Tuscan Hilltowns Hike
"Rich and robust" describes the character of Tuscany's landscape, its luscious wines and warm, engaging people. From Florence to Siena, we'll see the finest expressions of Renaissance culture, and hike in beautiful areas of countryside beloved by local Tuscans. This is a region brimming with natural and historical splendors that surround us on each day's hike. Gentle hills dotted with olive groves and poppy fields line our way to medieval hilltowns. We're rewarded with superb views from ancient monasteries such as San Gimignano, which overlooks the sun-warmed Elsa Valley. At museums and galleries, Renaissance and Etruscan artifacts vie for attention. And life moves at a leisurely pace on Siena's magnificent central piazza: "Il Campo"—a perfect place to relax over cappuccino and watch the world go by.
Important Notice: Day 1 is the day you should plan to arrive at the meeting point for the trip. This may require departing your hometown one or more days in advance and traveling on an overnight flight.
Tuscan Hilltowns Hike Itinerary:
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Day 1
Your trip begins in Florence, Italy. Arrive anytime and transfer on your own to our hotel. Founded in 59 B.C. as a strategic garrison by Julius Caesar, Florence evolved into the cultural capital of Italy during the Renaissance and is still considered to be a nexus of Italian art, culture and history. Depending on your arrival time, you may have the opportunity to explore this lovely city independently today and visit the Duomo, the Uffizi Gallery or Michelangelo’s sublime statue of David. Dinner and transfer on your own. Hotel included.
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Day 2
Meet our guides and traveling companions at 12 p.m. for the 1½-hour transfer to the outskirts of Volterra where we begin our first hike up to the city, picturesquely situated on a plateau overlooking the surrounding countryside. One of the oldest and most historically significant hilltowns in Tuscany, Volterra was founded by the Etruscan's around the 8th century B.C. We have a guided walking tour of the city where you will be introduced to the town's 3,000 years of history, visible still to this day in the Etruscan walls, Roman theater, Medieval and Renaissance buildings. The city also contains several noteworthy museums, palazzos and churches, some dating back to the 13th-century. After a late afternoon check-in at our hotel, we have some time to freshen up before reconvening for a short walk to an enoteca (wine bar). We have a welcoming glass of Tuscan wine and an orientation meeting to discuss the weekly itinerary, followed by dinner. Overnight in Volterra the next two nights. Breakfast and dinner included.
Hiking: 4 miles, mostly uphill. -
Day 3
Today features a beautiful rolling hike through the Tuscan landscape. We enjoy fantastic views as we walk through fields of wheat and past solitary Cypress trees before eventually entering the woods. Our day's hike ends with a short transfer to Volterra by minivan. Free time late this afternoon to further explore Volterra or unwind at the hotel before we meet for tonight's dinner. Breakfast and dinner included.
Hiking: 9 miles. -
Day 4
We bid farewell to Volterra and transfer by van to Colle di Val d'Elsa for a walk to enchanting San Gimignano. The uphill approach to the town is fantastic, passing through cypresses and vineyards as 13 medieval towers draw ever closer, piercing the Tuscan sky. San Gimignano has dominated the hill above the Elsa Valley since Etruscan times and we have an opportunity to learn about its colorful history and explore its museums and piazzas before transferring back to Colle di Val d'Elsa, a charming walled town and home to Italy's finest crystal makers. We spend the next two nights in Colle. Breakfast and dinner included.
Hiking: 6-7 miles. -
Day 5
Central Tuscany is well known for its delicious wines and today's scenic loop walk from Colle includes a tour and tasting at a small "boutique" winery located at the site of a 13th century monastery. After lunch at the winery, we have free time in the afternoon to either peruse Colle's crystal shops or enjoy another short walk before dinner. Dinner tonight is on our own providing an opportunity to choose from Colle's numerous eateries including the two-star Michelin restaurant Arnulfo. Breakfast included.
