Siena Standard 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 Standard Tours & Trips

105 Siena trips. Tours from 48 tour companies. 90 reviews. 4.7/5 avg rating.

Filter by trip style:

Design custom trip
53 trips exactly matchall of the the filters you selected.
My selections:
Standard
8 Day Tuscany Fly & Drive with Milan (Chicago)
Save this trip to your favorites or other list

8 Day Tuscany Fly & Drive with Milan (Chicago)

By Gate 1 Travel
none
3.7/5 Great
100+ reviews
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Lucca, Milan, Parma, Pisa, San Gimignano, Siena

Themes

50 plus, Cultural

What travelers are saying

"We have loved Gate 1 and always sing their praises. We've been on 7 tours with another one booked for fall. We were supposed to leave for Ecuador this week, however the country is in a 60 day state of emergency with the escape of 2 infamous gang members. Tourists are advised to stay indoors and there is a daily curfew from 11pm-5am. (our flight was to land at 11:15pm). Our trip included stays in 2 of the main cities of unrest. There have been shootings, car bombings, hostage taking, closing of embassies, and other countries issuing do not travel warnings. Other tour companies have cancelled tours or offered refunds or rescheduling. Travel insurance does not cover wars or civil unrest, but we are clearly afraid to go there. Both we and our travel agent have reached out multiple times with our concerns and asked if we could reschedule or get some sort of credit. We continue to get the same reply either in person or via email...Gate 1 has your safety as our highest priority and we feel you are safe ("they are not targeting tourists") and your itinerary should not be impacted. What? Their highest priority is $ and not our safety. There is no way that's the tour we anticipated. We cancelled the trip and took a 90% penalty, loss of deposit, and $276 airline penalty. It's a LOT of money, but we would have been terrified, and it's not worth getting hurt or worse. Sorry, but it's not the company I want to do business with in the future."

Trip dates & details
Save this trip to your favorites or other list
8 days From$969
Price updated 1 year+ ago
More
8 Day Tuscany Fly & Drive with Milan, Thanksgiving Special
Save this trip to your favorites or other list

8 Day Tuscany Fly & Drive with Milan, Thanksgiving Special

By Gate 1 Travel
none
3.7/5 Great
100+ reviews
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Lucca, Milan, Parma, Pisa, San Gimignano, Siena

Themes

50 plus, Cultural

What travelers are saying

"We have loved Gate 1 and always sing their praises. We've been on 7 tours with another one booked for fall. We were supposed to leave for Ecuador this week, however the country is in a 60 day state of emergency with the escape of 2 infamous gang members. Tourists are advised to stay indoors and there is a daily curfew from 11pm-5am. (our flight was to land at 11:15pm). Our trip included stays in 2 of the main cities of unrest. There have been shootings, car bombings, hostage taking, closing of embassies, and other countries issuing do not travel warnings. Other tour companies have cancelled tours or offered refunds or rescheduling. Travel insurance does not cover wars or civil unrest, but we are clearly afraid to go there. Both we and our travel agent have reached out multiple times with our concerns and asked if we could reschedule or get some sort of credit. We continue to get the same reply either in person or via email...Gate 1 has your safety as our highest priority and we feel you are safe ("they are not targeting tourists") and your itinerary should not be impacted. What? Their highest priority is $ and not our safety. There is no way that's the tour we anticipated. We cancelled the trip and took a 90% penalty, loss of deposit, and $276 airline penalty. It's a LOT of money, but we would have been terrified, and it's not worth getting hurt or worse. Sorry, but it's not the company I want to do business with in the future."

Trip dates & details
Save this trip to your favorites or other list
8 days From$979
Price updated 1 year+ ago
More
8 Day Tuscany Fly & Drive with Milan (Los Angeles)
Save this trip to your favorites or other list

8 Day Tuscany Fly & Drive with Milan (Los Angeles)

By Gate 1 Travel
none
3.7/5 Great
100+ reviews
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Lucca, Milan, Parma, Pisa, San Gimignano, Siena

Themes

50 plus, Cultural

What travelers are saying

"We have loved Gate 1 and always sing their praises. We've been on 7 tours with another one booked for fall. We were supposed to leave for Ecuador this week, however the country is in a 60 day state of emergency with the escape of 2 infamous gang members. Tourists are advised to stay indoors and there is a daily curfew from 11pm-5am. (our flight was to land at 11:15pm). Our trip included stays in 2 of the main cities of unrest. There have been shootings, car bombings, hostage taking, closing of embassies, and other countries issuing do not travel warnings. Other tour companies have cancelled tours or offered refunds or rescheduling. Travel insurance does not cover wars or civil unrest, but we are clearly afraid to go there. Both we and our travel agent have reached out multiple times with our concerns and asked if we could reschedule or get some sort of credit. We continue to get the same reply either in person or via email...Gate 1 has your safety as our highest priority and we feel you are safe ("they are not targeting tourists") and your itinerary should not be impacted. What? Their highest priority is $ and not our safety. There is no way that's the tour we anticipated. We cancelled the trip and took a 90% penalty, loss of deposit, and $276 airline penalty. It's a LOT of money, but we would have been terrified, and it's not worth getting hurt or worse. Sorry, but it's not the company I want to do business with in the future."

