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Chianti to the Coast



Chianti to the Coast

Siena and the Tuscan Coast

Surrender to the magic of Tuscany as you cycle along quiet roads bordered by rolling hills, lush with vineyards and olive groves.

Stay in the heart of Chianti, renowned for its rich wines - the perfect accompaniment to the delicious cuisine. Explore the medieval hilltop village of Radda; discover the breathtaking beauty of Siena, Italy; and marvel at the landscape of the Crete Senesi on your journey to the coast. Blessed with charming locals, the warm Tuscan sun and the deep blue Mediterranean this alluring region is sure to capture your heart.

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6 days | 5 nights
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Start | End

Florence, Italy | Grosseto, Italy

Daily Itinerary



Today's Ride:

Radda to Lucarelli Loop
Approximately 17 miles with 1,200 feet of climbing

Avid Option:

Radda to La Piazza to Lucarelli Loop
Approximately 24 miles with 1,600 feet of climbing


Your Trek Travel guides will meet you at the Hotel Palazzo Vecchio (via Cennini 4, 50123, Florence, Italy) at 11:00 AM on the first day of the trip. After a 1 hour shuttle, you arrive in Radda in Chianti, once the capital of the Chianti League and one of the region’s historic gems. Enjoy a simple lunch of tasty Tuscan specialties at our favorite trattoria, before your guides familiarize you with your high-end Trek bicycle for the week and ensure you and your bike a perfect fit. Outstanding views surround you today as you cross the tranquil countryside, covered with vines heavy with Sangiovese grapes and traverse a ridge on the way toward Castellina, another famed Chianti town. Later a rewarding descent will take you into a lush green valley and through Lucarelli before beginning your final climb back into Radda. This evening you’ll gather with your guides and fellow guests for drinks on the hotel’s terrace overlooking the surrounding rolling hills before enjoying an al fresco Tuscan feast together.

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Palazzo Leopoldo
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Today's Ride:

Chianti Loop
Approximately 53 miles with 4,900 feet of climbing

Short Option:

Radda to Castelnuovo B
Approximately 25 miles with 4,900 feet of climbing

Avid Option:

Chianti Loop with Nusenna
Approximately 70 miles with 6,000 feet of climbing


Your ride today will take you above the vineyards to Monteluco, the highest point in Chianti, before enjoying a well-deserved descent offering unparalleled views of the Tuscan countryside. Ride on to Felsina Winery in Castelnuovo Berardenga for a tour of the cellars before settling in for a signature picnic prepared by your Trek Travel guides, replete with tastes of Fèlsina’s famed wines. Later it’s back into the saddle to ride through the small towns on the southernmost border of the Chianti Classico region, through enchanting villages before climbing to the tiny village of Lecchi, to mingle with the locals over a mid-afternoon espresso. Alternatively you can also continue directly through town to pedal up the hills, or collines, surrounded by vineyards. This evening, Radda in Chianti is yours to explore to discover your own classic dishes! Tempt your taste buds with a local ribollita or relax in the town square and watch the world go by with a simple pizza, the choice is yours.


Palazzo Leopoldo
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Today's Ride:

Radda to Mensanello
Approximately 35 miles with 3,000 feet of climbing

Avid Option:

Radda to Mensanello to Casole D'Elsa
Approximately 56 miles with 4,000 feet of climbing


The heart of central Tuscany awaits today, as you ride south along quiet ribbons of road past silver green olive groves and gently undulating vineyards. Relax and immerse yourself in the beauty of this region as you glide past myriad blooming wildflowers, ancient stone walls and lush shady forest. Stop at Hotel Villa Cipriani for lunch and relax by the pool, or keep going to Casole D'Elsa - where you can explore the local bistros of this Etruscan settlement featuring ancient brick buildings and panoramic views of the surrounding farmland.. This evening a private shuttle will take you to Siena where you will meet Andrea, our knowledgeable tour guide who will lead you and your fellow guests on a tour of discovery through Italy’s best preserved medieval city. Choose from Siena’s many dining options tonight to reward yourself with a leisurely meal in the heart of this living time capsule.


