15-Day Rome Tuscany, Amalfi Coast Cinque Terre and Italy’s Boot
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Alberobello, Ostuni, Polignano, Matera, Sorrento, Amalfi, Ravello, Positano, Pompeii, Rome, Florence, Siena, Chianti and Cinque Terre.
This unforgettable trip takes you on a grand tour of Italy, offering the chance to see some of the country’s finest locations and experience a range of different Italian towns, cities, landscapes and attractions.
Beginning in Apulia, you will travel through the Val d’Itria and enjoy its picturesque countryside filled with vineyards, villages, and fields, as well as a specialist wine and cheese tasting session in rural Masseria. Next, explore the historical underground city of caves in the World Heritage Site of Matera, followed by a trip to the ancient ruins of Pompeii to see some of the famous remains that survived the eruption of Mount Vesuvius.
After enjoying the hospitality of Sorrento, you will travel to Rome and spend a few days exploring Italy’s capital city both with a guide and independently, giving you the chance to see some of its most popular sights and discover a few hidden gems of your own. From Rome, you will travel to the Tuscany region of Italy, visiting two of its most popular locations; Florence and Siena.
Finally, enjoy the scenic coastal towns of Cinque Terre and the wineries of the Chianti countryside, before returning to Florence at the end of your trip.
This is a fully customized tour, starting in Bari and ending in Florence. You will have a local support, private local guides for your days of sightseeing and private transportation between locations. Local assistance will also be on hand 24/7 throughout your trip in case you need anything else. You can choose any departure date.
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Day 1 - Arrival
Important Note: This tour starts in BARI, Italy and ends FLORENCE. We will be happy to assist you with airfare and connections.
You will arrive in Italy at Bari airport, and be privately transferred to your hotel in Alberobello, Apulia. check in and relax at your hotel. Free this evening.
Day 2 - Alberobello, Locorotondo and Cisternino
Your first full day of this tour will start with breakfast at your hotel, after which you will be met by a private driver-guide who will take you around the Val d’Itria. This is a beautiful drive through woodlands and vineyards in the countryside, and your first stop will be in the village of Locorotondo.
Locorotondo is one of Italy’s most beautiful settlements and is an ideal place to spend a morning people-watching from a shaded cafe or exploring the historic town centre. This ancient area is circular and right at the top of the hill and is a maze of whitewashed streets that are full of the interesting old buildings and baroque architecture.
Next, you will visit Cisterno, which is thought to have been inhabited right back in the Middle Palaeolithic period. Today, Cisterno is a charming town that maintains a historic atmosphere, full of pretty white houses, beautiful churches and a central square that offers panoramic views of your surroundings. From here you can admire the hills that overlap into the distance, and try to spot the trulli huts amongst the fields that you will better be able to explore later in the day
Lunch will be served after a wine and cheese tasting session, sampling some of the area’s best produce. You will eat at a local Masseria, looking out over olive groves that are backed by views of the Adriatic sea. On your return to Alberobello, you will be given the rest of the afternoon to explore the town on your own.
Alberobello is best known for the whitewashed trulli huts that can be found everywhere with their distinctive, conical roofs. Each structure was built without cement or lime to hold the material together, and visiting one is a must for your time in Alberobello to experience a piece of truly unique architecture.
You will spend the evening in Alberobello as well and stay another night at your hotel.
Day 3 - Ostuni, Polignano and Monopoli
Your third day will be spent with more excursions from Alberobello to nearby towns in the Apulia area, again getting the chance to see more of the beautiful Italian countryside as you travel.
First visit Ostuni, which is spread out across three hills over 200 metres above sea level and has the nickname the ‘White Town’ because of the whitewashed houses that make up the town’s historic centre. A must-see for this visit is Ostuni’s Romanesque-Gothic cathedral from the 15th century, but there are also many elegant houses and churches are particularly lovely to look at in the old town as well, along with ancient town gates still allowing visitors in through the Aragonese walls that guard the settlement.
