From

US $2,250 per person

Florence & Tuscany Explorer - 5 days

5 days

•

Start and end in Florence

4.6 (2,649 reviews)

Florence & Tuscany Explorer - 5 days - On The Go Tours

From

US $2,250 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Booking needs min. 2 travelers

Select departure month

1 Adult2 Adults, 1 Child2 Children

Pay only $400 today. The rest is due 70 days before departure. Learn more

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Plan your adventure:

Platinum Operator: On The Go Tours
City & Culture: Immerse yourself in rich history and local traditions
Group Tour: Join a group and forge lifelong friendships
Partially Guided: Independent travel, featuring selected guided excursions
Low Intensity: Travelers can expect some light physical activities
Guided in English
Group Size 4 - 24
All Ages Welcome

Image of a map showing the route of the tour

Itinerary

Intro
Introduction
Day 1
Florence
Florence
Included Activities
- Orientation walk of Florence including Duomo, Piazza della Signoria, and Ponte Vecchio
Optional Activities
- Dinner at a traditional trattoria
- Florentine aperitivo with spritz and regional specialities
Landmarks
Duomo
Piazza della Signoria
Ponte Vecchio
Day 2
Florence
Florence
Meals
Breakfast
Optional Activities
- Visit Florence's iconic sights (galleries, museums, landmarks)
- Browse artisan boutiques
- Explore historic centre at leisure
Day 3
Florence - Siena - Cortona - Montepulciano - San Gimignano
Florence - Siena - Cortona - Montepulciano - San Gimignano
Meals
Breakfast, Lunch (Food tasting at a local farm in Montepulciano)
Included Activities
- Group tour of Siena, Cortona & Montepulciano
- Stroll through medieval streets of Siena to Piazza del Campo
- Visit Siena's Gothic cathedral
- Browse artisan shops in Cortona
- Food tasting at a local farm in Montepulciano
- Explore Montepulciano at leisure with views over Val d'Orcia
Optional Activities
- Additional exploration of Siena's historic streets
- Extended time in Cortona for artisan shopping
- Wine tastings in Montepulciano beyond the included tour
Landmarks
Piazza del Campo
Siena Cathedral
Cortona
Val di Chiana
Lake Trasimeno
Montepulciano
Val d'Orcia
San Gimignano
Day 4
San Gimignano - Chianti Wine Country
San Gimignano - Chianti Wine Country
Meals
Breakfast
Included Activities
- Chianti region group tour with wine and olive oil tasting in two wineries
- Guided tasting of Chianti wines paired with regional specialties
- Meet and learn from passionate local winemakers
- Sample award-winning wines at a family-run estate in Chianti
Optional Activities
- Extended exploration of Chianti region
- Additional wine purchases from wineries
- Explore San Gimignano at leisure in the afternoon
Landmarks
Chianti Region
Day 5
San Gimignano - Florence
San Gimignano - Florence
Meals
Breakfast, Lunch (Meal prepared during hands-on cooking class accompanied by local wine)
Included Activities
- Hands-on Tuscan cooking class with a local chef
- Learn to prepare traditional regional dishes

Landmarks
Duomo
Piazza della Signoria
Ponte Vecchio

Landmarks
Piazza del Campo
Siena Cathedral
Cortona
Val di Chiana
Lake Trasimeno
Montepulciano
Val d'Orcia
San Gimignano

Landmarks
Chianti Region

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What's Included

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Accommodation
Guide
Meals
Additional Services
Transport

What's Not Included

Flights
Additional Services

Operated by

On The Go Tours

Platinum Operator

Rating: 4.6 (2,649 reviews)
Response time: within 1 day
Response rate: 68%
Cancellation policy: Learn more