Trip dates & details
Save this trip to your favorites or other list
8 days From$1,199
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

8 Day Tuscany Fly & Drive with Milan (New York)
Save this trip to your favorites or other list

8 Day Tuscany Fly & Drive with Milan (New York)

By Gate 1 Travel
none
3.7/5 Great
100+ reviews
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Lucca, Milan, Parma, Pisa, San Gimignano, Siena

Themes

50 plus, Cultural

What travelers are saying

"We have loved Gate 1 and always sing their praises. We've been on 7 tours with another one booked for fall. We were supposed to leave for Ecuador this week, however the country is in a 60 day state of emergency with the escape of 2 infamous gang members. Tourists are advised to stay indoors and there is a daily curfew from 11pm-5am. (our flight was to land at 11:15pm). Our trip included stays in 2 of the main cities of unrest. There have been shootings, car bombings, hostage taking, closing of embassies, and other countries issuing do not travel warnings. Other tour companies have cancelled tours or offered refunds or rescheduling. Travel insurance does not cover wars or civil unrest, but we are clearly afraid to go there. Both we and our travel agent have reached out multiple times with our concerns and asked if we could reschedule or get some sort of credit. We continue to get the same reply either in person or via email...Gate 1 has your safety as our highest priority and we feel you are safe ("they are not targeting tourists") and your itinerary should not be impacted. What? Their highest priority is $ and not our safety. There is no way that's the tour we anticipated. We cancelled the trip and took a 90% penalty, loss of deposit, and $276 airline penalty. It's a LOT of money, but we would have been terrified, and it's not worth getting hurt or worse. Sorry, but it's not the company I want to do business with in the future."

Trip dates & details
Save this trip to your favorites or other list
8 days From$969
Price updated 1 year+ ago
More
8 Day Tuscany Fly & Drive with Milan (Miami)
Save this trip to your favorites or other list

8 Day Tuscany Fly & Drive with Milan (Miami)

By Gate 1 Travel
none
3.7/5 Great
100+ reviews
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Lucca, Milan, Parma, Pisa, San Gimignano, Siena

Themes

50 plus, Cultural

What travelers are saying

"We have loved Gate 1 and always sing their praises. We've been on 7 tours with another one booked for fall. We were supposed to leave for Ecuador this week, however the country is in a 60 day state of emergency with the escape of 2 infamous gang members. Tourists are advised to stay indoors and there is a daily curfew from 11pm-5am. (our flight was to land at 11:15pm). Our trip included stays in 2 of the main cities of unrest. There have been shootings, car bombings, hostage taking, closing of embassies, and other countries issuing do not travel warnings. Other tour companies have cancelled tours or offered refunds or rescheduling. Travel insurance does not cover wars or civil unrest, but we are clearly afraid to go there. Both we and our travel agent have reached out multiple times with our concerns and asked if we could reschedule or get some sort of credit. We continue to get the same reply either in person or via email...Gate 1 has your safety as our highest priority and we feel you are safe ("they are not targeting tourists") and your itinerary should not be impacted. What? Their highest priority is $ and not our safety. There is no way that's the tour we anticipated. We cancelled the trip and took a 90% penalty, loss of deposit, and $276 airline penalty. It's a LOT of money, but we would have been terrified, and it's not worth getting hurt or worse. Sorry, but it's not the company I want to do business with in the future."

Trip dates & details
Save this trip to your favorites or other list
8 days From$939
Price updated 1 year+ ago
More
8 Day Tuscany Fly & Drive with Milan (Chicago)
Save this trip to your favorites or other list

8 Day Tuscany Fly & Drive with Milan (Chicago)

By Gate 1 Travel
none
3.7/5 Great
100+ reviews
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Lucca, Milan, Parma, Pisa, San Gimignano, Siena

