Discover Italy's Historic Cities and Coasts - 19 Days



Trip Snapshot
Age range
0 - 100Start / End
- Rome
- Venice
Physical rating
Guide style
Self GuidedMeals included
1
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
Discover the best of Italy on this 19-day journey from Rome to Venice, blending history, art, coastlines and culture. Begin in the Eternal City before crossing the Apennines to explore Puglia’s whitewashed towns and Matera’s ancient cave dwellings. Cruise to Capri, admire Mount Etna from Taormina and uncover Sicily’s treasures in Palermo. Returning north, travel through Umbria and Tuscany to Florence, Pisa and the stunning Cinque Terre. End your adventure among the romantic canals of Venice. With guided tours, scenic drives and plenty of leisure time, this tour offers an unforgettable sweep through Italy’s most captivating regions.
Itinerary
Day 1
Rome
Welcome to Rome! Upon your arrival, we will arrange your transfer to the hotel, allowing you some leisure time to settle in and relax. Later, you can check the hotel reception for important details regarding the start of your tour, conveniently displayed on the boards. Enjoy exploring Rome at your own pace before the exciting adventures of the coming days unfold.
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
Exploring Rome
On the second day of our journey, we embark on a fascinating exploration of Rome, the Eternal City. Our morning unfolds with a three-hour guided tour that seamlessly blends walking through the heart of Imperial Rome with a panoramic bus ride. This immersive experience showcases the profound influence of this ancient metropolis on Western civilisation. We begin by visiting the exterior of the colossal Colosseum and the historic Arch of Constantine before proceeding to the grand Imperial Forums. Our adventure continues as we observe the remnants of the Circus Maximus and the Baths of Caracalla, before admiring the intricate Baroque facade of the Basilica of Saint Mary Major. Discover the intriguing Pyramid of Cestius and the iconic Castel Sant�Angelo as our tour guides us to the sovereign Vatican City, where we conclude at approximately 11:00 a.m.
Following this, you have the option to delve deeper into the rich history by joining an optional visit to the Vatican Museums and the awe-inspiring Sistine Chapel.
As the day wanes, we whisk you to the vibrant Trastevere district, known for its charming eateries and lively ambiance � a perfect setting to unwind and reflect on the day�s discoveries. We will return to the hotel around 8:30 p.m., ensuring you enjoy a restful night.
Day 3
Rome at Leisure
Enjoy a free day to continue exploring Rome at your own pace. Take this opportunity to wander through its enchanting streets, discover hidden corners steeped in history, and experience the timeless magic that fills the city. Whether you choose to revisit favourite landmarks, relax at a café, or simply watch the world go by in a lively piazza, Rome’s beauty and charm are sure to captivate you at every turn.
Day 4
Rome to Puglia
Today, we journey eastward towards the Adriatic Sea, traversing the picturesque Apennine Mountains. Our first stop is the San Giovanni in Venere Abbey, a splendid 11th-century monastery built on the site of an ancient Roman temple - admission is included. From there, we will visit Termoli, a delightful coastal town where golden sands meet the charming walled old town. In Termoli, you'll see its 13th-century castle and Romanesque cathedral, plus enjoy time for lunch and a leisurely stroll. Our travels then take us to Bari, a historic port city with origins predating Roman times. Here, you can explore the old town, with its maze of narrow streets, beautiful churches, and lively atmosphere, encapsulating the essence of Southern Italian charm.
Day 5
Bari to Lecce
Today, our journey continues along the picturesque coast to the historic port city of Brindisi. Here, you can meander along the seafront, gaze upon the notable Roman column, and discover the charm of the old quarter. Afterwards, we head to Lecce, a city celebrated for its exquisite baroque architecture that has earned it the nickname "Florence of the South." As you explore the historic centre, you'll be surrounded by ornately decorated baroque buildings and churches, with time to enjoy a leisurely walk and lunch.
In the afternoon, we visit Gallipoli, a city on the Ionian Sea with Greek origins - the name itself means "beautiful town." Its old town, influenced by Arab, Norman, and Aragonese cultures, is connected to the mainland by a charming 17th-century bridge. The area is a labyrinth of narrow streets and historic landmarks, including a striking cathedral, an impressive castle, and ancient city walls. Our day concludes with a return to Brindisi for the evening.
Day 6
Alberobello & Matera
Today, we embark on a journey to explore two remarkable towns that exemplify the authentic charm of southern Italy. Our first destination is Alberobello, renowned for its distinctive trulli, cone-shaped stone houses. Recognised as a UNESCO World Heritage Site, the trulli represent a unique form of rural Italian architecture.
