Sometimes you have a clear idea where you want to go and what you would like to do. Other times it may be that you just would like to see more of the world and have to figure out where do you want to go next, and what you can do there. Tours are the easy way out, and sometimes offer savings, but generally you're paying more for convenience. When you plan a nice long tour across multiple cities and/or countries then you start to appreciate paying someone else to figure everything out for you.
My wife and I have done a bit of both types of travel, but for the most part, we like to plan everything ourselves.
Fortunately the web makes a lot of the travel tasks so much simpler. Previously we had to rely on books by Lonely Plannet, Frommers, DK and the like, which were all very good. But now we use sites like TripAdvisor, Expedia, Viator, AirBnB, Skyscanner and Street view on Google Maps.
Getting there.
We always look for good value flights, but try to keep the number of stops to the absolute minimum, as well as the total flight time. Time of year that you're travelling is likely limited by your work requirements, so check out the usual climate you can expect during your travel time.
Staying there.
When picking a place to stay, for us, it has to be near the attractions that we're interested in, usually central, in the "old town" if the city has one. TripAdvisor will show you the map and you can have Expedia show you the map with acommodation, then wander around with street view to check out the area, back to trip advisor to read the reviews for the accommodation.
Attractions.
Does the city have a "Pass" that gets you into the attractions for free ... make a spreadsheet using Google Docs so you can share with your partner and all of your connected devices, work out what attractions you want to visit and will the pass be good value for you?
