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Tuscany: A Journey Through the Chianti Region Short Break (Self-Guided)

Explore the brilliance behind "Chianti Classico and Gallo Nero" wines by strolling through the picturesque vineyards where they originate. Nestled between the thriving art cities of Florence and Siena, the Chianti region unveils its natural splendour and unparalleled culinary treasures.

  • Tuscany

  • 4 nights
  • Bed and Breakfast
  • Culture

    Food & Wine

  • April - October

Moderate

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Walking grade

Grade 4

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.  

Usual daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

The above statistics are generalisations of a day’s key walk, it does not include distance covered during general sightseeing or daily activity. Detailed information of the daily walking requirements are specified in the specific holidays ‘Daily Itinerary".

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Self-Guided Collection

Expertly planned, flexible walking itineraries, led by you, with accommodation, route plans, and luggage transfers all taken care of by us.

Overview

Holiday Highlights

  • Florence, the birthplace of the Renaissance, and Medieval Siena with its grand Piazza del Campo.
  • Fiesole featuring the Ancient Roman amphitheatre.
  • The scenic wine hills of Greve in Chianti and Radda in Chianti.
  • Explore exceptional wineries and savour a variety of wines.
  • Delight in captivating landscapes, medieval villages, and charming hamlets.
  • Experience the warmth of friendly locals, indulge in delicious salami, savour a Florentine steak, enjoy Cantucci with vinsanto, and, of course, revel in the exquisite wines!

Explore the brilliance behind "Chianti Classico and Gallo Nero" wines by strolling through the picturesque vineyards where they originate. Nestled between the thriving art cities of Florence and Siena, the Chianti region unveils its natural splendor and unparalleled culinary treasures, including the globally renowned Chianti wines and delightful homemade olive oil. Wander along country roads shaded by cypress trees and traverse gravel paths, winding through oak, beech, and chestnut forests. Under the Tuscan sun, casting its warmth on the golden Chianti landscape, you'll experience the sensation of stepping into a living Renaissance masterpiece.

  • 4 nights' accommodation in selected B&Bs, hotels and agriturismo with breakfast.
  • Private transfer (+ luggage) from Florence to Greve in Chianti on day 2.
  • Private transfer from Greve in Chianti to Badiaccia + luggage to Radda in Chianti on Day 3.
  • Private transfer (+ luggage) from Radda in Chianti to Siena on Day 4.
  • Digital detailed route notes and maps in English.
  • Access to route information on an app.
  • 24-hour telephone assistance.
  • Flights.
  • Travel insurance.
  • Travel to Florence and from Siena.
  • Trains and busses wherever necessary.
  • Lunches & Dinners.
  • Drinks and snacks.
  • Personal equipment.
  • Tourist taxes.
  • Printed detailed route information (available at an additional charge of £30, and is available at your first hotel).

Holiday Information

Click the button below for a detailed Holiday Information Sheet containing all the particulars about this trip.

NOTE: Itineraries and Holiday Information Sheets can vary by a specific date chosen

View Holiday Information Sheet

Tour Codes

66170

Itinerary & Travel

Itinerary Details

Whilst every effort will be made to adhere to the outlined itinerary and advertised programme, local conditions can change due to weather or other unforeseen circumstances. This may mean that routes and timings need to be amended or the order of days may change, sometimes at short notice.

Your Itinerary

Day 1

Florence

Accommodation

Arrive in Florence and seize a moment to inhale the essence of the Renaissance. We recommend an early arrival to embark on a city stroll encompassing the splendid squares and the renowned Arno River. Commencing and concluding at the Piazza della Signoria, this leisurely walk spans approximately 3.5 hours.

Day 2

Greve

Meals

Breakfast

Accommodation

Transfer with luggage from Florence to Greve at 09:30 included.

Following breakfast, a private transfer will transport you to Greve in Chianti, a charming market village and the epicentre of the Chianti wine-producing region. Complete the check-in process at the hotel and proceed to Le Cantine di Greve, where you can sample an array of over 50 distinct Chianti wines. Make the most of the daylight by exploring the picturesque surroundings, opting for one of two scenic routes.

Greve in Chianti loop via Uzzano: 7 miles, 425m ascent, 447m descent, 2.5 hours.

Greve loop via Montefioralle: 6.2 miles, 358m ascent, 355m descent, 3.5 hours.

Day 3

Badiaccia a Montemuro to Radda

Meals

Breakfast

Accommodation

Transfer from Greve to Badiaccia, luggage transfer to Radda at 09:00 included.

