Siena Small Group Tours & Trip Packages
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Siena Small Group Tours & Trips

26 Siena trips. Tours from 8 tour companies. 106 reviews. 4.7/5 avg rating.

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13 trips exactly matchall of the the filters you selected. We are displaying some similar trips.
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Small Group Tour
Tuscany: Cycle Siena & Chianti

Tuscany: Cycle Siena & Chianti

By Exodus Travels
premier
4.8/5 Excellent
100+ reviews
Small Group Tour
Why we love them
With a wide range of trip styles, Exodus caters to every type of traveler out there- even those with specific interests from cycling to winter hiking.
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

"Rick was really helpful and patient. He explained things clearly, was happy to answer questions. It is a long time since I last travelled solo but I felt confident that Rick understood what I wanted from the trip and reassured me."

Trip dates & details
Save this trip to your favorites or other list
26% OFF$3,949
8 days From$2,925
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Barcelona to Rome

Barcelona to Rome

By Intrepid Travel
premier
4.8/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.
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, Local Immersion & Homestays, High Adventure

What travelers are saying

"I did the EBC trek with Intrepid in September and October. Our group missed the first 3 days of the planned 12 day trek due to bad weather. There was a real fear we would not be able to do the trek at all. Intrepid sorted out additional accommodation and flights once we were able to fly. Our group made it to EBC by missing the 2 acclimation days on the accent and descending in 3 days instead of 4. This was only possible because of the awesome staff (guides and porters) employed by Intrepid and by Intrepid's backroom staff making alternative accommodation and flight arrangements for us."

Trip dates & details
Save this trip to your favorites or other list
26% OFF$7,324
15 days From$5,425
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Premium Rome to Dubrovnik

Premium Rome to Dubrovnik

By Intrepid Travel
premier
4.5/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Full schedule

Visits

Colosseum, Croatia, Dubrovnik, Florence, Forum, Lake Bled, Ljubljana, Pisa, Rome, San Gimignano, Siena, Split, Tuscany, Venice

Highlights

  • Visit the home of a Roman nobleman during an Exclusive Experience. Your aristocratic host will show you around the opulent interiors and explain the rich history of the residence, before sitting down for lunch in his dining room.
  • Enjoy two memorable Feature Stays - a hotel in the rolling vineyards of Tuscany's Chianti region, and an exquisite1776 building in Split.
  • Delight in a truffle tasting in Motovun during an Exclusive Experience. Truffles are combined with local speciality dishes and a sommelier will pair your tasting with suitable Istrian wines to try.
  • Explore scenic Croatian towns with glittering harbors and ancient facades, including the resort town of Opatija and seaside Sibenik, where you'll explore the 15th century stone Cathedral of St. James, decorated with 71 sculpted faces.

Themes

High Adventure

What travelers are saying

"I did the EBC trek with Intrepid in September and October. Our group missed the first 3 days of the planned 12 day trek due to bad weather. There was a real fear we would not be able to do the trek at all. Intrepid sorted out additional accommodation and flights once we were able to fly. Our group made it to EBC by missing the 2 acclimation days on the accent and descending in 3 days instead of 4. This was only possible because of the awesome staff (guides and porters) employed by Intrepid and by Intrepid's backroom staff making alternative accommodation and flight arrangements for us."

Trip dates & details
Save this trip to your favorites or other list
26% OFF$18,353
23 days From$13,595
More
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Secrets of San Gimignano Cycling

Secrets of San Gimignano Cycling

By Exodus Travels
premier
4.7/5 Excellent
100+ reviews
Small Group Tour
Why we love them
With a wide range of trip styles, Exodus caters to every type of traveler out there- even those with specific interests from cycling to winter hiking.
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

"Rick was really helpful and patient. He explained things clearly, was happy to answer questions. It is a long time since I last travelled solo but I felt confident that Rick understood what I wanted from the trip and reassured me."

