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Siena Cycling & Biking Tours & Trips

109 Siena trips. Tours from 48 tour companies. 94 reviews. 4.7/5 avg rating.

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Cycling & Biking
Tuscany: Cycle Siena & Chianti
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Tuscany: Cycle Siena & Chianti

By Exodus Travels
premier
4.8/5 Excellent
100+ reviews
Small Group Tour
Why we love them
With a huge range of trip styles and themes, they cater to basically every type of traveler out there- even those with super specific interests.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Florence, Siena, Tuscany

Highlights

  • Explore the cultural cities of Siena and Florence
  • Enjoy Tuscan cuisine and wine
  • Visit some of the most beautiful hilltop towns in the region
  • Ride along the scenic country roads of classic Tuscany

Themes

Cultural, Cycling & Biking

What travelers are saying

"Discover Costa Rica is a great itinerary, covering varied habitats around the country and staying 2 nights each at 6 centres. Their birdwatching specials are led by local experts who really know their stuff."

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-15%$3,450
8 days From$2,925

Health Safety +

Generous cancellation

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Secrets of San Gimignano Cycling
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Secrets of San Gimignano Cycling

By Exodus Travels
premier
4.7/5 Excellent
100+ reviews
Small Group Tour
Why we love them
With a huge range of trip styles and themes, they cater to basically every type of traveler out there- even those with super specific interests.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

San Gimignano, Siena

Highlights

  • Exhilarating cycling through open and totally unspoilt countryside
  • San Gimignano's soaring towers; Volterra's Etruscan treasures; great art cities of Florence, Pisa and Siena
  • Fabulous hotels all with stunning pools; superb cuisine and fine wines
  • Cypress-studded hills, sun-drenched olives, row upon row of sunflowers and world-famous vineyards
  • Pretty hamlets, hidden chapels, timeless vermilion villas

Themes

Cycling & Biking

What travelers are saying

"Discover Costa Rica is a great itinerary, covering varied habitats around the country and staying 2 nights each at 6 centres. Their birdwatching specials are led by local experts who really know their stuff."

Trip dates & details
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-26%$4,300
9 days From$3,185

Health Safety +

Generous cancellation

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Classic Chianti Cycling
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Classic Chianti Cycling

By Exodus Travels
premier
4.7/5 Excellent
100+ reviews
Small Group Tour
Why we love them
With a huge range of trip styles and themes, they cater to basically every type of traveler out there- even those with super specific interests.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

San Gimignano, Siena

Highlights

  • Quintessential, Italian landscapes: rolling hills, endless vines, beautifully preserved honey-hued hamlets
  • Mostly 4-star hotels; gorgeous swimming pools; superb local cuisine
  • Scenic cycling through olive groves, fruit orchards and sunflowers
  • Spend 4 nights in Colle di Val d'Elsa: charming piazze, Sienese frescoes, easy access to Florence and Siena
  • Etruscan, Roman, Renaissance and Mediaeval art and architecture

Themes

Cycling & Biking

What travelers are saying

"Discover Costa Rica is a great itinerary, covering varied habitats around the country and staying 2 nights each at 6 centres. Their birdwatching specials are led by local experts who really know their stuff."

Trip dates & details
Save this trip to your favorites or other list
-26%$4,867
11 days From$3,605

Health Safety +

Generous cancellation

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Tuscany Biking
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Tuscany Biking

By Butterfield & Robinson
none
5/5 Excellent
74 reviews
Small Group Tour
Lodging level
Luxury - 5 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Florence, Siena, Tuscany

Highlights

  • Enjoy tasting of Tuscan reds
  • Explore vine-covered hills of Chianti
  • Explore Siena
  • Visit a private wine estate for a tasting

Themes

50 plus, Cycling & Biking

What travelers are saying

"Butterfield and Robinson just planned and executed a great, great trip for us to the Amalfi coast. All the services and hotels were wonderful and the guides were great fun and and well informed. Many nice surprises along the way and an itinerary we would have had trouble putting together on our own was effortless. All guides were well trained the transportation and drivers were polite and on time. The recommended hotels were amazing. We loved every minute of our vacation."

