Tuscany By The Sea Walking & Hiking Tour

Walking & Hiking

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Tuscany by the Sea Walking & Hiking Tour

From Chianti to the Mediterranean

Couples, Friends & Solos

6 days 5 nights

Activity Levels 1-3

Premiere Hotels

From: $5,799 - $6,199 pp dbl occ

($1,300 for sgl occ)

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.

Detailed Itinerary

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 Radda and Gaiole and incomparable Siena
Lounge on white sand at our seaside oasis in Punta Ala, where the Mediterranean meets lush emerald hills
Taste the region's best flavors, from classic Tuscan wines and fare to the Maremma's fresh-caught frutti di mare

Detailed Itinerary

Itinerary

Accommodations may vary based on departure date.

6 Days Premiere Hotels

Accommodations may vary based on departure.

Days 1-3

An unforgettable hiking tour through an iconic Tuscan landscape | Revel in the natural beauty on scenic hikes past cypress trees, olive orchards and legendary Chianti Classico vineyards | Linger in the vibrant Chianti towns of Gaiole and Radda and taste fine Tuscan wines | On a guided tour, learn more about the legendary Palio in Siena | Travel south and marvel at 14th-century frescoes in the Monte Oliveto Maggiore Abbey | Follow trails overlooking the region's otherworldly Crete Senesi | Discover the fine art of the truffle hunt with our local friend then savor its delicate flavors over dinner at an organic farm | Vacation at a beautifully restored Tuscan monastery-turned-hotel.

Castel Monastero

Monastero d'Ombrone

| Premiere Hotel

Stunning views of the Tuscan countryside and exceptional hospitality await at this elegantly restored castle-hotel. (pool, spa)

Days 4-6

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.

Baglioni Resort Cala del Porto

Punta Ala

| Premiere Hotel

A luxurious resort overlooking the harbor and the Tyrrhenian Sea with classic Tuscan styling and a private beach club. (pool)

Detailed Itinerary

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.

2022

May 8 - May 13

Scheduled Departure

Space is available — Book online

May 22 - May 27

Scheduled Departure

Going fast — Book online

Jun 5 - Jun 10

Scheduled Departure

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Jun 5 - Jun 10

Private Departure | 8+ Guests

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Jun 12 - Jun 17

Scheduled Departure

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Jun 12 - Jun 17

Private Departure | 8+ Guests

Space is available — Book online

Jun 19 - Jun 24

Scheduled Departure

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Jun 19 - Jun 24

Private Departure | 8+ Guests

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Jun 26 - Jul 1

Scheduled Departure

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Jul 3 - Jul 8

Scheduled Departure

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Sep 4 - Sep 9

Scheduled Departure

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Sep 11 - Sep 16

Scheduled Departure

Space is available — Book online

Sep 11 - Sep 16

Private Departure | 8+ Guests

Space is available — Book online

Sep 18 - Sep 23

Scheduled Departure

Space is available — Book online

Sep 25 - Sep 30

Scheduled Departure

reserved

Sep 25 - Sep 30

Private Departure | 8+ Guests

reserved

Oct 2 - Oct 7

Scheduled Departure

Space is available — Book online

Go Private

Go custom

Detailed Itinerary

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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 vineyard footpaths, wooded trails and narrow well-maintained coastal trails.

Daily Route Options

* Includes shuttle.

Day 1

Walking & Hiking

Level 2 | 4 miles | 900 ft. gain

Day 2

Walking & Hiking

Level 1 | 4 miles* | 400 ft. gain

Level 2 | 6 miles* | 700 ft. gain

Level 3 | 7 miles | 1100 ft. gain

Day 3

Walking & Hiking

Level 1 | 3 miles* | 400 ft. gain

Level 2 | 5 miles* | 700 ft. gain

Level 3 | 7 miles | 1000 ft. gain

Day 4

Walking & Hiking

Level 1 | 4 miles* | 400 ft. gain

Level 2 | 7 miles* | 800 ft. gain

Level 3 | 9 miles | 1000 ft. gain

Day 5

Walking & Hiking

Level 1 | 5 miles* | 700 ft. gain

Level 2 | 7 miles* | 900 ft. gain

Level 3 | 9 miles | 1100 ft. gain

Day 6

Walking & Hiking

Level 1 | 3 miles | 400 ft. gain

Detailed Itinerary

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

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Tuscany by the Sea Walking & Hiking Tour