Themes

50 plus, Cultural

What travelers are saying

"We have loved Gate 1 and always sing their praises. We've been on 7 tours with another one booked for fall. We were supposed to leave for Ecuador this week, however the country is in a 60 day state of emergency with the escape of 2 infamous gang members. Tourists are advised to stay indoors and there is a daily curfew from 11pm-5am. (our flight was to land at 11:15pm). Our trip included stays in 2 of the main cities of unrest. There have been shootings, car bombings, hostage taking, closing of embassies, and other countries issuing do not travel warnings. Other tour companies have cancelled tours or offered refunds or rescheduling. Travel insurance does not cover wars or civil unrest, but we are clearly afraid to go there. Both we and our travel agent have reached out multiple times with our concerns and asked if we could reschedule or get some sort of credit. We continue to get the same reply either in person or via email...Gate 1 has your safety as our highest priority and we feel you are safe ("they are not targeting tourists") and your itinerary should not be impacted. What? Their highest priority is $ and not our safety. There is no way that's the tour we anticipated. We cancelled the trip and took a 90% penalty, loss of deposit, and $276 airline penalty. It's a LOT of money, but we would have been terrified, and it's not worth getting hurt or worse. Sorry, but it's not the company I want to do business with in the future."

Trip dates & details
Save this trip to your favorites or other list
8 days From$1,189
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
8 Day Tuscany Fly & Drive with Milan (New York)
Save this trip to your favorites or other list

8 Day Tuscany Fly & Drive with Milan (New York)

By Gate 1 Travel
none
3.7/5 Great
100+ reviews
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Lucca, Milan, Parma, Pisa, San Gimignano, Siena

Themes

50 plus, Cultural

What travelers are saying

"We have loved Gate 1 and always sing their praises. We've been on 7 tours with another one booked for fall. We were supposed to leave for Ecuador this week, however the country is in a 60 day state of emergency with the escape of 2 infamous gang members. Tourists are advised to stay indoors and there is a daily curfew from 11pm-5am. (our flight was to land at 11:15pm). Our trip included stays in 2 of the main cities of unrest. There have been shootings, car bombings, hostage taking, closing of embassies, and other countries issuing do not travel warnings. Other tour companies have cancelled tours or offered refunds or rescheduling. Travel insurance does not cover wars or civil unrest, but we are clearly afraid to go there. Both we and our travel agent have reached out multiple times with our concerns and asked if we could reschedule or get some sort of credit. We continue to get the same reply either in person or via email...Gate 1 has your safety as our highest priority and we feel you are safe ("they are not targeting tourists") and your itinerary should not be impacted. What? Their highest priority is $ and not our safety. There is no way that's the tour we anticipated. We cancelled the trip and took a 90% penalty, loss of deposit, and $276 airline penalty. It's a LOT of money, but we would have been terrified, and it's not worth getting hurt or worse. Sorry, but it's not the company I want to do business with in the future."

Trip dates & details
Save this trip to your favorites or other list
8 days From$829
Price updated 1 year+ ago
More
8 Day Tuscany Fly & Drive with Milan (Miami)
Save this trip to your favorites or other list

8 Day Tuscany Fly & Drive with Milan (Miami)

By Gate 1 Travel
none
3.7/5 Great
100+ reviews
Self-Guided / Independent Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Lucca, Milan, Parma, Pisa, San Gimignano, Siena

Themes

50 plus, Cultural

What travelers are saying

"We have loved Gate 1 and always sing their praises. We've been on 7 tours with another one booked for fall. We were supposed to leave for Ecuador this week, however the country is in a 60 day state of emergency with the escape of 2 infamous gang members. Tourists are advised to stay indoors and there is a daily curfew from 11pm-5am. (our flight was to land at 11:15pm). Our trip included stays in 2 of the main cities of unrest. There have been shootings, car bombings, hostage taking, closing of embassies, and other countries issuing do not travel warnings. Other tour companies have cancelled tours or offered refunds or rescheduling. Travel insurance does not cover wars or civil unrest, but we are clearly afraid to go there. Both we and our travel agent have reached out multiple times with our concerns and asked if we could reschedule or get some sort of credit. We continue to get the same reply either in person or via email...Gate 1 has your safety as our highest priority and we feel you are safe ("they are not targeting tourists") and your itinerary should not be impacted. What? Their highest priority is $ and not our safety. There is no way that's the tour we anticipated. We cancelled the trip and took a 90% penalty, loss of deposit, and $276 airline penalty. It's a LOT of money, but we would have been terrified, and it's not worth getting hurt or worse. Sorry, but it's not the company I want to do business with in the future."

Trip dates & details
Save this trip to your favorites or other list
8 days From$1,179
Price updated 1 year+ ago
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
53 trips exactly matchall of the the filters you selected.
My selections:
Standard

First

...

1

2

3

...

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
90  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

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

Glorious Countryside

We rode through glorious towns and countryside with plenty of opportunities to take photographs. I really enjoyed the company of the other riders. I am so glad I t...

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

See all Siena reviews

Write a Review

Additional details

Top Siena Travel Companies
Exodus Travels 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
Nancy Aiello Tours Reviews

Always Find the Best

On Travelstride you can find 105 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!