Your guides will meet you in the lobby of our guest house near Rome's Leonardo da Vinci–Fiumicino Airport. (FCO) After introductions and brief orientation, we will head to a local restaurant for some fine Roman food and discuss the trip details further.

Overnight: Capitani Guest House Flumicino

Meals: Dinner

After breakfast, we depart for the 90-minute drive northeast into the Maremma region of Tuscany and Porto Santo Stefano. Launching our kayaks near the harbor of picturesque Porto Sant'Ercole, we 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. Leaving the coastline, we'll drive a short distance inland to our hilltop agriturismo, surrounded by olive groves and vineyards; it is part of the ancient "Podere" system of land management. We'll enjoy a farm-to-table meal of classic Maremma Tuscan cuisine this evening. 

Overnight: Fattoria La Capitana

Meals: Breakfast, Lunch and Dinner

Today, we launch from the fishing village of Talamone and 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 were built to protect against invaders. This evening, we'll stop for dinner in the pre-Roman town of Ortebello at the head of the causeway connecting Monte Argentario with the mainland and holding one of the most unusual small wetlands in all of Italy. 

Overnight: Fattoria La Capitana

Meals: Breakfast, Lunch and Dinner

After a one-hour drive, we arrive in the Medici town of Pitigliano and set out for an easy 7 km hike along a mysterious sunken road to the village of Sovana, the site of a vast Etruscan necropolis. After lunch, in Sovana, we'll continue on to our accommodations in the town of Bolseno at a mill that dates from the 1500s. Depending on timing, there may be time for a paddle along the Bolsena waterfront before dinner. We dine at a lakeside restaurant specializing in fresh-caught local fish this evening.

Overnight: Casale 1541 Hotel

Meals: Breakfast, Lunch and Dinner

Today, we paddle the southwestern shores of Lago Bolsena, explore the beautiful ancient towns of Marta and Capodimonte, and visit the submerged ruins of a lakeside Etruscan settlement. Kayaking offshore to Isola Bisentina, which has been occupied since Etruscan and Roman times and, since the 9th century, has acted as a refuge for popes, nobility, and religious orders. Today, there are several chapels set amid centuries-old gardens and the Octaganol church of Santa Caterina atop a headland. This evening, we will drive to the stunningly situated Civita di Castellana for spectacular views and a memorable dinner.

Overnight: Casale 1541 Hotel

Meals: Breakfast, Lunch and Dinner

A scenic 3-hour drive takes us to the crest of the Appennine Mountains at Monte Catria for a stunning view of the central Italian countryside to the west and the blue-green waters of the Adriatic to the east. Descending, we arrive at the seaside Roman town of Senigallia, characterized by narrow winding alleyways and the well-preserved gothic fortress of Rocca Roveresca. Our accommodations are at a beautifully restored 19th-century country house turned agriturismo. We'll enjoy a farm-to-table dinner on the terrace amid sweeping views of the Marche countryside.

Overnight: Casa Vacanze La Meriggia

Meals: Breakfast, Lunch and Dinner

Today's paddling route takes along the spectacular coastline of what is known as the Conero Riviera past the iconic spires, the Due Sorelle (Two Sisters). A crystal-clear blue-green Adriatic contrasts with dramatic cliffs of white limestone and deep green woods. Hidden beaches beckon swimmers, and the tiny fishing village of Portonovo is fronted by one of the most beautiful beaches in Italy, and restaurants serve a dish of locally harvested mussels. This evening, we'll have dinner at a special local restaurant in the heart of Senigallia. 

Overnight: Casa Vacanze La Meriggia

Meals: Breakfast, Lunch and Dinner

A short drive takes us to Urbino, a UNESCO Heritage Site and a masterpiece of Renaissance design and craftsmanship set in the rolling Marche countryside. We'll wander the narrow streets of city and visit the Palazzo Ducale gallery to see paintings by Urbino's native son Raphael. Returning to the coast, there will be time for a late afternoon paddle before a classic Marche Brodetto fish stew for dinner.

Overnight: Casa Vacanze La Meriggia

Meals: Breakfast, Lunch and Dinner

 Our final day of Adriatic kayaking takes us to a unique landscape of cliffs and beaches known for both biodiversity and historical significance. In Parco Naturale Monte San Bartolo, long stretches of sandy beach are accessible only by water and protected by offshore breakwaters, producing a sublime paddling and swimming experience. This evening, we celebrate the completion of our coast-to-coast kayaking journey with a festive dinner in a tiny walled medieval hilltop town in Le Marche.

Overnight: Casa Vacanze La Meriggia

Meals: Breakfast, Lunch and Dinner

After breakfast, transfers to either the city of Ancona Airport (AOI) or train station, where 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

Tofino Expeditions was the highest rated sea kayaking adventure travel company in a National Geographic Adventure survey of international outfitters based on:

• Quality of Service
• Education
• Sustainability
• Spirit of Adventure