Hiking and Cultural Adventures on Italy's Ancient Trails

Rome and Tuscany Private Journey

Italy

7 Days

From $5,295

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It&#39;s the perfect base for village-to-village hikes across Tuscany&#39;s luminous landscape, familiar from a thousand Renaissance paintings, with its rolling vineyards, olive groves, rows of cypresses, and backdrop of hill-perched medieval towns. Every day, you&#39;ll have your choice of activities so you can tailor the day to your own taste, whether you want a deep dive into culture or a beautiful hike on an ancient trail. A fun add-on option includes a private cooking class at a local vineyard in San Gimignano, where you'll learn to make a typical Tuscan meal with fresh local ingredients. 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Find the Toucan Club tab on the home page of our website and choose Helpful Links: <a href=\"https:\/\/www.wildernesstravel.com\/ toucan\/links\">www.wildernesstravel.com\/ toucan\/links<\/a>.<\/p>","System_About_Private_Journeys":"<!-- Generated by XStandard version 3.0.0.0 on 2023-02-17T11:00:24 --><p>Wilderness Travel Private Journeys are designed for people who want to travel with their own small private group, but who still want to experience the same superb itinerary design, great accommodations, and signature quality of Wilderness Travel's escorted group trips. These Private Journeys allow you to choose your own dates and your traveling companions -- even if it's just the two of you -- yet still enjoy a guided adventure.<\/p>","System_About_New_Trips":"","System_Social_Media":"<!-- Generated by XStandard version 3.0.0.0 on 2023-03-29T11:33:43 --><p><strong>SOCIAL MEDIA:<\/strong> We invite you to share your adventure with us on social media. 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Refer to the Emergency Contact Information listed in this Final Bulletin.<\/p>","System_Valid_Passport":"<!-- Generated by XStandard version 3.0.0.0 on 2023-06-16T10:26:21 --><p><strong>VALID PASSPORT:<\/strong> Check that your passport is valid for at least six months from the last day of your trip, and that you have at least two blank pages for any necessary visa or entry and exit stamps.<\/p>","System_Insurance_Policy":"<!-- Generated by XStandard version 3.0.0.0 on 2023-03-29T11:36:23 --><p><strong>INSURANCE POLICY:<\/strong> If you have purchased the Travelex Travel Protection Plan, you should have received an email confirmation of your policy. Please bring a digital or printed copy of this policy with you. If you cannot find your email confirmation, please contact Travelex's Customer Solutions team at 844-877-1885 or e-mail customersolutions@travclcxinsurancc.com. 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Overview

    Contact Us Download Itinerary

    Call 1-800-368-2794 or contact us for any questions

    Overview

    You'll get an “insider” view of the unrivalled heritage of Rome and sublime beauty of Tuscany on this delightful private journey. With your own private guide, head out on foot to see Rome's lesser-known sites, hike an ancient Roman road, and discover the treasures of Tivoli, where Roman emperors built lavish villas. Moving to the heart of Tuscany, you'll be based in the phenomenal medieval city of San Gimignano, a World Heritage Site. It's the perfect base for village-to-village hikes across Tuscany's luminous landscape, familiar from a thousand Renaissance paintings, with its rolling vineyards, olive groves, rows of cypresses, and backdrop of hill-perched medieval towns. Every day, you'll have your choice of activities so you can tailor the day to your own taste, whether you want a deep dive into culture or a beautiful hike on an ancient trail. A fun add-on option includes a private cooking class at a local vineyard in San Gimignano, where you'll learn to make a typical Tuscan meal with fresh local ingredients. Your Trip Leader knows this land as home and will unlock its secrets for you!

    Arrive: Rome, Italy

    Depart: Florence, Italy

    Highlights

    • Enjoy a Trip Leader who knows all the hidden sites, best trails, and local delicacies!
    • Walk the Appian Way in the footsteps of the Roman legions
    • Visit the World Heritage Sites of Villa Adriana and Villa d'Este in the hills of Tivoli
    • Follow the ancient Francigena pilgrim trail from San Gimignano to the fortified village of Monteriggioni
    • Optional private cooking class with a Tuscan chef

    Itinerary

    Download Itinerary Expand All Days
    Stretch your legs on a full day's walk as your private guide brings you to some of Rome's most important sites as well as hidden sites that tell ancient stories. On the following days, choose cultural or hiking options, including a hike on the ancient Roman road called the Appian Way, a hike through Monte Catillo Nature Reserve to the top of Monte Catillo in the Apennine Mountains, and an out-of-town trip to explore Tivoli's fabulous Roman and Renaissance villas.

