Trip Itinerary

We begin our trip in the town of Grosseto, which is easily accessible in roughly two hours by train from Roma Termini station or Santa Maria Novella station in Florence. Grosseto is a historic Tuscan city whose origins date back to the Etruscans. It gained prominence in the Middle Ages when it became the capital of the Maremma region. The city's main attraction is its remarkable 16th-century Medici walls, which you can walk along for panoramic views, along with its charming historic center featuring the Duomo di San Lorenzo and an archaeological museum. Grosseto is an authentic, working Tuscan town without the tourist crowds of Florence or Siena. The walled historic center is compact and walkable.

Overnight: N/A

Meals: N/A

Your guides will meet you outside the central Grosseto train station at 11:00 am. We'll take a short drive and check into our agriturismo accommodations, then have a light lunch before heading to our launch point at the fishing village of Talamone. From there, we'll paddle the shoreline of the Parco Naturale della Maremma to beaches only accessible by water and do a short hike into the pine forests the park is known for, and explore the system of watchtowers that the Medici built in the 16th century to protect against the Barbary Pirates. This evening, we'll visit the beautifully preserved medieval hilltop town of Magliano in Toscana for a walk along the top of the 15th-century walls that encircle the historic center and have dinner at a family-run restaurant on one of the town's narrow streets, serving classic Maremma cuisine.

Overnight: Case Cordovan

Meals: Lunch and Dinner

Today, we launch our kayaks near the harbor of picturesque Porto Sant'Ercole and pass the imposing walls of Fortress Filippo, one of three fortresses built in the 16th century to guard the Port against pirates. Gliding through crystalline blue water along the peninsula's cliffs, we explore sea caves, including the stunning Gotta Azzura. After a swim and a beach picnic, we return to Porto Sant'Ercole for a celebratory gelato. Returning to our hilltop agriturismo, surrounded by olive groves and vineyards, for a farm-to-table meal of locally produced Tuscan cuisine and wine.

Overnight: Case Cordovan

Meals: Breakfast, Lunch and Dinner

After a one-hour drive, we arrive in the Medici town of Pitigliano and set out for an easy hike along an ancient sunken road to the site of a vast Etruscan necropolis. After lunch, in Pitigliano, we'll continue to the town of Bolsena and our accommodations in the village of Bolsena at a boutique hotel created from the restoration of an ancient mill dating back to the 1500s. After checking in, we'll have our first taste of paddling the remarkably clear, clean waters of Italy's largest volcanic lake, formed around 300,000 years ago in the collapsed caldera of the ancient Vulsini volcano. Paddling the lake offers beautiful views of medieval hilltop towns, areas rich with birdlife, and volcanic rock formations. Dinner this evening is at a family-run restaurant specializing in locally caught, fresh lake fish, prepared with traditional recipes that offer an authentic taste of the area's culinary heritage, along with beautiful lake views.

Overnight: Casale 1541 Hotel

Meals: Breakfast, Lunch and Dinner

Today, we paddle along the southwestern shores of Lago Bolsena, exploring the beautiful ancient towns of Marta and Capodimonte and visiting the submerged ruins of a lakeside Etruscan settlement. We'll kayak offshore to Isola Bisentina, an island inhabited since Etruscan and Roman times that has served as a refuge for popes, nobility, and religious orders since the 9th century. Today, several chapels nestle amid centuries-old gardens, and the octagonal church of Santa Caterina crowns a scenic headland. Dinner this evening is at another family-run restaurant in Bolsena.

Overnight: Casale 1541 Hotel

Meals: Breakfast, Lunch and Dinner

Our journey across Italy continues today with a two-and-a-half-hour drive to the crest of the Central Apennine mountains, at Monte Catria, which stands 1,702 meters above sea level. The mountain offers spectacular views across Central Italy, stretching from the Sibylline Mountains to Lake Trasimeno and the Adriatic Sea. Nearby, we'll visit the Monastero di Fonte Avellana, established around 980 by a group of hermits, and tour the restored complex, including the magnificent 13th-century scriptorium where monks copied manuscripts by the light of the sun, as well as a historic library founded in 1733 that contains over 10,000 volumes. After lunch at the monastery, a one-hour descent takes us from limestone peaks and mountain meadows to the verdant rolling valleys and foothills of the Marche region, to the azure and turquoise waters of the Adriatic, and to our seaside accommodation in the city of Senigallia. This evening, we'll celebrate the completion of our cross-country journey with a glass of chilled Verdicchio wine from Marche and enjoy a dinner at a trattoria on one of the narrow alleys of Senigallia's historic center.

Overnight: Hotel Cristallo

Meals: Breakfast, Lunch and Dinner

With our kayaks on board, we drive to the dramatic limestone promontory of Monte Conero, which rises 572m above the crystal-clear, turquoise waters of the Adriatic. Our paddling route follows the spectacular coastline of the Conero Riviera, passing the iconic limestone spires known as the Due Sorelle (Two Sisters). The clear, vividly hued waters contrast dramatically with the rugged, white limestone cliffs and deep, green Mediterranean forests above. As we paddle, hidden coves and pristine beaches beckon us to stop to swim and snorkel, while the tiny fishing village of Portonovo, fronted by one of Italy's most beautiful beaches, awaits us. Lunch is at a beachside restaurant that specializes in a regional dish prepared with locally harvested mussels. This evening, we'll enjoy dinner in a tiny walled medieval hilltop town in Le Marche.

Overnight: Hotel Cristallo

Meals: Breakfast, Lunch and Dinner

Today's paddle takes us past Senigallia's iconic, elegant art nouveau pier Rotonda a Mare and the 15th-century Renaissance fortress of Rocca Roveresca, then along Senigallia's famous "spiaggia di velluto" (velvet beach). Protected by breakwaters, our beach paddle allows us to revel in the warm, clear waters of the Adriatic and stop at will for a refreshing swim. This evening, we'll enjoy a celebratory farewell dinner at a special restaurant in the heart of historic Senigallia, which boasts the highest concentration of gourmet dining in Italy relative to its size.

Overnight: Hotel Cristallo

Meals: Breakfast, Lunch and Dinner

After breakfast, transfers to Ancona Airport (AOI) are available. From Senigallia's central train station (located within walking distance from our hotel), high-speed rail connections to both Rome and Bologna are available. Returning to Rome Airport (FCO) is easy via the direct Leonardo Express train from Roma Termini station to the main terminal. Arrivederci

Overnight: N/A

Meals: Breakfast