1. Exceptional 4-Star Accommodations
  2. 15 Meals including 7 Breakfasts, 5 Lunches, and 3 Dinners
  3. 3 Wine Tastings, Cooking Class, Pizza Party
  4. Guided Tour of Siena, Excursions to the Chianti Region, San Gimignano, and Volterra
  5. Guided Tour of Pompeii and Excursion to Capri
  6. Excursion to Ravello, Montepertuso and Positano
  7. Most Gratuities Included

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8 Days

Explore the two vastly different regions of what many travelers consider to be the best Italy has to offer in scenery, culture, food and wine.

Classic Tuscany… birthplace of the Renaissance, home to some of the world’s best cuisine, wine, and postcard landscapes. We’ll explore this magical land from the cobblestone streets and romantic squares of the historic city of Siena to the countryside dotted with ancient castles, vineyard covered hillsides, and tiny walled towns that date to Roman times.

After Tuscany we walk into a completely different world of cuisine, culture and scenery as we journey to the Amalfi Coast, one of the most beautiful coastlines on the planet. You’ll explore tiny pastel villages perched precariously on impossibly steep hillsides that plunge into the blue water of the Mediterranean, discover new delights in the local food and wine scene, and wander the amazing city of Pompeii, preserved by a volcanic eruption and covered in ash for almost 2000 years.

True to our “get lost” philosophy, we’ll ease into the pulse of the Italian experience and find the real Italy.

You’ll be pampered with premier 4-Star accommodations, local guides to show you the secrets of the area, and a Go Get Lost tour leader to make it all run smoothly.

Tour Dates & Pricing

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Day 1 - Siena

Your Italian adventure starts in the afternoon today with a short meeting in the lobby of our hotel in the medieval city of Siena. (You'll be provided with detailed arrival and departure instructions to help you coordinate your flights and travel.) You'll meet your private guide and get to know your fellow travelers. Afterwards we'll have a private guided walking tour of Siena by one of its citizens, who will explain all of its amazing history and customs. When you combine the history of Siena with the current traditions of its inhabitants, you'll find that Siena is arguably one of the most fascinating, one of the most unique, and one of the most vibrant cultures in all of Europe! The Senese have kept alive the customs of their ancestors, and in fact live it every day. As you explore the city you'll marvel at the huge span of history represented in its architecture, from the Romans to the Renaissance to the Goths, Siena is a landscape of all the civilizations that have dominated here.

After our tour we'll head to one of our favorite local out-of-the-way ristorante for an excellent arrival dinner. Tuscan cuisine, like all Italian regions, reflects the best of the local area. Fresh pasta is prevalent, along with salami, prosciutto, chicken, beef, and pork, with nearly everything organic and free-range, which has always been the natural way for Italians. Of course you'll find some of the world's best olive oils here, along with tomatoes, peppers and melanzane that are bursting with flavor. And the cheeses of this region are legendary, with literally dozens of varieties running the gamut from fresh and creamy to aged and robust...truly an epicurean's heaven! Italian wines need no introduction...during your time in Italy with us you'll be introduced to some exquisite wines that can be found nowhere else, from marvelous honest farmhouse productions to wines from some of the top estates in the world, and everything in-between.

An after-dinner stroll through Siena's magnificent piazza Il Campo, will cap off your first day in Italia!

Day 2 - The Chianti Region

After breakfast today we depart on our private coach for a day of exploring the renowned Chianti region and its quaint villages. Famous for its scenic beauty and wine production, Chianti typifies the perfect balance of cultivated vineyards, forested hills, and quaint medieval towns. Our first stop is one of the most historic castles in all of Italy, Castello di Brolio. The original formula for Chianti Classico wine was developed here by the "Iron Baron" Bettino Ricasoli in 1872, and in fact the Ricasoli family still lives in part of the castle! Our friend and local sommelier will accompany us today to explain grape and olive cultivation and harvesting, all while strolling on a picturesque country lane and admiring the stunning Chianti views.

Eventually we’ll arrive at the Cantina of the Brolio Castle, where we’ll enjoy a tour of their winemaking facility. No wine tasting here, though, because we’ll save that for after the tour, when we visit the massive Brolio castle perched on top of the mountain! While you wander the grounds of the castle and take as many pictures as possible, the guides will be preparing a picnic of regional delicacies. You’ll enjoy your lunch while relaxing on the walls of the castle, overlooking the vineyards and forests of the surrounding countryside. To make our picnic even more elegant, our resident sommelier will host a wine tasting of some of the fantastic wines of Toscana.

You'll have the rest of the day free in Siena to explore and get lost.

