Adventurous Italy tour with some historical places of Rome and Pisa.

Day to Day Itinerary

  • Day 1: Arrive Portofino

    Meals: None Arrive in Portofino, the glamorous jewel of the Italian Riviera. Enjoy your first family meal together this evening in Portofino’s lively harbour, a great place for people-watching among the luxurious yachts. Overnight: Hotel Splendido
  • Day 2: Private Motor – Yacht in the Cinque Terre

    Meals: Breakfast The Cinque Terre is one of Italy’s most precious treasures. Its five lands, or villages; Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore are linked by a rugged, 12 mile coastal path that winds past steeply terraced olive groves and vineyards, white-sand beaches, colourful higgledy-piggledy houses and the most spectacular rocky seascapes imaginable. The best way to explore the villages and the coast of the Italian Riviera is on-board a skippered motor-yacht. Spend the day sailing on the sparkling Mediterranean with your expert guide, taking in the beauty of the Cinque Terre. Overnight: Hotel Splendido
  • Day 3: Hiking in the Portofino National Park

    Meals: Breakfast The promontory of Portofino National Park is one of great natural beauty and a paradise for walkers. Ancient walking paths lead through olive groves and vineyards up to chestnut forests. Join your guide for an invigorating hike to the San Fruttuoso Abbey, only accessible by foot or by the sea. The abbey dates back more than 700 years and includes a defence tower to protect it from pirates! Overnight: Hotel Splendido
  • Day 4: Off-road Experience in the Marble Mountains, Leaning Tower of Pisa, Pisa’s Chocolate Valley

    Meals: Breakfast The mountains between Portofino and Tuscany offer the most highly demanded of the famous white Italian marble, loved by the great sculptors such as Michelangelo and Bernini. Today we have a high octane 4x4 off road experience into the vast marble quarries. Your expert driver will bring you up the along steep, winding, roads. See trucks manoeuvring in the quarries at death-defying angles, and gaze in awe at dazzling landscapes. After climbing nearly 4000 feet you are rewarded with an amazing view, on a good day to the island of Corsica. Continue your journey onwards to the world famous city of Pisa with time for lunch and climbing the iconic leaning tower. The last visit of the day is in Pisa’s ‘chocolate valley’ for tastings at an artisanal producer of fine Italian chocolate. The day ends at your exclusive private villa on the Castiglion del Bosco estate, pride of the esteemed Ferragamo family. Overnight: Castiglion del Bosco
  • Day 5: Siena Sightseeing, Evening Pizza Party at your villa

    Meals: Breakfast Depart for Siena for a guided tour of the great city. Siena was built on three hills and is enclosed by a set of walls and gates. See the Piazza del Campo, one of the finest main squares in Italy, and the Palazzo Pubblico which has served as Siena's Town Hall since the 1300s. Visit Siena's Duomo, considered to be one of the finest Gothic cathedrals in Italy with unforgettable frescoes in the Piccolomini Library. A highlight of your day in Siena will be private access into one of the Contrada Museums, dedicated to one of the quarters of the city that participates in the bi-annual Palio horse race. Here you can gain an insight into the centuries of pomp, pride and pageantry behind today’s spectacle. Return to your luxury villa in the afternoon with your private pool inviting you in for a dip. In the evening a pizzaiola will arrive to fire up the pizza oven and create a freshly baked private pizza party for you in the grounds of your villa! Overnight: Castiglion del Bosco
  • Day 6: Balloon Flight and Activity Day

    Meals: Breakfast This morning, enjoy a special experience, floating above the rolling Tuscan countryside during a private hot air balloon flight (subject to weather conditions). The peace and serenity of exploring Tuscany in this way is one not to be missed. Return to the hotel for breakfast. The remainder of the day is at leisure to take advantage of the many on-site activities (payable locally) or simply relax and drink in the special atmosphere. Activities on the estate include:Tours of the winery,Championship members/guests only golf course, Horseback riding, Hiking trails, Mountain biking trails, Extensive spa, Cooking school Academy, Kids Club. Overnight: Castiglion del Bosco
  • Day 7: Pienza and Wineries of the Val d’Orcia