    Visit medieval Siena, with its famous shell-shaped main square, on your way to San Gimignano, a hilltop gem that makes the perfect base for your cultural and hiking options. For a cultural option, explore the walled city of Lucca, birthplace of Puccini, and Pisa, with its iconic Leaning Tower. Hiking options from San Gimignano bring you through olive groves in the Tuscan countryside with striking views of the San Gimignano towers, along the Via Francigena (pilgrim trail) to Monteriggioni, or along the Via del Sale, the medieval salt trade route, to the Etruscan town of Volterra. For an optional add-on, enjoy a private cooking class at a local vineyard near San Gimignano. Depart via Rome on Day 7.

  • Private cooking class at a vineyard near San Gimignano
  • Dates & Pricing

    Best months to go: January to December. For our Private Journeys, you choose your own group and your preferred dates. Prices are per person and not guaranteed until services are confirmed. Contact us for availability, questions, or to book your adventure!

    Payment & Cancel Schedule

    At time of reservation: 25% of trip cost
    90 days prior to departure: Balance

    *Please note that this differs from our standard policy.

    Cancellation & Transfer Schedule

    Minimum fee: 25% of trip cost
    90 days or less: 100% of trip cost

    *Please note that this differs from our standard policy.

    Included
    • Expert leadership of local guides
    • Accommodations in hotels
    • All meals included except 5 dinners as indicated in Detailed Itinerary
    • All ground transportation and baggage handling from meeting until departure
    • All activities as indicated in Detailed Itinerary
    Not Included
    • Travel to and from the arrival and departure location as indicated in Detailed Itinerary
    • Additional hotel nights outside the trip's scheduled dates
    • Optional gratuities to Trip Leaders or staff
    • Optional travel insurance
    • Other expenses of a personal nature (some alcoholic beverages, laundry, etc.)
    • Any activities and services described as an upgrade or optional

    Accommodations

    Listed below are our signature accommodations for this trip. Although it is highly unlikely, we may make substitutions when necessary.

    Hotel Forum

    Days 1-3 (3 nights)

    The location of the Hotel Forum can't be beat—it's right in the heart of Rome's centro historico, directly across the street from the Forum and just steps from the Colosseum and other monuments of the Eternal City. Watch Rome come to life in the morning as you enjoy breakfast at the rooftop restaurant and marvel at the stunning views (you can even see the spot where Caesar was assassinated). Several good restaurants (and gelaterie!) are located nearby. Guest rooms vary in size but offer a comfortable place to rest after a busy day of exploring this enchanting city.

    Hotel La Collegiata

    Days 4-6 (3 nights)

    Set in a beautiful park-like location just outside San Gimignano, this former 16th century convent for Capuchin friars and, later, a private family summer residence, is a wonderful retreat that retains an air of quiet elegance. Each of the 20 guest rooms rooms are individually decorated in Tuscan country style, but offer all the amenities you would expect in a fine hotel. After a busy day exploring, take advantage of the outdoor swimming pool and relax in the lovely gardens.

    1/2

    Trip Leaders

    Gianluca Canalicchio

    View Profile

    What the Trip is Like

    This trip is rated a Level 2-3 (Moderate) according to our trip grading system, and offers a choice of in-depth walking and cultural tours and easy to moderate optional hikes. This trip has a good blend of hiking and cultural exploration. The cultural walking tours will keep you on your feet for 4 to 6 hours over a mix of streets and stairs.
    Review Trip Level Details

    If you choose the hiking options, you must feel comfortable hiking 3 to 5 hours, with recent experience hiking five miles in a day. You need to be able to hike on uneven surfaces, occasionally downhill over loose rocks, so good balance is important. The hikes explore a mix of terrain, from dirt roads to paths across rolling hills to ancient stone staircases, which can be quite steep.