Trip dates & details
Save this trip to your favorites or other list
26% OFF$4,361
9 days From$3,230
More
Premium Rome to Split

Premium Rome to Split

By Intrepid Travel
premier
4.5/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Full schedule

Visits

Colosseum, Croatia, Florence, Forum, Lake Bled, Ljubljana, Pisa, Rome, San Gimignano, Siena, Split, Tuscany, Venice

Highlights

  • Nestled in the rolling vineyards of Tuscany's Chianti region, spend two memorable nights in a converted castle hotel and dine on a multi-course gourmet meal at the onsite restaurant.
  • Visit the home of a Roman nobleman during an Exclusive Experience. Your aristocratic host will show you around the opulent interiors and explain the rich history of the residence, before sitting down for lunch in his dining room.
  • Delight in regional specialties during a wine-tasting at a family garden vineyard in Tuscany and a truffle and Istrian wine tasting in Motovun.
  • Take advantage of local knowledge when you travel with expert local leaders who will share the best of their countries, bring history to life and know all the best places to eat.
  • Enjoy your own slice of paradise at your feature stay hotel. The stunning Hotel Istra sits on its own private island, with world class service, fantastic facilities and beautiful grounds to explore.

Themes

High Adventure

What travelers are saying

"I did the EBC trek with Intrepid in September and October. Our group missed the first 3 days of the planned 12 day trek due to bad weather. There was a real fear we would not be able to do the trek at all. Intrepid sorted out additional accommodation and flights once we were able to fly. Our group made it to EBC by missing the 2 acclimation days on the accent and descending in 3 days instead of 4. This was only possible because of the awesome staff (guides and porters) employed by Intrepid and by Intrepid's backroom staff making alternative accommodation and flight arrangements for us."

Trip dates & details
Save this trip to your favorites or other list
26% OFF$13,028
16 days From$9,650
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Premium Italy in Depth

Premium Italy in Depth

By Intrepid Travel
premier
4.5/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.
Lodging level
Standard - 3 star
Physical level
Easy

Visits

Bar, Colosseum, Florence, Forum, Lecce, Matera, Naples, Pisa, Pompeii, Rome, San Gimignano, Siena, Tuscany, Venice

Highlights

  • Stay in spectacular places including a Feature Stay in an historic property in Nardo – that was once a Baronial Palace – as well as a countryside hotel nestled amid the rolling vineyards of Tuscany.
  • Visit the home of a Roman nobleman during an Exclusive Experience. Your aristocratic host will show you around the opulent interiors and explain the rich history of the residence, before sitting down for lunch in his dining room.
  • Get a taste for Italy’s celebrated cuisine and viticulture during an olive oil tasting on a farm that’s been active since Roman times and a trip to the celebrated wine-growing region of San Gimignano to visit a family-run winery and sample their world-class drops.
  • Take a step back in time and explore the ancient ruins of Pompeii, destroyed and preserved by the eruption of Mt Vesuvius in 79 AD.
  • Join a group of like-minded travellers on a tour takes a deep dive into the history, culture and natural beauty of southern Italy with one of our most experienced locally based leaders (legends) guiding the way.

Themes

High Adventure

What travelers are saying

"I did the EBC trek with Intrepid in September and October. Our group missed the first 3 days of the planned 12 day trek due to bad weather. There was a real fear we would not be able to do the trek at all. Intrepid sorted out additional accommodation and flights once we were able to fly. Our group made it to EBC by missing the 2 acclimation days on the accent and descending in 3 days instead of 4. This was only possible because of the awesome staff (guides and porters) employed by Intrepid and by Intrepid's backroom staff making alternative accommodation and flight arrangements for us."

Trip dates & details
Save this trip to your favorites or other list
26% OFF$12,670
15 days From$9,385
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Premium Sicily and Italy in Depth

Premium Sicily and Italy in Depth

By Intrepid Travel
premier
4.5/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.
Lodging level
Standard - 3 star
Physical level
Easy

Visits

Agrigento, Bar, Catania, Colosseum, Florence, Forum, Lecce, Matera, Naples, Pisa, Pompeii, Rome, San Gimignano, Sicily, Siena, Tuscany, Venice

Highlights

  • Take a step back in time and marvel at some of Italy’s most fascinating ancient monuments including discovering the ancient ruins of Pompeii with a local guide.
  • Get a taste for Italian specialties and visit a family-run winery to sample world-class drops in Tuscany, discover a local olive oil producer and taste their specialties on a farm that has been active since Roman times in Puglia and dig your hands into a traditional cooking class in Sicily.
  • Come face-to-face with Europe’s largest active volcano, Mount Etna, as you walk into the centre of an extinct crater and visit a lava cave.
  • Get the inside scoop on the best places to eat and explore with your locally-based leader joining you on orientation walks in some of Italy’s most captivating cities.
  • Stay in style with 3 Feature Stays, nestled in the heart of the rolling Tuscan hillside, in a once 13th-century Baronial Palace in Nardo and in a countryside estate built within a medieval watch tower in Baglio della Luna Foresteria.

