Siena 50 plus Tours & Trip Packages

Siena 50 plus Tours & Trips

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

19 trips exactly matchall of the the filters you selected.
My selections:
50 plus
The Beautiful and the Powerful of the Italian Renaissance
Save this trip to your favorites or other list
4.4/5 Great
100+ reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Very Easy
Trip pace
Full schedule

Visits

Naples, Rome, Siena, Tuscany, Venice

Highlights

  • Examine the wealth and power of the Medici family — believed to have been the wealthiest family in Europe — and their influence as patrons
  • Compare and contrast the different artistic schools of Florence, Siena, Venice, Naples and Rome
  • Discuss the influences, techniques, designs and styles of the Renaissance’s most prominent artists including Botticelli, Brunelleschi, da Vinci and Michelangelo

Themes

50 plus, Education / Learning

What travelers are saying

"Our family of four, including two adult children, took the Bicycling: Day Trips to Paradise in Canada. This trip is entirely outsourced to the owners of the inn, there are no Road Scholar employees involved in the trip. Two of us have taken bicycle trips all over the world and the bicycling component of this trip was disorganized, haphazard and almost unsafe. We all filled out forms giving details regarding our bicycle fitting months before the trip. On the first day, the leader Stephen, went around the room and asked the same questions and said everyone would get fitted in the morning before we began the first ride. The morning brought a rack of bikes, all different types in various levels of readiness. There were road bikes, hybrid bikes, mountain bikes and e-bikes. The rides were all on paved surfaces and the mountain bikes were heavy and the additional suspension added weight. The bike I received had rust on the chain and rear sprocket. When I asked about it, was told they were waiting for another van to show up with tools and equipment. Once it arrived, they gave me the lubricant to spray on the rust. My wife’s bike would not shift into the high gear on the front sprocket. Instead of adjusting the derailleur, they suggested spraying it with lubricant. Our one son is over six feet and needed a larger frame bike, even though he detailed it in the bike form months ago, there was no bike to fit him. One of the guides, then went home and brought a larger bike that was a full suspension mountain bike for him. The bike was very heavy, hard to control on the road and he felt unsafe. After two days, one of the guides convinced Stephen that they could adjust a hybrid bike to fit him. Clearly there was no work done to prepare the bikes for the trip. Many of the bikes needed adjusting and all needed lubricant to function easily. For every day, there was a tray of snacks placed out for us to take along the ride. None of the bikes had any baskets or attached bags, so if you didn’t bring a small day pack, there was no way to carry the snacks. For lunch on the rides, they brought exactly one sandwich for each rider. Since most of us get hungry while doing a day of exercise, it would have been helpful to have a few extras. On one day, they ran out of sandwiches and one of the leaders that were riding with us did not get lunch. Do NOT take this trip if you are expecting it to be a bicycling trip. We have used VBT and Discovery Bicycle Tours many times over the past 25 years and they are excellent bike tour companies. Lastly, after sharing these details with Road Scholar after the trip, their response was weak at best. After doing the full reviews and having to call them, their response was to give us $200 credit after spending $8000 on this trip. Not only was that insulting, they assumed that I would take another trip with their organization."

Trip dates & details
Save this trip to your favorites or other list
More
Italy: Classic Tuscany and the Treasures of Florence
Save this trip to your favorites or other list
4.4/5 Great
100+ reviews
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Wheelchair Accessible
Trip pace
Full schedule

Visits

Lucca, Pisa, Siena, Tuscany

Highlights

  • Visit the famed quarries of Carrara to learn why this marble is the material of choice for great sculptors and architects
  • Explore the villa of Lorenzo de'Medici at Poggio a Caiano, and visit a winery in the Tuscan countryside to sample Tuscan wines
  • View the great masterpieces in Florence: works by Donatello, Brunelleschi, Ghiberti, Caravaggio, Cellini and Michelangelo’s iconic sculpture, “David

