Enchanted Journey Through Italy's Heritage
Start location – Rome End location – Rome Total number of days – 21 Key experiences or destinations – Rome and the Vatican; Capri and Sorrento; Matera and Alberobello; Sicily’s Taormina and Palermo; Tuscany with Siena, San Gimignano and Florence; Pisa and the Cinque Terre; Portofino and Genoa; Milan and the Italian Lakes; Verona and Venice; San Marino and Perugia. Begin and end in Rome on a 21–day circuit of Italy – a brilliant blend of classics and coastal charm. You’ll explore Rome’s ancient icons, then head south for Lecce’s baroque beauty, Alberobello’s trulli and Matera’s cave dwellings. Sail to Capri, linger in Sorrento and hop over to Sicily for Etna views, Taormina’s terraces and Palermo’s golden mosaics. Back north, you’ll visit Tuscan hill towns and Florence, see Pisa’s Leaning Tower, ride the Cinque Terre trains and cruise to Portofino. Expect Milan’s style, peaceful lakes, romantic Venice and storied Verona – with a dash of San Marino and medieval Perugia.
For a detailed itinerary and information about visas, money, weather and more.
Tour Overview
Duration
21 daysHotel Rating
4 star hotelsStarts
RomeEnds
RomeMinimum Age
No minimum ageMaximum Age
Tours have upper age limits for several reasons, such as but not limited to: tour pace, activity level, and accommodation standards. If you fall outside of this age limit, we do have lots of other tours in Italy that are suitable for all ages!
Arrival Transfer
YesDeparture Transfer
NoTour Guide
Yes - English speaking guides (guiding may be in additional languages to English)Country
ItalyPassengers
$5,236.00
$400.00
Tour Style
Group Size
Min 2 / Max 65
Trip Type
Large Coach Tours
Range
This tour is operated by our trusted local partner and has been handpicked by us to deliver you an unforgettable trip.
Guiding Style
This tour includes scheduled sightseeing with expert guides in key destinations as per the Inclusions, as well as transportation (either with a driver or public transport), plus of course your accommodation. There is no single tour guide or tour leader throughout the trip. You’ll have support where it counts, and more freedom in between. Our cruise tours also fall into this category where you will be looked after by a crew. For more information, check the Inclusions of this tour.
Tour Pace
A balanced pace, with a mix of free time and visits to multiple locations, allowing for both relaxation and exploration. Generally doesn't visit more than one or two destinations per day.
Physical Rating
A moderate amount of walking is required during sightseeing, with some free time, offering a balance between activity and relaxation. As a general rule, you should be able to walk 2-kilometres without stopping.
Tour Guide
Yes - English speaking guides (guiding may be in additional languages to English)Group Size
Min 2 / Max 65Range
This tour is operated by our trusted local partner and has been handpicked by us to deliver you an unforgettable trip.
Guiding Style
This tour includes scheduled sightseeing with expert guides in key destinations as per the Inclusions, as well as transportation (either with a driver or public transport), plus of course your accommodation. There is no single tour guide or tour leader throughout the trip. You’ll have support where it counts, and more freedom in between. Our cruise tours also fall into this category where you will be looked after by a crew. For more information, check the Inclusions of this tour.
Tour Pace
A balanced pace, with a mix of free time and visits to multiple locations, allowing for both relaxation and exploration. Generally doesn't visit more than one or two destinations per day.
Physical Rating
A moderate amount of walking is required during sightseeing, with some free time, offering a balance between activity and relaxation. As a general rule, you should be able to walk 2-kilometres without stopping.
Trip Type
Large Coach ToursPlaces You'll See
Rome
San giovanni in venere abbey
Termoli
Bari
Brindisi
Lecce
Gallipoli
Alberobello
Matera
Naples
Capri
Sorrento
Salerno
Paola
Mesina
Taormina
Caltagirone
Villa Romana del Casale
Palermo
Orvieto
Castiglione del Lago
Siena
Monteriggioni
San Gimignano
Florence
Pisa
Cinque Terre
Genoa
Portofino
Milan
Lakes Region
Verona
Venice
Padua
San Marino
Gubbio
Perugia
Assisi
Included
Not Included
Itinerary
Day 1 - Rome
Welcome to Rome. On arrival, we’ll transfer you to your hotel, and you’ll have free time to settle in or start exploring at your own pace. In the afternoon, please check the information boards at hotel reception for details about the start of your tour.
