Siena Family Vacations

If you were cooking up the best Tuscan town for a kid-friendly vacation, Siena would have all the ingredients. Sprawling piazzas that practically demand pickup soccer games, boulevards lined with independent shops and cafes, and stunning art and architecture to impress the whole family mean that Siena is worthy of a full day, if not a longer stay to take it all in. A guided walking tour of Siena’s historic center is ideal, and be sure to experience the famed Duomo with your guide so you don’t miss some of the intricate details. Our favorite kid-friendly resort in Siena has just as much storybook appeal as the town itself. We can also recommend private villa rentals nearby for those who prefer a more independent accommodation experience.

Travel Planning

Experience the Best of Siena with Kids

Let Ciao Bambino! Plan Your Dream Trip

Our expert Family Travel Advisors are passionate about exploring the world with children — and empowering you to do the same. From handpicked accommodations to insider experiences, we can craft a custom vacation that’s uniquely suited to your family’s needs. Click to get started!

Get Started

Our Happy Travelers

"We had a brilliant holiday and we loved both Tuscany and our accommodations. The booking process was very easy and Katie was very helpful. Overall we had the most memorable and happy holiday!"

–Chantler Family Italy Trip

"Thanks again for all of your help! You made the trip easier for us to navigate as we went to unknown territory. It was definitely a trip of a lifetime and one we won't soon forget."

–Muse Family Italy Trip

"We loved everything about the trip! It was so wonderful and everything ran very smoothly. Thank you again for all your help!"

–Jones Family Trip

“I have been blown away with the services you provide. I first contacted Barbara last summer on a recommendation to Ciao Bambino from a friend. I wasn't sure what to expect as I had not used this type of service before. We were beyond impressed with everything Barbara set up for our family.”

–Detter Family Trip

"Katie planned the perfect trip. We all agree it was the best trip we've had, and the hotels were some of the best we've stayed in. We found that with a baby, it was only possible to get through about half of the suggested itinerary each day, which was great because it gave us options. We took time each night to debate what we would do the next day, and really enjoyed having those possibilities laid out for us."

–Beck Family Trip

Travel Blog

Build a Lifetime of Memories

View All

Amalfi Coast Family Vacations

Florence Family Vacations

Lucca Family Vacations

Milan Family Vacations

Puglia Family Vacations

Rome Family Vacations

Volterra Family Vacations

Umbria Family Vacations

Venice Family Vacations

Experiences

Immersive Family Activities Around the World

View All

Italy Family Vacations

Spain Family Vacations

Japan Family Vacations

Australia Family Vacations

Tuscany

Tuscany

Experience the Best of Siena with Kids

Let Ciao Bambino! Plan Your Dream Trip

Our Happy Travelers

"We had a brilliant holiday and we loved both Tuscany and our accommodations. The booking process was very easy and Katie was very helpful. Overall we had the most memorable and happy holiday!"

"Thanks again for all of your help! You made the trip easier for us to navigate as we went to unknown territory. It was definitely a trip of a lifetime and one we won't soon forget."

"We loved everything about the trip! It was so wonderful and everything ran very smoothly. Thank you again for all your help!"

“I have been blown away with the services you provide. I first contacted Barbara last summer on a recommendation to Ciao Bambino from a friend. I wasn't sure what to expect as I had not used this type of service before. We were beyond impressed with everything Barbara set up for our family.”

Top Articles About Siena with Kids

Build a Lifetime of Memories

Amalfi Coast Family Vacations

Florence Family Vacations

Lucca Family Vacations

Milan Family Vacations

Puglia Family Vacations

Rome Family Vacations

Volterra Family Vacations

Umbria Family Vacations

Venice Family Vacations

Immersive Family Activities Around the World

City Breaks for Families

Cultural Immersion Travel

Food & Wine Trips for Families

For Single Parents

Vacations with Babies & Toddlers

Vacations with School-Age Children

Vacations with Tweens & Teens

Italy Family Vacations

Spain Family Vacations

Japan Family Vacations

Australia Family Vacations

Siena Family Vacations

Tuscany

Tuscany

Experience the Best of Siena with Kids

Let Ciao Bambino! Plan Your Dream Trip

Our Happy Travelers

"We had a brilliant holiday and we loved both Tuscany and our accommodations. The booking process was very easy and Katie was very helpful. Overall we had the most memorable and happy holiday!"

"Thanks again for all of your help! You made the trip easier for us to navigate as we went to unknown territory. It was definitely a trip of a lifetime and one we won't soon forget."

"We loved everything about the trip! It was so wonderful and everything ran very smoothly. Thank you again for all your help!"

“I have been blown away with the services you provide. I first contacted Barbara last summer on a recommendation to Ciao Bambino from a friend. I wasn't sure what to expect as I had not used this type of service before. We were beyond impressed with everything Barbara set up for our family.”

Top Articles About Siena with Kids

Build a Lifetime of Memories

Amalfi Coast Family Vacations

Florence Family Vacations

Lucca Family Vacations

Milan Family Vacations

Puglia Family Vacations

Rome Family Vacations

Volterra Family Vacations

Umbria Family Vacations

Venice Family Vacations

Immersive Family Activities Around the World

City Breaks for Families

Cultural Immersion Travel

Food & Wine Trips for Families

For Single Parents

Vacations with Babies & Toddlers

Vacations with School-Age Children

Vacations with Tweens & Teens

Get the latest family travel news, exclusive deals & more!

Sign In

Create an Account

Coronavirus Update

Thanks for using Ciao Bambino!