Eclectic Italy

Day 1 – Arrive Florence

Airport Transfer from Rome, Milan or Pisa, Dinner

Welcome to Italy! Wherever you land you’ll be greeted by a JBT guide and transferred by train or car to your accommodation in Florence the first stop on your Tuscan and Cinque Terre journey. Today will be dedicated to settling in and getting familiar with your new surroundings. Your local born and bred guide will introduce you to the city and point out the fascinating details that make Florence special. Fabulous food is a hallmark here and your first dinner in a traditional Florentine trattoria will introduce you to the ingredients and dishes that distinguish the region.

Day 2 – Florence

Guided Tour

Your guide will be waiting to begin your journey and walk along the charming streets and stunning architecture of the historic center. You’ll browse leather markets and learn how to tell a handmade wallet or belt from a cheap import on the way to the Uffizi Gallery whose galleries are filled with masterpieces by Botticelli, Michelangelo, and da Vinci. Once you’ve experienced the artistic results of the Renaissance, you’ll stroll across the Ponte Vecchio to browse jewelry shops and see how the powerful Medici family once crossed the oldest bridge in the city. At lunch, you’ll savor Tuscan flavors like ribollita, a hearty vegetable soup, or indulge in a classic Florentine steak at a JBT recommended trattoria or discover one on your own. In the afternoon, you and your guide will explore the iconic Duomo and climb the to the top for an incomparable view of Florence. Afterwards you’ll learn how the cathedral was constructed at the adjacent museum and enjoy aperitivo (happy hour) from a rooftop bar overlooking the Arno River.

Day 3 – Florence

Guided Tour, Cooking class

This morning you’ll dive into Florence’s artistic legacy at the Accademia Gallery and see firsthand why Michelangelo’s David doesn’t disappoint. Your guide will recount the story of the masterpiece and the artist’s impact on the city. It’s a short walk to Basilica di Santa Croce, a grand church and the final resting place of Galileo and Machiavelli. Lunch will be dedicated to the pleasures of the city’s street food with stops at the Sant’Ambrogio Market where you can browse tempting stalls and watch hearty tomato stew being dished out to locals on their lunch hour. After a visit to the Bargello Museum to admire Donatello’s David you can decide which version you prefer over a cappuccino in an outdoor cafe overlooking one of the vibrant squares of the city center. Your guide will lead you across the Arno River through the quieter neighborhoods of Florence and up into the hillsides where few tourists tread. Once you’ve wandered the finely groomed paths of the Boboli Gardens, adorned with sculptures and fountains it will be time for dinner which you can create yourself with the help of a dedicated chef who will reveal how simple it to make pasta from scratch.

Day 4 – Chianti – Sip and Savor

Transfer, Guided Wine Tour, Lunch

It’s hard not to be seduced by Chianti. If the trademark rolling hills don’t get you the wine will. The region has no clear geographic borders, but is divided into Florentine Chianti in the north and Sienese Chianti in the south. The influence of the two cities can be seen in the architecture as well as on the tables of the region’s restaurants. Greve is the first town on the road from Florence to Siena and considered the gateway to the area. It’s an ancient market town notable for its architecture and gastronomy. This guided day trip takes you beyond the bottle and reveals the production process from grape to glass. You’ll dazzle your tastebuds and meet the vintners who have dedicated their lives to making Tuscan wine the finest in the world. There will be lots to sample and it will be served with locally produced cured meat and cheese at each vineyard stop. You can get your hands dirty and participate in the process or simply kickback and sip away. You’ll be driven back in time to watch the sun set over the Pontevecchio and can use your newfound knowledge at an enoteca in the Oltrearno neighborhood where Florentines young and old gather to enjoy life.

Day 5 – Lucca

Transfer, Guided Tour, Bicycles

Bid farewell to Florence and head to Lucca, a charming walled city near the coast. Your JBT Guide will be on hand to show you around the historic center taking in the picturesque Piazza dell’Anfiteatro, built over the remains of an ancient Roman amphitheater, the town’s ornate cathedral and a tower-house that provides stunning panoramic views of the town and surrounding countryside. After lunch you’ll hop on an electric bike to circle the city’s imposing ramparts and explore the bucolic paths along the Arno River. Dinner will be an opportunity to experience how distance affects menus in Italy and try the local staples.

Day 6 – Pisa

Guided Tour

In the morning you’ll take a short drive to Pisa along lovely back roads on your way to the iconic Leaning Tower in the center of the aptly named Piazza dei Miracoli (Square of Miracles). After climbing to the top of the tower you’ll tour the rest of the city which is often overlooked. Pisa owes its prosperity to the sea. It served as a naval base for the Romans and rivaled the maritime republics of Genova and Venice in the 12th century. Trade in those days financed the city’s monuments and the foundation of the university where Galileo Galilei contemplated gravity. There are Roman remains, Gothic churches, and Renaissance buildings that make interesting diversions from the usual trek towards the Duomo. Pisa was also one of Keith Haring’s favorite cities and the painter left his trademark images on the church of Sant’Antonio (Piazza Vittorio Emanuale). The visit includes a walk along both sides of the Arno and a stroll through all four of the city’s central neighborhoods.

Day 7 – Cinque Terre – Coastal Wonders

Transfer, Guided Tour

From Pisa you’ll hop a train to the Cinque Terre. The five coastal villages that give the area its name are Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore. Each is more charming than the next and deciding your favorite is one of life’s great pleasures. You’ll begin in Monterosso, the largest of the bunch, and arrive in time to savor a fresh seafood lunch at a cliffside restaurant. The Cinque Terre is best covered on foot and hikers will have no shortage of paths to explore. If you prefer swimming or sailing this is the perfect place to spend several days beach hopping and your guide can arrange a private cruise to remote inlets along the coast.