Day 3 - Volterra and San Gimignano

After breakfast this morning we head north to one of the most ancient cities in Italy, Volterra. Perched on a lofty rock platform, Volterra is an imposing fortified hill city with a dramatic, dominating view of the rugged countryside below. Built by the Etruscan civilization that pre-dated the Romans, Volterra in fact claims a history that goes back at least 3000 years. In Etruscan times it was Velithri, one of the twelve great cities of the Etruscan Confederation, with a domain that reached from the seacoast to the mountains.
Volterra still retains much of its ancient flavor, and of particular interest are the many alabaster work shops where local artisans can often be seen carefully working the delicate translucent stone into vases and ornaments. Mined in the area since Etruscan times, Volterran alabaster has been prized by the nobility for nearly 3000 years. We'll have the opportunity to tour one of the shops and learn how the ancient art is still alive.
During your free time here you'll have the chance to tour the world famous Etruscan Museum with the largest collection of Etruscan artifacts in the world. After having spent the morning getting lost in Volterra, we'll depart and wander east to stop at one of our favorite local family farms to have a visit of their operation and a tasting, followed by lunch. The farm covers ample acres of olive groves, vineyards, fields and forest. The farm's vineyards produce delicate white Vernaccia wine, a local specialty, along with several styles of robust Chianti. They also produce one of our favorite Tuscan olive oils, which along with the other farm products will figure prominently in our meal. The rule at their kitchen is you eat as much as you want, and then a little more!

After lunch we'll have the afternoon free for exploring 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 you can "get lost" in the maze of streets, shops, and cafes. San Gimignano is rumored to have one of the best gelato shops in all of Italy...may be worth a visit? 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.

Day 4 - Pompeii and Sorrento

After an early breakfast this morning, we board our private motorcoach and head south toward the coast. The scenery changes throughout the morning as we leave Tuscany behind us. We’ll wind our way through the rolling hills of Umbria and then into the Lazio region, heart of the ancient Roman Empire. This is a great chance to relax and enjoy the scenery after our previous days' adventures. Lazio soon gives way to the sunny south of Italy as we enter the Campania region.

After a brief stop for lunch we arrive this afternoon at one of the most famous archaeological sites of the world: Pompeii. The best local tour guides in Pompeii will take you on a fascinating journey back to the Roman Empire when Pompeii and the volcano Vesuvius were one of the most beautiful resort areas in Italy. On August 23, 79 AD, the eruption of Vesuvius buried the city of 20,000 inhabitants and entombed their culture for nearly 2000 years. Here, like nowhere else in the world, it's possible to see how the people of ancient times lived their daily lives. To visit to these world-renowned ruins is to experience life as it once was, on the shores of the Bay of Naples, in the early Empire. First, we will visit the Theater to imagine comedies and tragedies that played out upon the stage. Next, it’s on to the ornate Thermal Baths, with their dressing rooms, baths, toilets and athletic fields. These early health clubs were truly ahead of their time. The streets of Pompeii were alive with purveyors of food, clothing and - slaves. We’ll visit wine cellars, restaurants and bars. We’ll compare prices and learn of rare vintage recipes as we imagine life in this bustling metropolis of old. We’ll admire the ancient barracks, domain of gladiators, and even the infamous red light district . . .

From Pompeii it's just a short but breathtaking drive to the beautiful seaside town of Sorrento, situated on the cliffs overlooking the Bay of Naples. Across the bay the lights of Naples illuminate the horizon while the enormous looming bulk of Vesuvius dominates the skyline.

This evening your guide will have a casual pre-dinner wine tasting party to introduce you to some of the excellent but little-known local vintages. Tonight you’re free for dinner, but the guide can lead you to one of their favorite local "off-the-beaten-path" trattorias for another excellent meal in Southern Italy! Be prepared for a totally different taste experience from Tuscany, as southern Italy has always been considered a separate country, both politically and gastronomically. Sorrentine cuisine reflects the best of classical Southern Italian dishes, and many of the most famous of these are at their peak here! The region is famous for fresh Mediterranean seafood prepared as only the Italians can, with local fish, prawns, octopus and seafood salad that is nothing short of amazing. Buffala mozzarella, red peppers, olives and lemons all figure prominently in regional dishes which are best washed down with the silky white Fiano wine. The rich volcanic soil of the region produces fruits and vegetables of incomparable flavor. The best hazelnuts, almonds, and walnuts are grown here and find their way into many local pasta dishes and desserts. The extravagant pastries, gelatos, and ices of Sicily are also much in evidence. The crowning achievement of local culinary talent, however, is pizza, which was perfected here, along with the use of the tomato that was refined to an art by the local chefs. Along with Fiano and Falanghina, be sure to try the crowning achievement of the local vintners: Taurasi, one of the best red wines in Italy, and Lacrima Christi, (Tears of Christ), one of the most famous red and white wines in Campania.

