Historic Italian Cities and Coastal Retreats - 9 Days



Trip Snapshot
Age range
0 - 100Start / End
- Rome
- Milan
Physical rating
Guide style
Self GuidedMeals included
0
Everything you need to picture the adventure and pack with confidence — in one free PDF.
What's inside the PDF
Day-by-day itinerary
Every day mapped out, covering activities, travel times, meals and where you'll stay.Packing & kit list
Exactly what to bring, from clothing and essentials to luggage guidelines and what's available to hire locally.What's included
Accommodation, transport, guides and meals, so you can see exactly what your price covers.
Summary
Embark on a captivating 9-day journey through Italy, beginning in the timeless city of Rome and concluding in the vibrant Milan. Explore the grandeur of Rome with highlights including the Colosseum and Vatican City. Meander through the medieval charm of Orvieto and the striking landscapes of Umbria. Discover the iconic towers in San Gimignano and the Renaissance gems of Florence. Marvel at the Leaning Tower of Pisa before heading to the breathtaking Cinque Terre. Experience the exclusivity of Portofino and the fashion-forward streets of Milan. This tour offers a delightful blend of history, culture, and stunning natural beauty.
Itinerary
Day 1
Rome
Upon arrival in Rome, we'll ensure a smooth transfer to your hotel, where you can unwind and enjoy some leisure time. During the afternoon, be sure to check the hotel reception boards for essential information about the commencement of your tour. This marks the start of your captivating journey in one of history's most celebrated cities. Please note: This tour may have travellers joining or departing at various points along the route, meaning group composition can change during the tour. Please also be aware that depending on group composition, guiding may be in additional languages as well as English.
Day 2
Rome
On the second day of our journey in Rome, we begin with a three-hour guided tour of this remarkable city, reminiscent of its grandeur as a cornerstone of Western civilisation. Our exploration takes us through the heart of Imperial Rome, with a walking tour complemented by a panoramic bus ride. We will visit celebrated sites, including the Arch of Constantine, the exterior of the Colosseum, and the vast Imperial Forums. The tour also encompasses notable landmarks like the Circus Maximus, the immense Baths of Caracalla, the grandeur of the Basilica of Saint Mary Major, the distinctive Pyramid of Cestius, and historic Castel Sant'Angelo. Concluding around 11:00 a.m. at Vatican City, an optional visit to the Vatican Museums and the Sistine Chapel is available should you wish to delve deeper into these treasures.
In the evening, we ensure you experience the vibrant atmosphere of the Trastevere neighbourhood. Known for its inviting restaurants and lively ambience, Trastevere offers the perfect backdrop to unwind and soak in the local culture. We will arrange your return to the hotel at approximately 8:30 p.m., allowing for a leisurely dinner and some explorations.
Day 3
Rome
On day three, you have the freedom to shape your own adventure. You may wish to join an optional excursion and experience something unique. Between April and October, you can explore the stunning island of Capri, known for its breathtaking landscapes and vibrant atmosphere. From November to March, you might opt to delve into the history and culture of Naples and the ancient ruins of Pompeii instead. Wherever your choice leads you, the day promises exploration and discovery.
Day 4
Rome
On the fourth day of our tour, we venture into the charming region of Umbria. Our journey begins with a visit to Orvieto, a medieval city that sits proudly atop a flat hill. Before entering, enjoy the stunning panoramic views from the nearby viewpoint. We’ll then take the escalators connecting the lower town to the medieval centre, where the magnificent cathedral awaits—an exemplary piece of Italian Gothic architecture. Our adventure continues to Castiglione del Lago, beautifully situated on the banks of Lake Trasimeno. Here, you'll have the opportunity to take a leisurely walk and enjoy lunch at your own pace. After our stop, we proceed to the Tuscan city of Siena, celebrated for its iconic Piazza del Campo and splendid Duomo, spending the afternoon absorbing the unique ambience of this historic location.
Day 5
Siena
Leaving Siena, our adventure starts with a visit to Monteriggioni, a picturesque medieval village famed for its cobbled lanes and ancient fortified walls. Our journey then takes us to San Gimignano, renowned for its skyline of striking medieval towers. Following a delightful lunch, we head to Florence, the heart of Tuscany, with an expected arrival in the early afternoon. We suggest taking this opportunity to explore either the Uffizi Gallery or the Accademia Gallery, although please note both are closed on Mondays. As evening approaches, we invite you to indulge in a traditional local meal, rounding off your day with the tastes of the region.