Next, we travel to Matera, situated in the Basilicata region, famous for its ancient core, Sassi di Matera. These ancient dwellings and structures, carved into the rock, are considered one of the oldest continuously inhabited human settlements in existence, also a UNESCO World Heritage Site. After enjoying a delicious lunch in Matera, which is included, we continue our scenic journey through the picturesque mountain landscapes of Basilicata and Campania, ultimately reaching Naples by evening. Once in Naples, you will have some free time to explore at your leisure.
Day 7
Capri Day Trip
After breakfast, we will make our way to the port of Naples and take a ferry across to the picturesque Island of Capri. We recommend using the funicular to reach Capri town, where you can wander at your leisure while taking in the stunning views. Following lunch, we'll reboard and head to the charming town of Sorrento, nestled at the base of a scenic cliff. You'll have free time here to explore at your own pace. Our day concludes as we journey towards the Gulf of Salerno, staying in the vibrant city of Salerno for the night.
Day 8
Salerno to Sicily
We'll head south today, appreciating the captivating scenery of southern Italy as we traverse the Cilento National Park. Our first destination is Paola, situated along the Tyrrhenian Sea. Here, we'll visit the Sanctuary of St. Francis of Paola, followed by some free time to explore its charming historical centre and have lunch.
Our journey continues to Villa San Giovanni, where we'll enjoy a short ferry crossing to the island of Sicily. Upon reaching Messina, you'll have time to explore around the city's cathedral before we proceed to Taormina, where a delicious dinner awaits. Please note: Accommodation is typically in the Taormina region, but on certain occasions, you may stay in Messina.
Day 9
Taormina to Palermo
At the foot of Mount Etna lies the captivating town of Taormina, once described by Winston Churchill as “the most beautiful place on earth.” Early this morning, we’ll travel to Giardini Naxos, the first Greek settlement in Sicily, founded in 734 B.C. Enjoy its charming seafront promenade and inviting beaches before continuing on to explore Taormina’s lively old town. Here, we’ll visit the remarkable Greek Theatre, set against a backdrop of sweeping coastal and volcanic views—one of the island’s most unforgettable panoramas.
After lunch, we continue to the Roman Villa del Casale (admission and guided tour included), a UNESCO World Heritage Site celebrated for its exceptionally preserved 4th-century mosaics. Once a grand estate representing agricultural prosperity in the Roman Empire, the villa’s intricate mosaics—adorning nearly every room-are considered among the finest in the ancient world.
Crossing the mountainous heart of Sicily, we make our way to Palermo, arriving in the evening. Dinner included.
Day 10
Exploring Palermo
In Palermo, we'll set off on a guided tour of the city with a local expert. Our journey will feature the magnificent cathedral, renowned for its stunning blend of architectural styles and royal tombs - admission is included. We'll then visit the Palazzo dei Normanni, the grand former royal palace, surrounded by splendid fountains, vibrant markets, and lush gardens.
A venture to Monreale is also on the cards, where we'll admire its cathedral, famed for its breathtaking golden mosaics that beautifully cover the interior, and is recognised as a UNESCO World Heritage Site - entry is included here too. With these enriching explorations accomplished, the afternoon is yours to spend as you wish. Please note that if the group size is small, the city tour might be part of a local company's regular excursion rather than a private one.
Day 11
Fly to Rome
We will transfer you to the airport at the designated time for a domestic flight, which is part of your tour. Upon arrival at your destination, we will arrange another transfer to your hotel. You can expect your guide to get in touch with you by the late afternoon, or you may refer to the hotel reception for any updates or further instructions. Please remember that the standard luggage allowance for domestic flights is a single suitcase weighing up to 20 kilograms. Any excess baggage will incur charges payable directly to the airline.
Day 12
Exploring Umbria
Today, we're heading into the heart of the picturesque Umbria region. Our adventure begins in Orvieto, a medieval town perched dramatically on a hilltop. Before we enter, we'll pause to take in the stunning panorama from its viewpoint. Once inside the town, we'll ascend via escalators to the historic centre, where the magnificent cathedral, a notable example of Italian Gothic architecture, awaits.
Afterwards, we'll journey to Castiglione del Lago, charmingly situated on the shores of Lake Trasimeno. Here, you'll have time to enjoy a leisurely walk and savour a delicious lunch. Our afternoon continues with a trip to Siena, located in Tuscany and famous for its remarkable Piazza del Campo and Duomo. We'll take in the rich history and vibrant culture of Siena before concluding our day.
Day 13
Siena, San Gimignano & Florence
Today, we bid farewell to Siena and make our way to Monteriggioni, a captivating medieval village encircled by ancient walls and cobbled streets. After taking in the village's historical charm, we continue to San Gimignano, renowned for its impressive medieval towers that dominate the skyline. You'll have the chance to explore its picturesque alleys before settling for lunch in this delightful town. In the early afternoon, we travel to Florence, the cultural heart of Tuscany. Once there, we suggest visiting either the Uffizi Gallery or the Accademia Gallery, where you can admire masterpieces from the Renaissance era (note that both museums are closed on Mondays).