Villa Sabolini
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Today's Ride:

Mensanello to Roccatederighi to Scarlino
Approximately 60 miles with 3,300 feet of climbing

Short Option:

Mensanello to Roccatederighi
Approximately 40 miles with 2,800 feet of climbing

Avid Option:

Mensanello to Scarlino via Roccastrada Loop
Approximately 75 miles with 5,000 feet of climbing


Your ride today traverses Colline Metallifere: the “Metal Hills” a densely wooded area, punctuated by small fortified medieval villages, named for its mineral resources. Enjoy quiet roads and peaceful riding as you climb from the Val d’Elsa into the forested hills, on a route offering views largely unchanged for hundreds of years. Leaving the forest behind, the route heads to the town of Roccatederighi, where the remains of its fortress walls enclose the jewel-like central square. After enjoying a lunch of seasonal specialties prepared by our friends Vincenzo and Anna, begin your descent into the plains of the Maremma, a region where Etruscan and medieval villages, vineyards and woods, sand beaches and blue sea characterize the landscape - long considered the wildest area of Tuscany. A final climb will lead you to your home for the next two nights, La Cianella. Tonight you’ll dine at the luxurious Relais Vedetta, with a view of the magnificent sunset over the sea that stretches from nearby Elba to Corsica.


La Cianella
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Today's Ride:

Scarlino to Castiglione della Pescaia Loop
Approximately 60 miles with 4,200 feet of climbing

Short Option:

Scarlino to Castiglione della Pescaia
Approximately 36 miles with 2,500 feet of climbing

Avid Option:

Scarlino to Castiglione della Pescaia Loop with Guernica Option
Approximately 65 miles with 5,200 feet of climbing


Today’s ride encompasses the rich vineyards, forested hills, and dense olive groves of this region before descending toward the sea.With plenty of time to explore the hilltop villages and centuries-old buildings that line the route, it’s a day to explore and ride at your own pace.You’ll ride to the crystalline waters of the Mediterranean town of Castiglione della Pescaia. Find a café or trattoria right on the beach to refuel and relax with a Tuscan lunch and perhaps a dip in the Tyrrhenian Sea. Later it’s back onto two wheels to explore the valley between the mountains and the sea, where the roads meander back to the hotel. Pick up some last minute necessities, like well-aged balsamic vinegar, or your favorite bottle of Tuscan wine or return to the hotel to enjoy a final luxurious afternoon by the pool. This evening join your traveling companions and guides for a farewell social hour on the terrace, before ending the day with glasses raised to toast a fantastic week and newfound friends before tucking into a magnificent feast at the hotel!


La Cianella
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Today's Ride:

Scarlino to Lago dell'Acesso Loop
Approximately 23 miles with 1,500 feet of climbing


If you have the energy, return to your bicycle and relish one last ride in Tuscany.This last challenge takes you down from the top of Scarlino before toward the rolling hills and beautiful country side which surrounds Lago dell'Acesso. If you’d rather, linger over a hot cappuccino and enjoy a leisurely morning. Perhaps the pool or tennis courts of the hotel will entice. You’ll say farewell to your guides at 11:00 AM at the Agriturismo La Cianella. You’ll then shuttle 1 hour to the Grosseto Train Station, arriving at approximately 12:00 PM. Please allow adequate time for any connecting travel to accommodate possible traffic delays.

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Dates & Pricing



Palazzo Leopoldo hotel on our Chianti bike tour

Palazzo Leopoldo

Radda in Chianti, Italy

Dating back to the 13th century and set in the historical center of Radda in Chianti, Trip Advisor award winner, Palazzo Leopoldo is an elegant villa with its own wine shop and spa. The hotel’s design melds ancient architectural details and contemporary comforts for an unparallelled stay. Enjoy the views of the surrounding Chianti hills from their specacular terrace with a glass of Prosecco in hand.
Borgo Pretale hotel on our Chianti bike tour

Borgo Pretale

Sovicille, Italy

Nestled in the tranquil forests of central Tuscany, this 13th century home has been restored into a beautiful hotel. The main tower and its surrounding buildings all share gorgeous views and the estate has a swimming pool, tennis court and walking paths for you to enjoy. Soak in the history of this ancient space that provides all the modern amenities you could want.
La Cianella on our Chianti bike tour

La Cianella

Massa Maritima, Italy

La Cianella takes its name from the 19th century fountain located on the grounds, "Fontana delle Cianelle." Surrounded by olive trees, La Cianella is set high on a hill with fantastic views of surrounding valleys. Intimate and inviting, the 19th century main structure now houses 12 charming, comfortable rooms. The outdoor swimming pool and tennis courts each offer scenic views of the surrounding countryside.

