Self Guided Walking Holidays & Cycling Holidays


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Florence to Siena Self Guided Walking Holiday
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Highlights

  • Exploring romantic Florence, cradle of the Renaissance.
  • Walking through the vineyard cloaked hills of Chianti.
  • Enjoying the lively atmosphere of an outdoor table on the piazza.
  • The serious business of food, wine and olive oil appreciation.
  • Strolling across the Piazza del Campo in Siena.

Discover the magic of Chianti; old farmhouses, medieval villages, rows of cypress trees, quiet forests of oak, beach and chestnut, the lively atmosphere of an outside table on the piazza and the cherry flavours of a glass of Chianti Classico. This is the definitive Tuscany!

Begin with two nights in Florence, the cradle of the Renaissance; romantic, intriguing and utterly beguiling. Explore the Etruscan and Roman ruins in Fiesole. Indulge yourself in the enotecas and picture perfect landscapes of Greve in Chianti. Walk through vineyards and medieval hamlets to Radda in Chianti. Stroll through the Piazza del Campo in Siena.

The very best way to discover the secrets of Chianti is on foot. Your walking holiday in Chianti includes hand-picked 3 * superior and 4 star charming hotels, all breakfasts, luggage transfers, private transfers as per your itinerary, comprehensive route notes and maps and a detailed pre-departure information pack and emergency support.

Read one writer's tale of his experience walking from Florence to Siena in Scotland's Herald newspaper: "What a pleasure it is, therefore, to slow everything down to walking
pace, literally, and enjoy the sights, smells and tastes....
meandering through the beautiful and captivating landscape of Tuscany."
.

DAY 1: Arrive Florence

Settle into your accommodation and then throw yourself into the delights of Florence. Priceless renaissance art, magnificent piazzas, narrow streets, the Ponte Vecchio over the River Arno and the designer shops, will have you wishing you had more time to explore.


Overnight: Hotel Park Palace****, Florence


Minutes away, and enjoying wonderful views of, the historic centre of Florence. The Hotel Park Palace is your Florentine Villa.


DAY 2: Settignano to Fiesole

A 25 minute local bus ride brings you to the village of Settignano, where your walk begins. A typical Tuscan landscape of olive groves, cypress trees and renaissance villas unrolls before you, with the city of Florence at your feet.


Fiesole, founded in the 7th century BC, boasts Etruscan ruins, Roman baths and amphitheatres, a Franciscan Monastery, Tuscan Renaissance art and outstanding restaurants. You've a choice of walks today.


Walk 1: 8 km | 347m Ascent 224m Descent | 3 hrs


Walk 2: 16 km | 567m Ascent 566m Descent | 6 hrs


Overnight: Florence


DAY 3: Greve in Chianti Circular Walk

After breakfast, a private transfer will take you to Greve in Chianti, a rustic market village in the heart of the Chianti wine producing region.


Check into your hotel and head over to Le Cantine di Greve where you can taste over 50 different Chianti wines.  In the afternoon, enjoy a circular walk through a picture perfect Tuscan landscape north of the town.


Overnight: Albergo del Chianti***, Greve in Chianti


Located in an old tower on the main square in Chianti the Albergo del Chianti is perfectly situated. The 16 rooms are located at the rear of the building and overlook a quiet courtyard swimming pool.


Walk 1 (Greve Loop via Uzzano): 11.5 km | 425m Ascent/Descent | 2.5 hrs


Walk 2 (Greve Loop via Montefioralle): 10 km | 358m Ascent/Descent | 3.5 hrs 


DAY 4: Panzano Circular Walk

Today's walk is a lovely loop walk in the classic tuscan hills surrounding the village of Panzano. Enjoy the Chianti landscape that alternates between forests and vineyards and discover ancient farmsteads along the way.


Walk: 12km | 385m Ascent /Descent | 4 hrs 


Overnight: Albergo Chianti, Greve in Chianti


DAY 5: Walk from Badiaccia Montemuro to Radda in Chianti

After breakfast, a short car transfer takes you to the highest of the Chianti hills, Monte San Michele. From Badiaccia you descend through a forested valley of century old chestnut trees and to the medieval hamlet of Volpaia, situated amongst vineyards and castles.Stop in for a glass of red at a fine Enoteca, and then continue on to Radda in Chianti.


Radda is perched atop a high hill in a comparatively rugged part of Tuscany. The Capital of the old League of Chianti, its concentric streets still surround the historic Piazza Ferrucci, where you will find the shield encrusted Palazzo Comunale.