  • Time

    5/3 hours

  • Distance

    8.6/7.4 miles

  • Ascent/Descent

    506/668m

Following breakfast, a brief car transfer brings you to the pinnacle of the Chianti hills, Monte San Michele. Descend from Badiaccia through a valley adorned with ancient chestnut trees, and proceed towards the captivating medieval hamlet of Volpaia, nestled amid vineyards and castles. Take a break to enjoy a glass of red at a distinguished Enoteca wine shop before continuing your journey to Radda in Chianti.

Day 4

Siena

Meals

Breakfast

Accommodation

Transfer with luggage from Radda to Siena at 09:30 included.

Following breakfast, a private transfer will guide you to the enchanting city of Siena, renowned for its biannual 'Palio' horse race hosted in Europe's most beautiful shell-shaped square, the Piazza del Campo. Ensure you explore the architectural gem of the Duomo and the imposing medieval palaces that grace the city. History unfolds as you wander through the narrow streets of this immaculately preserved Italian gem.

Day 5

Final day

Meals

Breakfast

After breakfast your holiday ends, however you are able to book additional nights in Siena to continue exploring the city and the many museums and churches.  

Travel Details

Florence, Pisa and Bologna Airports are all easily accesible by public transport. From Florence airport you can take the direct local bus to downtown. From Pisa airport you can take a direct bus or train to Florence. From Bologna Airport take the bus to Bologna Central Station and from there catch a train to Florence. 

To return from Siena to Florence there is a bus station nearby to your hotel which departs every 30 minutes.

Accommodation

Accommodation information

Below is an example of the type of accommodation you will be allocated on this holiday. Your final accommodation list will be confirmed on your travel documents, these will usually be with you around two weeks prior to departure.

Park Palace Hotel or similar

Nestled amidst the Tuscan hills, Park Palace stands as a historic villa in Florence, featuring an expansive garden with a pool. Situated just a 5-minute bus ride from the city centre, it offers a tranquil retreat. The grounds of the hotel offer the chance for relaxation whether that be reading by the hotels fireplace in the lounge or relaxing by the pool. Rooms are well equipped with ensuite facilities, toiletries, hairdryer, slippers, TV, minibar, desk, A/C, heating and Wi-Fi. 

Albergo del Chianti or similar

Located in the main square of Greve in Chianti, Albergo Del Chianti presents an outdoor salt-water swimming pool and opportunities for tastings of house-made wine, grappa, and olive oil. Albergo Del Chianti's central location means you can easily reach Greve's most popular restaurants and shops. Rooms are equipped with ensuite facilities, toiletries, hairdryer, safe, TV, minibar, A/C and heating. 

Hotel Palazzo San Niccolò or similar

Situated in the scenic village of Radda in Chianti, the refined Palazzo San Niccolò hotel features enchanting interiors adorned with authentic frescoes and period furnishings. The hotel also provides a spacious garden and complimentary Wi-Fi. Rooms are equipped with ensuite facilities, toiletries, hairdryer, safe, desk, TV, minibar, heating and A/C. 

Hotel Chiusarelli or similar

The 3-star Albergo Chiusarelli presents newly renovated rooms in a neoclassical style, located near the bus station it is the perfect location for exploring Siena. The hotel has its own bar and restaurant. Rooms are equipped with ensuite facilities, toiletries, hairdryer, desk, TV, minibar, heating and A/C.

Trip Information

All the details you need

Holiday Grade

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.  

Usual daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

The above statistics are generalisations of a day’s key walk, it does not include distance covered during general sightseeing or daily activity. Detailed information of the daily walking requirements are specified in the specific holidays ‘Daily Itinerary".

Spending Money

Holiday Budgeting

As you plan your holiday budget, it's essential to account for expenses such as drinks, meals not covered in the holiday price, entrance fees not included, optional local excursions, and any souvenirs or additional services like laundry. For a rough estimate, budgeting around £10-£20 per person per day for lunches and drinks is a helpful guideline.

If your holiday does not include dinners (see itinerary) we recommend budgeting an additional £25-30 per day.

Currency in Italy

The currency in Italy is the Euro.

Tipping

Tips are not included in the holiday price. Although entirely at your own discretion, tipping is an important aspect of tourism and hospitality life and expectations are fairly high.  We strongly recommend when receiving good service you make a tip to the local supplier.

Your Travel Details

Florence, Pisa and Bologna Airports are all easily accesible by public transport. From Florence airport you can take the direct local bus to downtown. From Pisa airport you can take a direct bus or train to Florence. From Bologna Airport take the bus to Bologna Central Station and from there catch a train to Florence. 

