Siena Small Group Tours & Trip Packages
Design custom trip
TrendingMachu PicchuAngkor WatDanube RiverMt. KilimanjaroRivers & SeasGalapagosMediterranean SeaCiudad Perdida (The Lost City)Mideast & N. AfricaMekong River
EuropeFranceItalyCroatiaIrelandGreeceSwitzerlandSpainPortugalScandinaviaSee all >
South AmericaPeruEcuadorBrazilArgentinaChileColombiaPatagoniaAmazon RainforestBoliviaSee all >
AsiaChinaIndiaCambodiaTurkeyThailandJapanIndonesiaNepalJordanSee all >
AfricaTanzaniaSouth AfricaKenyaMoroccoEgyptBotswanaRwandaMadagascarEthiopiaSee all >
North AmericaUnited StatesCanadaMexicoSee all >
Australia & PacificAustraliaNew ZealandPacific IslandSee all >
Antarctica & ArcticAntarcticaArcticNorwaySee all >
Caribbean & C. AmericaCosta RicaBelizeBahamasSee all >
See all destinations >
Top TripsTop 10 ListsEditor PicksMost Popular TripsAward WinnersCollectionsTop TrendingSee all activities, themes, and interests >
ActivitiesCycling & BikingSmall Ship CruisesSafariRiver CruisesClimbing and MountaineeringTrekking & CampingHiking & WalkingTrain & RailRiver RaftingYoga, Meditation & Wellness
Styles50+Family Friendly18-30LuxuryBudgetAdventure TravelSolo and Single TripsGroup Guided ToursCustom Tour PackagesIndependent Vacation PackagesPrivate Guided
InterestsCulturalWildlifeHistoryNatureBirding toursFestivals and Special EventsEco/Sustainable TravelVolunteeringLearning & EducationalRuins & ArchaeologyCulinary & Wine Tasting
See all activities, themes, and interests >
Member Savings ProgramTour operatorsRover TripFinder AIAffiliate PartnersTravel Trivia GameAbout UsTravel ArticlesContact Us
Gift Cards
ToursEuropeItalySiena

Siena Small Group Tours & Trips

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

Filter by trip style:

Design custom trip
40 trips exactly matchall of the the filters you selected.
My selections:
Small Group Tour
Italian Discovery
Save this trip to your favorites or other list

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
Save this trip to your favorites or other list
-19%$3,075
10 days From$2,500
Price updated 1 year+ ago

Health Safety

More
Tuscany: Cycle Siena & Chianti
Save this trip to your favorites or other list

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
Save this trip to your favorites or other list

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
Save this trip to your favorites or other list
-30%$1,892
7 days From$1,319
More
Plan Your Siena Trip
Top Tours
All Siena Trips
Attractions & Things to Do
Suggested Itineraries
Iconic Siena Landmarks
Tour Companies for Siena
Siena Reviews

All Siena, expedition cruises, self guided adventures and vacation packages. Find the best guided and expert planned vacation and holiday packages. Read more about Siena

Barcelona to Rome
Save this trip to your favorites or other list

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 +

More
Premium Rome to Dubrovnik
Save this trip to your favorites or other list

Premium Rome to Dubrovnik

By Intrepid Travel
premier
4.5/5 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
Full schedule

Visits

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

Highlights

  • Explore Rome’s iconic Colosseum under moonlight during an Exclusive Experience evening tour. Walk in the footsteps of gladiators without the jostling daytime crowds.
  • Enjoy three memorable Feature Stays - a converted castle hotel in the rolling vineyards of Tuscany's Chianti region, a tranquil hotel on a private island in Istria 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

"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%$22,741
23 days From$16,845

Health Safety +

More
Ultimate Italy
Save this trip to your favorites or other list

Ultimate Italy

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
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Cinque Terre, Colosseum, Florence, Lake Como, Lucca, Milan, Pisa, Rome, Siena, Tuscany, Venice