    The weather in Rome and Tuscany in late spring and early fall is usually very pleasant, with temperatures in the 70s°F (80s°F in Tuscany) during the day, and in the 50s°F and 60s°F at night. There can be cool breezes and occasional showers at any time during these seasons.

    Book your trip today

    Our Area Specialists know every detail about our tours. They will be happy to answer any questions and help you choose the journey that’s right for you. Contact us to learn more or book your trip today!

    Itinerary

    Submit the form below to download itinerary

    Hidden

    Hidden


    Trip Levels

    With more than 200 different adventures to choose from, we want to help you find the trip that’s right for you. Our Trip Level system ranks each trip in two ways: a number rating from 1 to 6 according to the activity, and general travel rigors. 1 is the easiest and 6+ the most difficult—see descriptions below for explanations of each number. A plus (+) sign means the trip is a bit more strenuous than other trips of that level. The detailed explanation of each trip—below the bar with the number rating—is perhaps more important, specifying activities, altitudes, hiking, and travel conditions. The Detailed Itinerary, available by download or mail, gives further information. Our Area Managers can also answer questions and guide you to the trip that best suits your interests.

    Level 1 – Easiest

    Non-camping journeys, optional walks, little elevation gain or loss.

    Level 2 – Easy to Moderate

    Hotel nights and/or safari-style camping, hikes of two to four hours on some days. Other physical activities are sometimes included, such as optional sea kayaking.

     

    Level 3 – Moderate

    Half- to full-day hikes (3-6 hours) over rolling countryside on most days, occasional steep trails. Many of our hotel-based walking tours are in this category, as are our snorkeling adventures.

    Level 4 – Moderate to Strenuous

    Full-day hikes (4-6 hours), mountainous terrain, significant elevation gains and losses (hiking up or down as much as 3,000 feet) on many days. Altitudes no greater than about 10,000 feet.

     

    Level 5 – Strenuous

    Full-day hikes (4-8 hours), mountainous, steep terrain (hiking up or down as much as 3,500 feet) on many days. Trips with hiking at average altitudes of 10,000 to 12,000 feet are in this category.

    Level 6 – Very Strenuous

    Full-day hikes (5-8 hours), mountainous, steep terrain (hiking up or down as much as 3,500 feet) on many days. Most hikes take place at altitudes above 10,000 feet, with some days ascending as high as 18,000 feet.

