One of the questions I’m most often asked is 'when's the best time to travel?' My quick responses are 'whenever you can get time off' or ‘early and often.’ Perhaps a more comprehensive discussion is in order.
If we're talking Europe, ‘the best’ times to go are shoulder season--when the weather's typically nice but the summer crowds haven't shown up yet. That's generally April-May, and September-October. I'd say May and late September are my faves as they afford the best balance of weather and crowds. One caveat: even in late May/early June, some of my favorite mountain trails in the Alps are not yet open because of snow. For these, September is better than May.
The most expensive times of year are around Christmas and New Year’s (especially the week in between), spring break (so, March), and then summer (for Europe, especially July and August—also the busiest months).
You know I love being in Europe during the Christmas market season (and I'm taking folks both this year and next--HMU for details or see here). The best times to go for these, I’ve found, are very late November (making sure first that the ones you want to visit are open) and early December.
When’s the best time to plan? The earlier, the better. Airfare releases roughly 330 days out, but most tours and cruises are bookable well over a year ahead of time. You don’t have to start that early, but if you want your pick of itineraries, hotels, cabins, etc. plan ahead, and let's book it early. I had a client wait to book a long trip for this summer—and the hotels ended up being astronomical as a result. When you know when/where you want to go, contact me to get started. [Seen below: happy people who contacted me to plan their trip. 😎]