Highlights

  • Experience medieval and renaissance delights
  • Discover a passion for regional wines and italian cuisine
  • Savour the sea views and tuscan hills
  • Explore the elegant countryside of lake como by boat
  • Wander over the canals and bridges of venice

Themes

Cultural, 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
Save this trip to your favorites or other list
-30%$4,015
14 days From$2,799
More

Unlock Community Benefits

Travel better together

  • Save favorite trips and itineraries
  • Get insider insights
  • Receive personalized recommendations
  • ... and much more
Join community
Premium Rome to Split
Save this trip to your favorites or other list

Premium Rome to Split

By Intrepid Travel
premier
4.5/5 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
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.
  • Explore Rome’s iconic Colosseum under moonlight during an evening tour. Walk in the footsteps of gladiators without the jostling daytime crowds.
  • 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

"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%$16,288
16 days From$12,065

Health Safety +

More
A Taste of Tuscany - Hilltop Towns and Vineyards
Save this trip to your favorites or other list

A Taste of Tuscany - Hilltop Towns and Vineyards

By Explore!
premier
5/5 Excellent
100+ reviews
Small Group Tour
Why we love them
They explore a place beyond the typical tourist traps and offer exciting activities that bring the “wow factor” intrepid travelers want.
Lodging level
Premium - 4 star
Physical level
Moderate

Visits

Pisa, Rome, San Gimignano, Siena, Tuscany

Highlights

  • Sample some of Italy's finest wines and dine on delicious Tuscan regional specialites
  • Explore captivating hilltop towns, Medieval San Gimignano and Siena
  • Visits to food and wine producers and tasting fresh produce at source

Themes

Cultural, Hiking & Walking

What travelers are saying

"The trip itinerary was well thought through with the right balance of challenging walks, rest time, cultural activities and time to socialise. Joao, our guide, was exceptional. He really took on board any feedback and made sure we had the best time. The scenery in Madeira surpassed my expectations. I would recommend this trip to anyone wanting an active weeks’ holiday."

Trip dates & details
Save this trip to your favorites or other list
-23%$3,469
8 days From$2,660

Health Safety +

More
Travelstride Gift Card
One card, thousands of extraordinary trips
Explore
Gifts Card

Want a tailor-made trip instead?

Your trip, your way, planned by an expert:

  • You choose budget, destinations, activities, transport & lodging type
  • Expert designs the itinerary for you, and once approved, takes care of logistics
Design custom trip
40 trips exactly matchall of the the filters you selected.
My selections:
Small Group Tour
...

1

2

...

Last

Best Siena Tours by Duration

1 Week
One Week in Siena 

Tours, Cruises & Private Trips

10 Days
10 Days in Siena 

Tours, Cruises & Private Trips

2 Week
2 Weeks in Siena 

Tours, Cruises & Private Trips

Best Siena Tours by Price

Best Siena Luxury Tours 
Best Siena Standard Tours 
Best Siena Budget Tours 

Siena Reviews & Ratings

4.7/5  Excellent
94  Reviews
Write a review
See all Siena tour reviews
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

See all Siena reviews

Write a Review

Additional details

Top Siena Travel Companies
Exodus Travels Reviews
G Adventures Reviews
Intrepid Travel Reviews
Explore! Reviews
Collette Reviews
Eskapas Reviews
Travel for All Reviews
Soleto Travel Reviews
Image Tours Reviews
Find Your Italy Reviews
Europamundo Vacations Reviews
Discover Your Italy Reviews

Always Find the Best

On Travelstride you can find 109 trips to Siena and more than 20,000 trips worldwide ranging from budget to luxury and private guided to group tours and everything in between. Only on Stride can you find and compare expert-planned trips from 1,000+ tour operators, cruise lines and local experts. Read traveler and professional reviews so you can confidently find your perfect trip.

Top Tour Companies on Travelstride:
All 1,600+ companies >
Sign in to reveal savings up to $700 per person!