Hiking and Cultural Adventures on Italy's Ancient Trails
Rome and Tuscany Private Journey
Overview
You'll get an “insider” view of the unrivalled heritage of Rome and sublime beauty of Tuscany on this delightful private journey. With your own private guide, head out on foot to see Rome's lesser-known sites, hike an ancient Roman road, and discover the treasures of Tivoli, where Roman emperors built lavish villas. Moving to the heart of Tuscany, you'll be based in the phenomenal medieval city of San Gimignano, a World Heritage Site. It's the perfect base for village-to-village hikes across Tuscany's luminous landscape, familiar from a thousand Renaissance paintings, with its rolling vineyards, olive groves, rows of cypresses, and backdrop of hill-perched medieval towns. Every day, you'll have your choice of activities so you can tailor the day to your own taste, whether you want a deep dive into culture or a beautiful hike on an ancient trail. A fun add-on option includes a private cooking class at a local vineyard in San Gimignano, where you'll learn to make a typical Tuscan meal with fresh local ingredients. Your Trip Leader knows this land as home and will unlock its secrets for you!
Arrive: Rome, Italy
Depart: Florence, Italy
Highlights
- Enjoy a Trip Leader who knows all the hidden sites, best trails, and local delicacies!
- Walk the Appian Way in the footsteps of the Roman legions
- Visit the World Heritage Sites of Villa Adriana and Villa d'Este in the hills of Tivoli
- Follow the ancient Francigena pilgrim trail from San Gimignano to the fortified village of Monteriggioni
- Optional private cooking class with a Tuscan chef
Itinerary
Stretch your legs on a full day's walk as your private guide brings you to some of Rome's most important sites as well as hidden sites that tell ancient stories. On the following days, choose cultural or hiking options, including a hike on the ancient Roman road called the Appian Way, a hike through Monte Catillo Nature Reserve to the top of Monte Catillo in the Apennine Mountains, and an out-of-town trip to explore Tivoli's fabulous Roman and Renaissance villas.
Visit medieval Siena, with its famous shell-shaped main square, on your way to San Gimignano, a hilltop gem that makes the perfect base for your cultural and hiking options. For a cultural option, explore the walled city of Lucca, birthplace of Puccini, and Pisa, with its iconic Leaning Tower. Hiking options from San Gimignano bring you through olive groves in the Tuscan countryside with striking views of the San Gimignano towers, along the Via Francigena (pilgrim trail) to Monteriggioni, or along the Via del Sale, the medieval salt trade route, to the Etruscan town of Volterra. For an optional add-on, enjoy a private cooking class at a local vineyard near San Gimignano. Depart via Rome on Day 7.
Accommodations
Scroll through our signature accommodations for this trip below. Although it is highly unlikely, we may make substitutions when necessary.
What the Trip is Like
This trip is rated a Level 2-3 (Moderate) according to our trip grading system, and offers a choice of in-depth walking and cultural tours and easy to moderate optional hikes. This trip has a good blend of hiking and cultural exploration. The cultural walking tours will keep you on your feet for 4 to 6 hours over a mix of streets and stairs.
Review Trip Level Details
If you choose the hiking options, you must feel comfortable hiking 3 to 5 hours, with recent experience hiking five miles in a day. You need to be able to hike on uneven surfaces, occasionally downhill over loose rocks, so good balance is important. The hikes explore a mix of terrain, from dirt roads to paths across rolling hills to ancient stone staircases, which can be quite steep.
The weather in Rome and Tuscany in late spring and early fall is usually very pleasant, with temperatures in the 70s°F (80s°F in Tuscany) during the day, and in the 50s°F and 60s°F at night. There can be cool breezes and occasional showers at any time during these seasons.
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Book your trip today
Our Area Specialists know every detail about our tours. They will be happy to answer any questions and help you choose the journey that’s right for you. Contact us to learn more or book your trip today!
Itinerary
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Trip Levels
With more than 200 different adventures to choose from, we want to help you find the trip that’s right for you. Our Trip Level system ranks each trip in two ways: a number rating from 1 to 6 according to the activity, and general travel rigors. 1 is the easiest and 6+ the most difficult.