To return from Siena to Florence there is a bus station nearby to your hotel which departs every 30 minutes.

Luggage Allowance & Travel Documents

Should you have decided to book any overseas flight arrangements through us, details of your travel arrangements and baggage allowance will be clearly outlined in your 'Final Travel Documents'. These will be sent to you approximately 10 days before your departure, ensuring you have all the necessary information for a smooth and well-prepared journey.

Personal Details Check

To ensure the accurate administration of your holiday arrangements, kindly verify that the personal details we have for you are current and correct. Confirm that you've given us all the necessary information for securing your travel and accommodation. Please review your passport details, date of birth, and any other pertinent information crucial for the management of your holiday.

Additionally, please make us aware of any dietary allergies or intolerances you may have. Your well-being is important to us, and this information will help us make appropriate arrangements for your meals during the trip.

You can access and update the provided information or add missing details through the "Manage My Booking" feature on our website at www.rambleworldwide.co.uk. Alternatively, reach out to our Sales and Reservations team at +44 (0)1707 331133. Upon receiving your booking confirmation, promptly check the details. Your cooperation ensures a seamless and enjoyable holiday experience.

Documentation

After booking your holiday, expect to receive a confirmation and holiday information sheet soon after.

Once you've settled your balance, about 2 weeks before your holiday, you'll get instructions on how to log into your ActiveNav App. Grab your Apple or Android smartphone and head to the app store for a quick download. Once installed, the app grants you access to all route information and provides guidance on how to navigate it.

Around 2 weeks prior to your departure, you'll also get a destination manual & road book. This comprehensive guide includes detailed information on your walking route and interesting facts about the areas you'll stay in. Alongside, a trip voucher will confirm all the services booked for you, complete with the names and addresses of your hotels and other service providers. Be prepared to present this voucher as confirmation at your accommodations, and don't forget to bring along a valid form of ID.

Passports and Visas

European Passport Advice

If you are planning to travel to an EU country (except Ireland), or Switzerland, Norway, Iceland, Liechtenstein, Andorra, Monaco, San Marino or Vatican City, you must meet the Schengen area rules.

Your passport must meet 2 requirements. It must be:

  • less than 10 years old on the day you enter (check the ‘date of issue’)
  • valid for at least 3 months after the day you plan to leave (check the ‘expiry date’)

For some Schengen countries your passport may need to be less than 10 years old during your whole visit, and the 3 months at the end of your visit may need to be within 10 years of your passport’s issue date.

Check both the issue date and the expiry date in your passport. If you renewed your passport early, extra months may have been added to its expiry date. This could affect the requirement for your passport to be less than 10 years old.

Non British Passport holders should consult the host country’s embassy for applicable passport and visa entry requirements.

Meals

In general all of our self-guided holidays are on a bed and breakfast basis with breakfast provided at your accommodation. Depending on the route you are walking and access to local services such as restaurants, cafes and supermarkets, your itinerary may include packed lunches, dinners or a mix of both. Please refer to the individual itinerary and what is included for accurate information.

Footwear & Kit List

Footwear

Footwear is a walker’s personal choice; however, we suggest lightweight waterproof walking boots with a good, moulded sole (such as Vibram or similar) and a deep tread and which provide ankle support and may be essential for some walks.

Luggage Transfers

On a self guided holiday, the days you walk from one property to another, your main luggage will be transferred for you as part of your holiday arrangements. This leaves you free to just carry what you need for the day. Please refer to your individual itinerary for which days your luggage will be transferred. Before you leave your accommodation in the morning, please speak with your host for where the luggage should be left and by what time. 

General Kit List

Outdoor activities are always safer and more enjoyable if you are prepared.

If you have not travelled with us before the following list might be of use:

  • Day sack (this should be able to carry all you would need for the day's activity)
  • Day sack liner
  • Waterproof jacket (Goretex or similar) and trousers
  • Compass
  • Map case
  • Whistle
  • Lightweight quick-drying trousers
  • Walking T-shirt/shirts
  • Walking socks
  • Fleece or jumper
  • Sun hat, sunglasses, lip salve and sun block
  • Warm hat and gloves (if appropriate)
  • Water bottle - at least 2 litre capacity (more may be required)
  • Basic first aid kit
  • Lunchbox
  • Walking poles (should you find them useful)
  • Sit mat
  • Mobile
  • Power Bank for charging mobile if needed.
  • Phone charging lead

This list is not exhaustive, and every walker is different and may have their own preference.

