Within a few hours of being onboard my Windstar cruise, I had pockets of new friends around our ship, the Star Legend. I don’t typically connect this quickly, but there’s something about not knowing where you’re going that really brings a group of strangers together. The mystery cruise I’m on is a first for the company. Well, it’s the first time that such a cruise was planned. On a trip to Tahiti last year, a trio of cyclones derailed the company’s 11-night voyage through the Society and Tuamotu Islands. The cruise was re-routed through the Marquesas. Guests and staff alike had to go with the flow. Every day was a new, unexpected adventure, and everyone loved it. From this chance experience, the idea to do it again – this time on purpose – was born.
Fast-forward to this spring, when my husband and I joined about 300 other passengers on an eight-day itinerary where the only thing we knew for sure was that we were boarding in Athens. I had never been on a Windstar ship – they are known for small luxury ships with off-the-beaten-path ports and delicious food (thanks to being the Official Cruise Line of the James Beard Foundation) – and the mystery cruise concept intrigued me. Most of my fellow shipmates (about 80 percent of those onboard) had taken other sailings with Windstar and trusted the company to deliver an experience to remember.
The President’s Mystery Cruise added an element that felt unique, and most travelling parties had at least one member who’d been keen on being surprised. Even so, for some – myself included – it felt strange to surrender control of the trip’s itinerary so completely. One passenger told me that he was shocked when his librarian partner brought the cruise to his attention. “She likes things in order,” he laughed. “I did not think she’d be interested in something like this.” He could have been describing me.
Many of us assumed that all the ports would be revealed once we were onboard, but that wasn’t the case. About 36 hours ahead of each new port, a clue was dropped in our cabins with a riddle we could try to solve. For example, “Nestled by the Ionian sea, this ancient city boasts a bridge that swings, a castle that stands guard and a history that dates back to the Spartans”, was our hint that our first port stop would be in Taranto, Puglia, a coastal city in southern Italy. Many of us became fixated on figuring out the secret ports. We would stop each other in the halls, consult during dinner and trade theories over drinks. Others remained unfazed; after all, we’d know where we were going with plenty of time to book excursions and listen to a port talk. And why worry when we could use that time to lounge in our 280-square-foot suite, dine on James Beard Chef Paul Berglund’s rack of lamb or pop into the spa for a sauna and a steam.
As each stop was revealed – there were four in total – people began to settle. It helped that many of the ports were new, even to the frequent cruisers among us. From Taranto and Giardini Naxos in Sicily, to Reggio Calabria (at the toe of Italy’s boot) and Kalamata in Greece our voyage was steeped in ancient history and classic Mediterranean beauty.
In Taranto, for example, I opted to visit Alberobello, A UNESCO site, thanks to the most preserved collection of 15th-century Trulli homes. With distinctive conical roofs and white foundations, the still-inhabited structures use a drystone building technique that is thousands of years old, and their distinctive silhouettes have a fairy-tale quality to them.
The other excursions on offer were equally tempting: a visit to the whitewashed hilltop fortress town of Ostuni, a wine-tasting in a family-owned vineyard or seeing the prehistoric stone dwellings in the ancient city of Matera, which is thought to be the world’s third-longest continuously inhabited human settlement, among them.
A mystery cruise made having my usual overly prepared itinerary checklist impossible. (What do you pack when you aren’t entirely sure where you’re going? As it turns out, Mediterranean-friendly sundresses, linen pants, comfy shorts and T-shirts do the trick.) We leaned into the adventure of it all, and the result was a trip that was equal parts enlightening, engaging and exciting. In a world where happy surprises are hard to come by, booking a trip where they’re guaranteed may be my new favourite way to travel.