What's Included

We Include More

Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that’s how we help you create more memories. Learn more

  • Gratuities for all scheduled special events, restaurants, hotels, local guides and transportation during your trip.
  • Private tours
  • Entrance fees to all group events/activities
  • All luggage transfers
  • All transportation during the trip, including private coaches
  • 5 nights of accommodation
  • In every region we travel, we uncover the area’s best, and most delightful accommodations. On our Chianti to the Coast trip, you will stay in three beautifully balanced hotels including an impeccably restored manor house in a medieval village and a charming country residence in the hills above the Mediterranean.
  • On our Chianti to the Coast trip, local cuisine is known for using fresh, seasonal ingredients brought together in simple but classic style. Lunch provides bountiful selections of delicious regional specialties, and dinners range from hand-made pasta dishes at intimate local trattoria to elegant flawless fine dining in truly superb restaurants. On other occasions, you’ll be free to explore the local ‘cocina’ at your leisure to discover your own personal favorites. Buon appetito!
  • The knowledge, support, and camaraderie of experienced guides
  • Daily route support
  • The use of Garmin Touring Plus GPS cycling computer
  • Paper route guides also available upon request
  • Comprehensive trip literature and complimentary Trek merchandise
  • The use of a Trek Domane 5.9 carbon road bike with Shimano Di2 electronic shifting, or Trek Domane 5.9 Women’s Specific Design carbon road bike with Shimano Di2 electronic shifting (limited selection), or Trek 7.6 FX Hybrid bicycle
  • The use of Garmin Touring Plus GPS cycling computer
  • The use of Trek bike helmets and other gear and equipment to make your ride comfortable
  • Trek Travel water bottles
  • $300 USD off any 2015 5 Series or 6 Series Trek Domane including Project One and the Trek Emonda SL6 and SL8 models.
  • Trek Travel Bontrager RL jersey

Thank your Guides, by tipping

Gratuities for your Trek Travel guides are not included in your trip price. Industry standard is 5-10% of the trip price which will be divided by your guide team. Please tip your guides at your discretion, based on their level of professionalism, guest care and service.

  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.
  • Gratuities for your Trek Travel Guides may be given at your discretion in response to their professionalism and leadership.Industry standard is for each individual guest to tip the guide team 5-10% of the trip price.


Trip Changes

Our itineraries are an approximation of our trips. Trek Travel strives to offer each and every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

  • Rider Type | 3
  • Average Daily Mileage | 46
  • Terrain | Hilly
  • Average Daily Elevation | 3,300

On all of our vacations, Trek Travel strives to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Chianti to the Coast is best suited for our Type 3 Riders. Our Trek Travel guides can also easily accommodate Type 2 Riders, who seek less mileage or fewer uphills, with a boost in the van. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option–you still get a workout but can climb alongside even the strongest rider. Type 4 Riders will enjoy the extra mileage the avid route options offer. The terrain is hilly, with quiet, narrow, and winding roads. Many towns sit atop hills and, although the ascents are not exceptionally steep, they are often upwards of 3 miles long. See Itinerary for specific daily ride distance and elevation options.

The fall brings pleasant daytime temperatures (70F-80F) and evening temperatures 10-15 degrees cooler. Tuscany’s northern location means that it can be hit with the odd cold spell or rain shower. Light layers and a waterproof shell are recommended.

On most Trek Travel trips, we offer non-riding options for riders who want to take the afternoon off, or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Expenses and/or related transportation to these activities may not be included in the trip price. See Included In The Trip Price for more information. Some non-riding options on this trip are:

  • Explore the walled city of Siena
  • Shop and explore the medieval villages of Radda, Lecchi, Monteriggioni and Casole D’Elsa
  • Discover why Tuscan wines and olive oils are so renowned during our private wine-tasting
  • Opt to spend a half day at a local spa

For an additional fee you may request to upgrade to the brand new Trek Emonda SLR with Shimano Di2 electronic shifting for the ultimate riding experience. Upgrades to Bontrager Aeolus carbon wheels and Trek Ride Plus electric assist bicycle are also available. Contact our trip consultants for more details.

We understand things happen in life and sometimes you have to cancel or change your bike tour. We want to make it as easy as possible to do so and below you will find our timeline. If you ever have a question, just give us a call, 866 464 8735. Read our cancellation policy.

Didn't find what you were looking for? Check out our General FAQs section. You will find answers to all the most common questions that don't necessarily pertain to a specific trip.

Travel Services

How to get there

We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into Florence’s Amerigo Vespucci Airport (FLR) which is located about 3 miles from the town center.You can take a bus, which departs hourly, or a taxi (~20 euros) directly to the hotel.

