The Pleasures and Perils of Planning

Yes, I do know how lucky I am (husband, house, reasonable and reliable income). Some days the ordinary round pleases me, some days I know intellectually that I’m grateful, and some days I actually feel my gratitude. But I’m a restless person, too. Novelty, change, and travel – they sharpen my mind, make me feel awake.

So despite being in the depths of winter and the pandemic, I am starting—cautiously—to plan our first post-Covid trip. (Like other restless types, I’ve already made and canceled several trips in the past year.) Some people happily find a good tour company, choose a time to go, send a credit card number, make plane reservations, and are done. The best of the tour companies (Rick Steves, Overseas Adventure Travel, Viking) are very good, too. Yet my husband and I are not fans. We enjoyed our Viking cruise down the Danube, but the time we remember with the most pleasure is the three days in Amsterdam before the cruise started. We prefer to tailor our destinations according to our own tastes and to set our own pace. (We incline towards the currently hip Slow Travel, but we definitely travel in a way that’s just plain slow.)

Which means a tour company doesn’t plan our trips. I do. And though it’s exciting for me to plan a trip, complications arise all the time. It’s like navigating a maze: I set off confidently in a direction, come face-to-face with a wall, sigh heavily, then set off again on a slightly different path. This year, there are added uncertainties. (Luckily, reservation sites have gotten pretty good about cancellations.)

Here’s my awkward, tangled, not-so-pretty process.

(The shirt–depressingly accurate, except that there’s snow on the patio now–is available from the Acorn catalogue.)

Step One – choosing when to go

For planning purposes this year, I am assuming that my husband and I (over 65 but not yet 75) will finally qualify for the Covid vaccine sometime in the next month. Then we will still have to wait for the second shot, then let it work its way through our systems. By May, we should be fully vaccinated. (Imagine me crossing my fingers as I say that.)

Will being vaccinated be enough to let us travel? It will certainly lower my anxiety about going to stores (still masked). It will be enough to let us visit the kid and grandkid in a neighboring state–carefully. It probably won’t be enough to travel internationally, at least right away. After all, a lot of countries still don’t want to admit citizens of the worst-hit country in the world. But surely by fall….

So – how about October? In fact, since the leaves are gorgeous here in early October, how about mid-October to mid-November?

Step Two – choosing where to go

Well, Italy, of course. Although there are plenty of new countries and regions I’d like to explore, Michael and I are hungry to amble through some narrow streets with vine-covered stone walls, sip wine while we watch the Italians promenade arm-in-arm after work, and converse with storekeepers in our halting Italian.

Since we adored Florence when we spent six weeks there, spending a week there is a given. My husband, in fact, would be happy to settle there for the whole month. I’m the one pressing to see new cites and new countryside. So we compromise: a couple of weeks in Florence, followed by two weeks in a couple of other places. Remembering the relentless, chilly rain that started to fall in Florence as we flipped the calendar to November, I suggest we move south for the following two weeks. We should go to Rome, I pronounce. We’ve flown through it and visited it on daytrips, but never stayed. It’s always seemed overwhelming to us—so urban, so crowded. But lots of our friends love it. We need to give it a chance. It’s time to stay a week and see what that feels like.

Step Three – choosing places to sleep

Just as we’re not really tour-company people, so we’re not really hotel people, either. If we’re just staying a night or two, hotels make sense. But while it’s nice to be fed breakfast, we hate being cooped up in a hotel room on a rainy day. For the same money, we can rent a nice little apartment. Yes, we have to come up with our own food, but there’s usually a café and a touristy little market nearby. And shopping makes us feel more like locals.

So next I spend some enjoyable hours on VRBO and Airbnb, combing through possible apartments in Florence for October 13 – 27. (That’s a Wednesday to Wednesday. Why? Because it’s easier to travel from place to place during the week rather than the weekend. Also, it’s often cheaper to fly midweek.) I filter for two bedrooms (in expectation of guests), some outdoor space (preferably a terrace), and an excellent cancellation policy (full refund if we cancel sixty or thirty days prior)–all somewhere within half an hour’s walk of the center.

In our middling price-range, I find some promising possibilities, all with trade-offs. There are gorgeous views from a rooftop terrace, but the apartment is on the sixth floor with no lift. Or there’s a nice kitchen but a small, ugly living room (or vice versa). Or we can get out of the crowded tourist center, into a quieter and leafier part of town, but there’s a steep walk uphill at the end of the day. Even as I mull over the trade-offs, I recognize neighborhoods in Florence—and sometimes even specific streets. The whole process makes me deliriously happy.

After taking copious notes and narrowing the list down to a few top contenders, I shift to looking in Rome. There I don’t know the neighborhoods, let alone the streets, so I send off another flurry of emails and check the invaluable Rick Steves. (He suggests somewhere around the Pantheon unless one has a rich budget.) I set the same filters and save a few places that look good.

I rub my hands with pleasure. Things are falling into place. What’s next?

After urban delights and challenges, we’ll probably be ready for some countryside. But where? Maybe Sicily? (Only a tiny portion of it, because we have only a week, and we’re not the types to drive around, changing hotels every night or two. Maybe a tour company makes sense after all?) But what about the Amalfi coast? Or Bari and Lecce?

Step Three: The Wall

I check the average monthly weather for November along the Amalfi coast. Then in Lecce. Then in Sicily. Bad news piles on bad news. November turns out to be the rainiest month of the year, not just in Florence but all over Italy. Just to be sure, I check blogs and sites that specialize in Italian travel; they try to be upbeat about November (fewer crowds, lower prices), but they admit it rains a lot. I imagine hiking around Greco-Roman ruins in the pouring rain. It sounds miserable.

I sigh heavily and go back to the drawing board.

Step Four: Take a Deep Breath and Recalculate

Do we take a shorter trip? Or do we move our start-date up to the beginning of October?

We choose the latter. After all, we got a good dose of New England autumn this past year. So move the Florence weeks up, and then? Hard to know. Maybe, since we’ll be leaving from Rome, save it for the final week?

Whatever we decide, for the next few days, I’ll be re-immersing myself in VRBO & Airbnb…..