Siena 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 Tours & Trips

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

Filter by trip style:

Design custom trip

109 Trips match your criteria (101 - 109 shown)

9-DAY BOTTICELLI TOUR - Milan, Venice, Florence and Cinque Terre in 9 days
Save this trip to your favorites or other list

9-DAY BOTTICELLI TOUR - Milan, Venice, Florence and Cinque Terre in 9 days

By Vitor Italy Tours
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
21 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Wheelchair Accessible
Trip pace
Flexible schedule

Visits

Cinque Terre, Florence, Milan, Parma, Pisa, Venice, Verona

Highlights

  • Milan, the 2,000-years-old trendy capital of Northern Italy
  • Verona, the city of lovers
  • Venice, the merchant city that ruled the Mediterranean
  • Florence, an open-air museum
  • Siena and San Gimignano, power in the Middle Ages
Show more

Themes

Culinary & Wine, Cultural

What travelers are saying

"After an international trip was postponed for a third time due to COVID, my wife and I decided, last minute, to book a trip to Italy. We reached out to three self-drive tour companies, two of which - including VitorItaly - were less than half of the third quote. Ultimately we decided to go with Marcello because of his quote and responsiveness. With only a few weeks to book all of the accommodations and tours, Marcello got everything done and was very communicative throughout. We drove over 2200 km on our trip throughout Italy and Marcello booked a fantastic variety of lodgings: for example a country house near Pienza, a luxury hotel on the lagoon in Venice, and a country estate in Urbino surrounded by an organic farm and vineyard. At an olive oil mill nera Florence, we really enjoyed our time and our large order of fantastic tasting olive oil arrived yesterday. Ughetta was fantastic and gave us a great tour of their facility! Furthermore, while in Italy we could reach out to Marcello via WhatsApp and he continued to be incredibly responsive. Thanks Marcello!"

Trip dates & details
Save this trip to your favorites or other list
9 days From$3,680
Price updated 1 year+ ago

Health Safety

More
AUTHENTIC ITALY GRAND TOUR SOUTH - Naples, Amalfi, Matera, Puglia in 12 days
Save this trip to your favorites or other list

AUTHENTIC ITALY GRAND TOUR SOUTH - Naples, Amalfi, Matera, Puglia in 12 days

By Vitor Italy Tours
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
21 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Wheelchair Accessible
Trip pace
Balanced schedule

Visits

Alberobello , Amalfi Coast, Matera, Naples, Pompeii, Rome

Highlights

  • Montecassino, rising again from the ashes of the war
  • Naples, Pizza time
  • Pompei, the Roman city fixed in lava
  • The Amalfi Coast, where divas are at home
  • Paestum, when Greeks ruled Italy
Show more

Themes

Culinary & Wine, Cultural

What travelers are saying

"After an international trip was postponed for a third time due to COVID, my wife and I decided, last minute, to book a trip to Italy. We reached out to three self-drive tour companies, two of which - including VitorItaly - were less than half of the third quote. Ultimately we decided to go with Marcello because of his quote and responsiveness. With only a few weeks to book all of the accommodations and tours, Marcello got everything done and was very communicative throughout. We drove over 2200 km on our trip throughout Italy and Marcello booked a fantastic variety of lodgings: for example a country house near Pienza, a luxury hotel on the lagoon in Venice, and a country estate in Urbino surrounded by an organic farm and vineyard. At an olive oil mill nera Florence, we really enjoyed our time and our large order of fantastic tasting olive oil arrived yesterday. Ughetta was fantastic and gave us a great tour of their facility! Furthermore, while in Italy we could reach out to Marcello via WhatsApp and he continued to be incredibly responsive. Thanks Marcello!"

Trip dates & details
Save this trip to your favorites or other list
12 days From$4,645
Price updated 1 year+ ago

Health Safety

More
Tuscany Italy Walking and Culinary Adventure
Save this trip to your favorites or other list

Tuscany Italy Walking and Culinary Adventure

By Walking Connection
none
5/5 Excellent
4 reviews
Small Group Tour
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Cinque Terre, Florence, Siena, Tuscany

Highlights

  • Tuscan Landscapes
  • Florence
  • Siena Piazza
  • Bagno Vignoni Hot Springs
  • Wine Tastings
Show more

Themes

Culinary & Wine, Hiking & Walking

What travelers are saying

"Our Azores trip was excellent except for a bit of rain :-); The volcano hikes were spectacular and the side trip notes were very helpful. Doing the volcano hikes was fantastic, especially being high enough to see the Atlantic Ocean to the south and the north, beautiful! We also enjoyed the beach walks and walking to town from our hotel, Santa Barbara Eco Hotel. We stayed at the Santa Barbara Eco Hotel which was excellent. The room, property, pool and spa and services were all excellent. We enjoyed meals everyday at their restaurant which where all excellent. A very relaxing and restful and comfortable hotel. The restaurant at the Santa Barbara Eco Hotel is excellent as is there sister property, The White House, were we enjoyed a spectacular sunset and dinner one night. Your selection of this company “Singular Resorts” is a very good choice. We have been using Intura Travel / Walk Inn Provence since 2014 and will use you again in the future. I have recommended you to family and friends and will continue to do so. You have excellent information and support for travelers. Fantastic trip to the Azores, it was a highlight of our vacation to Portugal."