Walk: 12-14km | 506m Ascent 668m Descent | 3-5hrs


Overnight: Hotel Palazzo San Niccolò, Radda


Located in the heart of Radda, on the Piazza Ferrucci, the Hotel Palazzo San Nicolo is a converted medieval palace dating back to 1400. Large authentically decorated rooms with a sense of place and sophisticated commuanal areas envelop you in a sense of place. This will be a highlight of your trip.


DAY 6: Radda in Chianti Circular Walk

Bask under the Tuscan sun, go for a scenic walk around the old centre of Radda in Chianti. Wind along the narrow alleyways and visit the church of Santa Maria Novella. Treat yourself by visiting a wine cellar and tasting the wine from the celebrated local vineyards.


Walk: 16km | 586m Ascent/Descent | 5 hrs


Overnight: Hotel Palazzo San Niccolò, Radda


DAY 7: Siena

After breakfast, a prearranged private transfer will take you to Siena. Siena is famous for its biannual “Palio” horse race, held in the shell-shaped Piazza del Campo.


History comes alive as you meander through the narrow streets of this enchanting city.


Overnight: Hotel Villa Liberty*** or Hotel Chiusarelli***, Siena


The recently restored Hotel Villa Liberty offers comfortable and elegant rooms only a few minutes walk from the historic centre of Siena.


DAY: 8

Your trip finishes after breakfast.


Extensions & Extra Nights

Florence and Siena both warrant additional nights. Just ask at the time of booking and we would be happy to arrange this.

Accommodation

We specifically choose our hotels for comfort, location and authenticity. All are three star and four star hotels, which are centrally located and offer a genuinely warm Italian welcome and real sense of place.


Accommodation Details

We will always try and accommodate you at the locations detailed in the brochure, but because of limited availability we may have to accommodate you at an alternative location of the same or better standard. We will confirm your accommodation details on confirming your reservation.


Single Rooms

Single rooms are available but attract a single supplement.


Solo Walkers

This is a great holiday for solo walkers. If you are travelling solo the holiday is slightly more expensive as some costs are not shared.


Meals

The delicious Italian food and wine available locally is undoubtedly a highlight of this holiday. The price of your holiday includes breakfast each morning. Lunch and dinner are not included so you are free to choose from the available options.

Availability

This holiday is available to start on any day from April until the end of October.


May and June are absolutely lovely and spring and early summer is a great time in Tuscany. September & October are also lovely as the vineyards change to a pallet of reds and golds. July and August can be very hot so you will have to start early to miss the heat of the day, although the towns and villages are buzzing which is great. We also suggest that if you choose to walk during the summer months you should take plenty of water, a hat and sunscreen as shade is limited on the walks.


Single Rooms & Solo Walkers

Single rooms are available but attract a single supplement  This is a great holiday for solo walkers. If you are travelling solo the holiday is slightly more expensive as some costs are not shared.


Grade and Fitness

This holiday is graded easy to moderate because the walks are relatively short and you can choose to shorten them. Tuscany is hilly and there are some steep descents and ascents so you should have suitable fitness. You will walk on city streets, dirt tracks, mule tracks and footpaths. The longest day is Day 6, with a loop walk of 16km.


Navigation

The walks are generally not way marked. We supply very detailed route notes and maps so navigation is straightforward.


Baggage Transfer

When required your bags will be transferred from your hotel and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.


Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.


General Information

The distances and ascent/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants),sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.

Getting to Florence

We recommend arriving at either Florence or Pisa Airports.


Buses and taxis from Florence Airport to the City Centre take 25 or 15 minutes respectively and cost 4.50/20 Euro).


From Pisa Airport buses/taxis connect to the station and trains to Florence take 1h30.


Direct buses from Pisa Airport to Florence (70 min) are also available.


Travelling by Car

The hotels we use do not have private parking. Parking is available in Florence and Siena and costs about 25 Euro per day.


Getting From Siena

Florence and Pisa Airports are closest. Siena has good road and rail links to all Italian destinations.

Included

  • 7 nights accommodation including breakfast
  • Luggage transfers as per your itinerary
  • Private transfers from Settignano to Greve in Chianti (Day 3), from Greve in Chianti to Monte San Michele (Day 5) and from Radda in Chianti to Siena (Day 7).
  • 24-hour telephone assistance
  • Detailed route notes and maps

Excluded

  • All lunches & Dinners
  • Flights and public transportation
  • Bus to the village of Settignano on Day 2
  • Travel insurance
  • Admissions and entrance fees to any museums
  • Personal expenses such as wine tasting, drinks, phone calls, etc
  • Any item that has not been specifically mentioned in the program

Extras

  • Private airport transfers
  • Additional nights
  • Guided tours of Florence or Siena with private local city guide.
  • Cooking lessons in Florence or Siena

We are often asked the following questions and I hope that you will find the answers useful. Don't hesitate to contact one of our Italy specialists if you have any further queries. 