Travel Documents Checklist

Documents and Information to take with you:

  • Passport (make sure it's yours and valid)
  • Your travel tickets or e-ticket itinerary
  • Any visa or electronic travel authorisation (if required)
  • Holiday money
  • Credit or debit cards (and separate details of who to call if lost)
  • Car parking ticket and car park directions (if prebooked)
  • Coach or rail travel tickets (if prebooked)
  • Your holiday Booking Confirmation document
  • Your travel insurance details
  • Alternative form of identification (such as a driving licence)
  • Photocopy of the personal details pages of your passport
  • A valid European Health Insurance Card (EHIC) if relevant
  • Details of any medical condition or allergy your holiday leader should know about

Electricity in Italy

Electricity in Italy is supplied at 220 Volts. If you wish to use electrical equipment you will need a European two pin adaptor with round pins. More information can be found at https://www.power-plugs-sockets.com/

Water To Go

Opting for filtered water from a reusable bottle with its built-in water filter, like the Water-to-go bottle available at www.watertogo.eu, is a sustainable alternative to single-use sealed water bottles. Simply refill it from any water source and contribute to saving the environment from disposable plastic bottles.

Exciting news: Water-to-go has introduced two new bottles to their collection. The Active bottle is designed to fit bike water bottle holders, and the Sugarcane bottle is an even more planet-friendly option. Crafted from fibrous cane, a by-product of liquid extraction, it undergoes a process to create plant-based plastic. Explore the details on the Water-to-Go website for this innovative new range.

As a token of appreciation for your commitment to the environment, we've secured an exclusive 15% discount with Water-to-Go for you. Visit www.watertogo.eu and use the code RWH17 during your order.                        

Note: If you're booked on a long-haul holiday you'll receive a complimentary Water to Go bottle, sent to your home address 2 or 3 weeks before your holiday. Thank you for being a part of our sustainable journey!

Maps, Guidebooks & Other Information

Weather

Visit the following websites for an idea of the climate in your destination:

Staying Healthy On Holiday

Health requirements in destination can change, and it's crucial for you to take responsibility in staying informed. Ensure that you consult a professionally qualified source and comply with any health requirements at least 6 to 8 weeks before your departure. Your GP can provide advice on vaccinations. Stay proactive about your health preparations to ensure a safe and enjoyable travel experience.

Health Advice for Italy

No compulsory immunisations are required for visits to Italy.

You should be up to date with the usual immunisations recommended in the UK. 

You may wish to consider immunisations against Tetanus and Tick-borne Encephalitis.

Further Travel Advice

For further advice please visit:

You might wish to take a small bottle of antibacterial hand gel with you for times when you're unable to wash your hands.

Travel Insurance

It’s a condition of booking that you obtain adequate travel insurance, from a reputable provider, to undertake the holiday, including UK trips chiefly due to the cancellation element of cover.

The policy must cover the period from the date of booking to the last day of your trip and should include, as a minimum, cover for: medical expenses (including the consequences of a Covid positive test result), mountain rescue including helicopter rescue, death, repatriation, cancellation and curtailment and shall not have exclusion clauses limiting cover for the activities you will partake in on your trip, including altitudes reached in the holiday arrangement. It is your responsibility to check that your policy is adequate for the nature and destination of the holiday booked.

Once you have obtained your travel insurance, please provide us with the name of your travel insurer, the policy number and the insurer’s 24 hour emergency assistance number.

In the event that you fail to obtain suitable Travel Insurance we shall not be liable for any costs incurred or claims made against us due to your failure to comply with this term.

If travelling outside the UK you must carry proof of insurance with you and produce it if reasonably requested to do so by RWH Travel staff, tour leaders or suppliers. No refunds will be made should you be excluded from the walking programme through being uninsured or you being unable to demonstrate that you are insured.

Our house broker MPI should be considered for whom we are an affiliate and contact information is on our website and will be referred to in your booking confirmation.

If you are travelling to an EU country or Switzerland please also ensure that you have either an existing valid EU EHIC card (European Health Insurance Card) or a valid UK GHIC (Global Health Insurance Card). You can apply for a UK GHIC free of charge on the NHS website at https://services.nhsbsa.nhs.uk/cra/start.

EHIC & GHIC Cards

Starting January 1st, 2021, you, as a UK traveller, can continue using your European Health Insurance Card (EHIC) throughout its valid five-year period, granting you access to medical assistance during your holiday until its expiry date. Be aware, though, that this coverage will no longer extend to Iceland, Liechtenstein, Norway, or Switzerland. In case you don't have a valid EHIC, you can apply for a new UK Global Health Insurance Card (GHIC), which will replace the EHIC as it gets phased out.

