@mdurette It sounds like we're in a similar boat (but I think my kids are younger) and I don't think I've been in the timeshare game as long as you. We haven't fallen into a rut yet, but we have gone to several places 10+ times in the last few years.
We have found the spots we love and are happy to go back to...Orlando, Gulf Coast of FL, Colorado Mountains (where we live). We have also intermixed that with new locations (well new to our kids -- Arizona, different Hawaiian Islands).
Here are my suggestions:
- Get into the credit card game. I had traditionally always been in the Chase ecosystem (which is fantastic), but I recently got a VentureX card and a platinum Amex. To make the annual fee worth it I need to book stuff through their travel portal, so it's kind of fun booking places I wouldn't normally stay. Also, the point bonuses account for potentially $1000's in travel.
If you have a spouse and each get cards separately (and refer each other), you can double up on things.
This only works well if you are disciplined about paying off cards in full.
- Hyatt Points tend to stretch pretty far. They are also a travel partner of Chase. Many Hyatt Places (almost always sleep 6) or Hyatt Houses (which often have kitchens too) go for 8000 points.
It's hard to do a full week in a hotel for us as well, but 2-4 nights is doable....so perhaps get out of the mindset of going somewhere for a week and go for a long weekend. Find some places that have good points values in places that your families have wanted to visit.
When we stay at Hyatt's that serve breakfast, we usually aren't hungry until 1 or 2PM and then we just get a late lunch and don't need to eat dinner.
- Try to find new timeshare locations. We are fortunate to live next to a lot of great timeshare resorts, but if we want to try something new it's either a flight or a long drive. We had a great time in Arizona and look forward to staying in different Phoenix area resorts.
- Others have suggested camping. Obviously the camping is great out west. I'm not sure what it's like in your neck of the woods, but I've found a few National Park Service cabins if you don't like the idea of staying in a tent. A lot of them don't have bedding, but if you use cots it can be pretty comfortable and it's nice to be out in nature for a couple of nights. The rates are around $50 a day.
- Travel in the off-season of popular tourist destinations...it's a different experience for certain, but it can be a lot of fun. Our family always looks forward to going up to the mountains of Colorado during mud season (part of the appeal is that it's ridiculously cheap via timeshares).
- Do activities you wouldn't normally do. We did this on our last visit to Orlando and had a blast. This is ridiculous, but our kids went to the world's largest McDonald's off I drive 3 different times on our last vacation (They have a good arcade with an unlimited card...they also liked trying the wood fired pizza and Waffles -- both quite good...considering it was McDonalds). We went to The Florida Aquarium, we did the Gatorland zip line and basically stuff that we wouldn't normally do.