Italy: Southern Tuscany & Giglio Island

7 days
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4.9/5 Excellent
100+ reviews  
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Group Tour
This original cycling tour of southern Tuscany has had its share of copycats. We’re flattered—but don’t be fooled; reproductions are never authentic as the original. With 20 years of experience cycling the Tuscan coast, we know the best seaside routes, award-winning vineyards, and masserias that reflect the Maremma’s unique character. Our local Tuscan trip le...
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Trip type
Group Tour
Lodging level
Premium - 4 star
Physical level
Trip pace
Full schedule


    • Savor fresh farm cuisine during stays at fattorie lodgings
    • Dip your toes, lounge in the sand, or swim in the Tyrrhenian Sea
    • Learn from a Tuscan chef how to prepare cantucci almond cookies
    • Taste locally pressed olive oil at a local oil mill
    • Walk a panoramic trail with a local guide on Giglio Island

What's this trip about?

    This original cycling tour of southern Tuscany has had its share of copycats. We’re flattered—but don’t be fooled; reproductions are never authentic as the original. With 20 years of experience cycling the Tuscan coast, we know the best seaside routes, award-winning vineyards, and masserias that reflect the Maremma’s unique character. Our local Tuscan trip leaders will take you to secluded swimming coves—including a delightful beach on Giglio Island where you can cool off after an afternoon’s guided walking tour. Pedal the shores of the Orbetello lagoon, learn to prepare Tuscan cantucci during a cooking class, and enjoy a tasting of Tuscany’s “liquid gold” at a local olive oil mill. This incredible cycling vacation has it all.


Itinerary focusActive
Group sizeSmall Group - max of 20 people
Age range13 to 80 years
Flights and transportN/A
Start CityOrvieto
End CityRome

Travel Themes

  • Culinary & Wine
  • Cultural
  • Cycling & Biking
  • Nature & Wildlife


  • Europe
  • Italy


  • Capalbio
  • La Parrina
  • Magliano
  • Orvieto
  • Pereta
  • Rome
  • Scansano
  • Tuscany


  • Cooking
  • Culture
  • Cycling
  • Educational/ learning
  • Nature
  • Winetasting
  • Guided Group

Trip includes

    • Custom VBT Bike and Helmet
    • Two Local, Bilingual Trip Leaders
    • Support Vehicle
    • Luggage Transportation
    • Ride with GPS and Daily Route Notes
    • Welcome Reception
    • Facilitated Cultural Experiences
    • Your Choice of VBT Branded Gear for Your Adventure


Travel Map
DAY 1: VBT Bicycling Vacation begins / Travel to Parrina / Warm-up ride / Welcome reception and dinner

Meet your VBT trip leaders inside the Orbetello-Monte Argentario train station at 2:15 p.m. Your trip leaders will be wearing VBT staff garments. Please plan to buy lunch on your own before this meeting.

If you prefer, you can meet your group at the hotel in Or...

DAY 2: Cycle by the Maremma Park / Talamone / Cooking class

After breakfast, you’ll leave La Parrina and cycle to the coast and Talamone, where you’ll discover the many Greek legends linked to this little fortress village. There’ll be time during the morning’s ride to swim in the glittering blue sea. The medieval hilltop town ...

DAY 3: Cycle to Feniglia and Orbetello

This morning, ride through the countryside toward the coast and Ansedonia, passing elegant villas and gardens and enjoying splendid views of the sea and the old watchtower that once defended this coast. Enjoy a picnic lunch along the way at a typical Maremma family-ru...

DAY 4: Porto Santo Stefano / Ferry to Giglio Island

Today, take a pedaling break from your Tuscany bike tour to enjoy the tranquility of the Giglio island. You’ll start this morning with a warm goodbye to your hosts at La Parrina before traveling to the bustling harbor and quaint village of Porto Santo Stefano. From th...

DAY 5: Capalbio / Wine tasting

After breakfast, cycle to the medieval town of Capalbio. Dating to the 11th century, historic Capalbio is surrounded by massive walls. Stroll along these ancient ramparts above the city and take in the panoramic views of the surrounding countryside. Then enter the his...

DAY 6: Follow the Wine Road / Magliano / Olive oil tasting

After a leisurely breakfast, set off on quiet country roads, passing fields of poppies and sunflowers and vineyards gently sloping down to the sea. Tour the wine roads south of Scansano, famous for red Morellino wine. Then stop at the Magliano olive oil shop and forme...

