By the time I got to my third Greek island of the week, I had a pretty good idea that tourist season there was gasping for its final breaths.
I was on a Star Clippers cruise in mid-October and was now familiar with the empty streets and knew not to trust Google Maps when it said a restaurant was open (it was probably closed for the season).
I'd scouted a magnet to bring home to adorn my fridge, and my travel companion and I were not just the only tourists in the souvenir shop but seemingly some of the only tourists in the whole town on Skopelos as our port call entered its final hour.
While the shopkeeper rang up my purchase, I asked him when the store would be closing for the season.
"Tomorrow," he said, with the same look of vague fatigue I'd received from so many local business owners during my trip.
"We've entertained you tourists all summer," those expressions seemed to say. "Why oh why are you still here?"
I had been curious myself about the experience of cruising in Greece and Turkey in October before embarking on the trip, a sailing out of the port near Athens aboard the Star Clipper.
I knew it was better to be in a European metropolis like Rome or Athens in February than in August. Those cities will be as vibrant as ever but without the heat and the peak crowds.
This cruise, however, would typically be a beach-heavy itinerary on small islands with small towns. The least touristy port would be Dikili, Turkey, and we'd also visit Lemnos, Skiathos, Skopelos and Poros in Greece.
A good time to visit?

Streets on the island of Lemnos were mostly empty during an October cruise call. Photo Credit: Teri West
Throughout the trip, my travel companion and I weighed the pros and cons of the unusual experience of visiting these small island destinations in the fall.
I was convinced that the October temperatures provided a more comfortable experience for nearly every activity I enjoyed on land than the conditions I would have experienced in the summer.
We scaled a fort on the island of Lemnos, exploring hidden nooks, soaking in views and sharing the space with wild goats. Later that day, we biked to a trail and then climbed to a church that was tucked into a rock overhang.
In Turkey, we visited the ancient city of Pergamon, a fascinating hourslong adventure that offered little shade.
In every town, we strolled winding streets and scouted for cats.
Throughout the trip, there was always plenty to do that didn't involve lounging on a beach, and the temperature was great for all of it.
Some of these activities I even did in shorts despite my weather app informing me that the temperature would only reach the high 60s. When the sun was shining, it felt 10 degrees warmer than what the app told me.
Still, temperatures that feel like they're in the 70s don't beckon me to swim. But my companion and I did so anyway on a couple of occasions, as did some other passengers who were eager to enjoy the picturesque beaches despite the time of the season. I found it quite cold and uncomfortable, but others seemed to enjoy the challenge, even getting a thrill from the chill.

Photo Credit: Teri West
The movie-themed tour of the island of Skopelos is the star of the Star Clipper sailing.
Continue ReadingStar Clippers also offered equipment like snorkeling gear, paddleboards and a small sailboat just like it would have in the summer, which a few guests -- me included -- enjoyed.
Dining, I have to admit, was sometimes a bit of a challenge. For instance, three restaurants on Skiathos that we were interested in trying were listed as open by Google Maps but were shuttered when we arrived. We eventually headed to one of the eateries on the strip of open restaurants right near the port.
On Skopelos, we experience the same issue for lunch. We settled on a tented space on the waterfront, where we perused a long menu where many of the dishes we were interested in weren't available and fought for the attention of the two or three waiters who were serving what felt like pretty much all of the tourists in town that day, which was maybe 10 different tables of guests.
There were more eateries open on Lemnos, where the shops and restaurants catered more to locals than tourists. We still chose to eat on the waterfront at a restaurant that had far more space available than the two occupied tables. I loved the shrimp pasta dish I ordered, a specialty of the island.
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Sports team crew members of the Star Clipper prepare to welcome guests to climb the mast while at port in Dikili, Turkey. Photo Credit: Teri West
Bundled up
Back aboard the ship, weather conditions were a different story. I never saw anyone swimming in the two pools on the Star Clipper; while we were underway, the wind made sweatshirts or even additional layers a necessity.
The cooler temperature also meant that lounging on the decks was not much fun while we were sailing. That makes a big difference on a ship like the Star Clipper, where the indoor spaces are limited to cabins, a small library and a bar with some neighboring booths.
Ultimately, considering a shoulder season cruise at small European island destinations will have a lot to do with one's priorities.
If those priorities are land-based exploration with fewer crowds, then why not? If they're swimming, lounging and dining? Maybe an end-of-season cruise isn't a good fit for clients.