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Home Italy Kayaking Tours Kayaking Tuscany Umbria and Marche Two Seas Tour

Kayaking Tuscany Umbria and Marche Two Seas Tour

July - September
9 days
Ancona (AOI)


Due Mari - Two Seas

Join us for a new kayaking and walking trip across the heart of Italy that links due mari, two seas, the Adriatic and the Mediterranean. Kayak the clear waters on the Adriatic coast of Marche at Ancona. Explore the cradle of the Renaissance, Umbria and Tuscany, and paddle in the warm Mediterranean Sea at Maremma.
Clear Adriatic Waters at Conero Near Ancona, Marche

Across the Cradle of the Renaissance

Along the way you’ll tour iconic Siena and Assisi and kayak lakes backed by a splendidly pastoral countryside, medieval fortresses and Roman ruins. Enjoying an insider’s perspective of local life by staying in agriturismos, you’ll experience a culture that is quintessentially Italian while sampling a cuisine defined by spectacular produce, savory black truffles, fine cured meats, rare formaggi (cheeses) and famous regional wines.
Tuscan Countryside Shrouded in Morning Fog

An Old World Paddling Adventure

Paddling in both the Adriatic and Mediterranean Seas as well as Lago Trasimeno, the largest lake in central Italy, kayaks provide a unique perspective to a journey that spans three provinces and includes three UNESCO World Heritage sites. This trip tours the historical heart of Italy in a way no one else does, visiting splendid villages, ancient walled towns and kayaking through some of the most beautiful scenery in the world.


Day 1

Arrival at Ancona

Located only 20 minutes away from Ancona airport (AOI) the Agriturismo Poggio Agli ulivi is our introduction to the pastoral beauty of central Italy. Surrounded by the rolling hills of Marche the agriturismo produces organic vegetables and olive oil and has kitchen that makes true farm to table cuisine. You’ll meet your guides in the courtyard for a glass of wine and brief orientation before adjourning to the dining room for the first in a series of memorable meals on this trip.
Overnight: Agriturismo Poggio Agli ulivi
Meals: Dinner
Day 2

Kayaking the Adriatic Sea - Monte Conero, Numana and Ancona

After a farmhouse breakfast we’ll set off towards Monte Conero, the highest promontory on the Adriatic coast of Italy, and descend to the warm waters of the Adriatic for our first day paddling. At the beachfront town of Numana we will get fitted with gear and kayaks before setting off along a coastline of dramatic cliffs, picturesque rock formations and inviting beaches. After rounding the headland marked by a pair of rock spires known as the “Two Sisters” we’ll have a beach picnic of local specialties and a swim before paddling back. Later we’ll stop for a coffee in the village of Sirolo, in ancient times a Greek colony, and then head back to the Agriturismo. This evening’s dinner will be in Ancona and there will be time to wander the city’s historic center before dining a popular seafood restaurant.
Overnight: Agriturismo Poggio Agli ulivi
Meals: Breakfast, Lunch & Dinner
Day 3

Kayaking the Grotte di Ancona

Our second day of paddling explores the coastline north of Monte Conero. Launching at the village of Portonovo we pass a sweeping stretch of beach and rock outcrops to the Grotte di Ancona, unique waterfront structures cut into the cliff face that were once used by fishermen but are now boathouses and vacation homes. On the way to dinner in the seaside town of Senigallia we’ll stop at beautiful the hilltop village of Mondavio for a visit to the 15th-century castle of Rocca Roveresca.
Overnight: Agriturismo Poggio Agli uliv
Meals: Breakfast, Lunch & Dinner
Day 4

The Apennines and Assisi, Umbria

Departing Marche we wind our way though the spectacular scenery of the Apennine Mountians and enter Umbria. We’ll stop for an extended visit to the town of Assisi, a UNESCO World Heritage Site and famously the birthplace of St. Francis. Lunch will be followed by a private tour highlighting the remarkable history, architecture and Roman ruins of this ancient community. Journeying westward in the late afternoon we’ll arrive at an agriturismo set in an olive grove near the shores of Lago Trasimeno. There will be time to relax before another memorable farm-to-table dinner.
Overnight: Agriturismo Le Terre di Isa
Meals: Breakfast, Lunch & Dinner
Day 5

Kayaking Lago Trasimeno – Isola Polvese

Launching at the village of San Feliciano we paddle along the shoreline of the largest lake in central Italy observing the bird life that is evidence of the Lake’s role as a stopover on migratory flyway from Africa. Our eventual destination is the medieval monastery and castle on Islola Polvese, the largest of the Lake Trasimeno’s three islands. Once ashore we’ll wander ancient olive groves fringed with hedges of rosemary and enjoy a picnic lunch in a sun dappled clearing. This evening we’ll go for a dinner of freshwater fish the specialty of a restaurant in the town of Passignano.
Overnight: Agriturismo Le Terre di Isa
Meals: Breakfast, Lunch & Dinner
Day 6