DAY 7: VBT Bicycling Vacation ends / Travel to Rome

After an included breakfast, complimentary transportation is provided back to the Orbetello-Monte Argentario train station by private motorcoach, arriving at approximately 9:30 a.m. If you prefer, you are welcome to board our coach to Rome and continue with your own travel plans from our Rome hotel.

Included Meals: Breakfast

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Dates & Availability

Price From $3,645
Price per day$521
Last Updated: 2/23/2024
Start Date
End Date
Shared Room
Single Supplement
26 Apr 2024
02 May 2024
10 May 2024
16 May 2024
24 May 2024
30 May 2024
Limited Spaces Left
21 Jun 2024
27 Jun 2024
Limited Spaces Left
28 Jun 2024
04 Jul 2024
06 Sep 2024
12 Sep 2024
13 Sep 2024
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20 Sep 2024
26 Sep 2024
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03 Oct 2024
04 Oct 2024
10 Oct 2024

Check Current Availability, prices, specials with VBT Bicycling Vacations.

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.

VBT Bicycling Vacations Reviews & Ratings

4.9/5  Excellent
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Other VBT Bicycling Vacations Reviews



Nov 2023

Written on

Absolutely stunning scenery with relatively easy cycling.

This tour was one of our favorites. The tour leaders (Claudio and Tiziana) were great. The Dolomites and Italian Alps were breathtaking and the bike paths and towns ...



Nov 2023

Written on

Fantastic intro to a bike vacation!

VBT came highly recommended by several friends and family so we took the plunge and did our first guided bike trip. We were never disappointed. Guides, hotels, bikes...



Nov 2023

Written on

life at its fullest

Unlike tours where you gaze at world class natural and historic wonders in another culture, this tour put us in intimate touch with them through cycling, eating, dri...

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Tour Operator

VBT Bicycling Vacations

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Since 1971, VBT has crafted immersive and authentic biking vacations for active travelers. When you travel with VBT, you’re not just another tourist—you’re a traveler. With us, you’ll experience your destination with the help of a local, bilingual trip leader with a passion for sharing their home with you. You’ll eat in local restaurants, stay in accommodations that have been family-owned for generations and cycle through vineyards, olive groves, and medieval villages. 

With VBT, you won’t just visit a place—you’ll immerse yourself in it. You might follow a centuries-old pasta recipe while taking a cooking class in Rome—or learn a folk dance in Croatia, followed by sharing a bottle of locally-produced Grk wine with your new friends. Exploring the world on two wheels lets you experience your surroundings on a deeper level.


VBT offers exceptional value without compromising on quality. Simply put, no other US-based active travel company offers an experience this rich for such a reasonable price. On our tours, you can see more sights, have more local experiences, and enjoy more delicious, authentic meals—all while staying in high-quality, boutique hotels and charming, family-run inns.


All you have to do is show up at the airport—we’ll handle the rest! From tour consultants who help you find the perfect vacation to expert local trip leaders who show you the best place for gelato, we take care of all the little details that make your trip memorable. We book your flights, arrange all your transportation and accommodations, and move your luggage between hotels. Our support vans are available to give you a lift up a hill or quickly fix a flat tire. VBT takes care of your travel details and creates unique itineraries so you can relax and enjoy your small-group vacation from start to finish.


Friendly camaraderie, cultural immersion, and casual comforts are the hallmarks of our vacations. Discover delightful people, beautiful hotels, foreign cultures, and fascinating lifestyles that will enrich your life and provide memories for years to come.

Why we love this operator
Their unique emphasis on immersive cultural experiences combined with active exploration with personalized cycling experiences.
What they’re known for
VBT Cycling are renowned for offering exceptional guided and self-guided bicycle tours worldwide.


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,6 nights in small country estates
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
Visa requirements vary depending on your country of origin and your country of destination. It is your responsibility to familiarize yourself with the relevant requirements. For a handy tool that can help you quickly find the requirements, please visit this link .
Meals Included

14 meals: 6 breakfasts, 3 lunches, 5 dinners

Age Requirements
13 to 80 years
Additional Information
This tour offers a combination of easy terrain and moderate hills, ideal for beginners and experienced cyclists. Our VBT support vehicle is always available for those needing assistance with the hills. The accommodations on this tour are on country estates that are not in or near towns, but in peaceful surroundings. The roads are well paved, and the total unpaved terrain is 3%. Please note: there is one non-biking day to explore Giglio Island. Daily Mileage: 15 - 47 miles| Biking: 1 - 4 hours| Group Size: 20
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