Come sail away
Sailing Collective
GETAWAYS • Greece
Our catamaran shoved off from the island of Kos and headed northwest en route to Kalymnos, about 20 nautical miles away. We’d embarked on a weeklong sailing trip across Greece’s Dodecanese, a slightly off-the-beaten-path archipelago scattered in the southeastern Aegean near mainland Turkey. Aboard our 46-foot Lagoon catamaran, my best friend and I were joined by two couples from Indiana, a solo traveler from San Francisco, and our captain and chef.
It was my third charter in about seven years with Sailing Collective, a company headquartered in New York City that organizes group and private sailing voyages around the globe. My first trip was their Sardinia & Corsica itinerary with founder Dayyan Armstrong at the helm. He runs his company with an ethos of bringing people to as many places around the world by water as possible for real cultural engagement. Summer is for the Mediterranean, winter for the Caribbean, with destinations spanning the globe from Nantucket to French Polynesia, Madagascar, and Thailand. No sailing experience is necessary, and you can choose to be as active or passive as you like (unless you’re on one of the designated sailing school trips).
My friend and I keep returning because, first and foremost, we’re both water babies whose idea of heaven is spending a week at sea, sailing, witnessing wild new landscapes, swimming in different exotic coves every day. We’re loyal to Sailing Collective because they run a tight ship, employing top-tier chefs and capable captains with deep knowledge of the sailing grounds. Chefs provision locally, creating meals that reflect the region’s culinary traditions, often surpassing anything we eat on land at the excellent local restaurants that they also scout out for us. (The chef on my first voyage has gone on to work as a development chef in Yotam Ottolenghi’s test kitchen in London, for example.)
A day aboard a Sailing Collective voyage typically begins at the dining table on the back deck over a delicious breakfast that might look something like zucchini blossom frittatas, a bitter green salad, grilled bread with mascarpone butter, nectarines, and green grapes. Soon, everyone finds places to sprawl out — the forward deck near the netting, the top deck beneath the boom, in the shade at the helm with the captain — and take in the scenery under sail. Eventually, we anchor in a picturesque cove or dock at a local marina, and set out exploring.
A few things to keep in mind when considering a Sailing Collective vacation:
It’s more salt life than lux life. These are big sailboats, but quarters are still tight, and marine heads are far from glamorous.
A Sailing Collective trip is best in destinations you’ve already explored by land. If it’s your first time in France, you might not want to start with the rock in the Mediterranean where Napoleon was born.
Same goes for group travel. Are you sure you can get along with people you’ve never met before in a confined setting?
Part of the beauty of a Sailing Collective trip is the idea of the collective. There’s a spirit of community in this ragtag group of mariners, swapping stories of other voyages and friends you’ve met along the way, especially if you become a repeat guest. On this last trip in Greece, it turned out that the captain of the other boat in our flotilla had lived and worked on the water in Key West during the same time period I had and we had a ton of mutual friends. To put that together on our last night at a taverna on a remote island in Greece 6,000 miles from home made this big world feel small in the most beautiful way. –Shayne Benowitz
→ Sailing Collective • Double cabins from ~$3,900 per person for weeklong voyage.
Photo: Ashley Camper