Cortona, Tuscany, Italy
    6 night stay for 2 people in Cortona, Tuscany
    2 guests
    6 nights
    1 bed, 1 bath
    Supporting events in all states

    Description

    Experience the essence of Italy with a 6-night stay in the charming medieval town of Cortona, famed from Under the Tuscan Sun. Enjoy a one-bedroom apartment with a full kitchen, cozy living space, and easy access to local cafes, restaurants, and boutiques—perfect for savoring Tuscany’s food, wine, and beauty.

    Package includes

    • 6 night stay in a one-bedroom apartment for 2 in Cortona (Tuscany)
    • Welcome cocktail in the coolest wine bar in town, on the main square of Cortona
    • 4-course gourmet tasting menu paired with 4 different wines at Il Tocco Restaurant in Cortona
    • Final cleaning and utilities
    • Concierge service to add extra activities during the stay
    • Airfare is not included

    Terms and Conditions

    Blackout dates

    Bookings are based on the availability of accommodations.

    Max occupancy

    The maximum occupancy for this package is 2 persons.

    Redemption terms and restrictions

    Travel dates must be booked and used within a 24 month window from the auction date.

    Refunds, transfers, and changes policy

    There are no refunds for unused bookings.

    Travelers' testimonials

    ·
    Reviewed 10/12/25
    We purchased this trip at a fundraising auction and were so pleasantly surprised. The company made great arrangements and we were in an amazing apartment in the heart of Lisbon. There were street performers outside our window and multiple restaurants and shops just minutes away. Can’t wait to go back and see more of this wonderful city and country.
    From Blake H
    ·
    Reviewed 10/01/25
    I bid on and won a trip to Croatia at a local Charity Event. Hill Town Tours was the Travel Agency assigned to arrange the trip. I was a little hesitant because they are based in Italy and I am in the USA. I must say, dealing with Hill Town Tours was the best experience. My contact Serena Pacchiacucchi, was very professional and helpful and arranged everything perfectly!! The Villa we stayed at was exceptional and perfectly located. The excursions that we choose were Top Notch!! We had a great private chef come to the villa, we did a yummy cooking class, a day long excursion to Bosnia Herzegovina with wonderful driver and tour guide, a sunset cruise with pick up from villa to a hilarious boat captain and an informative walking tour guide around Dubrovnik that happened to own and operate the restaurant where the amazing cooking class took place. Serena and Hill Town Tours knew of and recommended all these wonderful people, places and excursions. I have another trip coming up in April 2026 to the Amalfi Coast Italy and look forward to using Hill Town Tours again.
    From Maureen C
    ·
    Reviewed 08/18/25
    We had an absolutely wonderful and unique vacation in Cortona, Italy. We were rewarded with a week in an apartment and a lunch/wine pairing through a friend’s nonprofit fundraiser. As a nonprofit leader myself, I am grateful for companies like HTT that give back through these giveaways. Most importantly, the experience was EXACTLY as it was presented, something that is not always the case. Working with HTT in planning and scheduling the trip was an absolute breeze and the staff were responsive, accommodating and just great people. The apartment was right off the main square and it was lively and crowded, yet the apartment was quiet and lovely. Very well appointed, good AC and washer/dryer combo was used twice! We had everything we needed. The wine tour and luncheon was arranged and we were greeted warmly. Transfers to/from the train station were arranged for us and went smoothly. Transportation is very expensive, so we rented a car and were really able to explore the region at a much lower cost. The driving and parking were really easy. The highlight was Cortona itself. What a beautiful, medieval city, with lovely shops and restaurants with gorgeous views of Tuscany. Just be aware that it is at the top of a hill. A lot of climbing to reach the square but very much worth it! Arrevederci for now Cortona! We cannot WAIT to return. Ciao Bella 🥰
    From Sylvia Z

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