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
This morning we’ll take a guided tour of Rome lasting around three hours – combining a walk through Imperial Rome with a panoramic coach drive to admire one of the oldest and most influential cities in the West. We’ll see the Arch of Constantine, the exterior of the Colosseum and the Imperial Forums, the Circus Maximus, the Baths of Caracalla, the Basilica of Saint Mary Major, the Pyramid of Cestius and Castel Sant’Angelo. The tour ends at Vatican City at around 11:00. Afterward, you can join an optional visit to the Vatican Museums and the Sistine Chapel with our guide. In the evening, we include a transfer from the hotel to Trastevere – known for its cosy restaurants and lively atmosphere – with return to the hotel at around 20:30.
Day 3 - Rome
Enjoy a full free day in Rome to explore at your own pace – there are no scheduled group activities today. You can continue wandering its historic streets, seek out hidden corners and linger wherever you like, making the most of the city in your own time.
Day 4 - Rome - San giovanni in venere abbey - Termoli - Bari
Leaving Rome, we travel east across the Apennines to the Adriatic. Our first stop is the San Giovanni in Venere Abbey – an 11th–century complex built on the remains of a Roman temple – with admission included. We continue to Termoli, a coastal city where the beach is framed by a walled old town dominated by a 13th–century castle and a Romanesque cathedral; you’ll have time for lunch and a leisurely walk. We then carry on to Bari, a historic port settled before Roman times, where you can explore the old town’s narrow streets and churches at your own pace.
Day 5 - Bari - Brindisi - Lecce - Gallipoli - Brindisi
We follow the Adriatic coast to Brindisi, a walled port city – you can stroll the seafront, admire the impressive Roman column and wander the old quarter. We then continue to Lecce, renowned for its elegant baroque architecture and often called the Florence of the South. You’ll have time to explore the historic centre and find lunch. In the afternoon, we visit Gallipoli on the Ionian Sea, founded by the Greeks and later shaped by Arab, Norman and Aragonese influences. Its old town – linked to the mainland by a 17th–century bridge – is a maze of narrow streets and historic buildings, including the cathedral, the castle and the ancient city walls. We return to Brindisi at the end of the day for accommodation.
Day 6 - Brindisi - Alberobello - Matera - Naples
We leave Brindisi to explore two remarkable towns. Our first stop is Alberobello, famed for its conical trulli – distinctive dry‑stone houses with stacked roofs and a UNESCO World Heritage Site. We then continue to Matera in Basilicata to discover the Sassi di Matera, an ancient complex of rock‑hewn dwellings and churches that form one of the world’s oldest continuously inhabited urban settlements. Lunch in Matera is included.In the afternoon we travel through the mountain landscapes of Basilicata and Campania, arriving in Naples by evening – you’ll have free time to explore once we get there.
Day 7 - Naples - Capri - Sorrento - Salerno
After breakfast, we head to the port of Naples and board the ferry to Capri. On arrival, you can take the funicular up to Capri town to stroll and enjoy the views. After lunch, we reboard for Sorrento – a charming town at the base of a cliff – where you’ll have free time to wander. We then continue to the Gulf of Salerno and stay in the city of Salerno.
Day 8 - Salerno - Paola - Mesina - Taormina
We travel south through southern Italy, crossing the landscapes of Cilento National Park, before arriving in Paola on the Tyrrhenian coast. We visit the Sanctuary of Saint Francis of Paola, then you have free time for lunch in the historic centre. We continue to Villa San Giovanni to board a short ferry across to Sicily. On arrival in Messina, you’ll have a little time to wander by the cathedral before we continue to Taormina. Dinner is included. Accommodation is normally in the Taormina area – on certain dates it may be in Messina.