    Meals: Breakfast Today visit the pretty town of Pienza. The center of Pienza was redesigned by Pope Pius II, who wanted to build a model Renaissance Square in his native village. Nearby Montepulciano is an archetypal Tuscan hilltop town, set 605 meters above sea level and offering superb views over the surrounding countryside. Inside the ancient city walls and fortifications you will find winding streets and a wealth of Renaissance style palazzi and churches. During your excursion today you will have the opportunity to enjoy a tasting of some of the wonderful Brunello and Montalcino wines of this region. INSIDER ACCESS: The Real Italian Pecorino Today visit a typical Tuscan farmhouse, located in the hearth of Val d’Orcia, close to Pienza and Montepulciano, to enjoy a private cheese making demonstration. The owner will give you a brief introduction of what they do on their estate followed by an explanation about Pecorino and Ricotta making. You will be able to visit the laboratory and learn about the entire process of cheese making. Overnight: Castiglion del Bosco
  • Day 8: Tuscany to Rome: The Colosseum from a Gladiator’s Perspective

    Meals: Breakfast Travel through the countryside of Tuscany and Umbria today to the capital city of Italy, Rome. In the afternoon descend into the belly of the most famous and most visited ancient monument in the world, the Colosseum! Stories of the gladiatorial games will become more vivid as you visit where gladiators once held their final preparations before battling with wild beasts. These spaces are preserved in the condition they were in at the end of the fifth century AD, at which time they were covered over and only very recently opened up. Your guide will bring to life the atmosphere of Rome's pulsating heart, crowded with people from across the Roman Empire. Your guide will also explain the other nearby Emperor's forums; Traiana, Augusto and Cesare. Enjoy accommodations at Rome’s newest urban resort, believed to be the birthplace of Emperor Nero and just a short walk from the Vatican City. Overnight: Gran Melia
  • Day 9: Underground Rome

    Meals: Breakfast Take a journey back in time during your half day (4 hours) excursion accompanied by your expert guide and driver. Explore the unique church of St. Clemente as you descend down three levels and through two thousand years of history! The medieval church was built over the remains of a 4th century basilica which, in turn, covers buildings from the time of the emperor Nero and a sanctuary dedicated to the oriental divinity, Mithras. The medieval basilica houses one of the finest mosaics from the period, representing the Tree of Life. Continue to one of Rome’s’ most important catacombs, those of San Sebastiano. In burying their dead in underground cemeteries outside of the city walls, the early Christians were simply obeying the laws of time. They were not forced to use them because of persecution, as later popular myth has suggested. Many saints were buried here, and the catacombs later became shrines and places of pilgrimage. For your final evening in Rome, come together as a family once again with dinner on your own private terrace in an exquisite villa drinking in the panoramic views of the Eternal City. Overnight: Gran Melia
  • Day 10: Depart Rome

    Meals: Breakfast Privately transfer to Rome Airport today and fly towards your home town.


Each year a flood of visitors come to Italy to enjoy the pleasures of la dolce vita. With many natural and architectural treasures, Croatia has re-emerged to become the sparkling jewel of the Adriatic. Italy has drawn travelers in search of culture and romance for many centuries. From the northern snow-capped peaks of the Alps and the idyllic hilltop villages of the renowned central Tuscany and Umbria area, to the rugged southern shores of Sicily, lies a plethora of distinctive regions and people. From the sophisticated, vibrant cities to the simple elegance of the countryside, Italy’s culture abounds. As a united country, Italy is only a little over 150 years old which means that each region still has a strong cultural identity, resulting in a country of many different faces to delight repeat visitors. Exuberance for life and its simple pleasures endears Italy to its visitors; an appreciation of family, food, history and beauty are the core values at the heart of this popular country.

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