Ventimiglia is situated between the Mediterranean coast and the mountains. Part of the Italian Riveria, Ventimiglia showcases its history and culture through a variety of festivals each year. Ventimiglia festivals include flowers, music, sword-fighting, and chestnuts.

The Battaglia di Fiori, or Battle of the Flowers, is held in June and includes a parade of floats made of flowers. The once ancient festival has been supported by the flower industry. People on the floats throw or shoot flowers at the onlookers. Each festival has a different theme, for example Dante’s Inferno or, more broadly, music.

The annual Ventimiglia Jazz Festival is held in July at multiple locations in the old section of town and on the beaches. The event is attended by a variety of European jazz musicians.

August brings a medieval Ventimiglia festival, appropriately called "Medieval August." Teams from other Italian cities come to compete in traditional and non-traditional medieval games. Highlights of the festival include medieval dress, sword-fighting, and period music. Other events include a parade of drummers and flag throwers which moves through the city and a boat competition with traditional Lagurian boats.

After the height of summer in the coastal towns, some of the festivals move away from the coastal and more tourist regions.

• Camporosso, the town next to Ventimiglia to the north, celebrates the Feast of St. Sebastian in mid-January. Along with the town of Dolceacqua, the celebration consists of laurel trees covered in communion wafers which are paraded through the streets.
• A 20-minute drive into the mountain town of Pigno adds several festivals to the calendar. Pigno hosts an art festival in June, a comedy festival in July, and a mushroom festival in October.
• Ten minutes away from Ventimiglia are 2 bunkers which were used during World War II. The International Bunker Film Festival has been held each July for nearly a decade. The bunkers are located in an olive yard, and the award for the festival is appropriately called the "Golden Olive."
• Perinaldo, 15 minutes away in the mountains, hosts a chestnut festival in October. The town is perched in the mountains and is full of chestnut trees. The festival is held in the town's center and overlooks the sea. Roasted chestnuts are a "must" at the festival and may be enjoyed with local wine and snacks.