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6 days From$5,295
Price updated 1 year+ ago
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Cycle the Via Francigena - Siena to Rome
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Cycle the Via Francigena - Siena to Rome

By UTracks
preferred
4.8/5 Excellent
62 reviews
Self-Guided / Independent Tour
Lodging level
Basic - 2 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Rome, Siena

Highlights

  • Exploring the renowned cities of Siena and Rome
  • Admiring the sunset over Lake Bolsena
  • Cycling on the old Via Cassia and to ancient Etruscan roads
  • Discovering the thermal pool in Bagno Vignoni, the amphitheatre of Sutri, and the pilgrim district in Viterbo
  • Enjoying delicious Italian delicacies along the way

Themes

Cycling & Biking

What travelers are saying

"A really difficult company to communicate with, slow to respond and not able to accept accountability for poor service. Used Tee Travel in Spain which was even worse. Not able to organize support or assistance and harassed me about luggage that wasn't mine. There were other walkers who appeared to have more support and assistance from their travel providers. Definitely avoid this company as overpriced and no actual service."

Trip dates & details
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9 days From$2,190
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Cycle the Via Francigena - Parma to Siena
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Cycle the Via Francigena - Parma to Siena

By UTracks
preferred
4.8/5 Excellent
62 reviews
Self-Guided / Independent Tour
Lodging level
Basic - 2 star
Physical level
Strenuous
Trip pace
Flexible schedule

Visits

Lucca, Rome, San Gimignano, Siena

Highlights

  • Discovering Parma and its delicacies, such as the Parmigiano Reggiano and Prosciutto di Parma
  • Exploring Lucca and its city walls by bike
  • Soaking up the medieval atmosphere of Pontremoli and Monteriggioni
  • Enjoying stunning views of hilltop villages, open valleys, cypress woods and olive groves

Themes

Cycling & Biking

What travelers are saying

"A really difficult company to communicate with, slow to respond and not able to accept accountability for poor service. Used Tee Travel in Spain which was even worse. Not able to organize support or assistance and harassed me about luggage that wasn't mine. There were other walkers who appeared to have more support and assistance from their travel providers. Definitely avoid this company as overpriced and no actual service."

Trip dates & details
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9 days From$2,290
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Cycle Florence to Siena
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Cycle Florence to Siena

By UTracks
preferred
4.8/5 Excellent
62 reviews
Self-Guided / Independent Tour
Lodging level
Basic - 2 star
Physical level
Moderate
Trip pace
Flexible schedule

Visits

Florence, Siena

Highlights

  • Cycling through the vineyards of Greve and Radda in Chianti
  • Visiting wineries on route
  • Discovering the impressive medieval cities of Florence and Siena
  • Enjoying the friendly hospitality and sampling the local delicacies of the region

Themes

Cycling & Biking

What travelers are saying

"A really difficult company to communicate with, slow to respond and not able to accept accountability for poor service. Used Tee Travel in Spain which was even worse. Not able to organize support or assistance and harassed me about luggage that wasn't mine. There were other walkers who appeared to have more support and assistance from their travel providers. Definitely avoid this company as overpriced and no actual service."

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4 days From$1,060
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Classic Northern Italy
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Classic Northern Italy

By Culture Trip
none
5/5 Excellent
12 reviews
Small Group Tour
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Cinque Terre, Colosseum, Florence, Lake Como, Leaning Tower of Pisa, Milan, Rome, Siena

Highlights

  • Cycle past the famed architectural attractions of Rome on a guided tour
  • Stay overnight in the Tuscan hills overlooking Siena
  • Enjoy a San Gimignano vineyard tour, wine tasting and cooking class
  • Hike along the cliffs of the Cinque Terre National Park
  • Sip an aperitif on a boat tour of Lake Como
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Themes

Culinary & Wine, Cultural, Cycling & Biking, Hiking & Walking, Nature & Wildlife, Relaxing Retreats, Photography, Festivals & Special Events

What travelers are saying

"A Culture Trip curated trip is a must for anyone burnt out planning their own trips or going to a remote or unfamiliar area. Having a local insider was the highlight of the trip. From the moment we landed to the moment we had to go through security to leave, we were completely taken care of. Our insider gave us great recommendations for restaurants and was very adaptable to any situation that arose."

Trip dates & details
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10 days From$3,529
Price updated 1 year+ ago

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Escorted Tours Of Tuscany
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Escorted Tours Of Tuscany

By Alma Italia
Local Expert
Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.
5/5 Excellent
14 reviews
Private Guided
Why we love them
They focus on creating unique and exclusive experiences including one of a kind private tours, tastings of rare wines and local cuisine.
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Full schedule

Visits

Florence, Leaning Tower of Pisa, Lucca, Pisa, Rome, San Gimignano, Siena, Tuscany

Highlights

  • Florence Marvel at the grandeur of the architecture in the Renaissance capital of Italy and soak up the atmosphere of the most culture rich city in the world. Florence is a city of art and alluring elegance and like no other.
  • Siena The delightful hilltop Renaissance jewel. The perfect place to spend a Tuscan day
  • Maremma Leave the tourists behind and adventure into the wilder side of Tuscany. Serene countryside scattered with stunning ancient hilltop towns and vineyards to be explored.
  • Monte Argentario An island joined to the mainland by 3 sandy spits, enjoy island life without leaving Tuscany and discover the best beaches in Tuscany
  • Lucca Another picture perfect walled Tuscan town crammed with architectural treasures. Also our favorite boutiques to browse in Tuscany.
Show more

Themes

Culinary & Wine, Nature & Wildlife

What travelers are saying

"My first trip to Italy was beyond my expectations. Alessio (Alma Italia Travel) is knowledgeable, accommodating, and his love for his country is apparent in how he guides guests through each exquisite destination. Alessio thoughtfully coordinates and plans out each day and is respectful of the guests requests for adjustments to the agenda or rest time to truly take in the beauty of Italy. There isn't a day that goes by where I don't long to return to Italy and breathe in that Tuscan air, sip on the rich olive oils and bright wines, and watch the sun rise and fall through the hills. I highly recommend booking your trip of a lifetime with Alma Italia. You'll be gifted a true authentic experience!"

Trip dates & details
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-12%$6,270
12 days From$5,500
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Italian Discovery
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Italian Discovery

By Eskapas
preferred
4.7/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They introduce their travelers to real locals through their selection of guides and off-the-beaten-path restaurants and attractions.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Assisi, Bologna, Florence, Isle of Capri, Leaning Tower of Pisa, Naples, Padua, Rome, Siena, Sorrento, Venice

Highlights

  • - Most comprehensive itinerary of Northern and Southern Italy - Fully escorted - Private arrival and departure airport transfers - Free Rome walking tour by night

Themes

Cultural, Family Friendly, Photography

What travelers are saying

"Wonderful, we really liked it."

Trip dates & details
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-19%$3,075
10 days From$2,500

Health Safety

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Tuscany: Cycle Siena & Chianti
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Tuscany: Cycle Siena & Chianti

By Exodus Travels
premier
4.8/5 Excellent
100+ reviews
Small Group Tour
Why we love them
With a huge range of trip styles and themes, they cater to basically every type of traveler out there- even those with super specific interests.
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Florence, Siena, Tuscany

Highlights

  • Explore the cultural cities of Siena and Florence
  • Enjoy Tuscan cuisine and wine
  • Visit some of the most beautiful hilltop towns in the region
  • Ride along the scenic country roads of classic Tuscany

Themes

Cultural, Cycling & Biking

What travelers are saying

"Discover Costa Rica is a great itinerary, covering varied habitats around the country and staying 2 nights each at 6 centres. Their birdwatching specials are led by local experts who really know their stuff."

Trip dates & details
Save this trip to your favorites or other list
-15%$3,450
8 days From$2,925

Health Safety +

Generous cancellation

More
Local Living Italy—Tuscany San Gimignano
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Local Living Italy—Tuscany San Gimignano

By G Adventures
preferred
4.6/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They’ve partnered with well-known names like National Geographic and the Jane Goodall Institute to offer unique experiences unavailable elsewhere.
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Florence, Rome, San Gimignano, Siena

Highlights

  • Share an apartment in our local friend ugo's home
  • Eat delicious tuscan cuisine and sample regional wines
  • Stroll the lanes of medieval san gimignano
  • Walk along the beautiful tuscan countryside
  • Make new friends at your home away from home