Day 9 - Taormina - Giardini Naxos - Villa Romana del Casale - Palermo
At the foot of Mount Etna, we begin with an early drive to Giardini Naxos – the first Greek settlement in Sicily, founded in 734 BC – where you can enjoy the seafront promenade and beaches. We then continue to Taormina, described by Churchill as the most beautiful place on earth. You’ll have time to wander its lively old town and admire the views towards the ancient Greek Theatre.After lunch, we continue to the Villa Romana del Casale – admission and guided tour included – a UNESCO World Heritage Site renowned for its 4th–century layout and outstanding Roman mosaics preserved across almost every room.We then cross the island’s mountainous interior to reach Palermo towards the end of the day. Dinner is included.
Day 10 - Palermo
We embark on a guided tour of Palermo with a local expert, taking in the cathedral – entry included – renowned for its blend of architectural styles and royal tombs. We continue to the Palazzo dei Normanni – the former royal palace – along with the surrounding fountains, markets and gardens. We then head to Monreale to visit its cathedral – entry included – a UNESCO World Heritage Site celebrated for its extraordinary golden mosaics. The afternoon is yours to explore at your own pace. Note: For smaller groups, this tour may run as a regular shared excursion operated by local companies rather than a private tour.
Day 11 - Palermo - Rome
At the time advised by your guide, we’ll transfer you to Palermo airport for your included domestic flight to Rome. On arrival, we’ll provide a transfer to your hotel. Your guide will get in touch in the late afternoon, or you can consult the information at hotel reception. Note: on domestic flights the usual allowance is one suitcase of up to 20 kg in the hold – any excess luggage must be paid directly to the airline.
Day 12 - Rome - Orvieto - Castiglione del Lago - Siena
Today we travel through Umbria to Orvieto, a medieval city set high on a flat-topped hill. We pause at the viewpoint for panoramic views, then take the escalators up to the medieval centre to see the cathedral – a masterpiece of Italian Gothic. We continue to Castiglione del Lago on Lake Trasimeno, where you’ll have free time for a leisurely stroll and lunch. Afterwards we travel on to Siena in Tuscany and spend the afternoon there – renowned for Piazza del Campo and the Duomo.
Day 13 - Siena - Monteriggioni - San Gimignano - Florence
We leave Siena for Monteriggioni – a charming medieval village of cobbled lanes and ancient walls – before continuing to San Gimignano, famed for its striking medieval towers. You’ll have time for lunch at your own pace.After lunch we travel to Florence, arriving in the early afternoon at the Vittorio Veneto neighbourhood. Owing to city regulations on tourist buses, we disembark here and walk with our guide to the historic centre. You then have free time to enjoy the Florentine atmosphere – if you wish, visit a museum today as the major galleries are closed on Mondays. The Uffizi is often considered Italy’s finest art museum, while the Accademia houses Michelangelo’s original David. Dinner is included, and the transfer to the hotel is scheduled for 7.30 pm. Comfortable walking shoes are recommended.
Day 14 - Florence
We start at the Michelangelo viewpoint for sweeping city views – an ideal photo stop – before walking into the historic centre for a guided tour of Florence, the Tuscan capital and cradle of the Renaissance. We’ll take in the Gothic Cathedral – the Duomo di Firenze – the ancient Ponte Vecchio with its traditional goldsmiths’ shops, and Piazza della Signoria, the city’s political heart with its medieval town hall. After the tour, you’ll have free time to explore at your own pace. Comfortable walking shoes are recommended, as much of the visit is on foot.
