I love planning the holidays, almost as much as taking the holiday itself.
Here's (roughly) what I do.
1. We decide on a destination. Our current thinking is Greece and Turkey - whittled down from an epic journey through most of Eastern Europe.
2. Then we make a list of all the most worthwhile places to visit. As a guide, I use the UNESCO World Heritage List, and a couple of excellent books: 1001 Historic Sites You Must See Before You Die and 1001 Natural Wonders: You Must See Before You Die. We add to this anything of personal interest - for example, I have made a point of trying to see as many of Michelangelo's works as I can. I think I've only got four to go. We try to get a mix of natural and cultural places so that there's a good balance. We add to that any places that look interesting or unusual from our travel guides. The DK guides are great for this as they are pictorial as well as textual.
3. Get a map, and locate them all on the map.
4. To minimise travel, we find a centrally located cities and towns to form as a base. Sometimes, you just have to drive each day to get around the places you want to see. For example, we stayed in Seville as a base and travelled to Granada and Cordoba as day trips. It just saves repacking the luggage and hauling it around every day, and locating the new accommodation every day.
5. Join the dots. Link sights to their closest base town and estimate how many days will be required in each location, and how much time will be needed to travel between base towns.
6. We often do a lot of tweaking at this stage: trying to re-order the sequence in which we visit sights, or changing the route or direction of travel so that we spend the maximum time seeing the sights and less time on the road (or train / plane etc.)
7. Be prepared to leave something out if you just can't get it in. You will need to prioritise which sights are the "must see" ones, and which are a bonus.
8. Plan "vacant" days. You'll never know what you stumble across once actually travelling. In Quebec, we took an unplanned trip out to Parc Nationale de la Jacques Cartier and had a wonderfully relaxing day walking some of the trails and picnicking by the river.
9. Sometimes you're just going to have to drive (travel by train, etc.) to see those things you want to see. In our planning, we seem to have the uncanny knack of having "must see" sights which are located at the furthest extremities of our destination!
10. Map out the whole trip, including timing for travelling and every sight you want to see.
11. Check the opening hours, times and days for every sight. This is REALLY important so that you know you can actually get into a particular place on the day you are there. Sundays in Europe can be a bit tricky, and watch out for museums closed on Mondays (though some have different closed days).
12. Take into account what your children can cope with: jet lag at the beginning, general "down" time, sleeping, rest times and their walking limit.
13. Book ahead where possible. This limits time in queues - thus minimising fuss from the kids, and you get more time actually enjoying the sights. Where you cannot book ahead (such as the Eiffel Tower), plan to arrive before opening time. We had breakfast at the base of the Eiffel Tower and were first out of the lifts at the top. No fuss for us or the kids. Some useful "book ahead" ideas:
- City Passes (e.g. Paris Pass - www.paris-pass.com) if you're wanting to visit a lot of museums etc.
- Individual sights (we prebooked the Alhambra Palaces in Granada)
- Ferries, especially car ferries (we prebooked the Stranraer - Belfast and Wexford - Fishguard ferries)
- Tours which take in a number of places of interest to you
- Hotels / B&Bs / Accommodation if you have special requirements, such as cots, family rooms etc.
- Any shows you might want to see
- Trains which require reservations. We have no experience using Eurail, so I can't comment on that, but we took the New York to Albany Amtrak service and we needed to travel at a specific time so prebooked tickets reduced stress and hassle
14. Map your driving meticulously. I have successfully used Google Maps for driving in Spain and Portugal, and MapQuest for the UK, USA and Quebec. Google Maps was very reliable for driving directions, though it does take a bit of time to figure out the street numbers, names, and scale of distances on the ground. Have a print copy for ease of navigation, and use a tiny font size to keep the whole document as small as possible.
Our last trip to Paris, Spain and Portugal was planned in great detail before we left. Some people wouldn't be comfortable with this, but we found that it worked brilliantly. It reduced our stress over unexpected inconveniences, and made travelling with kids inherently enjoyable. The kids appreciate the element of predictability that planning gives. We felt confident in what we were doing because we didn't have to do any planning on the run.