Day 6
Florence
Beginning our exploration of Florence, we start the day with a photo opportunity at the Michelangelo viewpoint, offering one of the most stunning panoramas of this majestic city. We then proceed with a guided walk through the historic centre, delving into the heart of Florence, celebrated as the cradle of the Renaissance. The city has inspired luminaries like Leonardo da Vinci, Michelangelo, Botticelli, and Raphael. Our tour takes us to marvel at the Gothic splendour of the Florence Cathedral (Duomo di Firenze) and the iconic Ponte Vecchio, renowned for its vibrant array of goldsmith shops. We’ll also visit the Piazza della Signoria, the city’s political hub, showcasing its impressive medieval town hall. Following our guided tour, you’ll have free time to explore this enchanting city at your own pace. For a comfortable day of sightseeing, we recommend wearing suitable walking shoes.
Day 7
Florence
Today, we set off to explore Pisa. A charming tourist train will escort us to the Piazza dei Miracoli, where you can admire the world-renowned Leaning Tower of Pisa. Following this, we'll continue our journey to the stunning Ligurian Riviera, famed for its breathtaking coastline, considered among the most picturesque in Europe. Our destination is the Cinque Terre, a UNESCO World Heritage Site, comprising five enchanting villages that are nearly isolated by road and now thrive on tourism. We will travel by train, with tickets included, to one of these quaint towns—typically Vernazza, though during peak tourism periods, our visit might be to one of the quieter locales like Manarola or Corniglia. There's ample time to enjoy lunch in this delightful setting. Our adventure then continues as we catch another train to Levanto, from where we'll board a bus to Genoa. On arrival, you will have some free time to explore the historical city centre, a testament to its rich history as a formidable republic during the Middle Ages. Please note that the train services through Cinque Terre are standard commuter trains, not specialised tourist ones, and you might need to stand during busy times, as seats cannot be reserved.
Day 8
Genoa
Our journey continues to the picturesque town of Santa Margherita Ligure, where we will set sail for the chic haven of Portofino, renowned as one of Europe’s most exclusive destinations. Enjoy a leisurely seaside stroll and free time to soak up its unique ambiance. Following lunch, our adventure proceeds to Milan, an epitome of northern Italy’s modernity and cultural allure. Here, you have the opportunity to wander this stylish city at your own pace. We suggest visiting the majestic Gothic cathedral at Piazza del Duomo and exploring the elegant Galleria Vittorio Emanuele II, a historic shopping arcade named after Italy's first king. Please note, from 30th May to 2nd November, tourist buses can't access Santa Margherita Ligure, so we will begin our boat trip to Portofino from Rapallo instead. Be aware that the boat crossing may be cancelled in poor weather conditions or during winter months.
Day 9
Milan
After breakfast, we bid farewell as our journey reaches its conclusion. Take a moment to reflect on the unforgettable experiences and memories forged during your travels. Safe travels home, and carry these cherished moments with you.
What's Included
Meals
Breakfasts: 0, Lunches: 0, Dinners: 0
Vegetarian options are available on all meals throughout the adventure.
Vegetarian options availableLocal Guide
Self GuidedWifi
Wifi is available during the adventure. In some areas and / or accommodation / transport Wifi may be free.
Dates & Prices
Oct 2026
from £1,574Nov 2026
from £1,347Dec 2026
from £1,347Jan 2027
from £1,347Feb 2027
from £1,347Mar 2027
from £1,347
- Save 13%Wednesday 4 Nov 2026to Thursday 12 Nov 20266+ spaces of 65 left£1,670£1,456
- Save 13%Wednesday 11 Nov 2026to Thursday 19 Nov 20266+ spaces of 65 left£1,670£1,456
- Save 13%Wednesday 18 Nov 2026to Thursday 26 Nov 20266+ spaces of 65 left£1,545£1,347Best offer
- Save 13%Wednesday 25 Nov 2026to Thursday 3 Dec 20266+ spaces of 65 left£1,545£1,347Best offer

Make this tour private
Every departure on this trip can be booked just for your own group — your dates, your people, the same expert local guides.
What changes when you go private
Travel with just your own group
No other travellers on the trip — just the people you choose to bringTravel on your schedule
Pick your exact start date—no fixed group departures or rigid timetables.Exclusively for your party
Enjoy this handcrafted itinerary with a dedicated private guide just for you.
Essential trip information
Our Important Notes and Packing List cover all essentials, from necessary equipment to inclusions, ensuring you're fully equipped and informed for this extraordinary adventure and more.
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