Themes

High Adventure

What travelers are saying

"I did the EBC trek with Intrepid in September and October. Our group missed the first 3 days of the planned 12 day trek due to bad weather. There was a real fear we would not be able to do the trek at all. Intrepid sorted out additional accommodation and flights once we were able to fly. Our group made it to EBC by missing the 2 acclimation days on the accent and descending in 3 days instead of 4. This was only possible because of the awesome staff (guides and porters) employed by Intrepid and by Intrepid's backroom staff making alternative accommodation and flight arrangements for us."

Trip dates & details
Save this trip to your favorites or other list
26% OFF$21,715
24 days From$16,085
More
Tuscany, Cinque Terre & the Portofino Coast 2025

Tuscany, Cinque Terre & the Portofino Coast 2025

By Tauck
none
4.4/5 Great
100+ reviews
Small Group Tour
Lodging level
Premium - 4 star
Physical level
Moderate

Highlights

  • From under the Tuscan sun to the Italian Riviera
  • embark on a journey that fills your senses with art
  • cuisine
  • wine
  • and the best of nature – from rolling Tuscan hills with vineyards of grapes and olives to the magnificent Mediterranean Italian Riviera
Show more

Themes

Cultural

What travelers are saying

"My husband and I booked the Yellowstone tour with Tauck expecting so much more with the accommodations, food, and tour director based on the price point. We were sadly disappointed but still tried to enjoy the experience. Rooms were dirty, food were often buffets and other group dinners with some food inedible. We noticed other tours staying in our hotels and paying much less for their tours. One positive was we never touched our luggage which was nice but my small suitcase was damaged during one transfer. Word to the wise… read their emails thoroughly as the email we received a few weeks before our trip reads like a disclaimer for poor service and accommodations."

Trip dates & details
Save this trip to your favorites or other list
8 days From$6,290
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Other trips you may like [sponsored]
Tuscany: Cycle Siena & Chianti

Tuscany: Cycle Siena & Chianti

By Exodus Travels
premier
4.8/5 Excellent
100+ reviews
Small Group Tour
Why we love them
With a wide range of trip styles, Exodus caters to every type of traveler out there- even those with specific interests from cycling to winter hiking.
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

"Rick was really helpful and patient. He explained things clearly, was happy to answer questions. It is a long time since I last travelled solo but I felt confident that Rick understood what I wanted from the trip and reassured me."

Trip dates & details
Save this trip to your favorites or other list
26% OFF$3,949
8 days From$2,925
More
Barcelona to Rome

Barcelona to Rome

By Intrepid Travel
premier
4.8/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.
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, Local Immersion & Homestays, High Adventure

What travelers are saying

"I did the EBC trek with Intrepid in September and October. Our group missed the first 3 days of the planned 12 day trek due to bad weather. There was a real fear we would not be able to do the trek at all. Intrepid sorted out additional accommodation and flights once we were able to fly. Our group made it to EBC by missing the 2 acclimation days on the accent and descending in 3 days instead of 4. This was only possible because of the awesome staff (guides and porters) employed by Intrepid and by Intrepid's backroom staff making alternative accommodation and flight arrangements for us."

