When we first arrived in Ripatransone, we were struck by its nickname: the “Belvedere del Piceno.” Perched 494 meters above sea level, the town offers views that stretch from the turquoise Adriatic Sea all the way to the Sibillini mountains.

In our opinion, Ripa and its surrounding is breathing romance. Here is our personal list of 5 things to do in and around our favorite hilltop town.

Sunset wine tasting at a local cantina

Ripatransone has a deep-rooted wine culture, boasting the largest vineyard surface in the Marche region. For a romantic afternoon, we recommend visiting a local winery like Tenuta Cocci Grifoni or Le Caniette. Sipping on a chilled glass of local Offida Pecorino while looking out over the rolling hills is pure magic—and a great way to learn about the land we now call home.

Catch a show at the Luigi Mercantini theater

Located inside the 14th-century Palazzo del Podestà, this is one of the most beautiful historic theaters in Italy. It is small, intimate, and incredibly ornate, featuring a ceiling painted with local legends. It’s the ideal spot for a sophisticated date night if you can catch a live performance or even just a guided tour of its velvet-lined boxes.

Golden hour at the Cathedral Belvedere

If you follow the path toward the Ripatransone Cathedral, you’ll find several panoramic points. At “Golden Hour,” the light hits the brickwork of the town just right. It’s easily the most romantic spot in town for a quiet moment together before dinner.

A coastal escape to Cupra Marittima

Just a 10-minute drive down from our hill is the Riviera delle Palme. While many tourists flock to the bigger resorts, we love Cupra Marittima for its more relaxed, authentic feel. You can rent two loungers, grab a spritz at a beach bar, and enjoy the sandy shores. It’s the perfect contrast to the rugged, earthy work we do up on the farm.

Walk the open-air art gallery in San Benedetto

The south pier of nearby San Benedetto del Tronto has been transformed into the MAM (Museum of Art on the Sea). You can walk for over a kilometer past 130 sculptures carved directly into the travertine rocks of the breakwater. It’s art, sea breeze, and a great walk all in one—and completely free to enjoy.

    Come and visit us at:

    Contrada Ciapella 20, 63065 Ripatransone (AP), Italy

    This is exactly where you want to be.

    Call or text us at: +39 37 809 228 64.

    And don’t forget to like and subscribe:

    (c) 2025 – 2026 HOMESTEAD HILL. We value real connections and your privacy. Please read our privacy policy before accepting it.