I use Google Docs. It's very simple but effective. In it, I have:

* 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.

I like everything about your approach (excluding passport.png), please direct me to your travel blog! =)

Well, the passport cover page png lets you keep your actual passport in a safe place, while having ID on you while you roam around. Very useful in places that have a high rate of pickpocketing and theft.

Also if you lose your passport, you have a copy to show the embassy.

I don't have a travel blog unfortunately.

It remains a problem in need of a single, highly usable and smart interface that can collate all the disparate data and expedite the process of planning and booking.

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.

Next evolution of Kayak — by Kayak co-founder — is Lola, which was completely amazing.

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.

https://www.lola.com

https://www.lola.com/about

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. :-)

When less busy and an extended weekend seems in order, I go to ctrip.com (note: I live in China, but I'm sure there are equivalents for flight/train details where you are) and see where on a mental list of places I like / I would like to go in China / East / Southeast Asia seem cheap, and if something seems really cheap, I get a Friday and/or Monday leave approved then book the flight.

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.

Scott's Cheap Flights.

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.

Rome 2 rio - https://www.rome2rio.com/ is a great tool to see what the different transportation options are. Say, for example, you want to travel from Lisbon to Berlin, rome2rio will show you what your options are (fly, train, bus, etc) and what the respective costs are.

Especially useful if you are traveling to countries where public transport isn't a given.

Google Flights does a pretty good job (though it doesn't cover every airline, it does cover all the ones I use) of tracking my flights and flight prices.

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.

I check google flights, book them when they are cheapish and look for somewhere I could see myself staying for a night or two in my destination area. Couchsurfing, last minute hotel booking and AirBNB for accommodation. I don't really plan much for what I am doing apart from catching up with/meeting people.

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.

I don't really plan the travel itself, so no help there. As for where to go - keep in mind 90% of what you find is going to be someone trying to sell you on something for financial gain. That's fine, but leads to questionable honesty. I've had best luck asking someone from a country you're interested in, if you're lucky enough to know one. If not, perhaps try the subreddit. I find people tend to perhaps overstate attractions at home, but not as far as to be deceitful. And they'll call the bad places bad.

Try oyster.com. They send their own people to check out hotels, and give you their own photos. This lets you compare the unvarnished reality against the brochure photos.

I really like this idea, but I tried 2 searches and just got hotels. I'm more interested in the attractions themselves.

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.

Google trips + Google flights. Google trips is pretty cool. It fetches reservations from your gmail and automatically creates itineraries of things to do, places to visit, food to try etc. It gives other info too like local currency, health and emergency, getting around and travel, state of internet and connectivity etc. It's been pretty accurate and saves a lot of research on internet so far for cities i've been too (in India and U.S).

Check out backroads.com and their trip itineraries. If you can afford backroads try them out (they are great). If you can't afford them, piece together your own trip with cheaper lodging and self-booked activities.

For us road trips roadtripper works well to start. I typically end up using Google sheets docs and presentations to bring together all of the logistics. Things get a bit nutty though when you are organizing with a larger group

I find the cheapest combination of plane ticket & rental car I can find in countries I haven't been, and then I go there. I don't plan more than that.

Sygic Travel worked great for me and my girlfriend this winter.