Day 5 - The Isle of Capri

This morning you'll join your tour leader for a ferry boat ride to the beautiful island of Capri for a full day's exploration of this “paradise”. Capri is one of the most picturesque and visited locations in south of Italy. Its unique beauties were celebrated in ancient times and later published for the world in Homer's works. Odysseus (known in Latin as Ulysses) sailed past the island, narrowly escaping the fate of those who hear the voices of the Sirens. Thus the island has a mythical charm as well as its natural treasures, through the writings and legends of Ancient Greece. Its breathtaking landscapes and beauty stretch from the rocky caves around the island to the edge of the horizon, and has been an inspiration to poets, lovers and travelers throughout the centuries.

Your guide and private coach will await to whisk you from Capri's port to the beautiful town of Anacapri, perched high along the slopes of the island's mountainous terrain. Your private guide will take you on a marvelous tour of the island, with the possibility to take a chairlift to the peak of Monte Solaro, with stunning panoramic views of the mainland! You'll feel like a native as you ride the tiny island bus down to Capri-town, where you'll have a tour of the neighborhoods and sites of this timeless village. You'll also have time on your own to Get Lost and explore. Keep a sharp eye out, as this place is definitely the haunt of the rich and famous, as it has been for over 2000 years! You can easily shop til you drop, with every major fashion house in Italy represented here, often with tiny little shops barely large enough for their goods. You can be sure to find the perfect cafe to have a cool glass of wine and people watch, or enjoy a breathtaking view of the Mediterranean.

Tonight we'll head up into the hills overlooking Sorrento to visit a family farm and learn how to make homemade pizza, Napolitano-style! You've not lived until you've tasted the world's best pizza, pulled steaming hot from wood-fired ovens! They're quite proud of all of the other products of their farm, and all will combine with plenty of wine to make for a memorable evening.

Day 6 - The Amalfi Coast

After breakfast today we embark on a fascinating journey to visit the iconic towns along the Costiera Amalfitana.. or Amalfi Coast. We have a full day of exploration planned, and we'll start by sitting back and relaxing in our private coach as we experience one of the world's most breathtakingly beautiful roads, the Amalfi Coast Drive. Hewn from the cliffs hundreds of feet above the blue Mediterranean, the road is an engineering wonder that winds along the coastline from Sorrento to Amalfi, cutting through numerous unique and picturesque towns and providing endless breathtaking panoramic views.. You’ll feel like you’re dreaming when you will be immersed in paradisical landscapes surrounded by mountains, seas, trees, flowers, perfumes and distinctive architecture of the place, as in a timeless painting that you’ll never forget.

During your journey today your guide will lead you on a fascinating tour of some of the most interesting gems of the coast. First you'll explore the jewel in the Amalfi crown, Ravello. The town has been a destination for artists, musicians, and writers, including the likes of Grieg, Boccaccio, Woolf, Mirò, Bernstein and others. Adjacent to the Ravello Duomo, is the Villa Rufolo, that dates back to the year 1200. During your visit to the villa, you will feel the thousand years of Arab cultural influence. The main building, which contains a chapel and a reception hall, is built on three levels which in the past hosted high ranking persons such as Pope Adrian IV and King Robert of Anjou. Perhaps the most iconic part of the villa is the famous terraced garden that overhangs the sea.
Not to be outdone, we'll enjoy getting lost in the beautiful but bizarre town of Positano, literally built on the side of the mountain! Positano is said to be the only town in the world organized on a vertical rather than horizontal plan! Pastel houses, hundreds of balconies and flower bedecked patios, and the golden dome of the town church make Positano a memorable sight. We’ll have some time to wander the through the lanes, (and stairs), and shops of Positano, ( a barefoot stroll in the surf with the multi-hued town of Positano towering over you is something you won’t soon forget) before we head back to Sorrento.

Tonight the bustling and vibrant nightlife of Sorrento's streets and squares invites you to find a cozy ristorante and laugh about the day's adventures with your friends over a bottle of the local vino. and a plate of pasta. Finish your day with a late night gelato and a romantic stroll through the squares and cobblestone streets of town.

Day 7 - Go Get Lost Day!

For today's lunch we'll have a pleasant walk through Sorrento to arrive at the kitchen of Chef Carmen. Here we’ll roll up our sleeves and let her teach us how to create and cook a traditional Italian menu. Of course afterwards we’ll get to enjoy the fruits of our labors, along with some excellent local wines!

