A Taste of Tuscany - Hilltop Towns and Vineyards

8 days
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4.6/5 Excellent
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Small Group Tour
Take in the splendours of southern Tuscany, an iconic landscape of rolling hills, avenues of cypress trees and medieval villages on this cultural highlights tour with a foodie focus. Explore the captivating city of Siena, take a tour through the vineyards and olive groves of Chianti and taste your way around the hilltop towns of Montalcino, Pienza and San Gim...
$362 OFF
$3,272
From$2,910
See departure dates

Overview

Trip type
Small Group Tour
Lodging level
Premium - 4 star
Physical level
Moderate

Highlights

    • Sample some of Italy's finest wines and dine on delicious Tuscan regional specialites
    • Explore captivating hilltop towns, Medieval San Gimignano and Siena
    • Visits to food and wine producers and tasting fresh produce at source

What's this trip about?

    Take in the splendours of southern Tuscany, an iconic landscape of rolling hills, avenues of cypress trees and medieval villages on this cultural highlights tour with a foodie focus. Explore the captivating city of Siena, take a tour through the vineyards and olive groves of Chianti and taste your way around the hilltop towns of Montalcino, Pienza and San Gimignano. Val d'Orcia - Visit medieval hilltop towns set amongst a landscape of rolling hills and vineyards, stopping to enjoy wine tasting and tasting local dishes Wine tastings - Sample some of Italy's finest wines from Chianti to Brunello Farm to table dining - Visit agriturismi to enjoy fresh produce and delicious flavours at their source

Details

Itinerary focusOff the Beaten Path
Group sizeSmall Group - max of 20 people
Age range16 to 85 years
Flights and transport
Start CityPisa
End CityPisa Airport

Travel Themes

  • Cultural
  • Hiking & Walking

Destinations

Attractions

  • Pisa
  • Rome
  • San Gimignano
  • Siena
  • Tuscany

Activities

  • Hiking

Max Group Size

  • Max Group Size: 20

Itinerary

Travel Map

Day 1 Join trip in Pisa; orientation tour followed by welcome dinner

The trip starts today in Pisa at our centrally located hotel. Your tour leader plans to meet everyone at the hotel reception for a welcome meeting today at 6.30pm. After the meeting we'll head out on a brief orientation stroll taking in the beautiful Campo del Miracol...

Day 2 Central Market tour in Livorno with street food lunch. Visit hilltop Montalcino, optional tasting of Brunello wines

We head off after breakfast to the port city of Livorno, around 45 minutes drive from Pisa. Livorno is known for its seafood, its Renaissance-era fortifications and the canal-laced Venezia Nuova quarter. We'll spend time exploring the huge Neoclassical Central Market,...

Day 3 Ramble to agriturismo for lunch of local organic produce; cheese-tasting in Pienza

We'll take in the stunning Tuscan countryside today on a hike (approximately three kilometres, one hour) to a nearby farm, Pieve a Salti. With over 700 hectares given over to organic cereal production ( crops include oats, spelt, wheat and pulses) and a herd of cattle...

Day 4 Guided walking tour in Siena; pasticerria and pasta shop visits

We've a full day today to enjoy the fabulous medieval city of Siena. With its magnificent Gothic architecture, Siena was once a rival to Florence in power and trade, the city controlled the trade routes between France and Rome as well as the southern Tuscan wool indus...

Day 5 Wine estate tour and tasting in Chianti; optional olive oil tasting

This morning we head to the magnificent Ricasoli Wine Estate, centred around the medieval Brolio Castle. The cellars are located at the foot of the castle and we'll enjoy a tasting here following our estate tour. Castelli di Brolio is the flagship chianti classico win...

Day 6 Farm tour and lunch at an agriturismo; visit to Medieval Volterra

This morning we head to the Fattoria Lischeto farm in the countryside close to the medieval walled town of Volterra. The 240 hectare farm was established by Giovanni Canas in the 1980s and is known for its cheeses, made from the milk of the 800 plus sheep that graze h...

Day 7 Free morning in San Gimignano; gelateria visit, cooking class and farewell supper

This morning has been left free to enjoy San Gimignano. You may like to climb to the top of the Torre Grossa, the tallest of the town's towers. Originally there were 72 towers , some as tall as 50 metres, each built by San Gimignano's patriarch families in a competiti...

Day 8 Drive to Pisa Airport where the trip ends

Departing San Gimignano this morning we drive to Pisa Galileo Galilei International Airport (PSA) where the tour ends at 8.00 am. The earliest time you should book a flight to depart today is 10.00 am. If you have time to pass before your flight departs, there is an i...