Polignano is the next stop on the tour; a town which is thought to be one of the oldest settlements in the Puglia area. Perched on the edge of a rocky gorge, Polignano has a history of invaders that range from the Normans to the Huns, and is a lovely place to just sit and watch the waves, enjoy the architecture or visit some of the local shops.
Your final stop will be Monopoli, home to a ‘paese vecchio’ in the centre of the town that features multiple churches lined up next to one another. The domestic buildings in this area are charming and have been inhabited by generations of the same families who still work in fishing, farming and winemaking.
Your driver will drop you back off in Alberobello at the end of the day for your final night there.
Day 4 - Matera and Sorrento
Your driver will meet you at your hotel after breakfast this morning, and transfer you to your accommodation in Sorrento. On the way, you will stop off in the historic location of Matera and have free time to explore the city.
Matera is the third oldest city in the world and has over 10,000 years of history, the most fascinating element of which are the man-made caves that have been carved into the area’s limestone. You can visit these underground homes that have contributed to Matera’s title of a World Heritage Site, and also see evidence of early structures that were used to transport running water into the caves.
Matera was named the cultural capital of Europe in 2019, and along with the fascinating cave systems is also home to several beautiful churches, pedestrianised squares, and bustling streets of cafes and shops. You might also recognise some of the surrounding landscape from several films and television shows, as the area is a very popular location for filming because of its dramatic scenery.
You will have time for lunch in the city before returning to your driver and continuing to Sorrento, where you will spend the night.
Day 5 - Amalfi Drive
Today your driver-guide will take you between the scenic locations of one of Italy’s most popular destinations: the Amalfi Coast. Enjoy the dramatic cliffside landscape and seaside atmosphere, with miles of beautiful coastline, pretty villages and luxurious beach resorts.
You will first visit the town of Amalfi, with free time to discover some of its medieval architecture such as the huge dome of the cathedral dedicated to Saint Andrew. After Amalfi your next stop is Minori, where you will experience a dessert tasting session that centres around lemons, one of the region’s finest ingredients. This will take place at Sal de Riso, the restaurant of one of Italy’s most famous pastry chefs.
From Minori you will continue to the romantic location of Ravello, a town spread out across steep, terraced slopes cut into the cliffs. Filled with beautiful gardens and quiet corners to stop and catch your breath, Ravello is one of the best spots on the Amalfi Coast to enjoy panoramic views of the deep blue Tyrrhenian Sea.
You will arrive in Sorrento in time for an evening meal of your choosing, and spend another night at your hotel.
Day 6 - Pompeii
Today your driver will take you to Pompeii in the morning for a guided tour around one of the best-preserved ancient Roman settlements in the country, thanks to the eruption of nearby Mount Vesuvius in 79 A.D. It is also one Italy’s most popular towns with tourists, and has been named a UNESCO World Heritage Site because of its historical value as an archaeological site.
Once a holiday resort for wealthy Romans, Pompeii still contains the remains of the civic buildings in the town, showcasing some of the Roman Empire’s finest architecture. Amongst these iconic ruins is the House of Mysteries; a building named after the murals covering its interior that depict the initiation rites of a cult of Dionysus.
Pompeii is also known for the historic graffiti that can still be found on the walls of the majority of its buildings. At the time of the eruption, there were elections meant to be happening in the town and so much of the graffiti is related to political figures and events, as well as some more generic, crude writing!
On your return to Sorrento, you will be treated to a wonderful candlelit dinner on a terrace with a sea view, and enjoy some of the area’s best food and drink.
Day 7 - Optional Discovery
At the end of your first week in Italy, you have a day of free time to allow for rest and relaxation, or for the chance to visit different parts of the area.
If you do decide to carry on exploring the area, we recommend an afternoon visit to the Pompeii Archeological Park, a boat excursion in Capri or along the Amalfi Coast, or a combination of visiting Pompeii again with Vesuvio.
