We are a family of three and this trip was planned over 4 weeks leading up to the trip.
We needed a break and Labor day weekend was coming up. We had just enough time for a short Europe trip. We settled on Spain as we have already done trips in Italy and France of similar duration. We have a large travel bucket list but that's for exploring some other day!
First we made airline bookings. We used Google Flights extensively for price shopping and comparing as it was pretty convenient to see prices to multiple destinations from an origin and departure date. E.g. we could compare flights to Barcelona or Madrid easily by providing destination as Spain and opening the calendar we were able to see prices for multiple start and end dates.
Then we found per Google's suggestion that it was cheaper (not easier though) to book the flight as one-way tickets rather than a round trip from different points of sale of Norwegian airline's website. Onward was booked on Norwegian's US POS and Return flight was booked on Norwegian's Spain POS. Of course we had to use Google translate to help us with the booking process on the latter site. We booked flights from Chicago to Barcelona. Flight to Madrid were a wee bit expensive. Note on Norwegian everything is an upsell. As we were going for an almost last minute trip, this airline was the most viable option. I won't say cheap as we did pay through our nose. We paid extra for reserving seats together and getting meal options. We packed lightly and didn't have any checked bags. This is important if you want to travel by train between cities in Spain. Pack light!
Once the tickets were out of the way, hubby was out of the picture and it was left to me to come up with an itinerary for how to utilize our time in Spain. I read a variety of blogs and watched tons of Youtube videos especially the ones by Rick Steve. Slowly a plan formed of what I wanted to do.
Pro tip - use a Trello Board. You can sign up for a free account and organize all the details of your trip into nice lists.
I created a list for each city we wanted to visit. The cities I thought would work for us in terms of the time we had and what we like doing were:
Barcelona, Madrid, Seville, Granada, Cadiz, Toledo.
For each of these cities, I added all the relevant info that I found useful under each list. e.g. Things to do, Things to see, Where to Stay, What to eat, What to avoid etc.
Next came the question of how much time to spend in each city. The "Things to do" and "Things to see" sections helped us (Note: hubby and I joined forces again!) understand how much time we needed in each city. We reserved 2.5 days for Barcelona, 2 days for Madrid and 1 day each for the other cities. Remainder was for travel time etc.
Next using Google maps, we tried to determine what order of travel would be easier from one city to another.
We decided to use Renfe High Speed Trains to travel between cities. So that made us time bound to a certain extent to train timings. Pro-tip use the Renfe website. Try to do a simulated booking using Google Translate to understand the various options in english as not everything is translated properly when you switch to Renfe's english version of the site they offer. Especially the account creation process. Pay close attention to that. There are other sites for booking train but they charge fees etc. that you don't really need to pay when booking directly through Renfe and in addition you can accumulate loyalty points in Renfe.
With all the train tickets in place, we now knew which nights we were going to be in which city. This helped us understand what hotel bookings were needed. Pro-tip for families - I know a lot of folks use AirBnB but we stayed clear of that. Primarily because I don't want to take a risk of the unknown in a foreign country especially when traveling with family. I'd rather go with reputed/chain hotels. With AirBnB and such you don't know who else has access to the rooms etc. I had points on Orbitz and used them up on this trip. It pays to have loyalty points on a credit card or travel website you use often for such last minute trips. When shopping for hotels, try to be either near the attraction you are going to visit first, last or be near the train station (if you are traveling by train between cities). We used filters to look at hotels in specific neighborhoods and amenities such as breakfast or wifi etc. I also called up the hotel to see if they would hold our luggage till check-in time if we arrived a city in the morning and didn't have check-in until later in the afternoon.
Highlights of each city visited.
We arranged the order of sight seeing places in each city based on distance. This itinerary below is really a fruit of our labor, so to speak! If you follow the same order you should be able to cover more ground each day of your vacation. Tried and tested!