I always try to plan a holiday in winter and head somewhere warm. I live in Victoria, Australia and in winter it's usually about 15C. I tend to get quite grumpy in winter and a few weeks of sun puts me in a better mood. This year we are going to Cambodia in July. It's their wet season but it will still be hot and the rain should only come in short bursts (fingers crossed).
going to vacation is anytime my favorite, but if I have to choose than spring and autumn is my favorites. In summer to many people are crowding in places I would like to visit, in winter I don't like the cold and the fact that its dark so soon. I like to walk as much as possible and discover the places by foot, so winter is the worst for these activities
I'm going to have to go with Summer - As Christmas here is over the summer, it's the idea time to go on holidays, and it's when I go on them. Winter would be good if you could go to a warmer place. We don't get snow in this town - just terrible wind and rain!
Defintiely winter . We prefer tropical beaches which you can apppreciate so much more after escapig the winter weather. Plus my wife has seasonal mood disorder when it starts getting dark early and the sunlight is good to alleviate that.
Since I own my own business - it's hard to get away with the family. We take a family vacation during Thanksgiving Week! We can have several days off because most offices are closed for business. I live in the Midwest so it's usually freezing cold here in November - it is great to get away to a warm sunny location and it is usually not crowded at the resorts. The prices for inclusive packages are great as well. It also reminds our nuclear family how much we have to be thankful for! The Bahamas and Cancun have great weather during that time of the year as the hurricane season ends around October.
My favorite time to vacation is the fall; it's usually less crowded and there's always 'Indian Summer' in the fall, so if I'm lucky, I'll hit a week that's not hot, not crowded and be able to stay on off-season rates.
In the summer, which I think is the time when most people travel, the 'locals' get tired and grumpy. "Another tourist." Come fall, I'm usually met with HOWDY or some other, 'I'm glad you came to visit!"
If I can escape the winter weather to a warm destination then that's my favourite season to travel. If I on the other hand want to visit a famous tourist location in let's say Italy, spring and autumn are the best seasons to go. I think it is always the best season to go on a vacation - it's only a matter which is the best destination in which season!