Hiking: 5 miles. -
Day 6
We transfer by van this morning to magical Siena, one of Italy’s most vibrant and captivating cities. Conquered by the Medicis in 1585, Siena is now known to contain some of Europe’s finest remaining examples of Gothic architecture due to its high concentration of well-preserved buildings from the 12th, 13th and 14th centuries. We’ll spend the entire day here, with a private guided tour scheduled for this morning and early afternoon. The city’s history will be recounted and explained during the course of our walk including insight into the origins of the famous bareback Palio horserace and story of the 600-year old “New Cathedral”. We’ll also visit Il Campo, Siena’s main piazza (considered by many to be Italy’s most beautiful) where the Palio takes place twice each year. After lunch, we can choose to join our guide for an exploration of Siena’s city walls and hidden neighborhoods or venture out on our own to peruse the local shops or wander through the town’s gothic streets at leisure. Late this afternoon, we’ll transfer to our countryside home for the next two nights, the lovely Villa Lecchi. The Villa Lecchi is an authentic 18th-century Tuscan villa that has been transformed into a family run hotel. Enjoy a swim in the villa’s pool or soak up the view of the surrounding hills while enjoying a cool glass of prosecco on the terrace. Dinner tonight is a feast prepared by the villa’s chef, Nonna. Breakfast and dinner included.
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Day 7
We awaken in our country villa this morning and have breakfast in the garden. Our final hike of the trip takes us into the famous Chianti Classico vineyards beneath the village of Castellina in Chianti. We depart directly from the villa on foot along an ancient path and wander through olive groves, along forest tracks and past scattered farmhouses and wineries…classic Tuscany at its most appealing. A lunch stop in a renovated farming hamlet now belonging to the Rocca della Macìe winery offers another opportunity to sample an assortment of excellent Tuscan delicacies in a delightful setting. We loop back to the Villa Lecchi at the end of the day to soak up the atmosphere and relax before our farewell dinner. Breakfast and dinner included.
Hiking: 10 miles. -
Day 8
After breakfast, our trip concludes with a group shuttle transfer to the Poggibonsi rail station. From here, frequent daily rail connections are available to Florence (1 hour) or Siena (30 minutes). Our guides will be happy to assist you with purchasing your ticket if necessary. Depart for home this afternoon or continue your adventure in Italy. Breakfast included.
Although we do our best to adhere to the schedule listed above, this itinerary is subject to change for numerous reasons beyond our control.
Please check with us before purchasing your airline tickets to ensure your trip has the necessary minimum number of participants required to operate.
Hotel accommodations with private bathrooms; meals as noted in the daily itinerary; guide/leadership; luggage transfers; all transfers starting from Florence on Day 2 until Poggibonsi on Day 7; special wine tasting; local city guides in Volterra and Siena.
Air transportation to Italy; transfer to Florence hotel; 2 dinners and 6 lunches; entrance fees to museums, churches and other sites during leisure time; alcoholic beverages (except at wine tasting); travel insurance; excess baggage charges; gratuities and items of a personal nature.
If you are traveling alone and specifically request single accommodations, you will be asked to pay the full single supplement noted on the trip itinerary. If you wish to share accommodations, we will assign you a roommate if one is available. If a roommate cannot be found, you will be asked to pay a reduced single fee, which is half of the full single supplement. Please be advised that there are a limited number of single rooms available on most departures.
This trip is rated Moderate [3]. The daily hikes range from 4-10 miles and are over varied terrain - from grassy lanes to rocky, gravel pathways. Since some of the trails we hike can be steep and/or hilly, a conditioning regimen beginning at least 2-3 months prior to departure is highly recommended. Walking/hiking, running and biking are all great ways to physically prepare for this adventure. The better shape you are in, the more you'll be able to enjoy all that Tuscany has to offer!
