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8 Days

Even the best tours occasionally need updating, so during 2016 we’ll be working on our Tuscany & CinqueTerre tour to make it even more fun! Look for it to be back in 2017…

Explore two of our favorite areas on the Italian peninsula and enjoy the best Italy has to offer in scenery, culture, food and wine. On nearly every day you’ll have options for easy walks or more challenging adventures.
The CinqueTerre – five stunning towns perched on seaside cliffs overlooking the sparkling Mediterranean Sea. Breathtaking vistas await you around every bend in the trail as it winds through the vineyards and olive groves of the most picturesque part of the Italian Riviera. We’ll experience the unique culture that has made this coastline one of our favorite places to visit. Felicita’s cooking class, Gian Luigi’s wine tasting, Vittorio’s olives and cheese, and many other local characters will make you feel like you’ve come home. Monterosso, Vernazza, Corneglia, Riomaggiore, Levanto, Bonassola, Volastra… Then on to Tuscany, truly the heart of great Italian wine and cuisine. Tuscany’s warm beauty will seep into your heart and soul. Stroll through ancient walled towns, enjoy a picnic beside an olive grove while drinking in the magnificent Tuscan scenery or get lost on the cobblestone streets and squares of ancient Siena.
Each year we discover some new forgotten corners of Tuscany…we’re excited to take you to them!

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Day 1
Monterosso al Mare

You should plan to arrive in the picturesque seaside town of Monterosso al Mare on the beautiful Italian Riviera by midday at the latest. This evening you'll have a chance to relax and meet the others at the "get-acquainted" party and dinner. (When you book your tour, your guides can advise you on how to transfer from your arrival airport to the hotel in Monterosso.)
After checking in to the hotel, the rest of the afternoon is free to explore and check out the local shops, or maybe visit the beach and take a dip in the beautiful blue Mediterranean.
This evening we will meet in the hotel lobby for an orientation meeting over a bottle of the excellent local white wine. Afterwards we'll go to one of our favorite restaurants for a get-to-know-each-other dinner. Ligurian cooking is famous for several things; fresh seafood, pesto (Italy's best basil grows here), veal and liberal amounts of olive oil and garlic. Meals are often washed down with a glass of the light, crisp red wine produced on the slopes overlooking the town. All the great food and wine combined with a little jet lag will insure that you sleep well tonight!

Day 2
Levanto and the Punta Mesco

After breakfast, we meet at midmorning for our first walk. We'll start our adventure today at the seaside town of Levanto. The coastal path that connects Levanto and Monterosso is unique in that it winds through a national park and slowly gains elevation to provide excellent views of the cobalt blue Mediterranean. This forested route will offer a glimpse of what the landscape probably looked like before olive and grape cultivation began to dominate the scenery. A small group of ruins from an ancient lookout is a perfect venue for a short midday rest and photo stop. Continuing on we arrive this afternoon at our home-base town of Monterosso.
Tonight we will have a wine tasting that will feature several of the area's excellent but little-known vintages. The rest of the evening is free to explore and decide where to have dinner. With the many fine restaurants to choose from, this may prove to be a difficult decision! After dinner, the evening is free to wander the town, check out the local shops and perhaps find a nice quiet outdoor cafe to relax over a glass of cappuccino and talk over the days adventures.

Day 3
Sentiero Azzurro, Alta Via

Today we explore the renowned region south of Monterosso known collectively as the Cinque Terre. We will use the ancient and famous walkways of the area including the "Sentiero Azzurro" or "Blue Trail", so named for its stunning views of the blue Mediterranean. We will also often find ourselves on one of the many "Alta Via" or "High Ways" that wind above the towns and provide access to the many small farmsteads and towns in the higher elevations. These spectacular coastal walking routes will take us through vineyards, olive groves and along hillsides and cliffs with breath-taking views of picturesque villages perched on the edge of the sea. This seaside Mediterranean "maquis" climate is home to many unique plants, trees, and flowers.
At midday, we will enjoy a picnic of local delicacies while relaxing and taking in the view. At many of the towns we pass through, the local train station is available for anyone who wants to linger in the town and use the train to return to Monterosso. In the late afternoon, when we complete our walks, a short train ride will take us back to our base in Monterosso.

