A historic town with a prominent church tower, surrounded by rolling hills and vineyards.

Castiglion Fiorentino Vacation Packages

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    • Your Castiglion Fiorentino Vacation

    There's no better way to travel than with one of our vacation packages to Castiglion Fiorentino. The rich history and spectacular views are just two of the convincing reasons to visit this captivating city. If sightseeing is on the agenda during your trip to Castiglion Fiorentino, stop by top attractions like Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona. Whoever you're taking time off with and whatever you want to spend, your ultimate Castiglion Fiorentino vacation is just clicks away with Expedia.

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    Discover the most popular places to visit in Castiglion Fiorentino

    Tennis Club Castiglionese

    Catch an event at Tennis Club Castiglionese during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

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    Cassero Tower

    Rating: 9.4/10 (6 reviews)

    Find out about the history of Castiglion Fiorentino when you spend time at Cassero Tower. You can enjoy the wineries while in the area.

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    Agricola Buccelletti Winery

    Rating: 10.0/10 (2 reviews)

    You can enjoy a tasting or tour at Agricola Buccelletti Winery during your travels to La Strada-Santa Cristina. Discover the area's countryside and wineries.

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    Archaeological Museum

    Rating: 9.6/10 (5 reviews)

    You can browse the exhibits at Archaeological Museum, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.

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    Vasari Loggia

    Rating: 10.0/10 (2 reviews)

    You can find out about the history of Castiglion Fiorentino with a trip to Vasari Loggia. You can enjoy the wineries while in the area.

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    What to do in Castiglion Fiorentino

    Montepulciano Wine Tasting in the Tuscan Countryside

    Montepulciano Wine Tasting in the Tuscan Countryside

    CA $40

    per adult

    0% of travellers recommend

    Arezzo Gran Tour

    Arezzo Gran Tour

    CA $19

    per adult

    0% of travellers recommend

    Montepulciano: Wine Tasting with typical Tuscan Cold Cuts

    Montepulciano: Wine Tasting with typical Tuscan Cold Cuts

    CA $79

    per adult

    0% of travellers recommend

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    Castiglion Fiorentino Hotel Deals

    San Michele al Castello

    An outdoor event with people seated at tables, surrounded by stone buildings and greenery.
    • Address: via dell'Orto, 2, Castiglion Fiorentino, AR, 52043, IT
    • Location: 0.1 km from Castiglion Fiorentino
    • Guest rating: 9.8/10 (Exceptional, 15 reviews)
    • Price: CA $143, CA $164 total, includes taxes & fees, Nov 17 - Nov 18
    • Review: We were in Italy for two weeks and this was our favorite hotel/B&B. FIVE STARS. Everyone & everything were wonderful.

    Hotel Park

    A modern hotel lobby with a reception desk, seating area, and a large plant.
    • Address: Via Umbro Casentinese, 88, Castiglion Fiorentino, AR, 52043, IT
    • Location: 0.8 km from Castiglion Fiorentino
    • Star rating: 4/5
    • Guest rating: 8.8/10 (Excellent, 51 reviews)
    • Price: CA $148, CA $169 total, includes taxes & fees, Nov 15 - Nov 16

    Bed & Breakfast Viziottavo

    A breakfast buffet with various food items and beverages.
    • Address: Via San Michele 69, Castiglion Fiorentino, AR, 52043, IT
    • Location: 0.1 km from Castiglion Fiorentino
    • Guest rating: 10/10 (Exceptional, 9 reviews)
    • Price: CA $120, CA $170 total, includes taxes & fees, Nov 24 - Nov 25
    • Review: Very quaint, recently renovated B&B in a wonderful location. The staff is welcoming, happy and very helpful. I highly recommend this accommodation.

    San Michele al Borgo

    A couple relaxing in a spa setting with a visible logo on the wall, a reception desk, and a plant in the background.
    • Address: Via Dante Alighieri 32, Castiglion Fiorentino, AR, 52043, IT
    • Location: 0.2 km from Castiglion Fiorentino
    • Guest rating: 9.8/10 (Exceptional, 9 reviews)
    • Price: CA $187, CA $213 total, includes taxes & fees, Nov 15 - Nov 16
    • Review: Excellent staff and tasty breakfast!

