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Tuscany Hills and Sea-Luxury Cycling Tour

7 days
Start and end in Siena
5.0
1 traveler review

No departure dates available

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Plan your adventure:
Bicycle
Pedal-powered journeys for two-wheeled explorers
Fully Guided
An experienced guide will be with you for the entire tour
Medium Intensity
Travelers should be comfortable with somewhat-demanding activities
Guided in English
Group Size 2 - 7
Ages 18+
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Siena

    You'll arrive in Siena with your own transport and meet up with the tour staff. There's a presentation about what's coming up, then your bikes get prepared and checked over. After that, you'll have a welcome drink to get to know everyone, and the day wraps up with dinner.

    Meals
    Dinner (Local acclaimed restaurant)

    Included Activities

    • Bike preparation
    • Welcome drink
    • Dinner in local restaurant
    Landmarks
    Siena
  2. Day 2

    Siena to Chianti Hills Loop

    This morning after breakfast, you're cycling 74 km through the Chianti Hills with rolling vineyards and gentle climbs the whole way. You'll ride through Radda in Chianti, then keep going to Castellina in Chianti where you'll stop for a cappuccino. From there, it's back to Siena for the evening. Dinner is at a typical local restaurant that's well-regarded in the area.

    Meals
    Breakfast, Lunch (Lunchtime biker's snacks and drinks), Dinner (Local acclaimed restaurant)

    Included Activities

    • Cycling tour through Chianti Hills (74 km)
    • Visit to Radda in Chianti
    • Visit to Castellina in Chianti
    • Cappuccino break in Castellina in Chianti
    • Dinner in local restaurant
    Landmarks
    Radda in Chianti
    Castellina in Chianti
    Chianti Hills
  3. Day 3

    Siena to Volterra

    Starting from Siena after breakfast, you'll cycle through small hillside villages with views of Monteriggioni castle along the way. You pass by Abbadia a Isola, a medieval spot that was part of the old Via Francigena pilgrimage route. Then you reach San Gimignano, which sits at 324m and has those famous intact towers from the medieval period. Your final destination is Volterra, an ancient town over 3,000 years old with an Acropolis, Etruscan walls, a medieval cathedral, and the Medici Fortress. You'll have time to walk around town before dinner.

    Meals
    Breakfast, Lunch (Lunchtime biker's snacks and drinks), Dinner (Local restaurant)

    Included Activities

    • Cycling tour through Tuscan villages
    • Visit to Abbadia a Isola
    • Visit to San Gimignano
    • Visit to Volterra
    • Dinner in local restaurant
    • Time to visit Volterra
    Landmarks
    Monteriggioni Castle
    Abbadia a Isola
    San Gimignano
    Volterra
    Volterra Cathedral
    Medici Fortress
    Palazzo dei Priori
  4. Day 4

    Volterra to San Vincenzo

    After breakfast, you're cycling from Volterra through Saline di Volterra, known for its salt springs. You'll continue through Pomarance and Montecerboli, areas known for their geothermal energy sites, then pass through historical villages like Sarezzano, Monteverdi Maritimo, and Doronatico. By late afternoon you reach San Vincenzo on the Etruscan Coast, check into your hotel, and have time to relax. Dinner with the group features local produce from the region.

    Meals
    Breakfast, Lunch (Lunchtime biker's snacks and drinks), Dinner (Dinner with group based on typical local produce)

    Included Activities

    • Cycling tour from Volterra to San Vincenzo
    • Visit to Saline di Volterra
    • Visit to Pomarance
    • Visit to Montecerboli
    • Dinner in local restaurant with group
    Landmarks
    Saline di Volterra
    Pomarance
    Montecerboli
    Sarezzano
    Monteverdi Maritimo
    Doronatico
    San Vincenzo
    Etruscan Coast
  5. Day 5

    Eastern Part

    After breakfast, you take a ferry from Piombino across to Portoferraio on Elba Island, then start cycling the eastern part of the island. The landscape is green and quiet with beaches, cliffs, and small hilltop villages. You'll ride through Bagnaia, Nisporto, and Nisportino to reach Rio dell'Elba, a medieval hamlet with historic mills still there. From there, continue to Capoliveri at 167m elevation, a beautiful medieval village perched on the hillside. You return to Portoferraio, a 16th-century Medici town with museums, mansions, and fortresses. After checking your bikes, you'll have time to relax before dinner.

    Meals
    Breakfast, Lunch (Lunchtime biker's snacks and drinks), Dinner (Local food)

    Included Activities

    • Ferry transfer from Piombino to Portoferraio
    • Cycling tour of eastern Elba Island
    • Visit to Rio dell'Elba
    • Visit to Capoliveri
    • Visit to Portoferraio
    • Dinner in local restaurant
    Landmarks
    Elba Island
    Rio dell'Elba
    Capoliveri
    Portoferraio
  6. Day 6

    Western Part

    Starting after breakfast, you're cycling the western part of Elba Island heading toward Procchio and Marciana Marina, the island's smallest municipality. The route climbs through hills past Poggio with its century-old chestnut woods, then reaches Marciana at 375m elevation, one of the island's oldest inhabited areas. You descend through Chiessi on the Costa del Sole out toward the island's western tip, then return through Procchio back to Portoferraio. An excellent group dinner wraps up your time on the island.