Themes

50 plus, Education / Learning

What travelers are saying

"Our family of four, including two adult children, took the Bicycling: Day Trips to Paradise in Canada. This trip is entirely outsourced to the owners of the inn, there are no Road Scholar employees involved in the trip. Two of us have taken bicycle trips all over the world and the bicycling component of this trip was disorganized, haphazard and almost unsafe. We all filled out forms giving details regarding our bicycle fitting months before the trip. On the first day, the leader Stephen, went around the room and asked the same questions and said everyone would get fitted in the morning before we began the first ride. The morning brought a rack of bikes, all different types in various levels of readiness. There were road bikes, hybrid bikes, mountain bikes and e-bikes. The rides were all on paved surfaces and the mountain bikes were heavy and the additional suspension added weight. The bike I received had rust on the chain and rear sprocket. When I asked about it, was told they were waiting for another van to show up with tools and equipment. Once it arrived, they gave me the lubricant to spray on the rust. My wife’s bike would not shift into the high gear on the front sprocket. Instead of adjusting the derailleur, they suggested spraying it with lubricant. Our one son is over six feet and needed a larger frame bike, even though he detailed it in the bike form months ago, there was no bike to fit him. One of the guides, then went home and brought a larger bike that was a full suspension mountain bike for him. The bike was very heavy, hard to control on the road and he felt unsafe. After two days, one of the guides convinced Stephen that they could adjust a hybrid bike to fit him. Clearly there was no work done to prepare the bikes for the trip. Many of the bikes needed adjusting and all needed lubricant to function easily. For every day, there was a tray of snacks placed out for us to take along the ride. None of the bikes had any baskets or attached bags, so if you didn’t bring a small day pack, there was no way to carry the snacks. For lunch on the rides, they brought exactly one sandwich for each rider. Since most of us get hungry while doing a day of exercise, it would have been helpful to have a few extras. On one day, they ran out of sandwiches and one of the leaders that were riding with us did not get lunch. Do NOT take this trip if you are expecting it to be a bicycling trip. We have used VBT and Discovery Bicycle Tours many times over the past 25 years and they are excellent bike tour companies. Lastly, after sharing these details with Road Scholar after the trip, their response was weak at best. After doing the full reviews and having to call them, their response was to give us $200 credit after spending $8000 on this trip. Not only was that insulting, they assumed that I would take another trip with their organization."

Trip dates & details
Save this trip to your favorites or other list
More
The Splendors of Italy
Save this trip to your favorites or other list
4/5 Great
100+ reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Strenuous
Trip pace
Balanced schedule

Visits

Assisi, Florence, Orvieto, Pisa, Rome, San Gimignano, Siena, Tuscany, Umbria, Venice

Themes

50 plus, Cultural

What travelers are saying

"We've taken over 10 group tours using Cosmos and Gate1. This trip last month, 9000 was not very good. -During booking, incorrect information was given about airport-hotel transfers -The whispers (listening devices) didn't work from the get-go, so no whispers were used during the 13 day trip. - Porters are no longer hired to bring your luggage to and from your room. (Very elderly had to handle their own luggage. Our friends had to help many of them.) -A few days into the trip one couple left. At the end of the trip we found out they had covid. Cosmos did not let us know; a few people weren't feeling well and two of our friends then tested positive. -One hotel was awful and not even up to "budget" standards -Many of the stops had castles, churches... but were not included, so be sure to count that in when pricing.  don't plan to use Cosmos ever again. Gate1 is the best in my opinion. When my husband's passport was stolen, they assigned someone to go with him to the embassy, translate, etc...It was above and beyond what we expected  "

Trip dates & details
Save this trip to your favorites or other list
More
Village Italy in 14 Days Tour
Save this trip to your favorites or other list
4.2/5 Great
23 reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Strenuous
Trip pace
Balanced schedule

Visits

Assisi, Cinque Terre, Lucca, Padua, Siena, Tuscany, Umbria, Venice

Highlights

  • Discover Mosaics of Ravenna's San Vitale & Galla Placidia tour
  • Enjoy Basilica of St. Francis tour
  • Orvieto cathedral and Signorelli's frescoes
  • Experience Lucca bike ride andLigurian Coast boat excursion

Themes

50 plus, Cultural, Hiking & Walking

What travelers are saying

"We purchased two backpacks from Rick Steves Europe. One of them arrived damaged and unusable. Their website says that you must contact them if you receive damaged merchandise. I have attempted to email them through their website and I have left 3 voicemails (nobody answers the phone, ever!) and nobody has contacted me back. At this point, it seems like I've been ripped off. Buyer beware. Extremely disappointed."

Trip dates & details
Save this trip to your favorites or other list
More
Heart of Italy in 9 Days Tour
Save this trip to your favorites or other list
4.2/5 Great
23 reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Cinque Terre, Colosseum, Florence, Lucca, Naples, Pantheon, Rome, Sistine Chapel, St. Peter's Basilica, Tuscany, Vatican City

Highlights

  • Experience Ancient Rome walking tour
  • Discover Colosseum tour and Roman Forum tour
  • Visit St. Peter's Basilica ,Vatican Museum and Sistine Chapel
  • ExploreGuarnacci Etruscan Museum tour

Themes

50 plus, Cultural, Hiking & Walking

What travelers are saying

"We purchased two backpacks from Rick Steves Europe. One of them arrived damaged and unusable. Their website says that you must contact them if you receive damaged merchandise. I have attempted to email them through their website and I have left 3 voicemails (nobody answers the phone, ever!) and nobody has contacted me back. At this point, it seems like I've been ripped off. Buyer beware. Extremely disappointed."