Kayaking Lago Trasimeno Isola Maggiore – Val d'Orcia and Pienza

In the morning a short van ride takes us to a put-in point on the north shore of Lago Trasimeno for a paddle out to Isola Maggiore. After visiting the island’s single tiny village that is home to only 17 people we’ll paddle around to Castello Guglielmini, a structure that is impressive even within the context of the many castles surrounding Lago Trasimeno. For lunch we’ll visit the town of Castiglione del Lago before setting of by van through vineyard adorned hills to Val d'Orcia and our first foray in Tuscany. A UNESCO World Heritage Site, Val d'Orcia has some of the most iconic scenery on the planet and was celebrated by painters of the Renaissance. We’ll explore the hilltop town of Pienza, a UNESCO World Heritage Site in its own right and sample the famous Vino Nobile di Montepulciano at a vineyard whose cellars are housed in caves carved by the Etruscans.
Overnight: Agriturismo Le Terre di Isa
Meals: Breakfast, Lunch & Dinner
Day 7

Tuscany – Siena and Maremma

Packing up we’ll depart by van bound for Siena, yet another UNESCO Site, where we’ll spend the day exploring the town’s historic center including Piazza del Campo, site of the world famous Palio horse race, and have lunch at a classic Sienese Trattoria. Later in the afternoon we’ll drive southwest through the Tuscan countryside to the region of Maremma and the Tyrrhenian Sea. Our destination is an agriturismo on the peninsula of Monte Argentario. After settling in we’ll enjoy a meal in the farm’s excellent dining room.
Overnight: Agriturismo Monte Argentario
Meals: Breakfast, Lunch & Dinner
Day 8

Kayaking the Mediterranean Sea - Monte Argentario

We’ll launch our kayak at the harbor of picturesque Porto Sant'Ercole and dip our paddles into the clear waters of the Mediterranean Sea. Setting out along the coast of the Monte Argentario we’ll pass the imposing walls of Fortress Filippo, one of three fortresses built in the 16th century to guard the harbor from pirates. Gliding through crystalline blue water along the peninsula’s steep cliffs we’ll have a view of the southern most islands of the Tuscan Archipelago. After a swim and a beach picnic we’ll return to Porto Sant'Ercole and after a celebratory gelato there will be time to wander the town. This evening we’ll have our farewell dinner in the village of Orbetello that was long ago an Etruscan settlement, parts of the city walls date back to the 5th Century BC. Over a leisurely Italian meal we’ll have time to recall some of the many sights and experiences of our journey across the heart of Italy between the Due Mari.
Overnight: Agriturismo Monte Argentario
Meals: Breakfast, Lunch & Dinner
Day 9

Monte Argentario to Rome Fiumicino Airport

After breakfast we’ll board our van for the drive to Rome Fiumicino airport (FCO) with an expected arrival late morning (11am to 12 noon). The airport offers easy connections to flights home and Roma Centrale. Arrivederci!
Overnight: N/A
Meals: Breakfast


Agriturismo Poggio Agli ulivi

Agriturismo Le Terre di Isa

Agriturismo Monte Argentario


At this time we do not offer any extensions for this trip but please feel free to call us about added travel options at 1-800-677-0877. We have spent a lot of time in and around the destinations we offer and are more than happy to share our experience.

Dates & Availability

Trip Length
07/05/2017 - 07/13/2017
07/05/2017 07/13/2017 9 days
Sold Out
9/2/2017 - 9/10/2017
9/2/2017 9/10/2017 9 days
4 Places
NOTE: Trips showing as 'Available' have at least 4 places open. All prices are $USD unless otherwise stated.

What Is Included

  • All accommodations as specified in Itinerary
  • All meals as specified in Itinerary
  • Ground transportation and attraction entry fees
  • Expedition sea kayaks and equipment including PFDs
  • Group safety equipment including medical kit, radios, and cell phones
  • Luggage transfers

What Is Not Included

  • Airfares
  • Meals other than specified in the trip itinerary
  • Alcoholic beverages
  • Items of a personal nature
  • Single supplement if applicable ($850 US)
  • Tipping of guides
  • Insurance of any kind (we strongly suggest that you purchase travel insurance that covers medical and evacuation as well as cancellations for medical reasons)
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Total Deposit: $75000 USD
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