Tuscany Walking and Wine

8 days
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4.6/5 Excellent
100+ reviews  
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Small Group Tour
A walking holiday that takes in the splendours of southern Tuscany, an iconic landscape of a rolling hills, avenues of cypress trees and medieval hilltop towns. Ramble through the vineyards of Chianti, along ancient pilgrimage trails and explore the captivating cities of Siena and Florence. Wine tastings - Sample some of Italy's finest wines from Chianti t...
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$2,854
From$2,690
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Overview

Trip type
Small Group Tour
Lodging level
Premium - 4 star

Highlights

    • Enjoy short walks in the classic rolling landscapes of southern Tuscany
    • Spend time in historic hill-top towns and cities of Florence and Siena
    • Enjoy wine tastings and delicious Tuscan cuisine

What's this trip about?

    A walking holiday that takes in the splendours of southern Tuscany, an iconic landscape of a rolling hills, avenues of cypress trees and medieval hilltop towns. Ramble through the vineyards of Chianti, along ancient pilgrimage trails and explore the captivating cities of Siena and Florence. Wine tastings - Sample some of Italy's finest wines from Chianti to Brunello Hilltop towns - Discover San Gimignano, Pienza and Montalcino Local cuisine - Enjoy the fresh produce and delicious flavours of Tuscany

Details

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

Destinations

Attractions

  • Pisa
  • Rome
  • San Gimignano
  • Siena
  • Tuscany

Max Group Size

  • Max Group Size: 20

Itinerary

Travel Map

Day 1 Trip starts today in Pisa

The trip starts today in Pisa at our centrally located hotel. The city's famous leaning tower and beautiful Campo del Miracoli are stunning testaments to a time when Pisa was 1 of the Mediterranean's major maritime powers. Your Tour Leader plans to meet everyone at t...

Day 2 Walk to the hilltop town of San Gimignano; enjoy a wine tasting before driving to Castellina in Chianti

This morning we drive towards San Gimignano, parking our bus in the rolling countryside outside of the town. We set off on a hike along part of the Via Francigena cycle trail,(the Via Francigena is an ancient pilgrimage route running all the way from Canterbury to Rom...

Day 3 Hike along white gravel tracks typical of Tuscany; visit a winery for lunch and a tasting of Chianti wines

We head out from our hotel after breakfast this morning on an undulating route that takes us through the countryside south from Castellina past vineyards, fields and olive groves. Much of the trail is on 'strade bianchi', the rural backroads that wind their way across...

Day 4 Visit medieval Siena on market day; drive to Pienza in southern Tuscany

Our final destination today is Pienza in southern Tuscany, but we will stop for most of the day in the fabulous medieval city of Siena where our time is free to explore the Wednesday market and other sights. With its magnificent Gothic architecture, Siena was once a ...

Day 5 Take a panoramic walk from Pienza; optional cheese tasting

Our walk today makes a panoramic loop through the stunning countryside around Pienza and is known locally as the 'Gladiator hike' as scenes from that movie were filmed here. Along the route we pass by the iconic Vitaleta chapel, a tiny, secluded building perched on a ...

Day 6 Hike in the Val D'Orcia from San Quorico D'Orcia to hilltop Montalcino

Today we drive from Pienza to San Quirico D'Orcia a beautiful town that lies along the Via Francigena pilgrimage route. We'll have time for a look around here, before we set out on our walk. Descending from the town we cross the Asso river and follow undulating trails...

Day 7 Drive to Florence; orientation walk and free time to explore this fabulous city

Leaving the rolling hills of southern Tuscany behind we head for our final destination of the holiday, the fabulous city of Florence. The spiritual home of the Renaissance, Florence is considered by many to be 1 of the most beautiful cities in Italy. On arrival our le...

Day 8 Trip ends in Florence

The trip ends after breakfast this morning at our hotel in Florence. There are no actvities planned for today and you are free to depart at any time. If you are departing later in the day luggage storage facilities are available at our hotel. If you would like ...

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Dates & Availability

Price From $2,690
Price per day$336
Last Updated: 3/15/2025
Departure Date
Finish Date
Base Price
Single Room (Optional)
Availability
08 Jun 2025
15 Jun 2025
$2,690
$3,290
31 Aug 2025
07 Sep 2025
$2,690
$3,290
21 Sep 2025
28 Sep 2025
$2,900
$3,500
05 Oct 2025
12 Oct 2025
$2,690
$3,290
12 Apr 2026
19 Apr 2026
$3,050
$3,830
10 May 2026
17 May 2026
$3,050
$3,830
24 May 2026
31 May 2026
$3,050
$3,830
07 Jun 2026
14 Jun 2026
$2,840
$3,430
06 Sep 2026
13 Sep 2026
$2,840
$3,430
13 Sep 2026
20 Sep 2026
$3,050
$3,830

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

Oct 2024

Written on

Tuscany Walking and Wine

An excellent Tuscan holiday, packing a lot in, including Pisa, Siena and Florence, along with some excellent walking and wine, of course. Highlights for us were sta...

I

Iris

Oct 2024

Written on

Tuscany Walking and Wine

Gorgeous scenery! Very special area. I absolutely loved the towns on sites on the tour! Entire trip was good. Gionata a fabulous guide and very conscientious. He hel...

T

Trusted Customer

Oct 2024

Written on

Tuscany Walking and Wine

Want to explore Tuscany without a rushed itinerary? Want a small group? Want to hike to wineries and hill towns? Stay in interesting hotels that are hundreds of year...

T

Trusted Customer

Sep 2024

Written on

Tuscany Walking and Wine

An excellent holiday if you like walking beautiful countryside good company and food. The hilltop towns are stunning. A great mix of activity and history and a know...

Write a Review

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Logistics

Accommodation

Transportation & Flights

Minibus, Train,

Transportation & flights

Minibus, Train
Guides
Explore Tour Leader
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 and Canadian citizens. Other nationalities should consult their local embassy or consular office.
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
  • Lunch : 2
Age Requirements
16 to 85 years
Additional Information
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Trip ID
explore-LTY

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