Day 4
Go Get Lost Day

Today it’s all about freedom, exploration, and getting lost on your own! Your guides will offer some popular options for the day’s activities and you can choose to do as little or as much as you want. You could opt to take the ferry to the picturesque seaside town of Portovenere and enjoy the stunning cliffside views enroute. Or perhaps a day lounging on the beach in Monterosso or Levanto would provide the relaxation you need. Some of the other Cinque Terre villages such as Riomaggiore and Vernazza are easily explored by train. Shopping, dining, and just hanging out are wonderful in these breathtaking locales! You can take the train in the other direction and visit the gorgeous and fashionable seaside town of Portofino, where the rich and famous come to get away from it all. Just a few minutes from Portofino, the town of Santa Margherita provides some excellent shopping and dining opportunities, too. If you feel like you need another day of hiking, the guides can point out a couple of spectacular coastal trails in the area. For the more adventurous, a great way to spend the day is paddling a sea kayak along the coast to the town of Vernazza. Hidden bays, water filled grottoes, and small rocky islands abound alongside huge cliffs plummeting into the clear blue water. Be sure to have lunch at a sidewalk café in Vernazza before returning to Monterosso. For those of you certified to scuba dive, the entire coastline here is a National Underwater Park, and several local dive operators will take you on an exploration of the underwater wonders of the Mediterranean.
Whatever you choose to do today, be sure to take plenty of digital photos to share with the gang tonight!
This evening it's back-to-school as we gather in a local kitchen for a cooking lesson. We'll learn how to prepare some of the favorite family recipes of the area including authentic Ligurian pesto. Afterwards we will enjoy an incredible dinner of the dishes we helped create! An after-dinner stroll down to the bocce court to watch the locals compete (amid much arm-waving and arguing) will cap off another perfect day in Italia.

 Day 5
Tuscany, Lucca, Siena

After breakfast, we board our private coach for our journey south to Siena. During our drive, the beautiful scenery of the Alpi Apuane mountains will give way to classic Tuscan countryside; rolling hills covered with vineyards and dotted with castles and villas.
En-route, we plan to stop at Lucca, one of Tuscany's great historical cities. From the Roman Times, through the Dark Ages, the Renaissance, and the Napoleonic Era, Lucca has managed to maintain its power, wealth and independence (at least it avoided being destroyed in the many wars which swept up and down the Italian peninsula over the centuries). The result is a wonderfully preserved and intact town completely encased in its famous walls. The old ramparts and fortifications constructed in 1500 are now full of lawns and trees and are crowned by one of Tuscany's most famous walkways, the Passeggiata delle Mura, which runs the entire 4 km length of the wall. Today, we not only enjoy wonderful views of the grounds outside the walls, but we also see Lucca from every angle as we stroll along this most interesting path. Here you'll have the opportunity for a casual lunch stop at a local sidewalk café.

After our midday stop, we'll resume our scenic southward ride to Italy's most enchanting medieval city, Siena, our base for the remainder of our stay.
With and endless supply of winding cobblestone streets and squares, soaring medieval towers and one of the loveliest squares in all of Italy, Siena is arguably the most beautiful city in all of Tuscany. This afternoon a local guide will lead us on a fascinating walk through some of the 17 contrade (neighborhoods) of Siena while explaining the rich history and magic of this ancient city. We will also visit one of the neighborhood museums, (every contrada has one), to learn the history of the spectacular Palio horserace, held every summer since 1310. The “Days of the Palio” is the religious/cultural/political event that truly defines Sienese life. To understand the Palio is to understand Siena.

Afterwards you’re free to explore Siena to choose your ristorante for the evening meal. We spend so much time in Siena we consider it our second home, so we can certainly take you on a nice stroll and point out our favorite eateries. Sienese cuisine reflects the best of classical Tuscan dishes. Robust and flavorful, a wide variety of pastas, meats and cheeses are present in a staggering variety of dishes. Experiment and enjoy!

Day 6
Castelvecchio, Voltrona, San Gimignano

Today we go North from Siena to explore the hidden ruins of Castelvecchioand then visit the fattoria (farm) of Sebastiano and Malcolm Leanza. Our path takes us through field and wood to the mysterious and overgrown remains of an 11th century ruined castle hidden in the forested hills. Formerly an outpost for the city of San Gimignano to guard against raiding neighbors, it was abandoned during the dark ages as the black plague swept Europe and its population was decimated. In fact, Castelvecchio was blamed for starting the plague, and was shunned by the local population for centuries as a haunted city. These medieval ruins are definitely "off the beaten path!"
After poking through the ruins of the village, we continue on our walk to Fattoria Voltrona, where, after a short tour, the Leanza family will have a sumptuous Tuscan feast prepared for us! Sebastiano and Malcolm's farm covers 100 rolling acres of olive groves, vineyards, fields and forest. The farm's vineyards produce delicate white Vernaccia wine, a local specialty, along with a robust Chianti. Olive oil, jams, honey and sunflower seeds are among it's other products, and will figure prominently in our meal. The rule at Voltrona is you eat as much as you want, and then a little more!
Later this afternoon we'll travel through the splendid Tuscan countryside to visit the wonderfully bizarre town of San Gimignano. The high walls and narrow streets of this imposing fortress are typical of Tuscan hill towns, but the 14 medieval towers that dominate San Gimignano's skyline set it apart from all the rest. Here we will have the rest of the afternoon to "get lost" in the maze of streets, shops, and cafes. For the not-so-faint-of-heart, a tour of the fascinating (and gruesome) Museum of Medieval Justice will provide an interesting yet terrifying glimpse of the past.
We have the evening free to discover some of Siena's wonderful restaurants for dinner. As always, your tour guides will be heading for their favorite dining establishments, everyone is always welcome to join them! Late-night people-watching over a cappuccino in Siena's romantic Piazza del Campo caps another perfect day in Italia.