Day 8 - Rome
After breakfast in Sorrento, you will be transferred to Naples Railway Station and catch the high-speed train to Rome, taking you to Italy’s capital city in under two hours.
On arrival in Rome, you will be met at the station by private transportation and dropped off at your hotel in the city centre. You will have the evening free to relax.
Day 9 - The Vatican and the Heart of Rome
After breakfast in the morning, you will be met by a private guide and join a small group tour of the Vatican; an independent city-state in the centre of Rome that is home to the famous Vatican Museum and stunning Sistine Chapel. Your guide will give you unique insight into the collections and masterpieces of the Vatican Museum such as the Raphael Rooms, Belvedere Courtyard, the Galleries of the Candelabra, the Maps and the Tapestries and the ornate Sistine Chapel, home to some of Michelangelo’s finest frescos.
Your tour will end with the famous St Peter’s Basilica, considered by many to be one of the most magnificent churches in the world. After an independent lunch in Rome, you will join your tour guide again for a walking tour of the city’s Baroque Town, including visits to the Spanish Steps, Piazza Navona, the Italian Parliament, the Pantheon and the Piazza’s Navona and Spagna.
You can then either return to the hotel or carry on exploring Rome by yourself and choose somewhere to eat dinner.
Day 10 - Rome
This tour has been designed to combine days of guided sightseeing with leisure time that allows you to set the pace of your days exploring. The tenth day of this tour is left free so that you have some time to relax in one of Italy’s greatest cities, or choose your own activities to fill the day.
If you do decide you want to take a day trip, you can take an excursion to Capri or Pompeii for views of the coast, or travel by high-speed train back to Naples and explore this famous area. The nearby Viterbo area also offers wine tasting and vineyard tours, or you can stay in Rome and visit popular spots such as the Colosseum and Roman Forum.
On your final night in Rome, you can choose where to eat dinner, and then stroll back to your hotel through the darkening streets and admire some of the city’s famous monuments as they are lit up.
Day 11 - Experience True Tuscany
Today you will depart Rome and travel into Tuscany, meeting your tour host at your hotel and catching a private car to Florence. This journey allows you to see the famous Tuscan hills, scattered with medieval villages and castles and home to numerous vineyards.
This transfer to Florence includes a stop in Siena; one of Tuscany’s oldest and most beautiful cities. Centuries ago Siena was said to be the only rival to Florence in terms of wealth, power and culture, and it remains a fascinating city that is full of art and Renaissance architecture.
Your guide will take you on a walking tour of the city, that includes a visit to the Piazza del Campo which is used as the venue for the famous annual Palio horse race. You will then walk around some of the seventeen city districts that compete in this tournament each year, exploring Siena’s quieter back streets.
If there is the time your tour may also stop off in Monteriggioni in the afternoon. You will arrive in Florence in the early evening, and spend the night in the city.
Day 12 - Magnificent Florence: Between Food and Arts
After breakfast, your tour of Florence will begin in some of the lesser-known parts of the city, exploring back streets and visiting the San Lorenzo market. Fresh local produce arrives here each morning from the countryside, and it’s a great place to sample new flavours and pick up something for lunch.
In the afternoon your guide will meet you again at your hotel to journey into the city centre, and learn about how the ancient statesman Lorenzo de Medici brought writers, artists and architects to Florence in the 15th century, and secured its reputation as the birthplace of the Renaissance. Michelangelo, Leonardo da Vinci and Botticelli are just some of the famous names whose work is now on display in Florence.
Your tour will take you past the Palazzo Vecchio, over the Ponte Vecchio, to the Piazza della Signoria and end with a visit to the Accademia gallery. Here, your tickets will allow you to skip the queues and see Michelangelo’s influential statue of David, as well as other classic artworks.
You will return to your hotel after this full day of sightseeing, and spend another night in Florence.