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The view of San Gimignano from the breakfast terrace and swimming pool is magical and the onsite restaurant serves excellent fresh Tuscan cuisine.<\/body>","ItinBlock":"","VendorPhoto":"https:\/\/s3.us-west-1.wasabisys.com\/wildernesstravel\/vendors\/1-la-mormoraia-farmhouse-agriturismo-san-gimignano-vineyard-front.jpg","ProductPhoto":"","OnRequest":"Option","Overhead":false,"BookingNotes":"","TicketSession":"","TicketTimeOfDay":"","TicketRound":"","TicketCategory":"","TicketDate":"","TicketLocation":"","NotTicketOnly":false,"Inactive":false}],"CustomFields":{"Custom_Trip_Level_5":"","Custom_Trip_Name_Addendum":"","Custom_Welcome_Letter_Addendum":"","Custom_Welcome_Email_Send_List":"","Custom_Welcome_Insurance_Intro":"We recommend you purchase a travel protection plan to help protect your travel investment against the unexpected. 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If you have questions about the level of comfort or any of the activities described in this itinerary, please call Wilderness Travel at 1-800-368-2794 and ask for the<\/p>","System_References":"<!-- Generated by XStandard version 3.0.0.0 on 2023-01-27T07:50:51 --><p>We'd be happy to put you in touch with a past client that has traveled with us on this trip.<\/p>","System_Visit_Our_Website":"<!-- Generated by XStandard version 3.0.0.0 on 2023-01-27T07:51:32 --><p>At <a href=\"https:\/\/www.wildernesstravel.com\">www.wildernesstravel.com<\/a>, you can find out about added departures, last-minute deals, and special WT Expeditions that aren't listed in our catalog. You can also access a complete library of our detailed itineraries and browse the customized reading guides for each of our adventures.<\/p>","System_Helpful_Links":"<!-- Generated by XStandard version 3.0.0.0 on 2023-01-27T07:52:03 --><p>Wilderness Travel has compiled a list of useful websites for travelers. Find the Toucan Club tab on the home page of our website and choose Helpful Links: <a href=\"https:\/\/www.wildernesstravel.com\/ toucan\/links\">www.wildernesstravel.com\/ toucan\/links<\/a>.<\/p>","System_About_Private_Journeys":"<!-- Generated by XStandard version 3.0.0.0 on 2023-02-17T11:00:24 --><p>Wilderness Travel Private Journeys are designed for people who want to travel with their own small private group, but who still want to experience the same superb itinerary design, great accommodations, and signature quality of Wilderness Travel's escorted group trips. These Private Journeys allow you to choose your own dates and your traveling companions -- even if it's just the two of you -- yet still enjoy a guided adventure.<\/p>","System_About_New_Trips":"","System_Social_Media":"<!-- Generated by XStandard version 3.0.0.0 on 2023-03-29T11:33:43 --><p><strong>SOCIAL MEDIA:<\/strong> We invite you to share your adventure with us on social media. Tag @wildernesstravel and we may even feature your content on our pages!<\/p>","System_If_You_Miss_Your_Flight":"<!-- Generated by XStandard version 3.0.0.0 on 2023-03-29T11:34:09 --><p><strong>IF YOU MISS YOUR FLIGHT<\/strong><br \/>If you miss your flight or are otherwise delayed, contact our Wilderness Travel office as well as our local partners, with your new flight information. Refer to the Emergency Contact Information listed in this Final Bulletin.<\/p>","System_Valid_Passport":"<!-- Generated by XStandard version 3.0.0.0 on 2023-06-16T10:26:21 --><p><strong>VALID PASSPORT:<\/strong> Check that your passport is valid for at least six months from the last day of your trip, and that you have at least two blank pages for any necessary visa or entry and exit stamps.<\/p>","System_Insurance_Policy":"<!-- Generated by XStandard version 3.0.0.0 on 2023-03-29T11:36:23 --><p><strong>INSURANCE POLICY:<\/strong> If you have purchased the Travelex Travel Protection Plan, you should have received an email confirmation of your policy. Please bring a digital or printed copy of this policy with you. If you cannot find your email confirmation, please contact Travelex's Customer Solutions team at 844-877-1885 or e-mail customersolutions@travclcxinsurancc.com. If you have not purchased Travelex insurance already, you have the option to do so up to 24 hours prior to your departure.<\/p>","System_Covid-19_Travel_Requirements":"<!-- Generated by XStandard version 3.0.0.0 on 2023-04-19T13:27:44 --><p><strong>COVID-19 TRAVEL REQUIREMENTS:<\/strong> Please double-check COVID-19 entry requirements for any countries you may be traveling to or transiting through, on this website: <a href=\"apply.joinsherpa.com\/travel-restrictions\">apply.joinsherpa.com\/travel-restrictions<\/a><\/p>","System_Pre-Trip_Safety":"<!-- Generated by XStandard version 3.0.0.0 on 2023-03-29T11:37:06 --><p><strong>PRE-TRIP SAFETY:<\/strong> In the next weeks, we encourage you to do everything possible to stay healthy. Please practice social distancing, steer clear of potential COVID-19 exposure, and take an at-home antigen or lab based PCR test before you depart.