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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 kayaking and walking trip across the heart of Italy that links due mari, two seas, the Adriatic and the Mediterranean (technically the Tyrrhenian). Kayak the clear waters of the Adriatic coast of Marche, paddle Lago Trasimeno in Umbria, the largest lake in central Italy and explore the Tuscan coast at Maremma. Journey across the heart of Italy through an iconic landscape that resonates with history and is at the heart of the country's vibrant culture.
Clear Adriatic Waters at Conero Near Ancona, Marche

Across the Cradle of the Renaissance

Along the way you’ll tour Siena and Assisi as well as kayak an expansive lake 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

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.
Val d'Orcia, Tuscany


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 Marche. Surrounded by rolling hills of Marche the agriturismo produces organic vegetables, olive oil and fine wine and boasts kitchen that makes true farm to table cuisine. You’ll meet your guides on the terrace 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, Portonovo and Ancona

After a farmhouse breakfast we’ll set off through rolling hills towards Monte Conero and wind our way down through a thickly wooded slope to Portonovo and the warm waters of the Adriatic for our first day paddling on the "Conero Riviera". At the beachfront we will get fitted with gear and kayaks before setting off south 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. We’ll stop for a coffee in the village of Sirolo, a Greek colony in ancient times, 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

We’ll start our second day of paddling again at Portonovo, this time heading north along coastline of Monte Conero towards Ancona. Passing a sweeping stretch of beach and rock outcrops we’ll come to the start of the over four hundred Grotte di Ancona. Carved into the cliff face the Grottini are small caves once used by fishermen but are now a unique community of family owned boathouses and beach cottages. Like individual shadowbox tableaus each one is an expression of the family that owns it. Arriving back at Portonovo there should be time to enjoy a cold glass of Verdicchio before returning to the agriturismo. 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, Assisi and Lago Trasimeno

Departing Marche we wind our way through the spectacular scenery of the Apennine Mountains and enter Umbria. We’ll stop in Assisi for a private tour highlighting the remarkable history, architecture and Roman ruins of this UNESCO World Heritage Site that is famously the birthplace of St. Francis. After continuing westward to our agriturismo set in an olive grove near the shores of Lago Trasimeno there will be time for paddle to Islola Polvese before another memorable farm-to-table dinner.
Overnight: Agriturismo Le Terre di Isa
Meals: Breakfast, Lunch & Dinner
Day 5

Kayaking Lago Trasimeno

Today we explore Lago Trasimeno by kayak visiting lakefront villages and observing the bird life that is evidence of the Lake’s role as a stopover on migratory flyway from Africa. Along the shore there are ancient olive groves fringed with hedges of rosemary and vineyards dot the hillside. Castles, fortresses, monasteries and churches some dating back to the middle ages attest to the long rich history of this region. This evening we’ll enjoy one of the lake’s famous sunsets before 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

Montepulciano, Val d'Orcia, Pienza and Bagno Vignoni

Setting off early by van we'll climb through vineyard adorned hills to Montepulciano, our first stop in Tuscany, to visit winery cellars that are housed in caves original carved by the ancient Etruscans and sample the famous Vino Nobile di Montepulciano. For lunch we'll stop in picture-perfect Pienza, gateway to Val d'Orcia.  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.  To stretch our legs after lunch we'll do a gentle Tuscan hill walk before wrapping up the day at Bagno Vignoni, a hot springs resort popular back to Roman times where we'll stay in an elegant guest house.
Overnight: La Locanda del Loggiato
Meals: Breakfast, Lunch & Dinner
Day 7

Tuscany – Siena and Maremma

Packing up we’ll depart for the one hour drive to Siena, yet another UNESCO Site, where we’ll explore the town’s historic center, have a mid-morning coffee on the Piazza del Campo, site of the world famous Palio horse race, and have lunch at a classic Sienese Trattoria. Afterward we’ll drive southwest through the Tuscan countryside to the region of Maremma and the Tyrrhenian Sea. Our destination is an agriturismo located inside the Parco Naturale della Maremma. After settling in we’ll head out for our first paddle on the left coast of Italy on the shore of the Parco Naturale before returning for a memorable home-cooked meal of cucina Tipica Maremma in the farm’s excellent dining room.
Overnight: Agriturismo Fusini
Meals: Breakfast, Lunch & Dinner
Day 8

Kayaking the Tyrrhenian Sea - Monte Argentario

We’ll launch our kayaks near the harbor of picturesque Porto Sant'Ercole and dip our paddles into the clear waters of the Tyrrhenian 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 explore sea caves and 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 then go for celebratory gelato in the village of Orbetello that was long ago an Etruscan settlement.  This evening we’ll have our farewell dinner in Porto Sant'Ercole and there will be time to wander the town before we dine in a charming seafood restaurant overlooking the harbor.  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 Fusini
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 the Leonardo Express non-stop train service to Roma Centrale. Arrivederci!
Overnight: N/A
Meals: Breakfast


Agriturismo Poggio Agli ulivi

Agriturismo Le Terre di Isa

La Locanda del Loggiato

Agriturismo Fusini


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
Sold Out
6/20/2018 - 6/28/2018
6/20/2018 6/28/2018 9 days
09/02/2018 - 09/10/2018
09/02/2018 09/10/2018 9 days
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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