Day 13 - Cinque Terre
Today you will take a day trip from Florence to the northern coast of Italy, discovering incredible views and mouth-watering local cuisine in the fishing region of Cinque Terre. We will drive through the Tuscan Hills and along the Italian Riviera Coast until you can spot the southern part of the Alps, and arrive by mid-morning to make the most of the day.
Cinque Terre is best known for being a hiking and backpacking destination, and we will visit the area’s National Park and experience some of its popular trails across the cliffs and forests. The highlight of today’s itinerary is lunch, which will consist of wonderfully fresh seafood dishes cooked in the classic Ligurian style, accompanied by crisp white wine and views of the coast.
We will relax after lunch before travelling back to Florence, and spend another night in the city.
Day 14 - Wine and Oil Experience with Dinner in Chianti
After yesterday’s walking excursion, the morning of your final full day of this tour is left free to allow you to enjoy a late breakfast and gentle start to the day. After lunch, you will meet up with your local guide and spend the afternoon in the Chianti Wine Region.
A private driver will shuttle you through the grape-covered hills until you reach a boutique winery half an hour outside of Florence. Your group will receive a tour of the 500-year-old cellars beneath the estate, which are still used today to age some of the finest wines this area produces.
Next, you will enjoy an in-depth wine tasting session, sampling all of the different varieties that the estate produces and learning the correct techniques to distinguish the different flavours. The final treat of this winery experience is dinner, served at the estate.
Your meal will be a true celebration of the classic Italian flavours that come from Chianti; olive oil with unsalted Tuscan bread, a selection of local charcuterie and cheese served with balsamic vinegar and preserves, two delicious pasta dishes and then a traditional meat dish. Each of these courses will be paired with a carefully selected wine that compliments the flavours of the ingredients, including the world-renowned Supertuscan wine that is made on the estate.
After dessert, served with local sweet wine, you will return to Florence in the evening and stop off at the Piazzale Michelangelo Belvedere to take in breathtaking views of the city in the dark, as a final goodbye to the area.
Day 15 - Departure
After your last hotel breakfast, private transportation will arrive to take you to either Florence’s airport or railway station.
Departure Dates & Pricing
This tour is customized to your exact standards and budget. You can book it exactly as it is or change it. If you were to book it as it is starting pricing is below. Contact us for a custom quote for your exact date.
Prices starting from:
Pricing Guide from
Single Room: € 5,994
Double/Twin Room: € 4,731
Triple Room: € 4,580
This tour offers customized pricing which means that you can pick your own departure dates, level of hotels, add or remove days or book it as it is shown. Just contact us at email@example.com for a custom quote.
- 3 nights in Martina Franca, Apulia
- 4 nights in Sorrento
- 3 nights in Rome
- 4 nights in Florence
- Breakfast every morning in your accommodation
- Transfer to your hotel from the airport on arrival
- An excursion to the towns of Alberobello and Locorotondo
- A wine tasting session in Locorotondo
- An Italian farmer lunch near Cisternino
- Olive oil and cheese tasting experience in Cisternino
- An excursion to Ostuni and Polignano, with the option to visit Monopoli
- Transfer from Alberobello to Sorrento, stopping in Matera
- A diver guided tour of Amalfi and Ravello
- A ‘lemon delicacies’ tasting session in Minori, near Amalfi
- A half-day guided visit of Pompeii
- A special farewell candlelight dinner in Sorrento on a sea view terrace
- Private transfer from Sorrento to Rome
- A guided visit of Vatican Museum & Sistine Chapel
- Afternoon walking tour through the heart of Rome
- Transfer from Rome to Florence, stopping in Siena
- A wine and food experience in Siena
- Fresh food market’s tour in Florence
- A guided tour of the centre of Florence, including visiting the Accademia to see Michelangelo’s David
- Departure Transfer to Florence airport or railway station
- Local city tax
- The airfare to and from Italy. We can help you with booking your flights, just ask when booking
- Travel Insurance. This may be purchased from any source, and we do offer it, but it is required for all travel
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