Call 800-579-6178 to Learn More
Our hours of operation are Monday–Friday, 9 a.m.–6 p.m. ET.
10-Day Land Tour Roundtrip from Rome
Experience the heart of Tuscany. This immersive journey blends Italy’s rich cultural heritage with culinary delights, scenic landscapes and charming medieval towns. Enjoy hands-on experiences like cooking classes, wine and olive oil tastings and guided tours of iconic destinations such as Siena, Pisa and the Cinque Terre.
Call 800-579-6178 to Learn More
Our hours of operation are Monday–Friday, 9 a.m.–6 p.m. ET.
Stay
10 Days
9 Nights
Meals
9 Breakfasts
4 Lunches
4 Dinners
Travel Style
Motorcoach
Benvenuti in Italia! Upon arrival at Rome Fiumicino Airport, you’ll be welcomed by your HGV host, tour director and fellow travelers. After introductions, we begin our scenic journey into the heart of Tuscany.
Time and flight schedules permitting, stop in the medieval hilltop town of Orvieto. Here, enjoy a guided exploration of the underground grottos, a labyrinth of Etruscan tunnels and cellars beneath the town, followed by a light tasting lunch of Umbrian specialties at Il Labirinto di Adriano.
In the afternoon, continue to the Chianti region and check into your hotel in Radda in Chianti, nestled among vineyards and rolling hills. In the evening, gather for a welcome dinner with spectacular views and a seasonal menu at Ristoro di Lamole.
Travel to a peaceful farmhouse in the Tuscan countryside, Poggio San Polo, for a hands-on cooking experience. Under the guidance of local chefs, prepare classic dishes such as homemade pasta and meat with fresh herbs, followed by a relaxed lunch paired with wine.
Afterwards, enjoy wine tasting on-site and discover the characteristics that make Chianti Classico so special. The remainder of the day is yours to unwind at the hotel or explore Radda at your own pace.
Begin with a visit to the family-run Frantoio del Grevepesa where you’ll enjoy a guided olive oil tasting and learn about the centuries-old traditions behind this liquid gold.
Next, head to the vibrant Greve in Chianti market, held every Saturday in the picturesque Piazza Matteotti. Enjoy free time to browse local stalls, sample cheeses or meats and perhaps pick up a bottle of Chianti. Catch the beginning of the Chianti Classico Wine Festival, which usually starts today.
In the afternoon, a local guide will take you for a gentle walk through Greve’s history — including tales of Giovanni da Verrazzano, the explorer who first charted New York Bay.
In the evening, dine in style at the Michelin-starred Arnolfo Restaurant in Colle di Val d’Elsa, enjoying a refined tasting menu that showcases the very best of modern Tuscan cuisine.
Choose from two immersive Tuscan experiences:
Option 1: Leonardo’s Countryside by E-Bike
Embark on a scenic e-bike tour through the rolling hills of Vinci, the birthplace of Leonardo da Vinci. Pedal past olive groves and vineyards with frequent stops to admire the views. A light lunch with wine is included.
Option 2: Truffle Hunting and Gourmet Lunch
Join a professional truffle hunter and his dog in the woodlands around San Miniato. Discover the secrets of this prized delicacy and indulge in a three-course truffle lunch, accompanied by wine, olive oil and honey tastings.
In the morning, say goodbye to Chianti and travel west towards the Ligurian coast. En route, stop in Pisa for a guided visit to the famous Piazza dei Miracoli. You’ll enjoy entrance to the iconic Leaning Tower and time to admire the Cathedral and Baptistry. Lunch at leisure in Pisa before continuing to La Spezia, your base for the next two nights.
Settle in with time to stroll along the waterfront promenade or simply relax before exploring the coast tomorrow.
Experience the magic of the Cinque Terre as we explore this breathtaking coastal region by private boat.
Cruise along the Riviera’s rugged shoreline and visit four of the five villages, with time to explore Monterosso al Mare at leisure. Discover colorful harbors, cliffside homes and boutique shops as you soak in the views.
Enjoy lunch in one of the villages before returning to La Spezia for a relaxed evening.
Travel inland to the stunning Val d’Orcia, stopping in the historic city of Siena for a guided walking tour through its medieval lanes and grand piazzas. Learn about the Palio horse race, the city’s neighborhood “contrade” rivalries and visit a historic contrada museum. Afterwards, enjoy a three-course lunch with local wine.
Continue on to Pienza, a Renaissance gem known for its pecorino cheese and picture-perfect views. Check into your hotel, ideally located within the old town walls.
In the morning, enjoy time at your leisure in Pienza to explore charming alleys, sample local cheese or simply soak up the views across the Val d’Orcia.
In the afternoon, travel to nearby Montalcino to visit the Tempio del Brunello, an immersive experience telling the story of the region’s famed wine. Afterward, enjoy a tasting of Brunello wines accompanied by local snacks.
Dinner tonight is a group farewell meal at La Terrazza del Chiostro, offering panoramic views and a menu celebrating Tuscan flavours.
This morning, we visit the natural hot springs at Bagni San Filippo, known for their striking white limestone formations and forest setting — ideal for a peaceful walk or photo opportunity.