We have scheduled our departures to avoid the mid-summer heat and crowds while still traveling during periods that typically offer abundant sunshine and comfortable temperatures. Temperatures in Tuscany in May, June and September range from 70-80° F with evening temperatures dropping approximately 10 degrees. October departures will experience slightly cooler temperatures and fewer daylight hours.
This trip is subject to the booking information set forth in the current REI Adventures Reservation Information. Please read this information carefully and call us if you have any questions. A full gear list and pre-departure information is sent upon sign-up. We highly recommend the purchase of travel insurance through REI Adventures. If coverage is purchased within 21 days of your initial trip deposit, the 'Pre-existing Conditions Exclusion' is waived (certain exclusions apply).
We look forward to having you join us for the trip of a lifetime! Why wait? Space is limited, reserve your adventure today.
Tuscan Hilltowns Hike
The key to staying comfortable while on an active trip is layering. To get maximum comfort with minimum weight, you need versatile layers that mix and match to create the right amount of insulation, ventilation and weather protection. Try to bring only what is necessary—this will help you and the field staff.
Weather
We have scheduled our departures to avoid the mid-summer heat and crowds while still traveling during periods that typically offer abundant sunshine and comfortable temperatures. Temperatures in Tuscany in May, June and September range from 70-80° F with evening temperatures dropping approximately 10 degrees. October departures will experience slightly cooler temperatures and fewer daylight hours.
Gear Checklist
- Valid passport
- Airline tickets
- Medium-size duffel bag or soft sided suitcase (limiting luggage to one bag is recommended for ease in negotiating between airport and trains. Keep in mind that some train stations have numerous steps. Wheeled luggage is fine).
- Daypack (2,000 cu. in. to carry camera, water bottles, lunch and extra clothing)
- Luggage tags and luggage locks
- Passport pouch or money belt
- Bring a few lightweight, easily washable items for travel and evening wear
- Hiking pants - synthetic, quick-drying
- Hiking shorts - synthetic, quick-drying
- Long-sleeve shirts
- T-shirts
- Underwear
- Hiking socks
- Liner socks
- Casual socks
- Swimsuit
- Sun hat
- Bandana
- Rain jacket, waterproof and breathable
- Rain pants, waterproof and breathable
- Lightweight jacket or sweater
- Sturdy hiking boots, water resistant, lightweight, broken in, aggressive tread
- Comfortable shoes
- Two one-quart water bottle(s) or hydration pack
- Sunglasses and retainer strap
- Sunblock and lip balm
- Toiletry kit
- Small washcloth and small towel
- Personal first-aid kit
- Hand sanitizer gel
- Insect repellent
- Several Ziploc plastic bags
- Camera, film and spare batteries
- Spare contact lenses or glasses
- Reading and writing materials
- Travel pillow
- Hiking staff or trekking poles
- Ear plugs
- Watch with alarm or travel clock
- Electrical adapter plug/converter
Things to Consider
- Please remember to always pack essential items such as your passport, money, eyewear, a change of clothing, hiking boots and medications in your carry-on baggage, in case your luggage is delayed.
- Cotton is wonderful in warm weather. However, once it becomes wet, it will drain your body heat. Bring wool or synthetics such as Capilene®, MTS® and Thermax®.
- Always test your layers before a trip. Your outer layer should fit easily over the inside ones without binding and bunching up.
- Make sure boots are broken-in. Bring moleskin for foot treatment. Thin liner socks worn under regular hiking socks may minimize the risk of blisters. The liner sock should be synthetic, not cotton. Test your sock combination before you go on the trip.
- Stuff sacks are great for sorting gear. Use different sizes/colors to differentiate contents.
- Laundry facilities are not readily available during this trip and can be quite expensive. We suggest hand washing your clothes in your hotel room.
- Feel free to give us a call at (800) 622-2236 should you have any questions regarding the gear list. The staff at our stores or Direct Sales (800-426-4840) are happy to help you with gear questions. Or visit REI's website at www.rei.com. The Expert Advice section has great information to help you prepare for your trip.