Trip dates & details
Save this trip to your favorites or other list
More
Tuscany Biking
Save this trip to your favorites or other list
5/5 Excellent
74 reviews
Small Group Tour
Lodging level
Luxury - 5 star
Physical level
Moderate
Trip pace
Balanced schedule

Visits

Florence, Siena, Tuscany

Highlights

  • Enjoy tasting of Tuscan reds
  • Explore vine-covered hills of Chianti
  • Explore Siena
  • Visit a private wine estate for a tasting

Themes

50 plus, Cycling & Biking

What travelers are saying

"Butterfield and Robinson just planned and executed a great, great trip for us to the Amalfi coast. All the services and hotels were wonderful and the guides were great fun and and well informed. Many nice surprises along the way and an itinerary we would have had trouble putting together on our own was effortless. All guides were well trained the transportation and drivers were polite and on time. The recommended hotels were amazing. We loved every minute of our vacation."

Trip dates & details
Save this trip to your favorites or other list
More

Unlock Community Benefits

Travel better together

  • Save favorite trips and itineraries
  • Get insider insights
  • Receive personalized recommendations
  • ... and much more
Join community
Italy's Great Cities
Save this trip to your favorites or other list
4.7/5 Excellent
100+ reviews
Small Group Tour
Lodging level
Premium - 4 star
Physical level
Very Easy
Trip pace
Balanced schedule

Visits

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

Highlights

  • Rome : Special welcome dinner at a local restaurant; guided sightseeing, visit the Vatican Museums and Sistine Chapel, St. Peter’s Square and Basilica, and the Colosseum; farewell dinner at a local restaurant
  • Assisi : Visit St. Francis Basilica
  • Venice : Private boat ride; guided walking tour, visit St. Mark’s Square and Basilica, Doges’ Palace and the Bridge of Sighs; glassblower demonstration
  • Pisa: Marvel at the legendary Leaning Tower
  • Florence: Guided walking tour, visit Michelangelo’s David and Signoria Square, and Santa Croce Basilica; taste a traditional gelato
Show more

Themes

50 plus, Cultural

What travelers are saying

"Just returned from Italy. Guides were very informative. Hotels went downhill with each city. Dinners which were included were absolutely horrible - vegetable lasagna in Italy really? Worst part was our guide Alessandro did not wait for us when the group met for the taxi to the airport - we were 5 minutes late. He lied about calling our room - front desk said he had not. Our friends reminded him we were missing but he left anyway - could have been a costly disaster if we didn't run to catch up. Never again!"

Trip dates & details
Save this trip to your favorites or other list
More
Italian Treasures
Save this trip to your favorites or other list
4.7/5 Excellent
100+ reviews
Small Group Tour
Lodging level
Premium - 4 star
Physical level
Very Easy
Trip pace
Balanced schedule

Visits

Assisi, Cinque Terre, Florence, La Spezia, Lucca, Orvieto, Pisa, Rome, San Gimignano, Siena, Tuscany, Umbria, Venice, Verona

Highlights

  • Rome : Welcome and farewell dinners at a local restaurant; guided sightseeing, visit the Vatican Museums and Sistine Chapel, St. Peter’s Square and Basilica, and the Colosseum
  • Lucca: Orientation
  • Cinque terre : By boat (weather permitting) with a Local Guide, and train
  • Pisa: Marvel at the legendary Leaning Tower
  • Siena : Walking tour including Piazza del Campo
Show more

Themes

50 plus, Cultural

What travelers are saying

"Just returned from Italy. Guides were very informative. Hotels went downhill with each city. Dinners which were included were absolutely horrible - vegetable lasagna in Italy really? Worst part was our guide Alessandro did not wait for us when the group met for the taxi to the airport - we were 5 minutes late. He lied about calling our room - front desk said he had not. Our friends reminded him we were missing but he left anyway - could have been a costly disaster if we didn't run to catch up. Never again!"

Trip dates & details
Save this trip to your favorites or other list
More
Travelstride Gift Card
One card, thousands of extraordinary trips
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
19 trips exactly matchall of the the filters you selected.
My selections:
50 plus

Siena Reviews & Ratings

4.7/5  Excellent
94  Reviews
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, ...

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...

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...

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...

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...

Write a Review

Additional details

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!