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Dates & Availability

Price From $2,910
Price per day$364
Last Updated: 3/14/2025
Departure Date
Finish Date
Base Price
Single Room (Optional)
Availability
04 May 2025
11 May 2025
$3,460
$520
18 May 2025
25 May 2025
$3,460
$520
15 Jun 2025
22 Jun 2025
$2,910
$510
20 Jul 2025
27 Jul 2025
$3,390
$520
14 Sep 2025
21 Sep 2025
$3,050
$510
28 Sep 2025
05 Oct 2025
$3,050
$510
12 Oct 2025
19 Oct 2025
$3,320
$520
03 May 2026
10 May 2026
$3,110
$540
10 May 2026
17 May 2026
$3,110
$540
14 Jun 2026
21 Jun 2026
$3,110
$540

Check current availability, prices, specials & more.

The total tour cost includes the tour price (regular or promotional) and the compulsory local payment. The promotional price is subject to change. Check directly with the operator for the latest price offer. The tour operator requires you to pay only the tour price to purchase your travel. The compulsory local payment will be paid when you join the trip. All prices are based on double, twin or triple share occupancy. Solo passengers will be accommodated in a double, twin or triple room according to availability with a passenger(s) of the same gender. Single supplement only needs to be paid if the passenger does not want to share and requests their own room. Discounts can only be applied at the time of booking and cannot be added at a later date, regardless of any changes made to the original booking.

Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

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Explore! Reviews & Ratings

4.6/5  Excellent
Excellent
10,321
Great
3,322
Average
522
Disappointing
158
Terrible
79
T

Trusted Customer

Jun 2024

Written on

A Taste of Tuscany - Hilltop Towns and Vineyards

Great host, good company, beautiful scenery, medieval towns with lots of interesting restaurants,. All the tasting experiences were worthwhile, the optional oil tast...

T

Trusted Customer

Jun 2024

Written on

A Taste of Tuscany - Hilltop Towns and Vineyards

The tour delivers on its promise to provide an authentic experience of the towns, wines, and cuisine of Tuscany. It is well-paced with a nice balance of group activi...

H

Helen Furlong

Jun 2024

Written on

A Taste of Tuscany - Hilltop Towns and Vineyards

Super holiday with so much to see. Seamless organisation. Claudio a super driver and Esther our tour leader was very good indeed plus lots of fun. Plentiful wine and...

T

Trusted Customer

May 2024

Written on

A Taste of Tuscany - Hilltop Towns and Vineyards

This was a well paced trip around a beautiful part of Italy. Esther, our guide was excellent. She was welll organised, good fun and efficient. Lots of the ‘tastings’...

Write a Review

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Logistics

Accommodation

Transportation & Flights

Bus,

Transportation & flights

Bus
Guides
Driver(s), Local Guide(s)
Cancellation policy
These conditions are applicable to Discovery & Wildlife, Cycling, Walking and Family Trips. These conditions were updated November 2022. Booked a Polar trip? Please refer to our Polar booking conditions. To make it easy to know the detail of our flexibility, we’ve put it in a grid (these terms apply to all trips apart from our Polar Voyages.) Standard cancellations or changes within 69 days of travel If you’re getting closer to your trip, cancellation charges will apply as follows: For trips confirmed by 31st December 2022: 59-42 days before trip start date – 30%, or loss of deposit if higher 41-28 days before trip start date – 60% 27-14 days before trip start date – 90% Less than 14 days before trip start date – 100% For trips confirmed from 1st January 2023: 69 -42 days before trip start date – 30%, or loss of deposit if higher 41-28 days before trip start date – 60% 27-14 days before trip start date – 90% Less than 14 days before trip start date – 100%
Travel Insurance
We strongly recommend purchasing travel insurance alongside your travel package to safeguard against unforeseen circumstances such as medical expenses, trip cancellations, and other contingencies. It offers you peace of mind and ensures you are prepared for unexpected events that may occur before or during your journey
Visa requirements
Italy: Visas are not required by UK, E.U. Nationals, Australian, New Zealand, US or Canadian citizens. Other nationalities should consult their local embassy or consular office. All visa information is subject to change. You should confirm all visa related questions with the relevant embassy prior to departure.
Health & Safety
Nothing required. Tetanus recommended. Please check the latest requirements with your travel clinic or doctor prior to departure. The above is not an exhaustive list. Further information regarding vaccinations and travel health advice can be found by following the NHS and NaTHNaC links at <a href="https://www.explore.co.uk/essential-information/know-before-you-go/travel-health">Explore Travel Health</a> and from your local healthcare provider. Visa and vaccination requirements are subject to change and should be confirmed by you before travelling.
Meals Included
  • Breakfast : 7
  • Dinner : 2
  • Lunch : 3
Age Requirements
16 to 85 years
Additional Information
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Trip ID
explore-XTY

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