5 daysItaly City Break - 5 Days
Visits Rome, Assisi, Siena, Florence, Bologna and more.
RomeAssisiSienaFlorenceBolognaVeniceTuscanyMontepulciano
Italy Tours & Trips
Dreaming of Italy? Tell us when you want to travel, who is coming and what you enjoy, and our travel experts will design a tailor-made itinerary for you. Hotels, transport, guides and experiences are all taken care of.
Why book with TossnTrips
- ✓ Itineraries designed by Italy experts
- ✓ Free quote, no obligation
- ✓ 24/7 support while you travel
1Tell us your plans
Share your dates, group and interests in a couple of minutes.
2We design it for you
A travel expert builds a day-by-day itinerary around your trip.
3Travel with confidence
Hotels, transport and guides arranged, with support throughout.
Photos from Italy
Why travel to Italy?
Italy offers something for every kind of traveller, from well-known highlights such as Rome and Florence to quieter places worth discovering. A tailored itinerary lets you choose the mix that suits you.
Our team plans every detail around your dates, pace and interests, and is available 24/7 while you travel.
Popular Italy itineraries
Use these as inspiration. Every trip is tailor-made, so we will adjust the route, pace and hotels to suit you.
5 days8 daysWalking the Amalfi Coast 8 Days
Visits Bomerano, Amalfi, Naples, Mount Vesuvius, Pompeii and more.
BomeranoAmalfiNaplesMount VesuviusPompeiiRavelloPontoneCapriPositano
11 daysItalian Discovery 11 Days
Visits Rome, Assisi, Siena, Florence, Bologna and more.
RomeAssisiSienaFlorenceBolognaVeniceMontepulcianoPompeiiSorrento
5 days5-day Best of Italy: Rome, Florence & Venice
Visits Rome, Assisi, Siena, Florence, Bologna and more.
RomeAssisiSienaFlorenceBolognaVeniceMontepulciano
8 daysSicilian Secrets - Tour of Sicily 8 days
Visits Catania, Syracuse, Noto, Ragusa, Modica and more.
CataniaSyracuseNotoRagusaModicaPiazza ArmerinaAgrigentoMarsalaMonrealePalermoCefaluMount Etna
8 daysVenice & the Jewels of Veneto 8 Days
Visits Venice, Island of Mazzorbo, Burano, Chioggia.
VeniceIsland of MazzorboBuranoChioggia
4 daysDiscovering Taormina 4 Days
Visits Taormina, Mount Etna.
TaorminaMount Etna
7 daysVenice, Florence, Rome: signature 7 Days
Visits Venice, Florence, Rome.
VeniceFlorenceRome
Most popular places in Italy
Rome
Florence
Venice
Milan
Amalfi Coast
Tuscany
See Italy your way
Pick what you enjoy and we will build the trip around it.
Italy trips for every type of group
Italy itineraries by length
Italy trip FAQs
Contact our Italy travel experts
Our team has planned trips to Italy and knows the places worth your time. Tell us what you have in mind and we will send you a tailored itinerary, free of charge.
- ✓ Personal itinerary built around you
- ✓ Free quote, no obligation to book
- ✓ Support 24/7, before and during your trip