At Homestead Hill, our morning view is defined by the mountains. It’s the first we see when we wake up. However, because the coast is so incredibly close, we often find ourselves leading a double life. Just as the sky begins to turn a dusty pink, we’ll take a ride to catch the sunrise in Cupra Marittima (“Cupra”). There is something magical about watching the sun climb out of the Adriatic in total silence before the rest of the world wakes up.
By midday, that silence is gone. The blue side of the Marche transforms into the vibrant, high-energy Riviera delle Palme.
Cupra is our favorite starting point of that Riviera. When we leave Ripatransone, Cupra is within a 10-minutes drive. This is where we are greeted first by the salt air and the rhythmic sway of thousands of palm trees. But the Riviera is a trio: Cupra Marittima, Grottammare, and San Benedetto del Tronto are all linked by a stunning 15-kilometer seaside promenade. In the winter, this path is a sanctuary for silent walks. In the summer? It transforms into a moving mosaic of cyclists, skaters, and families out for the passeggiata.
Cupra is our favorite starting point of the Riviera delle Palme.
Join the crowd
The sheer energy of the coast in summer means the calendar is packed. The beaches are full, but in a good way. It’s easy to find free spots. In summer, many events take place. Look out for these:
- Festa della Madonna della Marina (San Benedetto | Late July): A massive tribute to the sea with a procession of decorated boats, a huge fair, and incredible midnight fireworks over the harbor.
- L’Antico e le Palme (San Benedetto | June & August): One of Italy’s premier antique markets. The city center fills with hundreds of stalls – a paradise for treasure hunters.
- Artocrisia & Marano Events (Cupra | July/August): Cupra celebrates its Roman and medieval roots with theater and markets in the hilltop Borgo Marano. It’s a beautiful, slightly quieter alternative to the big city parties.
- Cabaret Amoremio! (Grottammare | August): A legendary comedy festival in the medieval old town. The atmosphere in the piazza under the stars is electric.
In summer, beach life takes off in the Riviera delle Palme.
San Benedetto: Glitz, Grit, and Fish
When you want the full party mode experience, you head towards San Benedetto del Tronto. San Benedetto is the main city of the Riviera. Its center is perfect for shopping and sipping a Spritz in the pedestrian zone. It’s polished, fashionable, and very Dolce Vita. Less than 15 minutes walking from the boutiques, the atmosphere shifts. This is one of Italy’s most vibrant fishing ports. Here, the glitz is replaced by the smell of the sea and the sight of massive blue trawlers.
Skip the white-tablecloth restaurants for a night and head to one of the harbor fish shacks. These unassuming little friggitorie serve the freshest catch of the day. There is nothing like eating a fritto misto.
One of our favorite fish shacks: NUDO e CRUDO.
By the time the beach clubs start their midnight sets and the coastal heat lingers, we usually find ourselves retreating.
The beauty of the Riviera is that it’s right there when you want the music, the markets, and the vibrant Italian chaos. But the real luxury is the drive back. As you climb the hill and leave the sea behind, the humidity drops and the mountain silhouettes reappear. At Homestead Hill, the only soundtrack is the wind through the trees and the only lights are the stars above the peaks.