Biking tours


Tuscany Coast Bike Tour

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  • Location: Italy
  • Duration: 7 Days/6 Nights
  • Departing from: Florence, 9 a.m. Sunday, Day 1
  • Tour finishes: Grosseto or nearby train station, 10 a.m. on Day 7
  • Departures 2020: May 3, 17 & 31, June 14 & 28, July 12, Aug 23, Sept 6 & 20, Oct 4
  • Price 2020: Euro €3,300 per person in double occupancy and a group size of 6 or more (€3,600 if less than 6). Single Supplement Euro €300. Two guides accompany departures of 3 or more people (one guide for groups of 2).

Ride beside white sandy beaches, through charming seaside villages, and past terraced olive groves and lush vineyards as you explore Tuscany’s beautiful and lesser-traveled coast. The region’s gently rolling hills are scattered with medieval villages, seaside harbors, and famous wineries, making it ideally suited to biking. Of course, Tuscany’s wonderful cuisine, superb wine and charming inns provide a wonderfully relaxing end to the day. Our rides include flat coastal roads as well as some hillier terrain with long, gradual climbs. Optional rides are available for those wanting more miles, while more casual cyclists can return to the hotel earlier, or take advantage of our support vehicle. The tour takes in the renowned wine region of Bolgheri, home to the famous labels of Ornellaia, Sassicaia, and Grattamacco. We have incorporated visits to a winery and an olive oil mill so you can experience first-hand two of the key elements that make life in Tuscany so sublime. The beautifully preserved medieval towns of Castagneto Carducci, Casale Marittimo, and Suvereto feature in the first few days while the second half of the trip explores the heart of the Maremma, Tuscany’s “Wild South.” Our accommodations include two country hotels (with pools) which produce their own olive oil and wine, and a seaside villa just steps away from the beach.

Tuscany Coast Bike Tour itinerary

Day 1 – Sunday

Meet your guide(s) at 9:00 a.m. at the Hotel Orto de’ Medici (or similar), in Florence. We have a 1.5 hour van shuttle to the charming seaside town of Castiglioncello where we will check into our hotel by the sea. After a short orientation, we set out for our first ride along the sea and up to a nearby village for lunch. The afternoon ride ends back in Castiglioncello where you will have time to enjoy a swim and explore the town. Located on a promontory covered by pinewood and Mediterranean brush, there is a lovely promenade for an evening stroll. Our hotel is the Villa Leopoldo (or similar), a charming family-run hotel built in the early 1900′s on the seaside. Sit back, relax and admire the shimmering sunset, then enjoy dinner on the terrace perched above the water. Overnight Castiglioncello. Hotel, breakfast and dinner included.

Day 2 – Monday

Today we ride up into the low hills that rise up from the coastal plain, along quiet country roads with beautiful views of the verdant hills and the Tyrrhenian sea.  We’ll ride through several small villages and stop for lunch in a delightful trattoria in the town of Gabbro, a tiny village nestled in the Regional Park of the Monti Livornesi.  A beautiful downhill takes us back to Castiglioncello, where we can enjoy a swim and a walk along the promenade.  We dine together tonight in a local restaurant. Overnight Castiglioncello. Hotel, breakfast and dinner included.

Day 3 – Tuesday

This morning we bike through the “pineta,” a shady pine forest which stretches for miles along the coast.  We soon reach the “Strada del Vino,” the wine road of the Bolgheri area, a.k.a. the “Italian Bordeaux.”  Bolgheri village is full of artists, workshops and galleries, and of course tempting wine shops. We have lunch in a local trattoria that is popular with the local winemakers, then wend our way to the winery of Michele Satta for a wine tasting.  One of the most prestigious wineries in the area, its picturesque cellars are carved out of the natural rock wall.  After the tasting, we make our way to Tenuta La Bandita (or similar), our home for the next two nights.  It is a 17th-century villa set high in the hills of the Val di Cornia, with an elegant and tranquil atmosphere.  Have a dip in the pool then relax on the terrace before dinner featuring the Tenuta’s own organic produce. Overnight Tenuta la Bandita. Hotel, breakfast, lunch and dinner included.

Day 4 – Wednesday

This morning you can ride a challenging loop in the surrounding hills, or enjoy a later start and an easy ride to our lunch destination.  Whichever you choose, we will visit Castagneto Carducci, an ancient town perched dramatically above the sea. Its medieval ramparts offer breath-taking views which the Counts della Gherardesca might have appreciated less 600 years ago when they scanned the horizon for marauding Saracen pirates. We have lunch at the Fonte di Foiano, a family-run olive mill. We’ll learn why Olio di Oliva Extra Vergine is so special and then enjoy a lunch of their home-grown delicacies, After lunch, ride back to La Bandita and enjoy some downtime by the pool. Overnight Tenuta la Bandita. Hotel, breakfast, lunch and dinner included

Day 5 – Thursday

Our ride takes us on a beautiful road through dense chestnut and cork oak forests, as we head south toward the Tuscan Maremma. This is the wildest part of Tuscany, where until recently shepherds tended to their livestock – notably cattle and sheep – on horseback. Sassetta village, perched on an outcrop of rock high above the valley serves as a beacon as we make our way to medieval Suvereto. Its fortified walls, tower houses, and Gothic churches take you back a thousand years. A nice cappuccino at the café will ease you back into the present, and then we ride through the Montioni forest to a great little trattoria in the middle of nowhere – a favorite stopping point for local cyclists. Try their wild boar carpaccio! It’s delicious and will fuel your afternoon ride.  After lunch, we ride past the rock quarries of Scarlino on our way to our next hotel, the Agriturismo Montebelli (or similar), which is a gem. Our host, Alessandro, welcomes us to his family-run property with a glass of his own excellent wine and tells us a little about the estate’s long history. Overnight Agriturismo Montebelli. Hotel, breakfast and dinner included.