Day 8 – Cinque Terre – Village Hopping

Transfer, Guided Tour

Today you’ll hike north towards Vernazza, the Cinque Terre’s grandest town or board the ferry that operates between all 5 villages and can save you a blister or two. Explore the defensive walls that are still standing and have a look inside Castello Doria, which protected residents from marauding pirates in the Middle Ages. It’s another 45 minutes by foot to Monterosso, where you’ll be glad you packed your swimsuit. Before diving into the Ligurian Sea, have a look inside the gothic church of San Giovanni Battista with its austere interior favored by locals. Later you’ll relax under an umbrella at one of the stabilimenti (beach establishments) that offer light snacks and mixed drinks to bathers. You can take the ferry or train back to Corniglia and enjoy dinner that comes with a sunset.

Day 9 – Siena

Transfer, Guided Tour

You’ll get an early start taking the train to La Spezia where your JBT guide will be waiting to drive you through the heart of Tuscany. Wherever you enter Siena, you are inevitably drawn to Piazza del Campo. The main square has inherited its famous seashell shape from the whims and jerks of medieval urbanization. You’ll have lunch on the square overlooking Fonte Gaie fountain at the northern end before taking a tour of the town’s Duomo which would have been the largest in Italy had it been completed. In the afternoon you’ll visit a pristine hamlet a short drive away. Monteriggioni is what comes to mind when you imagine the Middle Ages. This magnificent walled village 15-kilometers from Siena has all its bricks in place. The 13th-century defenses were insurance against Florentines and now provide visitors with an instant medieval experience. Two restaurants on the inside serve delicious 3-course meals and there’s plenty of gelato.

Day 10 – Tuscan Hill Towns

Transfer, Guided tour

After a morning stroll through Siena’s lively market, you’ll continue to your agriturismo accommodation which will be a convenient base for exploring the towns and monasteries in the area. You’ll start with San Gimignano which could be mistaken for a miniature Manhattan. Height once mattered here and the skyscrapers made of stone reach a dizzying 50 meters. They’re the result of competition between patrician families trying to outdo each other back when pilgrims regularly passed the nearby Via Francigena trail and demand for saffron was high (it’s still grown and used in local dishes). Although only 14 of the original 72 towers have survived, the feudal atmosphere hasn’t faded. The medieval flashback begins as soon as you step through Porta San Giovanni.
In the afternoon you’ll discover Corsignano which owes a lot to Pope Pius II. In order to provide his birthplace with instant prestige, he commissioned Bernardo Rossellino in 1459 to transform the average medieval town into an ideal city. The construction that followed was the first based entirely on principles of Renaissance urban planning. Piazza Pio II and Palazzo Piccolomini presented a new way of treating public spaces that influenced architects for centuries. To complete the transformation the town was renamed Pienza. You’ll explore the outer walls and enjoy a sunset dinner before heading back to your countryside retreat.

Day 11 – Tuscan Hill Towns

Guided Tour, Wine Tasting, Bicycles

Montalcino is a pleasant detour on the way to Montepulciano and the curvy roads make for a wonderful scenic drive. Located in an idyllic Tuscan countryside, the town overlooks the Via Cassia. It was a key trading route and violently contested during the Middle Ages which explains the thickness of the outer walls. The town is one of the highest in the region and impressive fortifications are now used for admiring the views rather keeping anyone out. This is the home of Brunello wine and the grape tradition goes back centuries. You’ll stop in several wineries to learn about the famous vintage and how to recognize the flavorful Sangiovese grapes from which it is produced. You’ll then explore the timeless streets leading to Piazza del Popolo and Palazzo dei Priori notable for its fine loggia. Towering above is the Rocca, built in the 14th century by military architects. From the top on a clear day you can see all the way to the Lazio and Umbria regions. The ramparts of the Fortezza can be circumnavigated and the starting point of a bike tour through the surrounding countryside to Montepulciano and back.

Day 12 – Tuscan Hill Towns

Guided Tour

If Arezzo looks familiar, it’s because you’ve seen it in films like La Vita è Bella or The English Patient. If it doesn’t, prepare to get acquainted with one of the most picturesque towns in Tuscany. Although Arezzo was damaged during World War II everything was perfectly rebuilt to medieval standards. Piazza Grande was the site ‘f a Roman forum and the center of commercial activity. It still is and regularly hosts an antiques fair and the Giostra del Saracino festivities two weekends a year. At all other times, it’s a good place to watch locals coming and going and admire the ingenuity of Giorgio Vasari, who designed many of the 16th-century palazzi bordering the square.

After lunch you’ll visit one of the oldest hill towns in Tuscany, Cortona which also happens to be one of the most captivating. The Middle Ages left its mark here and signs of the town’s glorious heyday, when it managed to resist the advances of Siena and Arezzo, are evident throughout the maze of enchanting streets. If a lot of it starts to look alike, it’s because the same soft bluish-gray stone was used for medieval, Renaissance, and Baroque constructions, making it seem like everything was built at once. The Porta Montanina gate is as intimate as it gets, with views revealing rooftops and the entire Valdichiana Valley. You’ll find the Etruscan origins of the town on display at Museo dell’Accademia Etrusca.

Day 13 – Florence Farewell

Transfer to Rome, Milan or Pisa

Return to Florence for a farewell lunch at a local trattoria. Savor your favorite Tuscan dishes and raise a glass to unforgettable memories.