The Sailing Flotilla Charter That Wasn't

What To Do When Your Sailing Flotilla Doesn’t Go Where You’d Planned

Chesapeake sailors in Italy had to make a quick change of plan when their sailing charter changed direction…

family charter
The author's nephew and niece, Sherri and Brent, with daughter Claire at the helm of their charter sailboat in Italy.

Beginning, sulla terra

The Amalfi Coast for 15 glorious days; how lucky are we? The first week was, admittedly, a luxury land vacation with some good adventures for my husband Al and me as we traveled with our son and daughter-in-law, Dave and Jen. Our home base was lovely Sorrento where we had a full view of Mt. Vesuvius from our rented condo balcony. We packed in all the experiences we had hoped for—private boat tours of the Amalfi coast and Capri, must-see Pompeii, a pasta and tiramisu cooking class, a crazy drive up to Ravello, vineyard tours, and all the pasta, pizza, and Aperol Spritz we could handle.

Did you say, “When we head south”?

We said, “Ciao” to our son and his wife in Naples for our second week that was to be decidedly more adventurous and rustic. Our nephew and niece, who sail their own 40-foot Beneteau on the Chesapeake Bay, traveled to Italy with their mother and three teenage daughters. While they toured Pompeii, Al and I went on to Salerno—about an hour south of Naples—to check out our flotilla situation. With a flotilla, you sail your own charter boat, but there is a lead boat and skipper who knows the region, the customs, and the marinas. We appreciate this arrangement for international cruising, having joined one in Croatia a few years ago.

Herein started our adventure—the flotilla that wasn’t. Captain Al and I sat in an open-air bar at the very large and modern marina and called our flotilla captain. He off-handedly mentioned “when we head south in the morning.” What? No, no, our charter contract clearly had an itinerary for the Amalfi coast, basically west and north. No, he was certain we would head toward Sicily. This surprise plan (and agency mistake) was non-negotiable because our Maryland family had long yearned to sail on the Amalfi coast and particularly to Procida Island, which bears their family name. A quick sidebar resulted in our firm decision to do a bareboat charter on our own.


These Italian sailing cruising grounds offer dramatic views of rocky islands and the stunning coastline.

Setting their own course to adventure

Other than no local knowledge and infrequent experience with Mediterranean (Med) moorings, we felt confident we could manage. Med moorings are used widely in deep European waters; the boat is tied to an anchor rode fore and aft. In a mooring field the anchor rodes are already in place, but we discovered a quick call to the marina and help was always on the way to assist in this maneuver.

Our extended family arrived, alas with no luggage for four days (another story), but willing to go along with our plan, with an itinerary we would control. The weather was glorious, no rain for this part of our trip, pleasant breezes, and a boat that sailed well. Sailors don’t always appreciate self-tacking jibs, but on a vacation the Dufour monohull set up was just fine, as were the dual helm stations. We completed the boat orientation and had help dropping the four lines fore and aft, and off we went west towards Positano.

Our first sail was an easy beam reach the entire way. Our mooring field seemed pleasant enough, and we had a marvelous closeup view of Positano and the steep mountainside. We picked out a restaurant, took a launch to it, and had a tasty first dinner with some emergency clothing shopping afterwards. However, that was the only positive part of the night; we rocked and rolled all night long because of the continuous chop—and everyone woke up cranky.


Some daring swing and jumps into the clear water while anchored on a sailing charter near Procida Island, Italy.

Still no luggage, and delivery of it was made trickier by our boat being on the move every day. In addition, our family was required to complete customs forms before they could get the luggage. After studying the chart, we decided to go west around the point of the coast and head to Sorrento where Al and I had spent the prior week. We scored a marina, the women were all thrilled to go off shopping, and nephew Brent took an Uber to Naples airport to pick up the luggage. A lovely summer night in this quaintest of towns, another excellent seafood and pasta dinner, gelato, and a stroll down the cliffs to the marina. We had made lemonade (or limoncello) out of the lemons dealt us.

The next day was a three- to four-hour sail to Procida Island, the destination of which was quite a thrill for our Family Procida. We anchored outside of a village and rigged lines and a gangplank for some daring swing-and-jumps into the clear water. These teenagers are not typical; they thrive on adventure, love the water, steer the boat, and actually talk to older adults. We shopped for dinner which first mate Brent would cook onboard. A quick sail in the afternoon took us to the island of Ischia where we picked up more supper items after anchoring in the large bay where everyone jumped in the water. We didn’t have time to explore that island because we were anxious to start heading back southeast the next day, and we did not want to miss lovely Capri.

Capri (we learned to pronounce it as KAHpree) is gorgeous from the water, but the number of tourists was such that we did not want to go ashore. The “lesser” red, green, and white grottoes on the south side are beautiful, each different from the last. One brave guy swam inside one of them. Continuing on, but under motor because the wind was in the wrong direction and the waves too choppy to sail, we rejoined the Amalfi coast and moored in Nerano for another wonderful supper, highlighted by zucchini spaghetti, a specialty in that region. The mooring this time around was thankfully calm.


The author and her daughter-in-law Jennifer soak up the sunshine boating in Italy.

On to Amalfi the next day. We stuck to a tour of the picturesque town by sailboat, picked up a mooring ball, and took a launch to a beachside restaurant that is accessible by water only. More pleasant sailing under a light breeze delivered us back to Salerno to enjoy the pool and pizzas.

If you go…

For sailors interested in Italy, the skipper is required to have and submit evidence of ASA 104 sailing certification. The water is deep, hence the use of Med moorings. The distances between towns and islands are fairly short although there are many choices if you want to sail the whole day. As always, sailors need to be ready for a change of plans. We did use our translator phone app, but most Italians speak at least limited English. The variety of experiences cannot be beat—sailing, of course, but wonderful cuisine, swimming off the boat in clear water, and gorgeous sights every day. The weather in southern Italy in July is similar to Maryland, so a generator for A/C is quite a nice boat feature. We learned that the Italians in this region dress beautifully, especially in the evenings. No Grateful Dead tee shirts!

One last note: the Italians are friendly and outgoing, and everyone really does say "ciao" and "grazie mille." So, practice up. 

~By Betty Caffo

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