At 12:00 noon, you’ll depart by private shuttle for the Grosseto train station, arriving at approximately 1:00 pm.The train to Rome takes just over 2 hours, while trains to Florence require one change with the full trip taking approximately three hours. From both Rome and Florence, many other European destinations are easily accessible. Train schedules, fares and bookings can be made on the Trenitalia website at, or for other European destinations. Alitalia is the main operating airline connecting through Florence and you can find their schedules and other information on their website at

Hotel Palazzo Vecchio | Florence, Italy

Your Trek Travel guides will meet you at the Hotel Palazzo Vecchio (via Cennini 4, 50123, Florence, Italy) at 11:00 AM on the first day of the trip. You’ll take a one hour private shuttle to Radda in Chianti to enjoy a bountiful lunch featuring Tuscan specialties. Please have that day’s cycling clothes and riding gear easily accessible, separate from your luggage. After lunch, your Trek Travel guides will ensure you have a perfect fit to your bike before you head off for your first spin through the Tuscan countryside.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip start with their names and contact details. If you cannot reach them, please call our first hotel, Palazzo Leopoldo (+39 0577 73 56 05), and leave a message with your expected arrival time and contact details.You may take a taxi to Palazzo Leopaldo, the first night’s hotel in Radda in Chianti, for approximately 150 euros.

Grosseto Train station | Grosseto, Italy

You will say farewell to your guides at 11:00 AM at the Agriturismo La Cianella.You’ll then shuttle 1 hour to the Grosseto Train Station, arriving at approximately 12:00 PM. Please allow adequate connection time for any ongoing travel to accommodate possible traffic delays.

Before: FLORENCE, Italy

Florence is the majestic heart of Renaissance art and intellect. Several days can be spent wandering the streets in the shadow of Brunelleschi’s Duomo and alongside the famous Arno River. Along with the Duomo and Ponte Vecchio, the Uffizi is extremely worthwhile to visit as the pillar of the Renaissance and Medici era. Michelangelo’s David in the Galleria dell’Arte is not to be missed. Keep in mind while exploring Florence that opening hours vary and are quite often inconsistent. Different museums are open on different days and lines can be very long. It’s worthwhile to pay a few extra Euros and pre-book your tickets—this will enable you to pass all of the people waiting in line.We recommend the following accommodations for your pre-trip hotel:

J.K. Place Firenze

Hip and modern, Centrally located, within walking distance of Santa Maria Novella train station

Piazza S. M: Novella, 7, 50123 Firenze | +39 05 52 64 51 81 | www.JKPlace. com | ~$400

Hotel NH Porta Rossa

Built in the 12th century, the NH Porta Rossa hotel is one of the oldest hotels in Italy. Located in the pedestrian zone of Florence’s historical center it is well situated for visitors to experience all the sights and sounds of Florence.

Via Porta Rossa,19. 50123 Florence| + 39 05 52 71 09 11 | | ~$250

Hotel David

Just a short walk to the historic center or to the surrounding green hills, the Hotel David in Florence is a perfect place to begin and end the day in one of the world’s most beautiful cities. Housed in a completely renovated villa, the antique-filled Hotel David retains the charm of slower times.

Viale Michelangiolo 1, 50125 Florence | +39 05 56 81 16 95 | www.HotelDavid. com | ~$200

After: ROME, Italy

Rome is a powerhouse of stunning architecture and ancient history, beautifully told through its ruins and buildings. It seems that every street you walk down provides another unexpected glimpse of ancient times, yet modern bustle and energy abounds as well.The Coliseum, the Roman Forum, Vatican City and the Pantheon are some of the don’t-miss attractions. Be sure to linger on the Spanish Steps one afternoon and take advantage of great shopping and fantastic cuisine.We recommend the following accommodations for your post-trip hotel:

Hotel Barocco

This 37-room hotel is tucked away on central Piazza Barberini. It boasts a refined, simple style with all of the comforts and amenities needed for a relaxing Roman getaway.

via della Purificazione, 4 00187 Roma | +39 06 487 2001 | www.HotelBarocco. com | ~$285

Hotel Capo d’Africa

Located in the heart of Imperial Rome, between the Forum and the Domus Aurea, the Hotel Capo d’Africa boasts contemporary decor within a beautiful early 19th-century building. 64 rooms.

via Capo d’Africa, 54 00184 Roma | +39 06 772801 | www. | ~$350

Mecenate Palace

In front of the Basilica of Santa Maria Maggiore, this hotel is within walking distance of most of the important monuments and shopping areas found in Rome. Guests can enjoy a panoramic view of the city from the hotel’s roof garden. 62 rooms.

via C. Alberto, 3 00185 Roma | +39 06 44702024 | www.MecenatePalace. com | ~$260

* Hotels listed above are local properties we love. We do not have special rates available.

Experience It

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Trek Travel Difference

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the full-carbon, ultra smooth Trek Domane 5.9, to the comfortable Trek 7.6 FX Hybrid–both included in the trip cost, to our numerous upgrade options, you deserve the best ride on your vacation.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.