Rome and Tuscany Private Journey

Hiking and Cultural Adventures on Italy's Pilgrim Trail


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 trip to Rome’s Campo de'Fiori market with a professional chef to buy fresh ingredients for a private cooking class and lunch. Your Trip Leader knows this land as home and will unlock its secrets for you!

Itinerary at a Glance

Days 1-3
Roman Villas of Tivoli / Hike the Appian Way / Hike to Monte Catillo

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. For an optional add-on, enjoy a private cooking class with a Roman chef, including shopping for fresh ingredients in the historic Campo de’Fiori open market.

Days 4-7
Tuscany / Siena / San Gimignano / Lucca and Pisa / Village to Village Hikes

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. Depart via Rome on Day 7.

Hotel la Cisterna
San Gimignano, Italy
Days 4 to 6 (3 nights)
La Mormoraia Farmhouse
San Gimignano, Italy
Days 4 to 6 (3 nights)


  • Campo de’Fiori visit and private cooking class with a professional chef



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 Roman chef


Length: 7 days
Cost From: $4195  
Arrive: Rome, Italy
Depart: Florence, Italy
Lodging: 6 nights hotels
Meals: All meals included except 5 dinners as indicated in the Detailed Itinerary (B=Breakfast, L=Lunch, D=Dinner)
Activity: Walking, Hiking / Trekking
Trip Level:

Cultural explorations and walking tours, optional easy to moderate hikes of 2-5 hours