    Meals
    Breakfast, Lunch (Lunchtime biker's snacks and drinks), Dinner (Excellent dinner with group)

    Included Activities

    • Cycling tour of western Elba Island
    • Visit to Procchio
    • Visit to Marciana Marina
    • Visit to Poggio
    • Visit to Marciana
    • Visit to Chiessi
    • Dinner with group
    Landmarks
    Procchio
    Marciana Marina
    Poggio
    Marciana
    Chiessi
  7. Day 7

    Elba Island to Siena

    You'll have breakfast and then take the ferry from Elba Island back to the mainland. After that, a minibus transfer takes you back to Siena.

    Meals
    Breakfast

    Included Activities

    • Ferry transfer from Elba Island
    • Minibus transfer to Siena
    Landmarks
    Siena
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What's Included

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  • Accommodation
  • Guide
  • Insurance
  • Meals
  • Additional Services
  • Transport
  • Free eSIM
    TourRadar offers the lead traveler (the person who booked) a free 1GB eSIM for the trip. The eSIM is redeemable only through the TourRadar app 72 hours before departure.

What's Not Included

  • Flights
  • Optional
  • Additional Services
4.9
(15 reviews)

Number of tours

11

Age Range

18 to 90 years old

Response time

within 3 days

Response rate

50%

Road Bike Tours Italy was set up thanks to a desire to share our appreciation...

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Customer Reviews

  • Overall Rating
    Excellent
    5.0
  • Itinerary
    Excellent
    5.0
  • Guide
    Excellent
    5.0
  • Transport
    Excellent
    5.0
  • Accommodation
    Excellent
    5.0
  • Food
    Excellent
    5.0
  • 4.9
  • FL
    · June 20th, 2022
    This was such an amazing trip .... I would highly recommend Luca's hosting. Everything was top notch including organization, equipment, safety on the road, hotels, meals ... etc, etc. I will most certainly be returning for another tour.
    Show more
    Road Bike Tours Italy commented on this review
    Dear Fiona, Many thanks for your beautiful words. We spend an unforgettable time altogether, I hope to see you again on a new tour. Luca
    Trip date: May 2022

What our customers ask about this tour

The content in our FAQ section is subject to change.
All questions
  • M

    Megan

    Asked on June 2nd, 2022

    I'm a 69-year-old bicyclist. Active and fit. I've visited IT a few times. I am a vegan and I teach plant-based cooking so having access to vegan food choices is important. These days I ride 12-18 mph, don't hate hills, avg. distances per ride 20-60 miles. Does the Tuscany to sea ride seem like a good one for me (small group, friendly folks, not wannabe racers). I'd also entertain other rides as you might suggest.

    Group size
    Meals
    Tour Details
    • Road Bike Tours ItalyOperatorWritten June 2022

      We haven't confirmed that tour yet. Instead we confirmed the tour "A Fantastic Journey" dept on Sunday, September 25th. This tour is undoubtedly our best seller. This bike trip allows us to get in touch with the real Tuscany.

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Plan your adventure:

Good to Know

Tour ID: 97771

  • Currency
    Euro
    Italy
  • Plugs & Adapters

    As a traveler from New Zealand you will need an adaptor for type L.

    Type L
    Italy
  • Visa
    • Unfortunately we cannot offer you a visa application service. Whether you need a visa or not depends on your nationality and where you wish to travel. Assuming your home country does not have a visa agreement with the country you're planning to visit, you will need to apply for a visa in advance of your scheduled departure.
    • Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.
  • Payment information
    • For any tour departing before February 14th, 2026 a full payment is necessary. For tours departing after February 14th, 2026, a minimum payment of 20% is required to confirm your booking with Road Bike Tours Italy. The final payment will be automatically charged to your credit card on the designated due date. The final payment of the remaining balance is required at least 60 days prior to the departure date of your tour. TourRadar never charges you a booking fee and will charge you in the stated currency.
    • Some departure dates and prices may vary and Road Bike Tours Italy will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Road Bike Tours Italy" tours: Visa, Maestro, Mastercard, American Express or PayPal. TourRadar does NOT charge you an extra fee for using any of these payment methods.
  • Cancellation Policy
  • Accessibility
    Some tours are not suitable for mobility-restricted traveler, however, some operators may be able to accommodate special requests. For any enquiries, you can contact our customer support team, who are ready and waiting to help you.

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Western Europe Travel Guide

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2025

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec