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Siena Tours & Trips

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

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109 Trips match your criteria (21 - 40 shown)

Italy: Tuscany and Umbria Vineyard Walks
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Italy: Tuscany and Umbria Vineyard Walks

By G Adventures
preferred
4.8/5 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
Premium - 4 star
Physical level
Moderate

Visits

Rome, San Gimignano, Siena, Tuscany, Umbria

Highlights

  • Hike from the tiny village of strove along the ancient via fancigena
  • Sip wine on a vineyard terrace in tuscany during a lunch-time wine tasting
  • Walk through medieval towns like greve in chianti
  • Montefioralle and panzano
  • Sample local cuisines directly from the source within the many vineyards dotting the hills of tuscany’s chianti region

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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-25%$4,525
8 days From$3,399
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Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns - 2024
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Tuscan & Umbrian Countryside featuring Italy's Charming Hill Towns - 2024

By Collette
premier
4.7/5 Excellent
100+ reviews
Group Tour
Why we love them
With a history that spans back to 1918, they have unparalleled expertise in the guided tour industry and can cater to all types of travelers.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Assisi, Florence, Rome, San Gimignano, Siena, Tuscany, Umbria

Highlights

  • Experience a home-cooked meal in one of Umbria's country homes.
  • Sample pecorino sheep-milk cheese at a local farm in the Orcia Valley.
  • Savor the famous Brunello red wine during a musical tasting at a winery in Montalcino.
  • Behold the unique water-filled piazza in the village of Bagno Vignoni.
  • Enjoy 3 nights in a restored Tuscan villa.
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Themes

Cultural

What travelers are saying

"It was a wonderful trip and experience! We are still sorting all the pictures and memories about it, and some of them I would like to share with you - read my diary about this trip! My Diary about our trip to South Dakota shorturl.at/efoX1"

Trip dates & details
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-19%$3,627
11 days From$2,949
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Authentic Tuscany Trip
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Authentic Tuscany Trip

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, Lucca, San Gimignano, Siena, Tuscany

Highlights

  • The most famous Tuscany wine making region
  • The ancient walled city of Lucca, a 'hidden gem' of Tuscany
  • The most historic and prestigious olive groves in all of Tuscany
  • Enjoy cooking class to share with you some of their family secret

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%$3,420
6 days From$3,000
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Siena and San Gimignano Day Trip and Wine Tour
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Siena and San Gimignano Day Trip and Wine Tour

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, San Gimignano, Siena, Tuscany

Highlights

  • Drive through the beautiful Tuscan countryside until you reach stunning San Gimignano
  • Short walk from the town for wine tasting at an award winning family run vineyard
  • Enjoy a walk around the city discovering it's secrets with time to spare
  • Enjoy one of the world’s most unique piazzas

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%$314
1 days From$275
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Tuscany Wine Long Weekend
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Tuscany Wine Long Weekend

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
Wheelchair Accessible
Trip pace
Full schedule

Visits

Florence, San Gimignano, Siena, Tuscany

Highlights

  • Enjoy iconic products are without doubt its wine, pasta and olive oil
  • Explore hidden in the hill of the vineyard
  • Visit another family run organic award winning vineyard on the outskirts of San Gimignano
  • Visit one of the most loved by locals vineyards in the Bolgheri region where you will taste the newest blends of Tuscan wine

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%$2,280
4 days From$2,000
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Rome, Tuscany & Cinque Terre - 9 days
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Rome, Tuscany & Cinque Terre - 9 days

By On The Go Tours
none
4.7/5 Excellent
100+ reviews
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Cinque Terre, Florence, La Spezia, Rome, Siena

Highlights

  • Rome - 'Skip the line' for a guided tour of the Vatican City, including the iconic Sistine Chapel and the Galleries of Tapestries
  • Montalcino - Stroll around this pretty hilltop town and enjoy included wine tasting and light bites at one of the town's finest wine bars
  • Siena - See the magnificent Piazza del Campo and other highlights on a guided tour of this walled town
  • San Gimignano - Discover the pretty medieval buildings and fortified walls of this UNESCO-listed gem
  • Florence - Spend a free afternoon taking in the best of the city's Renaissance-era architecture, including the Duomo & Palazzo Vecchio
Show more

