My husband and I just returned from our first post-retirement road trip. Even though we mostly stuck to our planned schedule, it was very freeing to know that, because neither of us have a job to dictate our return date, we could stay away as long as we wanted… or at least until the money ran out.
We had a terrific several weeks in northern California; in Monterey at a car club “convention,” visiting my brother and sister-in-law in the Bay Area, and spending time in Santa Cruz with my husband’s family. In fact, we had such a good time we started to plan our next trip as we drove home. Yep, I think we could get used to this!
In addition to planning our next escape, we’ve been talking about what we can do to make it easier for us to just pack and go. We want to put a few things in place now so that, when the spontaneity spark hits us or a can’t-miss-it opportunity arises, we can take off at a moment’s notice.
We’ve already made the conscious decision not to have pets because of travel. Although I miss having a dog or a cat, the freedom has been a positive tradeoff.
Our landscaping is – by design – fairly low maintenance, so we don’t need to arrange for upkeep while we were gone as long as our plants don’t have to go more than a couple of weeks without water.
Seasoned travelers have told us that it’s best not to put a vacation stop on mail and newspaper delivery because it is an alert that we will be out of town. Because of this, we have a neighbor pick up our mail and paper while we are gone. Since we provide the same service to her when she’s on vacation, it doesn’t seem like an imposition. To make things simpler and to avoid overlapping vacations, we are considering cancelling the paper completely. Our mailbox is attached to the garage wall so we want to create an opening that will allow the mail to drop directly from the box into a container inside the garage.
Ideally, we’d like to have someone stay at our house for absences lasting longer than a week or so. Not much would be required beyond simple watering and generally keeping an eye on things, but having a presence in the home would make us more comfortable while away. Although we live in a pretty safe neighborhood, this is a big city and we’d be naive to think nothing could happen.
When I was younger, single, and living in a condo with my cat, I had plenty of friends who were happy to stay in my home while I was out of town. They either lived with their parents or with roommates and welcomed the opportunity to have their own space for awhile. They enjoyed the quiet and privacy and I received cat feeding, plant watering, and house watching services. Win-win.
Fast forward a few decades and circumstances have changed. Married or not, our friends tend to be happy with their living situations so are not available to house-sit.
House swapping is something we might explore in the future, especially for longer stays, but for now—and for shorter stays—we are looking for that perfect match; someone who is pet-free, trustworthy, responsible, and who would welcome the opportunity “get way” for awhile in our home.
Hopefully we can find someone before we take off again.
Retirementally Challenged 
I like your plan! You never know when the travel bug might bite and with the time to spend doing what you want it is a great idea to be ready to roll. We tried the AirBnB service for a recent trip to Paris and were very happy with the results. We are considering using them to possibly rent a room on occasion when we retire, not sure about renting the whole place while traveling…I am also reading about a lot of technology that allows you to keep tabs on your home while away – from video to lights, etc. Happy trails!
I’m glad to hear that you had a good experience with AirBnB – they are on my list of services to check out too. Not only can hotels be expensive but I think staying in someone’s home could add to the travel experience. I’ll check out the available security technologies. I don’t want to be paranoid, but you never know…
Glad you had a great trip — can’t beat the mixture of fun and family! The central coast is so wonderful! Even though it’s fairly close, it feels so different compared to the So Cal coast!
The cliffs of Monterey reminded me so much of La Jolla, but not nearly as crowded. San Francisco was magical, especially when viewed from the Marin Headlands, and Napa so lovely. We’re so lucky to have family up there with a guestroom always available.
Oh, you need to widen your circle of friends. Champers be yummy! Thanks for the heads up on our insurance. Definitely something to look into!
Anyone breaking into our house would be pretty disappointed too… but how creepy that would be anyway! Even if we don’t travel as often as we’d like, it really is nice to have the option and the flexibility.
Champagne tasting….ahhh. We are off to NY and the Fingerlakes Region next week and will be visiting a few New York wineries (no comparison of course), but it will be wonderful to get away again this summer. Love, love, love being able to grab a bag and go – no pets, no newspaper, no worries. Mother-in-law checks on the house in our absence and a neighbor has a key just in case. Love your mail slot idea. Happy for you that retirement is going as spontaneously unplanned as possible!
Lucky you! I have a friend who lives in Hammondsport and she loves it! I have a hard time understanding how she – Southern California born and raised – survives the winters there, but I guess the other seasons make up for it. Enjoy your trip… and the wine tasting!