For years we have helped retirees find their perfect retirement home in Jacksonville. It’s very enjoyable seeing their excitement as we tell them all about Jacksonville and Southern Oregon. Most of them have come from out of state so there is lots of education that goes on. From home prices, cost of living, weather, outdoor activities, theaters, restaurants, music scene, shopping, wineries, and culture; there can be lots to learn and lots of differences from the areas they are moving from.

This education has worked both ways as we have learned a lot from our retiring clients. We have seen a lot of smart planning, with some of our clients buying homes in Jacksonville years before they retire. They have us manage their retirement home as a rental home, giving them a yearly passive income until they are ready. When they do retire, they do so in a home that has appreciated in value and may be way beyond what they might currently spend for a retirement home. We have also seen retirees do a 1031 exchange from a rental property they own out of state to their future retirement home in Jacksonville giving them tax advantages.

We have also seen, from our newly retired clients, what a retired lifestyle looks like living in Jacksonville. One of my favorite stories is a day I walked into South Stage Cellars at two in the afternoon to pick up my credit cards I had inadvertently left the night before. As I entered the tasting room, I was greeted by four of my newly retired clients, all at the bar wine tasting. They quickly offered me a seat but I had to decline, telling them I had three more appointments to attend. It must be nice to be retired.

Just recently we had family visit us for a week and we decided to have a staycation and pretend we were retired without worries and with less responsibility. As it turned out, it might have been one of our best vacations. The first day started without the alarm going off and we wandered down the street to Good Bean for breakfast. There you could see tables of retired men and women, in what look liked a weekly gathering, catching up with each other. After breakfast we took our visitors on a tour of downtown, stopping at each eclectic store, buying gifts and gadgets you’ll never see in malls. Soon lunch came and we found ourselves in the sun on the back porch of Bella meeting up with the rest of our family. That evening we hiked up the hill to see The Little River Band at Britt, from our seats in front of the stage. It was a great concert, and I could only think of how lucky we are to live in a great town that just happens to have an amphitheater that attracts some of the best live music and comedy acts I have seen.

The next day involved an early morning hike in the Jacksonville woodlands, breakfast at Mustard seed, lunch outside at Jacksonville Inn and then on to wine tasting at South Stage Cellars. That evening we headed out to Red Lily to picnic on the Applegate River, hear live music and enjoy the beauty of the surroundings. We even watched a river otter swim up stream.

On the third day we woke up late, took a trolley ride around Jacksonville then headed to DANCIN for a great meal, great views and some great Pinot Noir. After that, we took our grandkids for ice cream under the La Fiesta restaurant. The kids were more enamored by the spoons that changed colors as they got cold than they were by the ice cream. For the adults, we were just grateful to hang out with the kids as an excuse to enjoy ice cream. After an afternoon nap we had a big BBQ at home for our guests and all of our family, then sat in our front yard and watched the energy build as 2000+ concert goers ascended up the hill to that evening’s concert. The evening was topped off when Jacksonville came alive with those 2000+ somewhat inebriated concert goers descending down the hill, many staying to enjoy the local restaurants, pubs and bars.

The staycation could have ended here, but on the fourth day, we headed up to Lake of the Woods for three more days. We swam, kayaked, boated, BBQed, hiked, roasted smores on the fire and reveled in the smells and sights of the high mountains. We even took a drive to Crater Lake, ending up at the historic lodge for lunch then sitting on the rocking chairs overlooking the lake.

We headed back to Jacksonville for the last day of our pretend retirement. We hung out at Daisy Creek Vineyards, listened to live music and talked about not what we did, but what we didn’t do. There wasn’t enough time to raft or Jet boat the Rogue River, go wine tasting in the Applegate Valley, see a play at OSF, go to a dinner show at the Cabaret, drive to the Redwoods or try the Jacksonville Segway tour.

The week went by too quickly, and when we dropped our relatives off at the airport, they vowed to do this again next year – another staycation in Jacksonville pretending we are retired. As we drove back into town, we realized Jacksonville is not a town, it’s an experience.