5-Nights Tuscany by the Sea Walking & Hiking Tour

From Chianti to the Mediterranean

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.

5 nights from $5799 per person

Supplier: Backroads

Click Here for Full Itinerary

Featured Destinations

Castelnuovo Berardenga

Castelnuovo Berardenga is a small town in the Province of Siena in southern Chianti, joining Italy’s finest vineyards since 1932. The name Berardenga comes from Count Berardo, of Frank who lived at the site of the town in the second half of the 10th century. Castelnuovo built in 1366, was a "new castle" of Siena acting as the border for Sienese territory.

Visitors can tour the countryside’s Landscape Museum. Full of charm and character, Castelnuovo Berardenga invites its guests to check out the Church of the Madonna del Patrocinio, the beautiful Italian Renaissance gardens, watch a musical performance at the Chigiana Musical Academy, cycle through Chianti Cycling Park, and just enjoy the scenic landscape of rustic villas, vineyards, churches and farmhouses.

Castiglione della Pescaia

Castiglione della Pescaia is a tranquil seaside village found on the Tuscan Coast of Italy. Developed around a medieval fortress and large fishery, Castiglione della Pescaia is known for its beaches and famed tourism. Castiglione was a city that held the defense along the Tyrrhenian coast building three towers protecting it from other Italian powers and the Spanish. In 1859, the town became an independent commune. Its pastel colored buildings, stretch to the port and wild grape vines, the town has been given the nickname “Svizzera della Maremma” or the “Switzerland of Maremma.” The town attracts visitors annually particularly throughout the summertime when the Tuscan Sun lures both locals and visitors to the crystal clear waters and eternities of coastal sand. Travelers can also visit the ancient remains of Vetulonia or stroll through the panoramic view of Casa Rossa Ximenes.

Valid Travel Dates

Departure Dates:
From Price
Prices Start at:
Number of Nights:
Vacation Inclusions:
  • 5-nights hotel accommodations in Premier Hotels
  • Meals: All breakfasts, 5 lunches, 4 dinners
  • Expertise and services of 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

Vacation 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

Air City:
Call for airfares from your city.
Vacation Rating:
Prices are per person, based on double occupancy, and subject to availability and change without notice. Prices reflect land only accommodations, airfare is additional. All prices are quoted in U.S. dollars. Single supplement applies. Call for single supplement pricing. Blackout dates/seasonal supplements may apply. Accommodations, inclusions and itinerary subject to change depending upon specific departure date. Private Trips, Custom Trips available; inquire for pricing and details. Please Note: Accommodations based on Premiere Hotels itinerary. 
Offer ID:

Reference this number when contacting our agency so we may better serve you. Also keeping this number handy will allow you to locate this document again quickly.

Company Info

House of Travel
17813 Biscayne Blvd.
Aventura, FL 33160
(305) 931-3002


Information and pricing is subject to change without notice. While we do our very best to ensure that information and pricing appearing in this website is complete and accurate, we cannot be responsible for incomplete and inaccurate representations, which may or may not be under our control. In the event of a pricing error, misrepresentation or omission, we reserve the right to adjust the pricing or make any other corrections.