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The names conjure romance:  Siena with its Palio and colorful medieval pennants. Monterrano, the Abandoned City, built by the Etruscans in the 8th century B.C.  All are surrounded by some of Italy’s most beautiful countryside bathed in light that painters try to capture and that you must see for yourself.  In splendid contrast, our time on the coast finds us walking along terraced hillsides, through fragrant olive groves and vineyards where the renowned Sciacchetra wines are made.  We relax along sunny beaches in secluded coves of stunning blue Mediterranean waters.  This trip offers you Italy’s best, from top to bottom!

DEPOSIT : To reserve your space, a $400 deposit per person is required.  Final payment is due 60 days prior to the trip departure date.  If applying within 60 days of the trip departure, full payment is required.

Sep 21-30, 2020


$3599 Double Occupancy

$3899 Single


Note: Includes 11 days/10 nights, ground transportation, most meals, all entrance fees & tours, full-time naturalist, guide & escort.  

Welcome to the heart of Italy!  Stroll with us through Italy’s sun-dappled countryside.  Share special times with local Italian farmers as they prepare for the grape harvest.  Be treated to their special wines, pressed olive oil, and fresh-baked breads.  Hike through some of Europe’s best vineyards, the vines bursting with grapes that will be used to make the famed Chianti and Brunello wines.  Visit such towns as Siena, Montepulciano, and Pienza.  Spend time walking through centuries-old villages, visit Etruscan tombs, and walk beneath Roman aqueducts.  Siena’s history will delight you, Rome’s Coliseum is one of the world’s marvels, and of course you’ll want to make sure you try some of the world’s best pastas.  You’ll be treated to a feast of food, wine, beautiful countryside, and ancient history hard to imagine.


We’ll also visit the quiet and remote fishing villages of the Cinque Terre, offering a variety of dramatic walks along cliffs overlooking the coastline of the Mediterranean.  “The Five Lands” of Monterosso, Vernazza, Vorniglia, Manarola, and Riomaggiore bring to life the ancient architecture of Italy’s earlier inhabitants.  Here where the mountains dive down into the sea, we’ll explore quaint villages, stroll through fragrant olive groves and terraced vineyards and relax along sunny beaches and in secluded coves.

This itinerary may be changed at the discretion of the trip leader. (B = Breakfast included,    L = Lunch included, D = Dinner included)

Day 1: Rome-San Quirico d’Orcia. Arrival day

As first day, group assemble in Rome airport or in your hotel in Rome. Leaving Rome we reach San Quirico d’Orcia in time for a brief exploration of this medieval town. Accommodation in hotel and dinner. L,D.


 Day 2: San Quirico-Bagno Vignoni

A uniquely different day spent crossing the Crete Senesi – one of the most amazing landscapes in Italy. The near desert region has a gentle bleakness with occasional houses and lines of Cypresses.  Stop for lunch in the farmhouse of Poggio Grande with olive oil, cheese and wine tasting.  Continue to Vignoni Alto until we reach the Unesco Heritage village of Bagno Vignoni.  A marvellous day to remember. B,L,D

14km, 300m ascent, 5h.


Day 3: San Quirico-Pienza

Departing San Quirico, with its twisted medieval alleyways, we follow gentle tracks through the vineyards by the town and across the renaissance ‘new town’ of Pienza.  B,L,D

Packed or picnic lunch. 12km, 150m ascent, 4h.


Day 4: Siena

After breakfast, a pleasant drive will take us to Sienna, where you can wander around the narrow streets and the wonderful monuments of one of the most beautiful city of the world, UNESCO heritage. B,D.


Day 5: Montalcino – Villa a Tolli – St. Antimo Abbey

Leaving San Quirico, after a short ride we reach Montalcino, home of the famous Brunello wine. From here, following ancient trails, we reach the panoramic area of the La Magia. We’ll stop for a lunch banquet in the small hamlet of Villa a Tolli. It’s in this area that the renowned Brunello wine is made. Then we follow an ancient route through typical wine country on our way to the abbey, one of the best-preserved medieval complexes.  B,L,D

12km, 200m ascent.


DAY 6 – San Quirico – Cinque Terre

Today we travel to Cinque Terre. Leaving San Quirico we will be surrounded by a warm countryside filled with fragrant olive groves, numerous vineyards, friendly locals and pastoral views you’ll long remember. After a stop in Cortona for a visit to the place of the famous “under the Tuscan sun”, we will continue our drive to reach the Ligurian coast.  Arrive in Cinque Terre by dinner time. B, D.



We start on foot from our hotel and head along an ancient pilgrim’s path towards Soviore.  We continue to Madonna di Reggio Sanctuary and stop for a picnic lunch.  In the early afternoon, we descend to Vernazza.  Depending on time, we’ll stop to enjoy a drink.  Return by train to Monterosso.  B,L,D.

11 km, 600 m ascent,4:30h


Day 8:  Levanto – Punta Mesco – Monterosso

A short ride on the train will take us to Levanto. From here, passing by a historic castle, we’ll walk along this beautiful and panoramic trail on the mountains over Levanto that follows an ancient way passing right on the edge of the cliff above the sea.  Savor panoramic views wherever you look. B,L,D.

8-12 Kms, 380m ascent.


Day 9: Monterosso- -Vernazza Soviore-Monterosso

Short train ride to Corniglia.  After a short visit of the village, we’ll start the walk to Volastra, climbing to the top of the hill above the village.  Once we reach Volastra we’ll have a light lunch before beginning our panoramic descent towards Manarola where we’ll ride the train back to Monterosso.  B,L,D.

10km, 420m ascent, 4:30 h


Day 10:  Departure day

After an early breakfast we drive to Pisa airport for our flights home or on to new destinations. B.





Visits to Montepulciano, Pienza and Montalcino

Visits to the Abbey di Sant’Antimo,

Visit to the famous Liguria Riviera

Cheese, Olive oil & Wine tasting

Walking through vineyards

Siena Visit



  • 5 nights in San Quirico d’Orcia, Hotel 3***.
  • 4 nights in Monterosso, Hotel 3***.



  • 9 continental morning breakfasts;
  • 7 packed or picnic lunches;
  • 1 light lunch in a wine cellar in Volastra (5 Terre) with wine tasting;
  • 9 dinners, wine & beverages included in hotels and restaurants
  • 1 Wine & cheese tasting in Tuscany.



  • Transportation in private van
  • All entrance fees and vat
  • Local trains in Cinque Terre
  • Professional Official Local Guide
  • Walking The World Guide
  • Duomo entrance ticket in Sienna
  • Great fun, companionship, unforgettable experiences


Beginning of Services:  Rome Fiumicino Airport, only one appointment for pick-up.

End of Services:  Pisa Galileo Galilei Airport, only one trip to suit most departures.

Transfer Times (approx): Rome to San Quirico d’Orcia:  3:00 hours.  San Quirico d”Orcia to Monterosso al Mare:  5:00 hours; Monterosso al Mare to Pisa: 1:45 hours

Trip Begins:                        Rome, Italy             

Trip Ends:                           Rome, Italy