Day 15 - Florence - Pisa - Cinque Terre - Genoa
We leave Florence for Pisa, where a small tourist train takes us to the Piazza dei Miracoli – home to the famous Leaning Tower. We then continue to the Ligurian Riviera to visit the Cinque Terre, a UNESCO World Heritage Site known for its dramatic coastline and five cliffside villages. We arrive by train – tickets included – at one of the villages, normally Vernazza, though on peak dates it may be Manarola or Corniglia. You’ll have time for lunch and a stroll. Afterwards, we take the train to Levanto and continue by coach to Genoa, where you’ll have free time to explore the historic centre – a reminder of the city’s power during the Middle Ages.Please note: the Cinque Terre trains are regular commuter services – there are no seat reservations, queues are possible and, at busy times, you may need to stand.
Day 16 - Genoa - Portofino - Milan
We leave Genoa for Santa Margherita Ligure, where we board the boat to Portofino. We’ll enjoy a relaxed seaside stroll and you’ll have free time to explore. After lunch, we continue to Milan, where you can wander at your own pace – we suggest visiting the Gothic cathedral in Piazza del Duomo and the Galleria Vittorio Emanuele II.From 30 May to 2 November, tourist buses cannot access Santa Margherita Ligure – during this period we stop in Rapallo to board the boat to Portofino. In adverse weather or during winter, the boat crossing to Portofino may not operate.
Day 17 - Milan - Lakes Region - Verona
From Milan, we venture into the Italian Lakes – one of Europe’s most scenic regions. Our first stop is Lake Orta and the charming town of Orta San Giulio. We take the train to the medieval centre, then a boat to tiny San Giulio Island to see its monastery. We continue to Lake Maggiore and pause in Stresa, where you can choose to visit the Borromean Islands – the highlight is Isola Bella with its palace and gardens (closed in winter). There will be time for lunch before we continue to Verona.
Day 18 - Verona - Venice
This morning we have time to explore Verona – the city of Romeo and Juliet – before travelling to Venice, arriving around 1 pm. We then take a boat to St Mark’s Square for a guided walking tour of the historic centre, including a visit to see Murano glasswork. You’ll have free time afterwards – perhaps take a gondola ride or simply wander the canals at your own pace. Accommodation is in the Mestre district.
Day 19 - Venice - Padua - San Marino - Gubbio - Perugia
We depart Venice for Padua, where we visit the Saint’s Basilica – an important place of pilgrimage. We then continue to San Marino, an independent country set on a fortified mountaintop. You’ll have time for lunch at leisure. In the afternoon we cross the Apennines to Gubbio, a well-preserved town noted for the Palace of the Consuls and its 12th century cathedral. We finish the day in Perugia.
Day 20 - Perugia - Assisi - Rome
This morning we take a panoramic tour of Perugia – the hilltop capital of Umbria and renowned for its chocolate – with a local guide. We ride the moving walkways up through the rocky hillside to the historic centre and explore its medieval underground city before continuing through stone paved streets and squares. Afterwards we travel to Rome, arriving in the afternoon.
Day 21 - Rome
After breakfast, our journey comes to an end – the tour concludes in Rome. We hope you depart with lasting memories of your time in Italy.
Tour Reviews
Extras and add-ons
If you'd like to add extras or add-ons to your booking, you can do this easily during checkout. Just review the available options and select any additional services or upgrades you'd like before completing your purchase.
Pre and Post Tour Accommodation
Extend your tour with us by booking pre and post-accommodation, available at a per-person, per-night rate.
Post-Tour Accommodation - Rome
Pre-Tour Accommodation - Rome
Hotels
The hotels listed below are examples which we frequently use on this tour. Alternative hotels of a similar standard may be used instead.
Confirmation of the hotels used may not be available until 48 hours before the tour departs.
If you are interested in booking pre or post-tour accommodation, here are some of the hotels we typically use.
Prices & Dates
Departure dates are guaranteed with 2 travellers. 'Double/Twin' prices are per person when there are 2 people on the same booking sharing a room. 'Single' prices are applicable to anyone wanting the privacy of their own room. 'Triple' prices are per person when there are 3 people on the same booking sharing a room. 'Shared' prices are for solo travellers who are happy to share with another solo traveller of the same sex in a twin room - a single room will be provided at no additional cost if there are no suitable travellers to share with.
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