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.
Walking & Hiking
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Tuscany by the Sea Walking & Hiking Tour
From Chianti to the Mediterranean
Couples, Friends & Solos
Activity Level: 1-3
Premiere Hotels
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.
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Italy Tuscany by the Sea Walking & Hiking Tour map
Italy
Start Arezzo / End Rome
Start/End locations may vary. Do not book flights until your trip details are confirmed.
Highlights
- Discover two distinct Italian landscapes on foot, from picturesque inland Tuscany to idyllic west coast beaches
- Hike through iconic farms and vineyards and explore medieval hilltop towns and incomparable Siena
- Lounge on white sandy beaches while gazing at the Mediterranean and lush emerald hills
- Taste the region's best flavors, from classic Tuscan wines and fare to the Maremma's fresh-caught frutti di mare
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Itinerary
Accommodations may vary based on departure date.
Premiere Hotels
Accommodations may vary based on departure.
Days 1-3
Description
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.
Accommodations
Castel Monastero
Monastero d'Ombrone
| Premiere 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)
Days 4-6
Description
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.
Accommodations
Baglioni Resort Cala del Porto
Punta Ala
A luxurious resort overlooking the harbor and the Tyrrhenian Sea with classic Tuscan styling and a private beach club. (pool)
Dates & Prices
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.
DATES COMING SOON
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From our Guests
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#MyBackroadsTrip
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Activity Level:
1-3
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.
Route notes
The terrain on this trip includes mainly gravel, rolling country roads and some sections of single-track forest paths with stone steps.
Daily Route Options
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.
Route notes
The terrain on this trip includes mainly gravel, rolling country roads and some sections of single-track forest paths with stone steps.
What's Included
- All breakfasts, 5 lunches, 4 dinners
- Expertise and services of our experienced Trip Leaders
- Snacks and beverages between meals
- Additional guides and experts from the region on many trips
- Van shuttles to support a variety of route options
- Comprehensive Travel Planner with detailed pre-trip information
- Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
- All gratuities at hotels and restaurants
- Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
- On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
- Trailercycles, carriers, and kid-sized helmets for Family Trips
- Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
- Park and other entry fees
- Fares for trains, ferries and other modes of travel as listed in the Travel Planner
- Select coach transfers
- Baggage transfers and porterage
- All breakfasts, 5 lunches, 4 dinners
- Expertise and services of our experienced Trip Leaders
- Snacks and beverages between meals
- Additional guides and experts from the region on many trips
- Van shuttles to support a variety of route options
- Comprehensive Travel Planner with detailed pre-trip information
- Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
- All gratuities at hotels and restaurants
- Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
- On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
- Trailercycles, carriers, and kid-sized helmets for Family Trips
- Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
- Park and other entry fees
- Fares for trains, ferries and other modes of travel as listed in the Travel Planner
- Select coach transfers
- Baggage transfers and porterage
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