My husband and I both retired in 2004. He was 55 and I was 58.
My impetus was two serious health conditions and a desire to enjoy what time I might have left. His was that I retired and he'd had it after 27 years at his employer. I'm still here at 74 and so is he at 72. It must've been a good decision.
From 2004-2009 we fixed up our house in the Tacoma WA area to sell, moved to Tucson, and rented for almost 4 years while we learned about the area, planned and had our house built.
Before we retired, we took advantage of the retirement training our respective employers provided. Of course there were the usual financial topics, but 3 bits of advice in particular stood out.
The first was to NOT move to where your kids live. That was easy because the 5 kids and their spouses lived in 4 different states at the time.
The second was to NOT buy a house in the first year of moving to a different place, even if you'd visited there many times over the years.
Renting the first year made very good sense to us.
The third piece of advice was given by one trainer who said as part of her session on what to do in retirement that she didn't want hear the 4 letter word, g__f.
We cheat on that third one. My husband's g__f is open wheel road racing. He typically spends May through September based in the Pacific Northwest racing the road racing tracks in WA and OR. He also makes sidetrips to other tracks in the US during those months or shortly after them.
And my g__f is travel. I took my first self-planned solo trip at the age of 31 in 1977. It was 4 months long. I quit my job and sold almost all my stuff to generate enough money to do it.
From 1982-1985 I lived and worked in Nuremberg. Although I had little vacation time at first, I could arrange my work schedule so I could have 5 days in a row off, so I was able to easily travel then. I used public transportation or my car.
After my husband and I got our house built and moved in, we took what was his first trip to Europe. We spent 2 months. From Iceland to Sicily to Ireland, I planned it all. He went on 4 additional 4+ weeks trips with me. Three of those I did all the planning. The last combined an RS week tour to Istanbul with 4 self-planned weeks in Greece.
He hates flying, so after that trip, he decided he didn't want to go to Europe anymore. Now I go on my own and have done 6 self-planned weeks in the UK and 4 RS tours with time in-country before and after since he opted out.
I love the dreaming and planning. The RS tours get me up and going in the morning. My self-planned time before and after may be in a B&B or a hotel and except for breakfast hour limits, are much more relaxed. I also stay in apartments and have never felt less safe in an apartment than in any other lodging by myself.
To answer your questions directly:
Yes, I travel more and for longer.
Two weeks are way too short, 6 weeks are just about right, but if I didn't have a dog, I'd probably stay longer.
No matter how long I'm gone, I have no problem filling the time when I'm not on a tour. I just like being there and prefer doing only 1 or 2 things a day.
We don't do family trips.
When we were working, all our trips were domestic ones and most were hooked onto my work travel. Others involved visiting family and friends.
Since we retired most have been to Europe. The rest have been connected to racing with friends and family visited along the way.
I thought of travel as a vacation when we worked. If I had more money, I'd travel longer and more often. Then I'd call it a lifestyle.