<\/p>","System_Wilderness_Travel_Office":"<!-- Generated by XStandard version 3.0.0.0 on 2023-03-29T11:38:07 --><p>Our office in Berkeley, California can be reached at 510-558-2488, or by email at info@wildernesstravel.com. We are available during regular business hours (M-F, 8:30 am-5:00 pm, PST). <\/p>","System_ECI_Travel_Insurance":"<!-- Generated by XStandard version 3.0.0.0 on 2023-03-29T11:38:31 --><p>If you have purchased the Travelex Travel Protection Plan through Wilderness Travel, please remember to bring your Confirmation of Coverages (COC) with you on the trip, including your Plan Number and important emergency contact information.<\/p><p>If you've purchased a travel protection plan on your own, we recommend that you bring a copy of your policy, including all coverages, with you on your trip.<\/p>","System_Face_Masks_and_Hand_Sanitizer":"","System_DidNotPurchase_Insurance":"<!-- Generated by XStandard version 3.0.0.0 on 2023-02-28T12:27:44 --><p>Travel Insurance: We recommend that you purchase travel insurance for this trip. For your convenience, we offer Travelex travel protection. Please let us know if you would like us to add the Travelex Travel Protection Plan to this final invoice. You can learn more about the policy on our <a href=\"https:\/\/www.wildernesstravel.com\/toucan\/travel-insurance\">website<\/a>.<\/p>","System_Purchased_Insurance":"","System_Questions?":"<!-- Generated by XStandard version 3.0.0.0 on 2023-01-27T13:47:31 --><p>Our Area Specialists are you single point of contact and would be happy to answer any questions about yout trip!<br \/>800.368.2794 | 510.558.2488<\/p>","System_Travel_Insurance":"<!-- Generated by XStandard version 3.0.0.0 on 2023-01-27T07:58:05 --><p>We highly recommend you purchase travel insurance. You can take advantage of a comprehensive Travel Protection Plan designed for Wilderness Travel by Travelex, or purchase other insurance on your own. See our website for details: <a href=\"https:\/\/www.wildernesstravel.com\/insurance\">www.wildernesstravel.com\/insurance<\/a><\/p>","System_Make_it_Your_Trip":"<!-- Generated by XStandard version 3.0.0.0 on 2023-03-29T11:44:18 --><p>The prices above are for the ready-to-book adventure outlined in this Detailed Itinerary, a popular option that has been handcrafted by our Area Specialists to include the best of every destination. While many travelers choose to book this tour as is, our Area Specialists are also happy to work with you to customize this Private Journey to suit your specific interests and style of travel. We can arrange for longer or shorter stays, offer hotel upgrades (see below for sample costs), or add an extension to additional places of interest. We can even add special activities or customize excursions depending on your interests. We invite you to contact us to discuss your options!<\/p>","System_Signing_up_for_a_Trip":"<!-- Generated by XStandard version 3.0.0.0 on 2023-03-29T11:44:42 --><p>Early reservations are recommended since accommodations often sell out far in advance. Please call 1-800-368-2794 and ask for our [Africa Manager] or email us at [africa@ wildernesstravel.com] with any questions that you may have about this trip. To reserve your Private Journey, we will need to know your preferred dates of travel. We will then check availability and send you a proposed itinerary with exact pricing for your adventure. We can typically hold a provisional booking for one week. At that time, we must collect your initial deposit or accommodations will be released. We accept Visa, Mastercard, or American Express card. Upon receipt of your deposit, we will send you a Welcome Packet that includes a letter of confirmation, Detailed Itinerary, Trip Application, Medical Form, and Pre-Departure Information Booklet with information to help you prepare for your adventure. Please see our Cancellations and Transfer Fee Schedule for specific payment information.<\/p>","System_Trip_Leaders":"<!-- Generated by XStandard version 3.0.0.0 on 2023-02-13T09:24:57 --><p>Wilderness Travel Trip Leaders have a passion and a joy for creating an unforgettable journey. We are extremely proud of them and the incredible travel experiences they make possible. The Trip Leader for each departure is listed on the &quot;Dates &amp; Prices&quot; tab on our Pilgrim's Way webpage:<\/p>"},"terms":{"PaymentSchedule":"<meta charset=\"utf-8\"\/><body><p>At time of reservation: 25% of trip cost<br>\r\n90 days prior to departure: Balance<br>\r<br><em>*Please note that this differs from our standard policy.<\/em><\/p><\/body>","CancelSchedule":"<p>Minimum fee: 25% of trip cost<br>90 days or less: 100% of trip cost<\/p><p><em>*Please note that this differs from our standard policy.<\/em><\/p>"}}