Day 14
Exploring Florence
Today we start by capturing a magnificent photograph from the Michelangelo viewpoint, offering one of the most spectacular vistas of Florence. We then stroll into the heart of this historic city for a guided exploration of Tuscany's capital, esteemed as one of Italy's most visited destinations.
Known as the birthplace of the Renaissance, Florence has been a source of inspiration for some of the most pivotal artists and thinkers in history, including Leonardo da Vinci, Michelangelo, Botticelli, and Raphael. As we wander through the city, you'll be captivated by the grandeur of the Gothic Cathedral (Duomo di Firenze) and the charm of the ancient stone bridge (Ponte Vecchio) with its vibrant goldsmith stores. We will also visit the bustling Piazza della Signoria, the political centre of Florence, renowned for its medieval town hall. After the tour, you will have some free time to explore at your leisure. Please note that comfortable shoes are recommended for today's visit to Florence.
Day 15
Pisa, Cinque Terre & Genoa
Today, we set off for the historic city of Pisa, where a quaint tourist train will take us to the iconic Piazza dei Miracoli, home to the renowned Leaning Tower of Pisa.
Following this visit, we journey towards the picturesque Ligurian Riviera, celebrated for its breathtaking coastline. Here, we'll enter the stunning region of Cinque Terre, a UNESCO World Heritage Site. This charming area is made up of five villages, renowned for their scenic beauty and unique charm, and remain largely unconnected by road but thrive through tourism. Our journey will take us by train to one of these beautiful towns, usually Vernazza, though on busier days, we may visit Manarola or Corniglia instead. You will have some leisure time to explore and enjoy lunch.
Afterwards, we continue our travels by train to Levanto before catching the bus to Genoa. In Genoa, you'll have the opportunity to wander and absorb the city's rich history, echoing its time as a powerful medieval republic. Please note, the train service to Cinque Terre is a standard commuter line, and during peak tourism periods, there may be standing room only as reservations are not available.
Day 16
Genoa to Milan
Today, we continue our Italian adventure by visiting Santa Margherita Ligure. From there, we'll take a boat to the glamorous Portofino, renowned for its picturesque harbour and vibrant atmosphere. You'll have some leisure time to wander the charming streets and soak in the breathtaking views.
After lunch, we make our way to Milan, Italy's fashion and culture capital, where you'll have free time to explore. We suggest a visit to the majestic Gothic cathedral in Piazza del Duomo and the elegant Galleria Vittorio Emanuele II. Please note that between 30th May and 2nd November, our bus access is restricted to Santa Margherita Ligure, and we will instead stop at Rapallo, another beautiful coastal town, for our boat journey to Portofino. Also, be aware that in adverse weather or winter conditions, the boat crossing may be unavailable.
Day 17
Italian Lakes & Verona
Today, we explore the enchanting Italian Lakes region, celebrated for its breathtaking landscapes. Our first destination is Lake Orta, situated in the charming village of Orta San Giulio. We will board a train to reach the medieval town centre before setting sail to the nearby Island of San Giulio. This picturesque isle is home to a serene monastery and offers a peaceful retreat.
Following our exploration, we'll continue to Lake Maggiore, stopping in the lovely town of Stresa. Here, you have the option to visit the Borromean Islands, with Isola Bella as a highlight, famed for its exquisite gardens and opulent palace (please note, these are closed during the winter months). Take some time for lunch and enjoy the views before we make our way to Verona, where the day's adventures conclude.
Day 18
Verona to Venice
You'll have time to explore the romantic city of Verona, renowned as the setting for Shakespeare's "Romeo and Juliet" and rich with historical and architectural wonders. Once you're ready, we'll depart for Venice, where we aim to arrive around 1:00 p.m.
A delightful boat trip to St. Mark’s Square is included, followed by a guided walking tour of the City of Canals, including a visit to see Murano glasswork. Afterwards, enjoy some free time to soak up Venice's unique atmosphere - perhaps you'd like to take a gondola ride through its serene waterways? Your accommodation for the night will be in the Mestre area, allowing you to easily access both Venice and its surrounding attractions.
Day 19
Venice
As our adventure concludes in Venice, relish a hearty breakfast as you reflect on the unforgettable experiences shared and the vibrant memories forged. While the journey officially ends today, the echoes of its remarkable moments will linger long after you bid farewell.
What's Included
Meals
Breakfasts: 1, 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 £3,780
- Save 13%Tuesday 20 Oct 2026to Saturday 7 Nov 20264 spaces of 65 left£4,335£3,780Best offer

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Essential trip information
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