For my 40th birthday, I was resolved to do something epic. So I rented a sailboat with eight of my closest friends, and we went island-hopping along the Dalmatian coast.
I first had this idea in 2008, when I visited Dubrovnik with Hannah on our “Children’s Crusade“. We enjoyed the walled city and a short trip to an island castle, then went inland and onward toward the Middle East. I left feeling that I had missed the best part of the coast, but knew that I would come back. Seventeen years later, it was time to return.
I started planning back in November, sending out feelers to folks I knew would be down for such an epic trip. Who would want to give a week of their vacation to me, a boat, and the winds and waves? This meant that friends with small kids were probably not compatible, but a few of my remaining child-free couples were keen. After a few false starts, we needed up with a crew of eight and a skipper named Toni. If you ever need a guy to drive your catamaran, he’s the best.
April is a little early in the sailing season for the Adriatic, but it’s my birthday and also Eid, so friends working in the Muslim calendar had a week free. With temperatures in the 50s and cold bura winds occasionally dropping off the mountains, it wasn’t going to be warm, but we’re from New England and made of hearty stuff. And besides, prices would be cheap and crowds low. I booked a 48ft Bali catamaran through a yacht broker, and got to planning island excursions.
We arrived on an overnight flight from Boston, stopping in Frankfurt for a nap in a pod and to change from Lufthansa to Croatian airlines. Flying into Split, you can see why it’s associated with the dog breed, there are thousands of lovely spots to check out. We got a taxi to the Kastel marina, where we met our skipper and got a tour of the boat. It’s a catamaran, which a sailor friend had warned me would be like “driving a bathtub”, but that doesn’t bother me much. It has six cabins, two with queen beds, two with twin bunks, and two in the front with hatch access to the outside. All were sufficiently comfortable, no “corner coffins” for us or our crew, and all had attached bathrooms.
Ruth and Debs went to get groceries, and I settled in with Toni to learn the non-metaphorical ropes. After a quick storm and a beautiful rainbow, I was glad we weren’t departing until the next morning.

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