinkedIn, WeChat, Facebook, etc, that there's invariably someone I've crossed paths with living where I want to do, so if I need a 'meat search engine' answer to a question I have it, or can suggest to hang out for those I know better.
So, that may or may not be applicable to you, but that's how I plan, or really don't plan much at all.
Do always have medical insurance when travelling. Check if your employer covers this. I've thankfully never needed to use it, but it gives a peace of mind for low probability high risk events.
It's an email list that tracks price wars and mistake fares, and sends you an email immediately when they're found. Saves on searching. They have free and for-pay tiers.
Especially useful if you are traveling to countries where public transport isn't a given.
Once I have something purchased (hotel, airline, event plans and tickets) I track the information in TripCase. I've been using that to good effect for years. I think the first time, though, was for work. The company had an integration between their travel office and TripCase to show me all my booking information in one spot. A nice thing here is that I can share out the itinerary with people (and I think, though I haven't done this, just share out partial information). This is helpful because my girlfriend and I can keep everything synced up using this.
I use YNAB for budgeting, so from a financial perspective that's where that goes. I create a category for the trip and subcategories for parts of it. This gets very detailed, but is only temporary (removed after the trip, I do a consolidation of the spending into my generic Travel category so my history isn't cluttered). If I don't have the money yet for the trip, I create goals based on my expectations and then start saving towards it. Like, I have bought my airline tickets and hotel rooms for my next big trip, so they're already funded. But I don't need to, in January, set aside the money for restaurants and miscellaneous spending yet for a trip in July.
For planning the trip, if it doesn't go into TripCase or YNAB, it goes into Omnifocus and through that my calendar. In fact, the whole planning activity usually ends up in Omnifocus too and then details for the actual event get added in later and pushed into YNAB and TripCase. This is also where I make sure I dot my i's and cross my t's by including every detail like double checking I have my passport and that it's up to date, get local currency, inform CC companies, etc.
If it's not in OmniFocus it's in an org file with a similar set of details. OmniFocus is just a bit easier to carry with me on the go. Since work is Windows and Linux only, I generally cover all work trips inside of an org-mode file in the same way I use OmniFocus for personal travel.
Planning a but that involves convincing a friend to tow a trailer across Australia for me and decking out my motorbike for camping off of.
My holidays are all winged. If I put too much effort into planning them or can't just relax and take my time it doesn't feel like a good holiday.
One other thing that's rarely captured anywhere is how crowded some places are. The benefits of a local is that they usually will tell you this, and sometimes even suggest a similar place that's less known.