Trip dates & details
Save this trip to your favorites or other list
26% OFF$7,324
15 days From$5,425
More
Premium Rome to Dubrovnik

Premium Rome to Dubrovnik

By Intrepid Travel
premier
4.5/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They're highly committed to sustainable tourism and contribute to crucial initiatives like climate action, focusing on local cultures and more.
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Full schedule

Visits

Colosseum, Croatia, Dubrovnik, Florence, Forum, Lake Bled, Ljubljana, Pisa, Rome, San Gimignano, Siena, Split, Tuscany, Venice

Highlights

  • Visit the home of a Roman nobleman during an Exclusive Experience. Your aristocratic host will show you around the opulent interiors and explain the rich history of the residence, before sitting down for lunch in his dining room.
  • Enjoy two memorable Feature Stays - a hotel in the rolling vineyards of Tuscany's Chianti region, and an exquisite1776 building in Split.
  • Delight in a truffle tasting in Motovun during an Exclusive Experience. Truffles are combined with local speciality dishes and a sommelier will pair your tasting with suitable Istrian wines to try.
  • Explore scenic Croatian towns with glittering harbors and ancient facades, including the resort town of Opatija and seaside Sibenik, where you'll explore the 15th century stone Cathedral of St. James, decorated with 71 sculpted faces.

Themes

High Adventure

What travelers are saying

"I did the EBC trek with Intrepid in September and October. Our group missed the first 3 days of the planned 12 day trek due to bad weather. There was a real fear we would not be able to do the trek at all. Intrepid sorted out additional accommodation and flights once we were able to fly. Our group made it to EBC by missing the 2 acclimation days on the accent and descending in 3 days instead of 4. This was only possible because of the awesome staff (guides and porters) employed by Intrepid and by Intrepid's backroom staff making alternative accommodation and flight arrangements for us."

Trip dates & details
Save this trip to your favorites or other list
26% OFF$18,353
23 days From$13,595
More
Italy's Treasures Art, Food & Wine of Italy - 2024

Italy's Treasures Art, Food & Wine of Italy - 2024

By Collette
premier
4.8/5 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

Bologna, Cinque Terre, Florence, San Gimignano, Siena, Tuscany, Venice

Highlights

  • Journey by boat to Isola dei Pescatori for a lovely welcome dinner.
  • Taste authentic Italian gelato from an award-winning ice cream parlor in San Gimignano.
  • Learn the art behind Tuscan cuisine during a hands-on cooking lesson.
  • Explore Lake Orta, one of Italy’s hidden treasures.
  • Discover colorful Cinque Terre, a UNESCO World Heritage site.
Show more

Themes

Cultural

What travelers are saying

"This was a tremendous trip. Nice mix of New Zealand s spectacular scenery and cultural highlights. In Australia Cairns was interesting for culture and great barrier reef, which is unfortunetely getting bleached due to rising ocean temps.The Sydney Opera house was amazing. Our Auastralian guide was knowledgeable and very organized. Only complaint was that at 37 folks the trip was too large in our opinion."

Trip dates & details
Save this trip to your favorites or other list
19% OFF$5,226
12 days From$4,249
More
Secrets of San Gimignano Cycling

Secrets of San Gimignano Cycling

By Exodus Travels
premier
4.7/5 Excellent
100+ reviews
Small Group Tour
Why we love them
With a wide range of trip styles, Exodus caters to every type of traveler out there- even those with specific interests from cycling to winter hiking.
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

"Rick was really helpful and patient. He explained things clearly, was happy to answer questions. It is a long time since I last travelled solo but I felt confident that Rick understood what I wanted from the trip and reassured me."

Trip dates & details
Save this trip to your favorites or other list
26% OFF$4,361
9 days From$3,230
More
13 trips exactly matchall of the the filters you selected. We are displaying some similar trips.
My selections:
Small Group Tour

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Siena Reviews & Ratings

4.7/5  Excellent
106  Reviews
Write a review
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Excellent
819
Great
269
Average
34
Disappointing
11
Terrible
6
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

Amazing adventure!

This was my first cycling tour and tour with Exodus. I had an amazing experience! The trip was well planned and I feel like it had the prefect balance of cycling, ...

Tour:  Tuscany: Cycle Siena & Chianti

A

Anonymous

Oct 2018

Provided byExodus Travels

Cycling in Tuscany

Excellent and memorable cycling trip! This was my daughter's first cycling trip. She is athletic but not an experienced cyclist. She had a wonderful experience wit...

Tour:  Tuscany: Cycle Siena & Chianti

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

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

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