Chianti Hilltowns

Chianti Hilltowns

The hills of the Chianti region are in the culinary and wine-producing heart of Tuscany.  This fertile land has been contested between Florence and Siena for generations. Striped with vineyards, dotted with olive trees and bordered with dark cypress and round-topped pines, this is the dreamy landscape behind every Renaissance painting. It is fascinating to hike through these hills and see how medieval settlements and castles sprang up along roadsides and river crossings, growing to become important fortified towns. The timeless stone work has withstood invasions and weather for centuries. Beautifully arranged grape vines and olive trees grow right up to the doors of both farm houses and elegant villas reminding us how important these elements are to the marvelous local cuisine. Here all roads lead to the kitchen and we are delighted to indulge in the simple, but always rewarding, Tuscan feast!

$6200 - $6800 (6-12 members)

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Tour Overview

Day 1-3

Meet in Florence for a brief afternoon visit to some small jewels of the Renaissance before our homemade dinner in the countryside. The following morning we transfer south to the Chianti area where four nights there include visits to ancient abbeys, hikes through vineyards and medieval towns and wonderful picnics.

Day 4-6

A morning visit to the remarkable towers in the medieval town of San Gimignano precludes our walk to an ancient abandoned settlement in the nearby woods. In these days we visit a cashmere goat farm, have a wine tasting in a family run cantina and hike to the enormous imposing Brolio castle which commands the local countryside.

Day 7-10

The golden Val d’Orcia  is a wide open landscape of pastures and grains. We chose Pienza for its Renaissance architecture and unique pecorino sheep cheese, and Montalcino for its views of the surrounding areas and its famous deep ruby Brunello wine. The towns are charming, the churches evocative, the food and wine divine.

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Dates and Prices


Trip Cost $6200 – $6800 (6-14 members)

Single supplement: $700

*Smaller groups and fewer days option are available upon request

Departures Spring: May

Autumn: September

Trip Payment Schedule At time of reservation: $800

60 days prior to departure: Balance

Cancellation  Fee Schedule Up to 91 days prior to departure: No charge!

61-90 days prior to departure: 25% of trip cost

46-60 days prior to departure: 50% of trip cost

45 days or less: 100% of trip cost

Trip Price Includes Expert leadership of a Journey Through Italy Trip Leader and local guides;

Accommodations in comfortable inns, hotels, homes, castles, mountain huts;

All meals included (breakfasts, picnic lunches and dinners);

Wine with meals;

All transportation during the tour (van, bus, boat, ferries, cable car or funicular);

All entry fees to: museums, historic sites and parks;

Trip Price Does Not Include  

Air and land transportation to and from the trip, and individual arrival or departure transfers;

Personal expenses, optional tipping or gratuities to leaders or staff;

Additional hotel nights that may be necessary due to airline schedule changes or other factors;

Travel insurance or passports;

Other expenses of a personal nature (alcoholic beverages and non outside of group meals, snacks, room service, laundry, etc.);

Clothing and Equipment You will receive a detailed list of suggestions for packing upon tour reservation.

Travel Details





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Clothing and Equipment

A detailed list will be supplied upon tour reservation

Travel Insurance

Journey Through Italy recommends that you consider purchasing a travel protection plan to help protect you and your travel investment against the unexpected. You may have some coverage through your personal insurance plan or credit card services. If not, the travel protection plan we recommend, provided by Berkshire Hathaway Travel Protection, includes coverage for Trip Cancellation, Trip Interruption, Emergency Medical Expenses and Emergency Evacuation/Repatriation, Trip Delay, Baggage Delay and more. You can purchase complete (comprehensive) coverage, just medical coverage, just travel coverage, cancellation, or any plan which suits your personal needs.

By clicking the following link you can find more information and an application form. Get a Travel Insurance Now!

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