I live 12 months a year, so I don't have a singularly favorite month. There's plenty to enjoy about every month, and though I can't in every year do everything I might want to do, I manage to get in enough of it that, barring unforeseen calamities, I pretty much enjoy every month of every year. What I try to do most years is:
- January - February --> Early part of the month is good for going to the Caribbean for a couple weeks and skiing in the U.S. and Western Europe.
- February - March --> Ski weekends in Europe or the U.S./Canada. Ideal times to visit myriad places in the Southern Hemisphere. Best time for African safaris and ballooning.
- April --> April's good to be in D.C. This tends to be a month when I do a fair bit of charity.
- May --> Good time to travel in the U.S. -- the Derby, the Preakness -- and close the month and bleed into June with a week and a half in Southern Europe culminating in a car race and/or a boat race/"raft up."
- June - July -- Ideal for weekends at the shore and/or backpacking/camping.
- August -- Toss up month. In years past it was all about getting the kids ready for school, but now that they're all grown and do that on their own, I play August by ear, so to speak. This is another charity work month. Sometimes that turns into nothing more involved than having one of my best friend's mentee families accompany me to the shore so they can have a vacation of sorts and get to see a part of the country they've never visited.
- September -- This has historically been my "get serious" and finish hitting my revenue goals for the year, or lay the foundations to make sure that come the first of December, I will have done. I tend to spend the weekends chilling and working in the solitude of the mountains.
- October -- Road trip weekends with my lady. We get in the car and drive until we see a bucolic place where we feel like stopping to spend time checking out a quaint town, or go apple or fruit harvesting or do whatever crosses our mind as we're driving down the road. Occasionally we'll visit friends in Canada for Thanksgiving, but that's not a road trip. Theatre season starts, so to at least be social, we try to go to "the big one" that opens the season. We tend to donate most of our tickets to local kids who are interested in the performing arts and might not otherwise get to go to the theatre.
- November -- Thanksgiving is the main event, along with weekend visits to or being visited by friends in the U.S. This is often another big charity month.
- December -- This is the time I most enjoy being in D.C. And, of course, there's Christmas, which makes December a big family month and a big charity month.
I'm all about what happens on weekends. The weekdays are work days, and that's all year long, sometimes even when I'm "officially" on vacation.
Regardless of how any given year pans out, it just comes down to deciding how one wants to live one's life -- whatever that means for oneself -- and then living it, without regard to what anyone else has to say about it (provided one's not harming others). If one is doing so, what's not to like about any month of the year? The stuff I've listed above is what I've been doing with my life in recent years. Fifteen years ago, I lived my life differently, but it was still the life I wanted to live. I suspect that fifteen years from now, I'll live my life differently than I do now, but it'll still be the life I want to live at that time. Perhaps there will come a time in my dotage when the life I must live isn't one I want to live. Hopefully at that time, I'll have a full bottle of sleeping pills in the nightstand and the fortitude and physical ability to consume them....And so will end a life well lived...And that too will be a good month.