Travel Guides: Italy Travel Guide: Overview
In Southern Europe—right in the heart of the Mediterranean—lies a boot-shaped country stuffed to the brim with culture, history and fine cuisine.
Couples, Friends & Solos
Activity Level: 1-3
A vacation in perfect harmony. Morning hikes through Tuscany's rolling vineyards and afternoons lazing under il sole. World-class traditional cuisine paired with the elegant flavors of Chianti's incredible wines. Iconic inland landscapes give way to white-sand beaches and the turquoise Tyrrhenian Sea. Balance out a classic Tuscan adventure with coastal hikes, sorbet sunsets and the magic of the Maremma. This hiking adventure in Italy doesn't miss a step.
Start Arezzo / End Rome
Start/End locations may vary. Do not book flights until your trip details are confirmed.
Relish an unforgettable hiking adventure through iconic Tuscan landscapes | Travel south and follow trails overlooking the region's otherworldly Crete Senesi | Discover an organic farm and taste their exquisite farm-to-table offerings | Visit a small, local brewery and sample their beers, crafted onsite | On a guided tour, learn more about the legendary Palio in Siena | Revel in the natural beauty on scenic hikes past cypress trees, olive orchards and legendary Chianti Classico vineyards | Linger in vibrant Chianti towns and taste fine Tuscan wines | Vacation at a beautifully restored Tuscan monastery-turned-hotel.
Stunning views of the Tuscan countryside and exceptional hospitality await at this elegantly restored castle-hotel. Leading Hotels of the World property. (pool, spa)
Journey to the coastal area of Tuscany’s Maremma, a seaside paradise on the Mediterranean | Discover the charms of the region—an abundance of stunningly beautiful scenery and sweeping views of the sea | Hike seaside trails that follow the contours of rugged cliffs above hidden bays | Sink your toes in the white sand of Cala Violina and Cala Martina, two postcard-perfect Mediterranean beaches | Soak up the unique atmosphere of life by the sea in la bella Italia | Explore the historic fishing village of Castiglione della Pescaia, the jewel of the Tyrrhenian Sea | Celebrate with an alfresco dinner of just-caught seafood | Sunbathe on a private beach at our luxury seaside oasis | Complete your journey exploring the inlet of Punta Ala and its dazzling coastline.
A luxurious resort overlooking the harbor and the Tyrrhenian Sea with classic Tuscan styling and a private beach club. (pool)
The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind — you won't be charged to transfer to a different trip before your final payment is due. View cancellation policy.
Click on dates for pricing, itinerary variations and to book your trip. Price is per person, double occupancy in USD.
Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.
Group size is required to show per-person pricing. Your group size can be approximate and can change.
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.
The terrain on this trip includes mainly gravel, rolling country roads and some sections of single-track forest paths with stone steps.