18-35 travel
Take the match
Italy

Italy City Break

Start & end in Rome 5 days Up to 45

About this trip

Five days across central and northern Italy, starting and ending in Rome, taking in Assisi, Siena, Florence, Bologna, Padua and Venice along the way. It's a fully guided group trip that moves at an easy pace, built around the main historical and cultural sights rather than off-the-beaten-track exploring.

You'll walk through Assisi's basilica, see Siena's UNESCO-listed old town, and spend proper time in Florence taking in the Duomo and the Renaissance streets around it. A Tuscan lunch in Piazza Santa Croce and a Montepulciano wine tasting break up the sightseeing.

The trip closes in Venice, with a wander along the canals and a look at the Doge's Palace and the Bridge of Sighs, before heading back to Rome to finish.

What you'll do

  • Visit the Basilica of St Francis in Assisi, with frescoes by Giotto and Cimabue
  • Walk Siena's UNESCO-listed historic centre, home of the Palio horse race
  • See Florence's Duomo, Campanile and Baptistery
  • Eat a Tuscan lunch in Piazza Santa Croce
  • Taste Montepulciano wines
  • Explore Venice's canals, the Doge's Palace and the Bridge of Sighs
Good to know
  • Fast-paced — you cover Rome, Assisi, Siena, Florence, Bologna, Padua and Venice in five days
  • Easy going and fully guided, suited to families and those who prefer sights handled for them
What travellers actually say

Worth it if you get a good guide and accept mediocre food. Think twice if communication matters to you—logistics and pre-trip info are genuinely patchy.

  • Guide quality is wildly inconsistent: some brilliant and helpful, others ignored groups entirely or pressured tip talk for days.
  • Pre-trip communication is unreliable. Ticket requirements change without notice; Venice entry pass confusion common; optional tour costs in euros only.
  • Food is mediocre across the board—lunches particularly weak—though rare standout meals in Montepulciano and final dinners redeem slightly.
  • Multiple cities in five days genuinely works; staying two nights in same hotel beats nightly moves. Venice, Florence, Assisi all memorable.

Distilled from real traveller reviews on TourRadar — we don't edit out the bad bits.

Tour dupe
Same trip, less money
£224 less all-in
Best of Italy: Rome, Florence & Venice
4.4from £6805 days
The trade-off: same length, a different operator.
See the dupe
How it compares

The same-vibe trips, side by side — price, value per day, and how each is moving. Only we can lay two operators' trips out honestly.

Sorted by fit — never by who paid. Price moves and availability come from our own daily tracking.

Best month to go

Departing in Jul is cheapest — from £904, about 17% below the priciest month (Sep).

Jul
Aug
Sep
Oct

Getting there

Rome
One-way · arrive 26 Jul 26

Opens Trip.com, pre-filled — one-way so you can book your return whenever. Prices & booking shown there.

Where to stay

A night before your tour in Rome · 26 Jul27 Jul

Booked on their own sites, separate from your tour. We may earn a commission — it never changes your price.

Find my best match

More trips like this

Ranked on real fit — in case this one isn't quite yours.

Powered by TourRadar

Booked with the operator via TourRadar · we may earn a commission.

Want longer in Italy?

Working holidays, volunteering & more — £50 off with code 18TO35TRAVEL.

See all →

Powered by Global Work & Travel · we may earn a commission on bookings.