Self-Guided Tuscan Trails - Florence to Siena

8 days
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Self-Guided / Independent Tour
Discover magnificent cities, picturesque villages and a landscape of rolling hills and vineyards on a self-guided walking holiday through Chianti country from Renaissance Florence to Medieval Siena. Hike along cypress-lined country roads and white gravel tracks, traversing forests of oak, beech and chestnut. Iconic cities - Explore Florence, cradle of the...

Overview

Trip type
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Trip pace
Full schedule

Highlights

    • Walk through iconic Tuscan landscapes of rolling hills, cypress avenues and vineyards
    • Explore fabulous Florence and Siena and medieval fortified towns
    • Enjoy the great wines and cuisine of Tuscany

What's this trip about?

    Discover magnificent cities, picturesque villages and a landscape of rolling hills and vineyards on a self-guided walking holiday through Chianti country from Renaissance Florence to Medieval Siena. Hike along cypress-lined country roads and white gravel tracks, traversing forests of oak, beech and chestnut. Iconic cities - Explore Florence, cradle of the Renaissance, and Medieval Siena with its imposing Piazza del Campo Medieval walls - Discover the fabulous fortified towns of San Gimignano and Monterissioni Food and wine - Taste the great wines and cuisine of Tuscany

Details

Itinerary focusClassic Highlights
Group sizeOperator does not provide
Age range30 years and up
Flights and transportN/A
Start CityFlorence
End CitySiena

Travel Themes

  • Cultural
  • Cycling & Biking
  • Hiking & Walking
  • Trekking & Expeditions

Destinations

  • Europe
  • Italy

Attractions

  • Pisa
  • Siena

Activities

  • Cycling
  • Hiking
  • Trekking

Popular Trips

Itinerary

Travel Map

Day 1 Trip starts in Florence

Your accommodation for the first two nights of your holiday is conveniently located in the heart of Florence. If you have time after checking-in, we recommend taking a walk around the city's magnificent squares and along the illustrious Arno River. This walk starts an...

Meals Provided :
None

Day 2 Walk from Settignano to Fiesole

After a twenty-five minute public bus ride to Settignano, your walk commences from this picturesque hillside village. Along your route, you will pass magnificent cypress trees, olive groves and Renaissance villas, with a view of Florence below you. Upon your arri...

Meals Provided :
Breakfast

Day 3 Transfer to Montespertoli; enjoy a circular walk

After breakfast, you take a private transfer by car to Montespertoli - a rustic market village set in the rolling green hills not far from Florence. Here, you will find your hospitable agritourismo accommodation that will be your base for the next two nights. Once you...

Meals Provided :
Breakfast

Day 4 Stroll through the Chianti Fiorentino area

Today's circular walk affords another opportunity to enjoy the picture-perfect landscape around Montespertoli. This time you walk south, through the Chianti Fiorentino area, passing by old parish churches and elegant country villas. You can expect today's 14 kilometre walk to take approximately four hours.

Meals Provided :
Breakfast

Day 5 Walk along the Via Francigena to San Gimignano

After breakfast, a short car transfer takes you to the village of Gambassi. From here, you will start your walk along the Via Francigena - a 700 year-old pilgrim route to Rome, which is thought to have originally started in Canterbury, England. The track affords spec...

Meals Provided :
Breakfast

Day 6 A choice of circular walks around San Gimignano

Today, you have the choice between two relatively gentle circular routes around San Gimignano. Both take you along cypress-lined country lanes and past vineyards and fields, taking in the picturesque hamlets of Monteauto and Santa Lucia. Depending on which route you choose, you can expect today's 10 and 14.5 kilometre walks to take approximately three and four and a half hours, respectively.

Meals Provided :
Breakfast

Day 7 Walk from Monteriggioni to Siena; explore the city

After breakfast, take a private transfer to the fortified village of Monteriggioni. From here, your walk takes you to the marvelous city of Siena, famous for its biannual "Palio" horse race, held in the beautiful shell-shaped Piazza del Campo. The narrow streets ...

Meals Provided :
Breakfast

Day 8 Trip ends in Siena

After breakfast, the organised part of your holiday comes to an end. Public transport and taxis can be easily organised to both Florence Airport (FLR) and Pisa Airport (PSA).

Meals Provided :
Breakfast

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Dates & Availability

Price From $1,230
Price per day$154
Last Updated: 2/23/2024

Check Current Availability, prices, specials with Explore!.

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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About Explore

We've been taking small groups on adventure vacations for over 41 years. Our authentic adventure travel experiences explore the sights and culture of a country, with hand-picked accommodation that balances comfort and location. Our average group tour size is just 11; perfect for meeting new people and getting to the heart of our destinations. Explore is one of the world's most trusted adventure travel companies with over 350 trips to more than 100 countries. We are passionate about travel and have developed a wide range of unique activities and adventures which give our customers an unforgettable experience with a team of award-winning Explore leaders. With Explore, you'll get to see your destination from a whole new perspective that takes you away from the typical well-trodden tourist track. You'll have the chance to meet, dine and stay with local people, rest in authentic accommodation with other like-minded explorers and travel to must-see destinations with a unique Explore twist. From family holidays to trips for solo travelers; cycling tours to wildlife safaris; trekking on mountains or exploring miles of scenic coastline, there is something for every kind of traveler with Explore. We will provide our expert knowledge, exciting itineraries and outstanding service as part of our sustainable travel experiences which take you under the skin of the country you're visiting for the adventure of a lifetime.


Why we love this operator
They explore a place beyond the typical tourist traps and offer exciting activities that bring the “wow factor” intrepid travelers want.
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Famous for our expert local guides that help ease the unknowns of adventure travel while bringing a unique richness and spontaneity to each and every

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Logistics

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, Australian, US, 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
Age Requirements
30 years and up
Additional Information
Trip ID
explore-WSTC

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