The rest of the day it’s all about freedom, exploration, and getting lost on your own! You can choose to do as little or as much as you want. This would be a perfect opportunity to explore the town of Sorrento, which has several interesting historical sites, dozens of fascinating nooks and streets, and literally hundreds of shops and boutiques to "get lost" in! As it's the last day, it's the perfect time to shop for gifts for the folks back home. You'll find no shortage of jewelry stores, designer fashion boutiques, and shops featuring local produce and wines in Sorrento's world-class shopping district! A stroll through the neighborhoods, gardens, and streets of this lovely coastal town will be just the thing to experience real Italian life. Truly a charming locale to get lost!

Or you could stumble into the small fishing village of Marina Grande, tucked into a small cove under the shadow of Sorrento. Marina Grande is a time capsule worth exploring, with colorful fishing boats parked in the narrow streets, nets drying in the sun, and Italian grandmothers selling handmade lace provide a glimpse of a typical working fishing village.

Another option for your day’s exploration might be to take the local Circumetnea train and re-visit Pompeii or the less-visited Herculaneum. One could easily spend an entire day tramping through the streets and squares of these enormous archaeological ruins and still not see it all! On your own you can explore at your own pace, take the time to photograph the mysterious buildings and streets, and spend as much time as you want contemplating the timeless tragedy that is Pompeii and Herculaneum.

This evening you'll want to return to your hotel, where you can refresh, relax, and get ready for your special farewell dinner at one of our favorite Sorrento ristorante. Adventures, (and misadventures), from the trip are re-lived and laughed about, everyone and everything is toasted, addresses and e-mails are copied, and heartfelt goodbyes are exchanged with all your new lifelong friends that you "Got Lost" in Italy with.

Day 8 - Arrivederci Sorrento

Your Go Get Lost tour ends this morning after breakfast. You have several options...you could depart on a private transfer to spend a few days in the eternal city of Rome on our Wonders of Rome extension. Or you could make your way to nearby Naples airport for a flight onwards, or you could head to the local train station to continue your travels in Italy. Your group leader can assist you with whatever arrangements you may need.


Due to availability at the time of booking, hotels listed may change to similar hotels

Siena – 4 Star Hotel Athena With a perfect location just inside the walls of Siena’s old city, the Athena is in a quiet residential neighborhood only a short walk from the center of Siena and its famous piazza, Il Campo. Modern rooms are tastefully decorated with dark woods and muted colors. With furnishings by local artisans, colors that echo the tones of the Tuscan landscape and the many comforts available, you will feel completely at home at ease, surrounded by the warmth of a welcome you will always remember.

Sorrento – 4 Star Hotel Plaza The Plaza Hotel is an original location to celebrate right in the heart of Sorrento. Set on the Gulf of Naples, this modern hotel lies 4 minutes' walk from Sorrento Cathedral and 8 minutes' walk from the art-filled Museum Correale. You will be guided to the most beautiful attractions of the charming land: Capri, Ischia, the Amalfi Coast, Mount Vesuvius, Pompeii and Herculaneum; without neglecting, places where time seems to stand still!


Sorrento – 4 Star Hotel Antiche Mura In a central yet peaceful position with access from the Piazza Tasso, heart of Sorrento, rises an elegant “art nouveau” building. The hotel combines sophisticated and elegant traditional decor with comfort and innovative technologies to satisfy the most demanding customer. 52 beautiful rooms divide in double, triple, family and interconnecting rooms. Located in the center of Sorrento and in walking distance from public transport and all amenities.

What´s Included

  • 3 nights stay in Siena in 4-Star Hotel
  • 4 nights stay in Sorrento in 4-Star Hotel
  • 7 Breakfast, 5 Lunches, 3 Dinners, 3 Wine Tastings
  • Tour of Chianti vineyard and cellars
  • Guided tour of Siena
  • Full day excursion to Volterra and San Gimignano
  • 2 hours guided tour of Pompeii
  • Hands on cooking class in Sorrento
  • Pizza party at a Sorrento farm
  • Full day excursion to Capri as per itinerary
  • Full day excursion to Ravello, Montepertuso and Positano as per itinerary
  • Farewell dinner at a restaurant in Sorrento
  • All transfers as per itinerary
  • All gratuities for meals and coach drivers (Gratuity for primary local guides not included)

What´s not Included

  • Airfare package
  • Arrival and departure transfers
  • Visa fees, if applicable
  • Meals not 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.
  • Gratuity for primary local tour guides
  • Any costs associated with optional activities on Go Get Lost day

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