A luxury sightseeing trip to Italy

A luxury sightseeing trip to Italy is built from the top third of what is on offer: San Gimignano, Chianti and Montalcino Day Tour from Siena, Hot air balloon experience over Tuscany from Florence. Activities in this plan start from about $159.

What kind of trip
Pace
How long
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Price bands are thirds of what Italy itself charges, not a fixed dollar figure - the cheapest third in Vietnam and in Norway are nowhere near the same number. Flights and accommodation are not included.

Your 5-day sightseeing plan for Italy

Where you stayToscana 5 nights

5 days · packed · 12 of 12 bookable now · activities from about $7,113

  1. Day 1 Toscana

    1. San Gimignano, Chianti and Montalcino Day Tour from Siena in Siena, Italy

      morning

      San Gimignano, Chianti and Montalcino Day Tour from Siena

      Siena · from $226

    2. Hot air balloon experience over Tuscany from Florence in Toscana, Italy

      afternoon

      Hot air balloon experience over Tuscany from Florence

      Toscana · from $435

    3. Hot air balloon experience with breakfast from Siena in Toscana, Italy

      evening

      Hot air balloon experience with breakfast from Siena

      Toscana · from $564

  2. Day 2 Toscana

    1. Pisa and Lucca Private One-Day Tour from Florence in Pisa, Italy

      morning

      Pisa and Lucca Private One-Day Tour from Florence

      Pisa · from $1,273

    2. From Siena: Best of Tuscany Wines & Lunch in Montepulciano in Siena, Italy

      afternoon

      From Siena: Best of Tuscany Wines & Lunch in Montepulciano

      Siena · from $178

    3. Pisa, Siena and San Gimignano Tuscany tour from Florence with Traditional Lunch in Siena, Italy

      evening

      Pisa, Siena and San Gimignano Tuscany tour from Florence with Traditional Lunch

      Siena · from $263

  3. Day 3 Toscana

    1. Private hot air balloon flight experience in Tuscany in Toscana, Italy

      morning

      Private hot air balloon flight experience in Tuscany

      Toscana · from $2,819

    2. Hot air balloon flight experience over Tuscany from Lucca in Toscana, Italy

      afternoon

      Hot air balloon flight experience over Tuscany from Lucca

      Toscana · from $483

    Where to eat

    • Breakfast

      Loggia del Mercato Nuovo

      So called to distinguish it from the Mercato vecchio (pronounced [merˈkaːto ˈvɛkkjo]; "Old Market") that used to be located in the area of today's Piazza della Repubblica.

      Florence · 0.7 km away

    • Lunch

      Enoteca Pinchiorri

      Has been awarded three stars by the Michelin Guide in 1993 and 1994 and perennially since 2004.

      Florence · 0.1 km away

  4. Day 4 Toscana

    1. Pasta and tiramisu cooking class in Chianti in Toscana, Italy

      morningalso worth doing

      Pasta and tiramisu cooking class in Chianti

      Toscana · from $217

    2. Pasta and tiramisu cooking class in Montepulciano in Toscana, Italy

      afternoonalso worth doing

      Pasta and tiramisu cooking class in Montepulciano

      Toscana · from $208

  5. Day 5 Toscana

    1. Pasta and Tiramisu Class in Pisa in Pisa, Italy

      morningalso worth doing

      Pasta and Tiramisu Class in Pisa

      Pisa · from $159

    2. Pasta and tiramisu cooking class in Siena in Siena, Italy

      afternoonalso worth doing

      Pasta and tiramisu cooking class in Siena

      Siena · from $288

Prices are indicative and in Australian dollars. Flights and accommodation are not included. Distances between stops are straight-line, so a walking or driving route will be longer, and they are shown only where both stops have a known location. Items marked also worth doing sit outside the sightseeing theme and are there because they are among the best things to do in Italy.

Before you fly to Italy

The part an itinerary app leaves out. These are Italy's rules for Australian passport holders, re-read from the official source and dated below.

Entry

No - Australian passport holders can enter Italy without a visa for up to 90 days in any 180-day period.

Italy visa and entry rules

Passport

Italy wants 3 months of validity beyond the day you leave. A fare is non-refundable long before a passport renewal is.

Check your passport against this rule

Your checklist

22 things to sort for Italy, built from these same rules, 3 of them essential.

Italy travel checklist

  • Passport valid - valid for at least 3 months beyond your planned departure from the schengen area, and issued within the last 10 years
  • Take out travel insurance
  • Get an International Driving Permit

Last reviewed 2026-10-24. Entry requirements change without notice. Always confirm with the official sources below before you book or fly.

Sort these before you go

The two things worth having arranged before a sightseeing trip to Italy, compared on price.

Italy airport transfers

FL1 regional train Cheapest

Cheaper but doesn't go to Termini - good for Trastevere and Ostiense.

45-55 minEvery 15 minDirect
$14 AUD

Leonardo Express Fastest

Non-stop to Roma Termini. Validate your ticket before boarding.

32 minEvery 15 minDirect
$25 AUD

Fixed-fare official taxi

A regulated flat fare of €55 applies to anywhere inside the Aurelian walls. Only use the official white taxi rank.

45-70 min24/7Door-to-door
$90 AUD

Driving in Italy

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Luxury sightseeing questions

What makes an activity luxury in this plan?

Price, measured against the rest of that country - the top third of what is worth doing there. It is not a hotel rating and it does not include flights or accommodation, both of which usually dwarf the activities.

Is the expensive option always better?

Often it buys time rather than quality: a private guide, a skip-the-queue entry, a small group instead of a coach. Everything here is still ranked on its review score first, so a luxury plan is the best-reviewed expensive things, not simply the dearest.

Are the big landmarks worth the queue?

Some are, some are not, and the difference is usually timing rather than the place. Where a timed ticket exists the plan flags it, because the same sight at nine in the morning and at midday are different experiences.

How much sightseeing needs a car?

It depends on the destination, and the plan tells you which items sit outside the main city. If you are driving, check the International Driving Permit rules for the country first - several require one alongside your Australian licence.

Other ways to do Italy

Sightseeing trips in other countries

Still deciding where to go? These are built the same way - real activities, in an order that works, with the entry rules for Australians attached.

All sightseeing itineraries

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