Themes

Cultural, Education / Learning, Local Immersion & Homestays, National Parks, Nature & Wildlife, Rafting, Kayaking, Canoeing, Transformative

What travelers are saying

"We spent two wonderful weeks touring several of the best destinations in Portugal & Spain with a group of 16 people. Our guide (Fredy) was from Spain and intimately familiar with the region, including its rich history, attractions, and food/beverages. The tour was well-paced using a combinations of private vehicles (small buses and cabs), trains, and an airplane ride as well as a fair amount of walking to get around these two beautiful countries. We extended our stay in Lisbon to see more attractions and took a side trip to Fatima, Obidos, and Nazare that was also excellent. Would have liked to have a bit more time in a couple of the cities, but we'll just have to plan another trip!"

Trip dates & details
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-30%$1,892
7 days From$1,319
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Barcelona to Rome
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Barcelona to Rome

By Intrepid Travel
premier
4.8/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They’re very committed to sustainable and responsible tourism and contribute to important initiatives like climate action.
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Arles, Barcelona, Cinque Terre, Florence, La Spezia, Nice, Pisa, Rome, Siena, Tuscany, Vatican City

Highlights

  • Spend your free time in Barcelona visiting Gaudi's modern basilica, La Sagrada Familia – a Gothic masterpiece that embodies the city’s artistic and progressive heart.
  • Hike in the majestic Spanish Pyrenees mountains, revelling in the fresh air, panoramic views and an exhilarating sense of freedom.
  • Explore the idyllic Provencal landscapes of southern France and gain an understanding as to why this part of the world is so adored by artists.
  • The Leaning Tower may be Pisa’s most iconic image, but there’s so much more to discover – The Piazza dei Miracoli and Pisa Baptistry are masterpieces in Medieval-Italian architecture.
  • Enjoy plenty of free time in Rome to discover the ancient Colosseum, stroll through Vatican City and gaze up towards the gods inside St Peter's Basilica.

Themes

Cultural, High Adventure, Local Immersion & Homestays

What travelers are saying

"We joined the Intrepid “Real Italy Food Tour” and enjoyed it thoroughly. Our tour guide, Micol, was very knowledgeable and provided us with lots of good information. It seems Micol knew many of the staff of the venues we visited, including the pasta making class we attended. Our group of 11 travelers was extremely compatible, which greatly added to the fun and enjoyment."

Trip dates & details
Save this trip to your favorites or other list
-26%$7,290
15 days From$5,400

Health Safety +

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8 trips exactly matchall of the the filters you selected. We are displaying some similar trips.
My selections:
Cycling & Biking

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Siena Reviews & Ratings

4.7/5  Excellent
94  Reviews
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Excellent
819
Great
269
Average
34
Disappointing
11
Terrible
6
A

Anonymous

Oct 2018

Provided byExodus Travels

Excellent hol

Great weather. Lovely group of people. Superb tour leaders (Bex and David). Food and wine was great. Ditto scenery. Really sorry to come home. If you are reasonabl...

Tour:  Tuscany: Cycle Siena & Chianti

A

Anonymous

Oct 2018

Provided byExodus Travels

Cycling Siena and Chianti

Great cycle routes, well planned stops, good climbs and descents. Reaching the tops of some of the more challenging hills Jon was a fabulous group leader, well org...

Tour:  Tuscany: Cycle Siena & Chianti

A

Anonymous

Oct 2018

Provided byExodus Travels

Lovely Hol

Second trip with Exodus. Lovely holiday cycling through Tuscany, finishing in Florence. Lots of clmb, but not too severe. Great weather, food & wine. Group we...

Tour:  Tuscany: Cycle Siena & Chianti

A

Anonymous

Oct 2018

Provided byExodus Travels

Siena cycle trip review

organised and well supported cycle trip through beautiful tuscan countryside with visits to Florence and siena. Not one specific thing but generally enjoyed the cha...

Tour:  Tuscany: Cycle Siena & Chianti

A

Anonymous

Oct 2018

Provided byExodus Travels

Great trip, difficulty rating a bit misleading

Our second trip with Exodus. A really good group of cyclists to ride and socialize with. Leaders Becs and David did a great job supporting us and handling both t...

Tour:  Tuscany: Cycle Siena & Chianti

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