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as this area is extremely popular. You will find up to date availability on our website and we will always try and accommodate your plans so just ask.

How fit do I need to be?

This walking holiday is graded easy and involves between two and five hours of walking each day. Most of the walks can be shortened or extended as required. Some walks are totally optional. There are some steeper ascents and descents so you should enjoy a reasonable level of fitness to get the most from this holiday.

When is the best time of year?

May and June are absolutely lovely and spring and early summer is a great time in Tuscany. September & October are also lovely as the vineyards change to a pallet of reds and golds.

July and August can be very hot so you will have to start early to miss the heat of the day, although the towns and villages are buzzing which is great.

What personal equipment do I need?

You will need good walking shoes/boots, comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc.

How do the baggage transfers work?

When required your bags will be transferred from your hotel and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

Which is the best airport?

Pisa and Florence are the best airports to fly into. Rome is also a possibility, but transfer times are longer.

REVIEW SNAPSHOT®

by PowerReviews
macs adventureTuscany: From Florence to Siena
 
4.6

(based on 13 reviews)

Ratings Distribution

  • 5 Stars

     

    (8)

  • 4 Stars

     

    (5)

  • 3 Stars

     

    (0)

  • 2 Stars

     

    (0)

  • 1 Stars

     

    (0)

100%

of respondents would recommend this to a friend.

Pros

  • Great accommodations (12)
  • Well organised (12)
  • Fun (10)
  • Once in a lifetime experience (6)

Cons

No Cons

Best Uses

  • Holiday (13)
  • Trying something new (8)
  • Relaxation (6)
    • Reviewer Profile:
    • World traveller (5), Occasional traveller (4)

Reviewed by 13 customers

Displaying reviews 1-10

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4.0

Recommended

By Summer Wine

from Holmfirth, Huddersfield West Yorkshire

About Me World Traveller

Verified Buyer

Pros

  • Beautiful Scenery
  • Fun
  • Great Accommodations
  • Interesting vilaages, towns and cities
  • Well Organised

Cons

  • None

Best Uses

  • Holiday
  • Relaxation

Comments about macs adventure Tuscany: From Florence to Siena:

Very well organised with a variety of walks interspersed with sightseeing in villages, towns and cities.

 
5.0

What an adventure

By Joanne

from Melbourne

About Me Enjoy holidays doing different adventures

Verified Buyer

Pros

  • Amazing scenery
  • Great Accommodations
  • Well Organised

Cons

    Best Uses

    • Holiday

    Comments about macs adventure Tuscany: From Florence to Siena:

    This is an amazing trip where you stay in great accomodation, see amazing scenery, enjoy fantastic local food and wine and get some exercise along the way. Some days are longer and more tiring than other but in all it's fantastic.

     
    4.0

    A wonderful trip to Tuscany.

    By Einar

    from Kopavogur Iceland

    About Me Occasional Traveller

    Verified Buyer

    Pros

    • Fun
    • Great Accommodations
    • Once in a Lifetime Experience
    • Well Organised

    Cons

      Best Uses

      • Holiday
      • Trying Something New

      Comments about macs adventure Tuscany: From Florence to Siena:

      All the documents were very good. It took some time to notice the marking on the trees on the first walk from Settignano - Fiesole. We did not know where to look for the red/ white markings. It would be better to put the marking in the guide, as it looks :)

       
      5.0

      exactly as advertised!

      By Bob

      from New Zealand

      Verified Buyer

      Pros

      • Great Accommodations
      • great scenery
      • Well Organised

      Cons

        Best Uses

        • Holiday
        • Trying Something New

        Comments about macs adventure Tuscany: From Florence to Siena:

        This was pleasant walk through the beautiful Tuscan countryside on lots of varied terrain. The route notes were accurate (if just occasionally confusing), and the standard of accommodation was very good, interesting and friendly. Bags and taxis were always where they were supposed to be. The walks were suitable for 60+ walkers and the only real challenge was the heat in mid-June, with highs reaching over 30 everyday.I remember the walks in and out of Radda as paricularly warm and exposed. Nonetheless, there was a lot of forest shade on most the walks; however, it as well to take warnings about heat seriously, particularly if you are coming out of a NZ winter. In sum a pleasant walk and one that leaves you feeling you have earned a beer or two at the end.

