Jon and I had been talking for years about a sailing trip somewhere in the Med. His background in sailing was mostly west coast, between San Francisco and Puerto Vallarta while mine was mostly in the Med, sailing with our good friend Jack in Croatia, Italy, Greece and Turkey. When I decided to take the skipper’s course in San Francisco Bay (out of Berkley), I did the final back in Puerto Vallarta. To prepare for it I practiced with Jon on his 42’ sailing boat, and afterwards enjoyed many wonderful days sailing with him and friends in Banderas Bay.

Over the years things changed. We moved to Europe and Jon & Silvia moved their boat up to San Francisco. But we kept talking about the Med. Finally we put a trip together in the Spring of ’26, to sail the Pontine Islands off of Naples, Italy. 

But first we began with a land trip to Puglia. Flo and I landed in Naples while Jon & Silvia took the train down from Rome – they’d already been traveling around Europe for a few weeks. Flo and I spent a night in Naples first, arriving late in the afternoon. We checked in and then went out to explore the historic center of Naples. 

We stumbled upon the Spacconapoli pedestrian walkway, which is a mile-long series of streets in the heart of the historic center. Its narrow streets, lined with past-century buildings and packed with people, is the beating heart of the city, with piazzas, palazzos, centuries-old churches, and a vibrant local life. It isn’t just a single road but a sequence of historic streets stretching from the Spanish Quarters to the Forcella neighborhood. 

It was  a Saturday night so it was especially busy, meaning we had a difficult time finding a restaurant without a long line-up. We came upon the Piazza San Domenico Maggiore and in the back corner of the plaza was a restaurant (Palazza Petrucci Pizzeria) with just a few people waiting outside for a table. We were fortunate as a table for two on the upper terrace overlong looking the plaza became available quickly. It worked out well as their pizzas were amazing. In the center of the plaza is a very large obelisk, surrounded by what once were large noble palaces that are now individual apartments. Each building has a front large entrance that leads central courtyard where horse carriages were once kept.

I have to say that our first impression of Naples was rather dystopian with its run-down buildings reminiscent of Soviet-era structures. I kept thinking of Gotham City, expecting the Joker, Penguin or Batman to appear any time. I went back out in the morning for a walk through the same area and it was better, but still, Naples is not the prettiest of Italian cities.

Maradona

Naples loves Maradona. Tributes to him can still be found everywhere in the city. He arrived in Naples in 1984, welcomed by 75,000 fans who were convinced that the savior had arrived. Prior to this, Italian football was dominated by teams from the north and centre of the country and no team in the south had ever won a league title. 

At Napoli Maradona reached the peak of his professional career inheriting the captain’s armband and quickly becoming an adored star among the club’s fans. In his time there he elevated the team to having the most successful era in its history.  Napoli won their first ever Series A Championship in 1986–87 and won the 1987 Coppa Italia finala. Maradona was one of the key players of the campaign, scoring seven goals in ten matches.

Napoli would win their second league title in 1989–90 and later won the 1990 Italian Super Cup. Murals of Maradona were painted on the city’s ancient buildings, and newborn children were named in his honor. On 4 December 2020, nine days after Maradona’s death, Napoli’s home stadium was renamed Stadio Diego Armando Maradona.

Puglia

We picked up our rental car after breakfast and headed east to Puglia to meet up with Jon & Silvia. We’d rented a home just outside of Ostuni to serve as a base while we explored the hilltop towns such as Ostuni, Locorotondo, Alberobello, Cisternino, Martina Franco and the seaside town of Polignano a Mare. 

Although we enjoyed a few lunches and dinners in these towns, we much preferred buying local produce and cooking and eating at the house. There were a number of different places to dine around the property – by the pool, in the garden or inside – and we took advantage of them all. 

Towns visited:

Ostuni is one of the most striking hilltop towns in Italy, and certainly the most popular. Perhaps too popular as it can get quite busy with tourists. As with all of these towns, the cathedral sits at the top and the town is built around it. The old town is a maze of  whitewashed alleys, stone staircases, arches, tiny piazzas, and excellent restaurants..

It has a Greek feel to  in — bright, airy, sun-bleached. You stroll through narrow lanes lined with little wine bars, cafés tucked into corners, and artisan shops selling ceramics, leather goods, and local olive oil. The cathedral at the top is a beautiful blend of Gothic and Baroque. All of the towns we visited were mazes of meandering, winding narrow streets, and it was explained to us that this was on purpose, to confuse attackers. If they managed to break through the city walls, they then got lost in its labyrinth of restricted pathways.

Locorotondo is probably the best example of this, and its name says it all (at least in Spanish!), as crazily round. In Italian it actually means “round place” as the old town forms a perfect circle around the hilltop. Within this round peripheral streets is a maze of narrow streets so complicated that small maps are mounted regularly to inform people where they are. It is certainly one of the most elegant and impeccably maintained towns in the whole region. 

Martina Franca is one of Puglia’s hidden gems and well worth a visit. Located in the heart of the Itria Valley, it offers a nice contrast and break from the neighboring, more tourist-heavy towns. Even more than other hilltop towns in this region, Marina Franca really is a maze of whitewashed alleys, flowered courtyards, and grand stone gateways. It’s very easy to get lost in its meandering streets, fortunately it isn’t that large so you can find your way out!

Alberobello is something entirely different than the other towns in this region, as all the homes are made in stone with conical roofs (called truly), like something out o a fairy tale. It’s a UNESCO World Heritage site and quite unlike anywhere else in the world. The homes originally were constructed without grout, just stone upon stone, even the roofs. Folklore has it they were built this way so they could be easily dismantled in case the tax man showed up! Definitely one of the most interesting villages in Puglia.

Polignano a Mare is a small medieval seaside village that overlooks the Adriatic coast. Its historic center is built on limestone cliffs that rise dramatically above the sea. In Polgnano the streets are straight, but just as interesting as other Puglian towns, lined with shops, cafes and restaurants. It’s famous for its sea caves that have been carved into the limestone over time. 

After a week in Puglia, it was time to move on. Back in the car and a return to Naples – time to go sailing!