Trip dates & details
Save this trip to your favorites or other list
9 days From$4,698
Price updated 1 year+ ago
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

1-WEEK ITALIAN EXCELLENCES TOUR - NORTHERN ITALY
Save this trip to your favorites or other list

1-WEEK ITALIAN EXCELLENCES TOUR - NORTHERN ITALY

By Vitor Italy Tours
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
21 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Wheelchair Accessible
Trip pace
Flexible schedule

Visits

Lake Garda, Milan, Parma, Verona

Highlights

  • Franciacorta & Lugana, the wines of the lakes
  • Verona, crossroads of tastes
  • Parma, the art of food
  • Langhe, the land of strong flavours
  • Vercelli, where risotto was born

Themes

Culinary & Wine, Cultural

What travelers are saying

"After an international trip was postponed for a third time due to COVID, my wife and I decided, last minute, to book a trip to Italy. We reached out to three self-drive tour companies, two of which - including VitorItaly - were less than half of the third quote. Ultimately we decided to go with Marcello because of his quote and responsiveness. With only a few weeks to book all of the accommodations and tours, Marcello got everything done and was very communicative throughout. We drove over 2200 km on our trip throughout Italy and Marcello booked a fantastic variety of lodgings: for example a country house near Pienza, a luxury hotel on the lagoon in Venice, and a country estate in Urbino surrounded by an organic farm and vineyard. At an olive oil mill nera Florence, we really enjoyed our time and our large order of fantastic tasting olive oil arrived yesterday. Ughetta was fantastic and gave us a great tour of their facility! Furthermore, while in Italy we could reach out to Marcello via WhatsApp and he continued to be incredibly responsive. Thanks Marcello!"

Trip dates & details
Save this trip to your favorites or other list
7 days From$3,001
Price updated 1 year+ ago

Health Safety

More
AUTHENTIC ITALY GRAND TOUR NORTH - The Northern Lakes, Emilia, Florence, Tuscany, Umbria in 12 days
Save this trip to your favorites or other list

AUTHENTIC ITALY GRAND TOUR NORTH - The Northern Lakes, Emilia, Florence, Tuscany, Umbria in 12 days

By Vitor Italy Tours
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
21 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Wheelchair Accessible
Trip pace
Balanced schedule

Visits

Assisi, Florence, Lake Como, Parma, San Gimignano, Siena

Highlights

  • Lake Maggiore and Lake Como, a scenery for movie lovers
  • Parma, where Food is an art
  • Maranello, the legend of Ferrari was born here
  • Florence, an open-air museum
  • Chianti, winemakers for 800 years
Show more

Themes

Culinary & Wine, Cultural

What travelers are saying

"After an international trip was postponed for a third time due to COVID, my wife and I decided, last minute, to book a trip to Italy. We reached out to three self-drive tour companies, two of which - including VitorItaly - were less than half of the third quote. Ultimately we decided to go with Marcello because of his quote and responsiveness. With only a few weeks to book all of the accommodations and tours, Marcello got everything done and was very communicative throughout. We drove over 2200 km on our trip throughout Italy and Marcello booked a fantastic variety of lodgings: for example a country house near Pienza, a luxury hotel on the lagoon in Venice, and a country estate in Urbino surrounded by an organic farm and vineyard. At an olive oil mill nera Florence, we really enjoyed our time and our large order of fantastic tasting olive oil arrived yesterday. Ughetta was fantastic and gave us a great tour of their facility! Furthermore, while in Italy we could reach out to Marcello via WhatsApp and he continued to be incredibly responsive. Thanks Marcello!"

Trip dates & details
Save this trip to your favorites or other list
12 days From$5,038
Price updated 1 year+ ago

Health Safety

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

Our Italy

By ITM Journeys
none
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Cinque Terre, Florence, Rome, Siena, Sistine Chapel, Tuscany, Venice

Highlights

  • Visit of Vatican Museum & Sistine Chapel with skip the line reservation
  • Visit the main sights of the city but also to discover the real soul of Venice
  • Discover the most beautiful villages of Cinque Terre
  • Experience an amazing boat trip to take the most beautiful pictures of Cinque Terre from the sea

Themes

Cultural, Local Immersion & Homestays, Transformative

Trip dates & details
Save this trip to your favorites or other list
9 days From$3,189
Price updated 1 year+ ago
More

Unlock Community Benefits

Travel better together

  • Save favorite trips and itineraries
  • Get insider insights
  • Receive personalized recommendations
  • ... and much more
Join community
Tuscany bike tour around Siena and Chianti
Save this trip to your favorites or other list

Tuscany bike tour around Siena and Chianti

By Find Your Italy
none
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Siena

Trip dates & details
Save this trip to your favorites or other list
8 days
Inquire
More
Amalfi Coast, Rome & Tuscany
Save this trip to your favorites or other list

Amalfi Coast, Rome & Tuscany

By ITM Journeys
none
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Visits

Amalfi Coast, Florence, Naples, Sistine Chapel, Sorrento, St. Peter's Basilica, Tuscany, Vatican City

Highlights

  • Visit Amalfi was one of the maritime power in the Mediterranean Sea
  • Visit the Greek Temples and taste the original buffalo mozzarella
  • Exploration of the magnificent Sorrento
  • Explore Capri, a tour to Paestum

Themes

Cultural, Transformative

Trip dates & details
Save this trip to your favorites or other list
11 days From$4,599
Price updated 1 year+ ago
More
Travelstride Gift Card
One card, thousands of extraordinary trips
Explore
Gifts Card
Other trips you may like [sponsored]
Escorted Tours Of Tuscany
Save this trip to your favorites or other list

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
Save this trip to your favorites or other list
-12%$6,270
12 days From$5,500
More
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

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
-24%$4,050
8 days From$3,075

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
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
-33%$6,494
15 days From$4,328

Health Safety +

More

First

...

2

3

4

5

6

...

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

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

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

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

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!