I'm looking for a planning tool that works with my brain, and I'm struggling to find one. It seems like all the tools I've come across are focused on planning specific attractions and restaurant stops first then travel, then accommodations, with the entire trip only spanning a small number of locations. For me this doesn't work as I don't generally have specific things I want to do, just places I want to explore. I also don't get to travel often, so having a little sample of a bunch of places is more attractive. The travel to/from the region and between cities (4-7) matters more, then where I will sleep each night (potentially while en route to a new location), then once I know how much time I have in each place I will look for specific attractions to slot in while leaving lots of space to be flexible and just wander/experience the non tourist parts. I should also mention that I don't mind a larger than average number of travel/transition days when it is train travel. I come from a boring land locked, car-centric region and will enjoy the train journeys. Also I will be traveling solo, so flexibility is much easier.
You may not need to read the rest to provide a suggestion, but I wanted to provide lots of context.
Here's sort of the logic I've been using to plan so far, and I'm looking for a tool that will keep track of everything and help calculate total time needed for various items on the itinerary .
I earn time off hours at work based on number of hours worked, this will determine how long I can travel for (adding in weekends later). I select a region I would like to explore, based off posts I've seen online for my hobbies/interests, and any attractions I've heard of and found interesting in that region. (In this example Western Europe). I research what times of year are the best balance of cost, tourism traffic, and weather, usually the shoulder seasons (mid April to early June). Once I know the optimal periods to travel I calculate how many hours off I will have for a given period, this tells me how many consecutive working days I can travel in that period (say the standard 10 days or 2 weeks). I then account for weekends and any bank holidays that can give me an extra day and determine the total number of travel days. 15-17 in my example, 10 workdays, 4-6 weekend days, and a bank day on the Monday after the last weekend. Usually the exact start and end dates can slide forward or back by +/-3 days to add/remove a weekend while still maintaining my maximum days off work. This sliding range is then used to search for flights. Because I'm not tied to a specific list in of attractions in a specific order to see, my arrival and departure airports can be different, and can be any in the region. I use flight search tools to find the cheapest flights based on my sliding start and end dates, and all major airports in the region.
Once a likely pair of flights are selected, I plot a route from arrival airport to departure airport via any cities that have attractions I've noted, allowing 2-4 days per city. I optimize the order of cities to reduce or remove backtracking, and drop/swap cities that are too far out of the way to allow efficient travel (say a city that requires more than 10 hours travel between it and the cities before and after it). For example I would drop Vienna and Rome if my other cities were Paris, Brussels, Amsterdam, and Hamburg. Instead I would add London or Luxembourg. Now that I know what cities I am visiting, I need to know how much time will be needed for traveling between cities, and if night trains are available. I prioritize taking short trips (<4 hours) during the day and long ones (>7 hours) during the night. Next knowing if trains normally run all day or only at certain times is important so I can block out travel time in my day so I know if I will have an extra morning in City 1, or an afternoon/evening in City 2.
With all of this figured out I can now see all the nights I wont be sleeping on a train, and what city I will be in. I then find accommodations for those nights (likely a hostel) and pencil them in. Finally the plan is taking shape and all thats left is filling all the gaps with attractions, activities, and food. These are all roughed in with flexibility to swap what day each one happens in a city, with the exception of a few that may require reservations or date specific tickets.
In the end I'm wanting a plan that looks something like this:
Day 0 - Depature
Arrive at ABC airport by 18:00PST
Flight KLM441 departs from Gate C32 at 19:40 Duration: 9h50m
Time Change to GMT+1
Day 1 - Paris
Flight KLM441 arrives at CDG 13:30
Lunch: At airport after arrival
Afternoon: Walking tour
Accommodation: Le Hostel Paris
Check in by 20:00
Address - Contact Info
Dinner: cafe near hostel
Day 2 - Paris
Morning: Activity 1
Lunch: Options A-C
Afternoon: Activity 2 or 3
Dinner: Option A/B
Accommodation: Le Hostel Paris
Day 3 - Paris & Brussels - Travel
Check out of Le Hostel Paris
Morning: Activity
Go to XYZ station - Trains to Brussels leave every 30 min
Lunch: bag lunch on train
Afternoon: Travel to Brussels
Accommodation: Brussels International Hostel
Check in by 21:00
Address - Contact Info
And so on.