Themes

Cultural, Nature & Wildlife

What travelers are saying

"First time we (mom and daughter) have done a tour and first time with on the go tours. What a special trip we had doing the 13 day Casablanca to Essaouira Morocco tour (26 Nov - 6 Dec 2023). We started the first 8 days doing the totally Morocco tour and the last few days at our own pace with down time in Essaouira. Jamal our guide led the tour from start to finish and took us safely on a culture filled journey. His knowledge of the country, it’s history and people was informative and inspiring. Every request was “no problem” and delivered with a smile and happy demeanour. Everything in Morrocco was “no problem” and we felt safe and looked after. We were driven in a comfortable coach with enough stops along the way to not feel long by our competent driver Suleman. The hotels, Riad and Dar were extremely comfortable with exceptional service. We would not have had the same experience travelling on our own, we felt as though we truly experienced Morocco. Everything was a highlight for us and we will definitely book another on the go tour in the future. If you wanting to see true Morocco we would strongly recommend doing this tour."

Trip dates & details
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9 days From$3,455
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Treasures of Tuscany & Liguria - 7 days
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Treasures of Tuscany & Liguria - 7 days

By On The Go Tours
none
4.7/5 Excellent
100+ reviews
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Cinque Terre, Florence, La Spezia, Rome, Siena

Highlights

  • Montalcino - Stroll around this pretty hilltop town and enjoy included wine tasting and light bites at one of the town's finest wine bars
  • Siena - See the magnificent Piazza del Campo and other highlights on a guided tour of this walled town
  • San Gimignano - Discover the pretty medieval buildings and fortified walls of this UNESCO-listed gem
  • Florence - Spend a free afternoon taking in the best of the city's Renaissance-era architecture, including the Duomo & Palazzo Vecchio
  • Lucca - Head inside the town's fortified walls for a guided sightseeing tour, taking in the main attractions of the city
Show more

Themes

Cultural, Nature & Wildlife

What travelers are saying

"First time we (mom and daughter) have done a tour and first time with on the go tours. What a special trip we had doing the 13 day Casablanca to Essaouira Morocco tour (26 Nov - 6 Dec 2023). We started the first 8 days doing the totally Morocco tour and the last few days at our own pace with down time in Essaouira. Jamal our guide led the tour from start to finish and took us safely on a culture filled journey. His knowledge of the country, it’s history and people was informative and inspiring. Every request was “no problem” and delivered with a smile and happy demeanour. Everything in Morrocco was “no problem” and we felt safe and looked after. We were driven in a comfortable coach with enough stops along the way to not feel long by our competent driver Suleman. The hotels, Riad and Dar were extremely comfortable with exceptional service. We would not have had the same experience travelling on our own, we felt as though we truly experienced Morocco. Everything was a highlight for us and we will definitely book another on the go tour in the future. If you wanting to see true Morocco we would strongly recommend doing this tour."

Trip dates & details
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7 days From$2,965
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Private Gourmet Wine Tour in Tuscany
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Private Gourmet Wine Tour in Tuscany

By Soleto Travel
none
5/5 Excellent
49 reviews
Private Guided
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Visits

Florence, Pisa, Siena, Tuscany

Highlights

  • Visit medieval towns like San Gimignano and Siena
  • Taste the world known Brunello di Montalcino
  • Enjoy panoramic views onto Chianti Hills Discover the charming Tuscany's countryside
  • Try the authentic Tuscan's specialties and fiorentina steak

Themes

Culinary & Wine, Cultural

What travelers are saying

"Ci siamo affidati a Soleto Travel per un tour di Malta personalizzato e ritagliato su misura per noi. Eravamo in crociera in MSC. Abbiamo trovato ad attenderci al porto Dennis, espertissima guida di Malta anche se definirlo così è estremamente riduttivo. Ci ha meravigliosamente accompagnato con un minivan con autista a Marsaxlokk, alla grotta Azzurra, ai siti megalitici di Hagar Qim e Mnajdra, infine Medina. Ci ha trasmesso con passione l'essenza dell'anima di Malta, millenni di cultura sotto un sole rovente e all'ombra delle colorate bouganville fucsia. Un paesaggio senza tempo in cui predominano il colore giallo e il profumo della storia di diverse culture e civiltà che si sono succedute. Un'esperienza indimenticabile. Grazie di cuore Dennis e grazie Omar di Soleto Travel!"

Trip dates & details
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-19%$2,442
4 days From$1,985
Price updated 1 year+ ago

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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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