Tuscany at its best - Hilltowns, Castles and Vineyards Day Trip from Rome

Small Group Day Trip from Rome to Tuscan Hilltowns, with lunch and wine tasting

13 h
Day Trips & Excursions
difficulty Very easy
Wheelchair Not Accessible

Small Group Day Trip from Rome to Tuscan Hilltowns, with lunch and wine tasting

A soulful land with rich culture, gourmet food and lyrical landscapes, it is no wonder why Tuscany is a dream destination for most people. We have compiled the best of Tuscany's attractions into a wondrous day tour so you can immerse yourself in a memorable and authentic Italian experience.

Discover the medieval Tuscan hill towns of Pienza and Montalcino, each boasting stunning views of Tuscany
Partake on an enriching tour of an organic Tuscan farm, where you will indulge in an excellent range of Tuscan delicacies
Scale the ancient walls of the grandeur Montalcino Castle while marvelling at the panoramic views of the rolling hills and verdant countryside
Visit an aromatic and beautiful vineyard producing award-winning Tuscan wines followed by a delectable tasting session
Explore with a small group of 15 like-minded individuals or less with a professional English-speaking guide

With departure from Rome, go to Tuscany! Embark on a gastronomic morning as you journey towards the scenic Tuscan countryside.

Savour in superfine Tuscan delicacies

Your adventure starts at Pienza, a UNESCO world heritage town perched atop a hill, offering panoramic views of the surrounding countryside. Take a leisure stroll through its characteristic streets and pick up some authentic local produce and wines along the way. There will be ample opportunities to sample traditional Tuscan delights such as pecorino cheese and wild boar, and to drop by some of Pienza's famous ceramics shops. Next up, your guide will lead you to an organic, family-owned farm for an exciting tour and an enriching session with their resident cheese maker. Following the tour, you will be treated to a delectable Tuscan cuisine, prepared directly from farm to table. The most anticipated part of the meal is the full tasting session of their finest sheep's and goat's milk cheeses complemented with homemade honey and jam. Your tour of the farm comes to a perfect close with a tasting session of their finest local wines while overlooking the charming views of the picturesque Val d'Orcia region.

Keep your eyes peeled for the alluring Montalcino Castle

Prepare yourself for the next highlight of the trip after lunch. Your adventure continues towards Montalcino, a quaint hill town renowned for its beautiful castle – The Montalcino Castle. With full access tickets, you will be entitled complete access to the highest lookout towers for a breath-taking view of the surroundings.

Discover the secrets of wine-amking and indulge in a tasting session

To end off a memorable day tour, you will be visiting a famous winery for an exclusive guided tour and tasting session of the finest Tuscan wines. If you would like to bring the Tuscan flavour home and share it with your family and friends, don't forget to bag a few bottles of the excellent wines from here!

More Day Trips from Rome

If you are based in Rome, this is the perfect departure point to discover Italy with some Day Trips! Take a look at our Day Tour to Florence or to our Day Tour to Venice!

  • Pienza Town
  • Val d'Orcia
  • Montalcino Castle
  • Round trip transport from Rome
  • English-speaking tour leader
  • Lunch at an organic farm
  • Wine tastings at a Montalcino vineyard
  • Special access ticket to climb Montalcino Castle Walls
  • Tips (Optional)
Meeting point: 

Meeting point information and local telephone numbers at your destination are included on your Confirmation Voucher.


Please note that the tour meeting time is 15 minutes prior to the start time. No refunds or re-bookings can be provided for late arrivals or no shows after tour commencement or departure.
Unfortunately we are unable to accommodate guests with mobility impairments, wheelchairs or strollers on this tour.
Comfortable walking shoes recommended.

Confirmation will be received within 48 hours of booking, subject to availability. Once your booking is confirmed we will email you a voucher. This is your ticket and proof of purchase.