Day 6 – Friday

Bring your swimsuit because today we ride to the beach!  Our destination is Castiglione della Pescaia, a lovely seaside resort town surmounted by an imposing castle. It also has a sandy beach, so we make time for a dip in the Med before lunch, but save room for the best gelato in the Maremma. Tonight’s final aperitivo is on the terrace followed by a special barbecue feast. Overnight Agriturismo Montebelli. Hotel, breakfast and dinner included.

Day 7 – Saturday

We transfer at 9:00 this morning to Grosseto train station for rail connections to Rome, Florence, and beyond. Breakfast and transfer included.

Useful Links

The City of Florence: everything you need to know about the city
The Accademia:  home of Michelangelo’s David and other world-famous works and The Uffizi Gallery: one of the greatest collections in the world. We recommend you make reservations ahead of time. The official site for both the Uffizi and Accademia is  and where in addition to ticket reservations useful information about the museum the artworks, the events,
and what visitors need to know before visiting the gallery.
The Duomo: one of the wonders of the Renaissance, Florence’s cathedral.
The Maremma:  great site with photos and info about the Maremma region.
UNESCO World Heritage Sites: Italy has more sites listed than any other country!

Activity Rating: 3 out of 5 = Moderate. A mix of flat and gently rolling terrain with the occasional sustained climb of up to 4 kms with some short, steep ups and downs. Daily activity is 4 to 5 hours with max distance 60 kms. Note: This is easier than our Chianti bike tour but is probably the most challenging of our "moderate" tours.

Trip Cost Includes: 6 nights in 3-star hotels and country B&Bs; 6 breakfasts and dinners, 2 lunches; bilingual guides; support vehicle; visits as noted in the itinerary; all luggage transfers; hybrid bicycle rental (road bikes and e-bikes are available for a small supplement); and final transfer to most convenient train station for departures. All departures are accompanied by two guides.

Booking: e-mail us at to receive a booking contract (or use the 'Contact Us' link at the top of this page), or click on the 'Book Now' button to the right.

Insurance: We highly recommend the purchase of Trip Insurance. We recommend “Travel Guard” to our North American clients, just click on the logo below.  Australian, New Zealander, and British travelers, please consult your insurance brokers.

travel Guard insurance

Getting There: the trip starts in Florence at 9 a.m. in the lobby of the Hotel Orto de’ Medici. Florence is well connected by road, rail and air with the rest of Italy and Europe.

Air: Florence airport receives both domestic and international flights, through European hubs such as London, Paris, Frankfurt, Amsterdam, Munich and Brussels. You can also fly into Pisa (about an hour away by train) on many low-cost airlines. For a complete list of Italian airports and a selection of low-cost airlines, see our "Transport Info" page.

Rail: The Eurostar and new Italo high-speed trains connect Florence with Milan (travel time about 2.5 hours), Bologna (travel time 35 mins) and Rome (travel time 1.5 hrs). See the Trenitalia website (in English) at this link. For alternative high-speed rail travel, see the Italo website. For complete information on using the Italian train system, see our blog post.

Road: The A1 Autostrada connects Florence with the rest of Italy. Travel time from Milan is about 5 hours, from Bologna 1.5 hours, and from Rome about 3 hours.

Getting Away at the End of the Trip: the trip ends with a van transfer to the Grosseto or Pisa train station (depending on the group’s travel arrangements) after breakfast on Saturday. We arrive around 10:00 a.m. to make connections to Florence, Rome, or other destinations.

If you book a trip with us you will receive detailed information about how to get to and from the trip, and of course you can e-mail us with any questions.

5.00 out of 5
Ratings based on 3 Verified Reviews

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by N. O'Hearn from Canada
Posted Feb 17, 2015

I loved this trip. It had beautiful ocean, interesting scenery, great cycling, superb food and especially wine. I was \Ga Ga\ to be so close to the wineries of Sassicaia and Ornellaia and was able to taste these famous wines in the quaint town of Bolgheri. Fantastic!!! My idea of a wonderful trip.

by Evangelista from Canada
Posted Feb 12, 2015

Brett and company created this trip because we had already done a number of trips in Italy with Custom Walks and we were looking for something different. It became one of our favorite. We loved the oceanside. Of course, as always, the food, wine, scenery, riding, adventure, staff, etc was as awesome as with all other trips we have done with them. Custom Walks never disappoints

by T Breeze from Toronto, Canada
Posted Jan 30, 2015

This was my first trip to Italy and doing it as a cycling tour with Brett and CustomWalks was amazing. Well planned, safe, fun and interesting. A very special vacation.

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