It's essential to emphasize that the EHIC/GHIC, while valuable, should not be regarded as a substitute for comprehensive medical or travel insurance. For your peace of mind and comprehensive coverage, considering additional insurance is highly recommended.

For more information, please visit www.nhs.uk/ehic

Personal Safety

The UK Foreign, Commonwealth & Development Office is your go-to for the latest info on security, local laws, and the nitty-gritty of passports and visas at www.gov.uk/travelaware. Make sure to take a quick peek at the current advice for your upcoming destination—it'll only take a few minutes.

When you're out and about, stay aware of your surroundings. Take smart precautions with your credit cards and passport, and maybe tone down the flashy accessories. Less is more, especially when it comes to carrying cash—just enough for the day will do. Consider using a money belt for that extra layer of security. Stay alert, stay safe, and make the most of your travels!

Cultural Awareness

Italian Laws & Customs

In some Italian towns and cities you may be fined for dropping litter and in some towns or cities it’s an offence to sit on monument steps or to eat and drink in the immediate vicinity of main churches, historic monuments and public buildings. It’s also an offence to enter or bathe in public fountains.

In May 2019, the Municipality of Capri introduced a law forbidding the use of any disposable plastic objects such as bags, cutlery, plates, cups, food packaging, trays, straws on the island of Capri. Violations can incur a fine of up to 500 euros.

Illegal traders operate on the streets of all major Italian cities, particularly tourist cities like Florence, Venice and Rome. Don’t buy from illegal street traders. You could be stopped by the local police and fined.

It is illegal to remove sand, shells or pebbles from coastal areas in Italy. Doing so may result in heavy fines. It’s also forbidden to collect various species of flowers, plants and herbs from mountain and wooded areas. For more information, check with the regional authorities of the area you’re visiting.

The Ramble Worldwide Outdoor Trust

Unlike many other tour operators, we take pride in our unique approach. Ramble Worldwide channels its surplus profits back into various outdoor, walking-related, or environmental conservation projects in the UK through our own trust. When you choose us, you contribute to this impactful initiative.

The Ramble Worldwide Outdoor Trust is passionate about making the outdoors more accessible for more people from all communities. We grant funds to many organisations and have recently partnered with Mind Over Mountains, Adaptive Grand Slam and other groups to create an enduring impact on people’s lives and to support them to enjoy the outdoors. In addition, the Trust makes many small grants to local organisations such as Ramblers Groups, Walkers are Welcome, My kind of Books and recently provided a small grant, via his scouting group, to enable a young man whose family had fallen on hard times to complete his DofE Gold award.

Patron of the Trust is the renowned explorer, Mark Wood. Over 20 years Mark has undertaken expeditions to some of the most remote parts of our planet. Our shared values make for an exciting partnership, and we believe that by standing shoulder to shoulder we can encourage people from all communities to enjoy being active outdoors in whatever way suits them best.

For more comprehensive details, please visit the 'About' section on our website and click on the Charitable Trust link. Your choice to travel with us goes beyond a memorable vacation; it contributes to meaningful projects that have a positive impact on our community and environment.

Heart and Sole

We appreciate that we are in a fortunate position to be able to use our profits to help make a difference to people's lives. Heart & Sole is a venture managed by our office staff, whose aim is to reach the heart of the communities in the countries we visit. Through Heart & Sole, we hope to make more of a long term, direct impact to these communities, particularly in less developed countries where even a small amount goes a long way. See our website for more information and details of some of the projects we support.

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Useful Information

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Italy

  • Capital

    Rome

  • Currency

    Euro

  • Language

    Italian

  • Time Difference

    UTC +02:00

  • Flight duration

    2.5hrs from UK

Visas and Passports

No Visa Required

Average weather

  • January

    6°C

    Avg. Rain: 67mm

  • February

    7°C

    Avg. Rain: 62mm

  • March

    9°C

    Avg. Rain: 63mm

  • April

    12°C

    Avg. Rain: 61mm

  • May

    16°C

    Avg. Rain: 56mm

  • June

    20°C

    Avg. Rain: 47mm

  • July

    22°C

    Avg. Rain: 35mm

  • August

    22°C

    Avg. Rain: 48mm

  • September

    20°C

    Avg. Rain: 64mm

  • October

    15°C

    Avg. Rain: 89mm

  • November

    10°C

    Avg. Rain: 96mm

  • December

    7°C

    Avg. Rain: 82mm

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