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Tuscany Day Trip from Rome: Tuscan Hilltowns, Fortresses & Vineyards

If you want to see Tuscany without having to navigate all those winding country roads (and maybe enjoy a glass or two of that famous wine), this is the day trip for you. We'll whisk you out of Rome and show you the best of Tuscany including a scenic lunch in Val d'Orcia, a vineyard, two beautiful hilltowns and a historic fortress.

Tuscany is one of the true gems of Italy. From mouth-watering cuisine and world-class wine to a deep and fascinating history; this region is one of the country's most popular among tourists and locals alike. On this tour, you'll board a small, comfortable air-conditioned bus in Rome.

Travelling with one of our fun, engaging tour leaders, you'll head into the Tuscan countryside for a cultural and culinary adventure. As you drive, they'll give you some background about the region; from the destruction wrought in WWII to the incredible produce that grows here (wine and cheese in particular).

Starting in Pienza, you'll have an hour of free time to wander the beautiful streets, shop and taste world-famous pecorino cheese, honey and jams. Be sure to check out the Etruscan well and the phenomenal views that stretch across the region from 'Strada del Amore', the street of love.

Next, you'll head to a local farm to enjoy a lunch of hyper-local ingredients. When you show up you'll get a brief look around to see what is growing and being raised before sitting down to a proper Tuscan feast. The menu changes with the season so whenever you go, you can be sure you're eating only the freshest ingredients sourced from the surrounding hills and right there on the farm.

After lunch, you'll visit Montalcino Fortress, where you'll climb the ancient walls for expansive views of the countryside. And let's not forget the wine! The most famous export of Tuscany, and this micro-region in particular. After the fortress, you'll visit a nearby vineyard for a guided tasting of Tuscan wines including Montepulciano and Barolo grapes.

Tuscany has a lot of cultures to experience, but this is as close as you can get to distilling its essence into a single day. We'll take you to the best spots where you'll meet the people behind the region's most famous exports and learn what makes them so special. Travelling with a local tour leader throughout the day, you'll get all the inside knowledge with none of the hassle so that all you'll have to worry about is which wine you're bringing home (don't worry, they ship internationally!)

Sites Visited: Pienza Town Organic farm in Val d’Orcia Montalcino Fortress Renowned vineyard in the Montalcino region.

Experience Includes

  • Explore the ancient Tuscan hill towns of Pienza and Montalcino
  • Special access ticket to climb the walls of the famous Montalcino Castle
  • Tour an award winning vineyard with a guided tasting of famous Tuscan wines
  • Small groups of max 18 people
  • Lunch at an organic farm
  • Comfortable, air-conditioned transport
  • Expert, English-speaking tour leader

Experience Excludes

  • Gratuities
  • Hotel Pick-Up/Drop-Off


Varies, please see calendar.

Departure location

Please meet your tour guide in front of Caffè Vergnano 1882 at Piazzale Flaminio n. 5/6, nextdoor to Intesa San Paolo bank.

Start times



Around 13 hours

Terms & Conditions

  • You will receive a voucher for this experience. Please read it thoroughly.
  • Itinerary subject to change without notice.
  • Gratuities to guides are appreciated but never obligatory.
  • Comfortable walking shoes are recommended.
  • 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.
  • Hotel pick-up/drop-off is NOT included. Please meet your guide in front of Caffè Vergnano 1882 at Piazzale Flaminio n. 5/6, nextdoor to Intesa San Paolo bank.
  • Please notify us if you have food allergies or other special requirements and we will do our very best to accommodate you.
  • Please ensure that all members of your party have a valid ID on them on the day of the visit. This is particularly important for guests who have qualified for child reduction.
  • Cancellation Policy: A full refund will be given on cancellations made more than 72 hours prior to tour commencement. Cancellations received within 72 hours prior to the tour are non-refundable. We will, however, do our best to reschedule you for another tour. Please note, this is subject to availability and price changes.
  • Tours depart precisely at the scheduled tour start time. If you show up late or cannot find the meeting point, for any reason, refund requests are not honoured per policy. For most tours, it is not logistically possible to join the group after it has started.