         
        5.0

        Great trip

        By Wendy

        from A Wales

        Verified Buyer

        Pros

        • Fun
        • Great Accommodations
        • Once in a Lifetime Experience
        • Well Organised

        Cons

          Best Uses

          • Holiday
          • Trying Something New

          Comments about macs adventure Tuscany: From Florence to Siena:

          Great hotels. The walking instructions are generally good but there are a few errors/confusing instructions. Chose a cool time of year for this holiday. It was hotter than predicted in early/mid June with temperatures in early to mid 30's which made a few walks hard work. Take snacks on the walks of walking early as the cafes/restaurants mentioned don't open until midday, we got caught out with this on the last long walk. Overall we had an amazing experience!

           
          5.0

          Beautiful Countryside and Charming Villages

          By Joy

          from Oregon, USA

          About Me Active Senior Citizen, Occasional Traveller

          Verified Buyer

          Pros

          • Beautiful Scenery
          • Great Accommodations
          • Well Organised

          Cons

          • Only one glitch in instructions

          Best Uses

          • Great Exercise
          • Holiday
          • Trying Something New

          Comments about macs adventure Tuscany: From Florence to Siena:

          We added an extra day in Florence to help figure out the logistics for the first day's hike. While the Park Palace Hotel is a lovely accommodation, it is not conveniently located for accessing the first hike, especially if you are using the city bus lines.

           
          4.0

          Some difficult parts, but rewarding by the end.

          By JAG

          from Halifax

          About Me World Traveller

          Pros

          • Fun
          • Great Accommodations

          Cons

          • Exhausting

          Best Uses

          • Holiday
          • Trying Something New

          Comments about macs adventure Tuscany: From Florence to Siena:

          Some of the hilly trails had a lot of wood debris/rocks/earth - there probably had been heavy rains that cascaded material down the paths making the uphills difficult. We did it early June and it was starting to get warm/humid (~25 C). Doing it in May or September may be cooler.
          Hotels were great, so were restaurants.
          We were 6 people: 4 in late 60s/early 70s, 2 in late twenties.

          (1 of 1 customers found this review helpful)

           
          5.0

          Fantastic holiday in Italy

          By Chris

          from Seattle, WA

          About Me Occasional Traveller, World Traveller

          Pros

          • Fun
          • Great Accommodations
          • Well Organised

          Cons

            Best Uses

            • Holiday
            • Relaxation

            Comments about macs adventure Tuscany: From Florence to Siena:

            My wife and I loved this trip. It was a perfect blend of cities and countryside - Florence and Siena were both wonderful places to explore with so much art/culture, but we were also glad that we got to experience smaller towns in Greve and Radda. The hiking directions were usually very clear - we only hit one snafu going from Baddacaria to Radda with a gate being closed. The accommodations were really nice - Our hotels in Florence and Radda were beautiful and felt luxurious. Our hotel in Greve was more simple, but the location right on the town square really couldn't be beat, we had a great view of the square. Our hotel in Siena had a great location as well.

            Macs was a pleasure to deal with, and we really enjoyed working with Erin. They were very understanding and flexible with changes to our itinerary when we found out my wife was pregnant! The trip was very organized and our taxi driver Stefano was always early to pick us up. He was one of our favorite people we met on the trip!!

            Macs is perfect for the way we like to travel - taking the headache out of organizing / coordinating logistics, but still giving the freedom to travel away from big tour groups and adapt activities to personal tastes. We have been recommending Macs to everyone we know and would absolutely book another trip with them!!

            (1 of 1 customers found this review helpful)

             
            5.0

            All that we hoped it would be.

            By Rae

            from Aberdeen

            About Me Occasional Traveller

            Verified Reviewer

            Pros

            • Fun
            • Great Accommodations
            • Great Walking Experience
            • Once in a Lifetime Experience
            • Well Organised

            Cons

              Best Uses

              • Holiday
              • Relaxation
              • Trying Something New

              Comments about macs adventure Tuscany: From Florence to Siena:

              Organisation was like clockwork. Walks were easy to follow and well designed. Perfect scenery, friendly hotels.

               
              5.0

              Amazing adventure!

              By Yoga Joan

              from Calgary

              About Me Avid Adventurer, World Traveller

              Pros

              • Fun
              • Great Accommodations
              • Once in a Lifetime Experience
              • Well Organised

              Cons

                Best Uses

                • Holiday
                • Relaxation
                • Trying Something New

                Comments about macs adventure Tuscany: From Florence to Siena:

                Enjoyable, yet challenging walks. Beautiful hotels and amazing views.

                Displaying reviews 1-10

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