Enjoy lunch at leisure, then visit La Fonte Agriturismo, a family-run farm and brewery producing craft beer from locally grown ingredients. Sample their unique beers during a guided tasting and tour, then return later for a farewell dinner featuring a hearty three-course Tuscan menu.
After breakfast, depart Pienza and travel by private coach back to Rome, where your journey concludes.
All Members have the option of paying for any hosted trips with annual, biennial, borrowed and rented points, a credit card or any combination of these. Click here to learn more.
From $14,699/£10,900 per person, based on double occupancy
Book by February 13, 2026, to secure your spot.
Limited single accommodation upon request; call for special pricing.
Call 800-579-6178 to Book Your Trip
Our hours of operation are Monday–Friday, 9 a.m.–6 p.m. ET.
Terms and Conditions
HOSTED RESORT TRIPS POINTS FOR TRAVEL: Reservations must be booked by February 13, 2026. Nonrefundable, nontransferable deposit of $1,500/£1,125 per person is due at the time of booking. Final payment due by May 1, 2026. Any combination of annual, biennial, borrowed or rented points and/or a cash/credit card are applicable forms of payment towards a hosted trip vacation. Point values applied under this benefit are subject to change and may vary based on tier level. All trips are subject to availability and will be conducted in English. All participants are required to sign the General Activity Release and Indemnification Agreement acknowledgement. Price is per person based on double occupancy, land tour only, for tour dates outlined above. Fares shown are in U.S. dollars and British pounds for new reservations only and are subject to availability. Prices, additional fees, itineraries and availability are subject to change without notice. Certain terms, conditions and restrictions may apply. Please call us at 800-579-6178 or +44 1524-386423 for additional information.
Hosted trip package includes all Big Journey Company inclusions plus these additional inclusions: some meals; one ticket per paying passenger for included excursions as noted in itinerary which may require an extra waiver to participate and have other restrictions/qualifications based on height, age and weight; on-tour motor coach transportation; gratuities for Big Journey Company tour director, tour guides and drivers; taxes; and airport transfers. Rome arrival transfers are included on the tour start date of September 2, 2026, and Rome departure transfers are included on the tour end date of September 12, 2026, provided that Guest arrival and departure flight or alternative travel details are received at least, 90 days for domestic travelers and 120 days prior for international travelers before tour commencement. Not included: airfare; airline baggage fees; airport or departure taxes; travel insurance; car rental; gratuities for hotel housekeepers; alcohol, beverages and food outside the contracted Big Journey Company menu as presented at a dining venue; optional excursions; and all other items of a personal nature.
Tour itinerary activities in this region may be subject to favorable weather conditions. Alcoholic beverages are only available to travelers 18 years or older. Hotels may differ from those listed by the tour provider, but the accommodations selected are of equivalent standard. Your hotels will be available in your final documents approximately two to three weeks prior to departure. No compensation is provided for alternative hotel stays not listed in the tour provider’s documentation.
A passport valid for six months past the end date of this tour is required for all guests. Entry requirements may vary for passport holders from other countries. Entry visas are not required for U.S. residents. Entry visas for other nationalities may be required. Visa requirements are subject to change at any time. International visitor entry requirements are subject to change at any time. In addition to passport and visa requirements, some countries may have additional requirements. It is the responsibility of the traveler to obtain and pay for all required entry documents prior to travel. Yellow Fever vaccinations are required if arriving from certain countries in South America or Africa. U.S. citizens, please refer to travel.state.gov or additional information, and non-U.S. citizens, please refer to your country's authority. Any requirements imposed by countries visited or traveled through are the responsibility of each traveler, and Great Vacation Destinations, Inc. cannot be held responsible for failure to comply or qualify for entry.
PICK YOUR EXPERIENCE: One excursion per person unless otherwise noted. No refunds on unused excursion(s). At least one excursion choice will be included at no additional cost, some excursion choices will be available with a surcharge beginning at $50. Excursion choices will vary based on the tour and specific excursion details will be available 60–90 days prior to the tour departure date. Tour providers may require an extra waiver to participate and have other restrictions/qualifications (“Qualifications”) based on height, age and weight. Failure to meet applicable Qualifications may result in ineligibility for this offer with no credit or refund issued. Visiting and participating in excursions in this region may be subject to favorable weather conditions. Inclement weather and/or other factors beyond the control of the tour operator may result in excursion cancellation such that this benefit will be lost and not substituted or replaced and no credit or refund will be issued.
THE BIG JOURNEY COMPANY: This is The Big Journey Company provided tour being sold by Great Vacation Destinations, Inc. Please visit The Big Journey Company’s website for full terms and conditions.
GREAT VACATION DESTINATIONS, INC.: Great Vacation Destinations, Inc. is a full-service travel agency that is a seller of travel providing vacations to Hilton Grand Vacation Members and Guests. Great Vacation Destinations, Inc. is the seller of these vacation trips and is located at 4960 Conference Way North, Suite 100, Boca Raton, FL 33431. Great Vacation Destinations is a Washington Seller of Travel No. 602-283-711; Florida Airlines Reporting Corporation (ARC) registration No. 15-72225-4, California Seller of Travel registration No. 2068362 (Registration as a Seller of Travel does not constitute approval by the State of California). Void where prohibited or restricted by law and/or where state registration and/or licensing requirements have not been met.
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