Reviews from other tours by On The Go Tours

Tour Operator
4.6

Matthias4.0•October 2026
All the transfers went smoothly, the city tour was interesting, the hotel was centrally located, and the rooms were...
Show more
Melissa5.0•October 2026
We booked through Tour Radar and then thought we were using On The Go Tours. When we arrived in Milan we learned that...
Show more
Pam4.0•October 2026
We had a good time. I think giving better directions to the Hop on-hop off bus would have been a big help. There are...
We had a good time. I think giving better directions to the Hop on-hop off bus would have been a big help. There are several different companies in Rome. Also let people know about the subway. We found it to be exceptional and had we known about it day one our trip would have had a much smoother start. Contracting to another company was interesting. We had 53 on our bus, it slowed everything down and limited our time in stop locations. With that many people, getting food served took forever and getting people through the bathroom stops was a challenge. Also there was no bathroom on the bus. The Raffaello in Florence was a dump! I would give it 2 stars. The first room stunk like someone threw up or meat was left spoiling in it. They did change our room but the hotel on a whole needs a good deep cleaning and updating. The breakfast was horrible, the coffee (made in a machine) was more tea like than coffee, the staff was split 50/50 on politeness. Day two we went to a local cafe for breakfast because when we went to get coffee we saw no improvement from the day before and the breakfast was not worth it. One other thing we thought, when we stopped for shorter stops we would have preferred the option to break away from the group and be given a meet up time & location. I don't remember the stop but we really wanted to explore more of the little town but sticking with the group we got to see the town square... wasn't horrible but it wasn't a spot I would have chosen to spend my time. The shops were calling our name and we didn't have time to stop in them after the long walk to the square. Over all it was a good trip.Show more

Dates & Prices

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1 Adult2 Adults, 1 Child2 Children

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23 Oct, 2026
To Tuesday
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To Tuesday
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To Saturday
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20 Nov, 2026
To Tuesday
24 Nov, 2026
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From Tuesday
24 Nov, 2026
To Saturday
28 Nov, 2026
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From:
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Price based on Private Double Room

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Trip essentials

Good to know

Tour ID: 354981

The practical details for your trip across Italy: money, plugs and flexible ways to pay, all in one place.

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Pay in installments
Spread the cost in interest-free biweekly installments of $113.
Deposit only
Book now with just a $400 deposit. The remaining balance is due 70 days before departure.
€ - Euro
You’ll encounter Euro in Italy.
Plug type L
You’ll need an adapter for these sockets in Italy.

Currency
€
Euro
Italy
Plugs & adapters
As a traveler from USA, Canada, England, Australia, New Zealand, South Africa you will need an adaptor for type L.
- Type L
  Used in Italy
Visa
Whether you need a visa depends on your nationality and how long you stay. We can’t process visas for you, but here’s a quick indication for this trip.
This is only an indication. Visa rules depend on your passport, trip length and purpose. Always confirm with the official embassy or consulate before you travel.
Payment information
Pay now
A $400 deposit
Balance due
70 days before departure
Installments
Interest-free, every two weeks
Currency
USD
Booking fee
None
Book now with just a $400 deposit and pay the rest later. The remaining balance is due 70 days before departure, charged automatically to your card, or you can split it into interest-free biweekly installments of $113 at checkout. Everything is charged in USD, and TourRadar never adds a booking fee. Any trip departing before December 29th, 2026 will need to be paid in full at checkout.
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Insurance
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From

US $2,250 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Booking needs min. 2 travelers

Select departure month

1 Adult2 Adults, 1 Child2 Children

Pay only $400 today. The rest is due 70 days before departure. Learn more

Best price guarantee Learn More

Plan your adventure:

Florence & Tuscany Explorer - 5 days

Itinerary

Included Activities

Optional Activities

Optional Activities

Included Activities

Optional Activities

Included Activities

Optional Activities

Included Activities

Want to read it later?

Explore our featured adventures

What's Included

What's Not Included

Reviews from other tours by On The Go Tours

Dates & Prices

Want to read it later?

Why book with TourRadar?

Pay in installments

Deposit only

€ - Euro

Plug type L

Currency

Plugs & adapters

Visa

Payment information

Accepted for On The Go Tours tours

Cancellation Policy

Insurance

Best price guarantee

How it works

Your quote needs

What doesn’t count

Accessibility

People also viewed

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