How about Spring AND Autumn? I’m in a position now where I can take 3-4 weeks off from work each year. Spring and Autumn are best because the attractions are less crowded, flights and lodging are cheaper, and the weather for hiking and biking is more pleasant. Traveling during both shoulder seasons also gives the illusion of an extended summer, one that begins in April and ends in October.
January to anywhere south - less crowds at tourist traps and far cheaper. May run in to problems with return flights to up north if there is a major snow storm but cheap and relaxing. Got stuck before even returning on a cruise back to Florida - snow storm and got stranded in Orlando for 3 days before we could fly back.
Used our timeshare but got to stay in Hilton Head one year in a suite for 1 week in January and it was like 15 points and the weather was amazing. Kids had a fantastic time with no crowding at all, great southern food (low country boils, shrimp and grits, oysters…so good…)
@blndfayth I think timeshares get sort of a bum rap. IF you know/understand the system you can get some incredible vacations at much better digs than what you would get if you pay for a crappy room in a hotel. We have stayed in some AMAZING resorts in Orlando, Oregon, the Poconos, St. Martin, Spain, Uruguay, Hawaii, Nashville, Hilton Head. Williamsburg … well, you get the idea.
Generally like to travel in the off or shoulder season. Less crowds, less cost, more good times.
We even have specifically booked cruises on a small sailboat in ‘hurricane’ season due to the available discounts, with the understanding that the itinerary may change at the last moment.
Like to go to places before schools let out (or after they resume) but since my wife has been a teacher (and now a student herself) over the past several years that has been harder to swing.
Overall, I will have a good time anywhere, anytime so no big sweat… A bad day on vacation is still better than a good day at work…