Day 7
Pienza, Monticchiello, Farewell Dinner

After breakfast, we meet our coach for an early morning drive through the splendid countryside south of Siena to the compact Renaissance town of Pienza. Originally named Corsignano, Pienza had the good fortune to be the hometown of Pope Pius II in the 15th century. Pius renamed the town and proceeded with a grandiose rebuilding scheme to transform the humble village into his ideal Renaissance city. Unfortunately Pius died before his plans were completed, but enough magnificent buildings were erected to give Pienza a place in history.
Among Italians, though, Pienza is most famous for producing some of the best hard cheeses in Italy, called pecorino. An abundance of winding cobblestone streets, a picturesque square and numerous cheese shops makes Pienza an ideal place to explore before our days walk begins.
The countryside between Pienza and Monticchiello will fulfill anyone's expectation of classic Tuscan countryside. Rolling hills, cypress-lined lanes, vineyards and views of medieval walled cities provide a constant visual treat as we stroll. At midday we’ll stop for a break, and your guides will host a trailside wine, cheese, and honey tasting pairing the incredible Nobile wines of Montepulciano, the world famous pecorino cheeses of Pienza, and the luscious farm honeys from the area. This should put us in the proper mood for this afternoons visit to the charming little village of Monticchiello. Perched high on a hill and surrounded by tremendous panoramic views, Monticchiello, a warren of cobblestone alleys, handsome palazzi, vine-covered walls and unique shops. The most important feature, (and the base of the local economy), is the famous wine Vino Nobile di Montepulciano produced on the slopes of the surrounding hills. Prized for over a thousand years and considered one of the great vintages of Italy, Nobile can be tasted in one of the small wineshops found in the village.
As this is our final evening in magical Siena, tonight we have an incredible farewell dinner planned at one of our favorite local restaurants. Adventures and misadventures from the previous week are re-lived and laughed about, everyone and everything is toasted, addresses are copied and goodbyes are exchanged with all your new lifelong friends that you "Got Lost" in Italy with!

Day 8
Arrivederci Siena

After breakfast, your Lost in Italy tour comes to a close. If you plan to depart today, your tour leader can help with any arrangements you need for a transfer to the airport or with any other travel plans you may have.

What´s Included

  • 7 nights, Double Occupancy Accommodations at Listed Hotels or Similar (All Hotels with Private Bathrooms)
  • Meals as Specified, 7 Breakfasts, 2 Lunches, 2 Trailside Picnics, 3 Dinners, 4 Wine Tastings
  • Italian Family Style Farm Lunch at Fattoria Voltrona
  • Picnic Lunch in Volastra featuring local Ligurian specialties
  • Welcome Dinner in Monterosso al Mare
  • Group Dinner in Monterosso al Mare
  • Farewell Dinner in Siena
  • Levanto-Punta Mesco Park Walk
  • Sentiero Azzurro-Alta Via Walk
  • Bonassola Walk
  • Pienza-Monticchiello Walk
  • Voltrona-Castelvecchio Walk
  • Visit to Lucca, Passegiatta della Mura Walk
  • Visit to Medieval Town of San Gimignano
  • Visits to Lots of Unique Villages; Manarola, Corneglia, Levanto, Volastra, San Donato, Bonassola, etc.
  • Cooking Class in Monterosso al Mare featuring traditional Ligurian dishes
  • Wine Tasting in Monterosso al Mare Featuring Ligurian Vintages
  • Sommelier Wine Tasting in Chianti Countryside
  • Guide’s Wine Tasting in Cinque Terre
  • Trailside Wine, Cheese, Honey Tasting near Montechiello
  • Entrance to a Siena Contrade Museum
  • Transportation once the tour has begun. The motorcoaches we use are modern, air-conditioned and roomy. Our tour groups are usually between 8-18 people which means we'll have plenty of room to get comfortable
  • All train, ferry and taxi transfers as specified in itinerary
  • Sightseeing and entrance fees as specified in itinerary
  • Completely escorted by a Lost in Italy Tour Leader with local guides at specified sites throughout itinerary
  • Lost in Italy trail-friendly wine glass

What´s not Included

  • Airfare package
  • Departure taxes
  • Arrival and departure transfers, tour begins at the hotel in Monterosso in the afternoon of Day 1, and the tour ends at the hotel in Siena on the morning of Day 8
  • Gratuities for meals, porterage, local guides, coach drivers, etc.
  • Any costs associated with options on Go Get Lost Day.
  • Visa fees, if applicable
  • Meals not specified in itinerary
  • Beverages at meals unless specified in itinerary
  • Trip Cancellation/Interruption and Medical Insurance (strongly recommended), call for details
  • Single supplement charge
  • Items of a personal nature; phone calls, laundry, etc.

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