Late season vacations offer many advantages: fewer crowds, easier access to popular sites and favored restaurants, lower prices on hotels and easier upgrades. They also mean more variable weather!
Yesterday, reports of rain ranged from 60% at 8 am to 80% by 11 am. We figured we’d play the odds and venture out in our new rain jackets for an early morning walk along Fira’s cliff-hugging, waterside promenade. The menacing clouds made for gorgeous photos of the volcano islands of the caldera.
Have I mentioned that there’s no such thing as a bad photographer on Santorini? Unless you are shooting the inside of a paper bag, you pretty much can’t help but catch a beautiful moment. There’s the blue domed, white walled churches spread across the island like Starbucks across NYC. There’s endless sea views, cliff dwellings, boats sailing, hidden alleys, weathered, painted doorways and charming shops. Even a pack of donkeys climbing the steep hills and the “hot patties” they leave behind the stone pathways are photo-worthy!
So, midway in our morning constitutional, 80% chances becomes 100% pouring rain and we hustle our way back to our car and head to the villa for breakfast.The glass surround of our dining room lets enjoy the wind and rain while we consume a daunting spread of breakfast offerings. We take our time!
Then back to our suite for a couple hours of creative pursuits. I to writing my blog about the previous days road trip and he to guitar playing. A bought a collapsible travel guitar he’s enjoying on its maiden journey (fits inside his carry on!).
Then, we do the second best thing you can do on a rainy day…we go wine tasting! The island is dotted with wonderful wineries growing its acclaimed assyrtiko white grapes in a ground-hugging farming style.

We try two: Domaine Sigales where our tasting menu was topped off with the best anchovy and tomato crostinis ever. Then we drive to Artspace where the historic winery’s interior has become a contemporary art gallery. Our engaging host Esmerelda tells us about the wines, the history, her recipe for tomato sauce and gives us a tasting of their wines all for just 5 euros!

We exit the winery at 4:30 and, miraculously, the  rain has stopped.

Later, we head to dinner at Metaxma Mas, a popular locals eatery. Unfortunately, it isn’t popular with google maps and we get hella lost on dark, winding roads and Andy must summon his superhero clutch skills to get us back on track! Finally, we park at a church, head down a dark, steep alley and end up at a cozy spot with excellent grilled octopus and a lamb shank for him.

We drive back to Fira for a last, quick walk along the now dark promenade and home to pack up our clean laundry that was just delivered.

And that’s how you spend a rainy day in Santorini.

Today, we head to Crete!