    La Cantina Relais - Fattoria Il Cipresso

    A restaurant with glass walls, tables set with white tablecloths, and chairs.
    • Address: Locaità Sassaia di Rigutino n 1, Arezzo, AR, 52100, IT
    • Location: 5.8 km from Castiglion Fiorentino
    • Guest rating: 10/10 (Exceptional, 121 reviews)
    • Price: CA $138, CA $161 total, includes taxes & fees, Nov 16 - Nov 17
    • Review: Great place to stay, felt rustic yet upscale. The location put you within a 45 minute drive of many Tuscan sights and towns. The restaurant offered some of the best dinners we had in Italy with a true farm to table experience. The staff were extremely helpful with suggestions for the area

    Locanda agli Amici

    A person in a white robe standing by a window with a view of mountains.
    • Address: Località Torreone 6, Cortona, AR, 52044, IT
    • Location: 9 km from Castiglion Fiorentino
    • Star rating: 4/5
    • Guest rating: 9.8/10 (Exceptional, 46 reviews)
    • Price: CA $137, CA $163 total, includes taxes & fees, Dec 1 - Dec 2

    Villa Santa Margherita

    An outdoor seating area with tables and chairs, potted plants, and a view of the sea.
    • Address: Viale Cesare Battisti 17, Cortona, AR, 52044, IT
    • Location: 9.3 km from Castiglion Fiorentino
    • Star rating: 3/5
    • Guest rating: 9.8/10 (Exceptional, 27 reviews)
    • Price: CA $151, CA $193 total, includes taxes & fees, Nov 21 - Nov 22
    • Review: Recommend do not arrive late at night into Cortona upon arrival. The roads are narrow and NOT like USA at all. GPS showed fastest route. However, part of the road are extremely narrow and hilly. There are no street signs at all. Local people are extremely helpful and friendly. We got lost and they showed us to the hotel.

    Hotel Le Capanne

    A large, two-story building with a symmetrical facade, a central entrance, and evenly spaced windows.
    • Address: Loc. Il Matto, 44/45, Arezzo, AR, 52100, IT
    • Location: 11.4 km from Castiglion Fiorentino
    • Star rating: 3/5
    • Guest rating: 9.4/10 (Exceptional, 67 reviews)
    • Price: CA $148, CA $173 total, includes taxes & fees, Nov 30 - Dec 1

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Frequently Asked Questions

    How much does a Castiglion Fiorentino vacation package cost?

    Offering great value package deals from CA $1,063 on Expedia, you'll be thrilled with how little a vacation to Castiglion Fiorentino costs! Expedia's packages make travel planning easier and save you more.

    What are the cheapest months to go to Castiglion Fiorentino?

    To score cheap Castiglion Fiorentino vacation packages, plan your trip outside of busy periods like public holidays and major festivals. You'll typically find lower prices and better availability in the off-season or when it's less busy.

    How many days is enough for Castiglion Fiorentino?

    With about 3 days, you'll have enough time to experience popular neighbourhoods like Cortona Old Town and Sodo during your Castiglion Fiorentino vacation. Make sure to also add Eremo Le Celle and Belvedere to your sightseeing list. Looking for more adventures? Consider venturing outside of Castiglion Fiorentino on tours and day trips.

    Is it worth booking a vacation package to Castiglion Fiorentino?

    Whether you're looking to explore top attractions like Cassero Tower and Municipal Art Gallery on your Castiglion Fiorentino vacation, or coming for its excellent nightlife, views and walking trails, there's something for everyone here. With so many things to see and do, you'll soon find out why so many families think Castiglion Fiorentino is a good vacation destination.

    How to find the best Castiglion Fiorentino package deals?

    Use Expedia's filters to help you find some tempting Castiglion Fiorentino package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Castiglion Fiorentino package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.

    Is it cheaper to book a Castiglion Fiorentino vacation as a package?

    Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Castiglion Fiorentino vacation by choosing your preferred airline, accommodation type and car class.

    When to book a vacation package to Castiglion Fiorentino?

    If you're considering a spur-of-the-moment Castiglion Fiorentino vacation, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking well in advance.

    How to plan a trip to Castiglion Fiorentino?

    1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Castiglion Fiorentino.
    2. Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to flights and activities. Your hotel will likely be the biggest expense during your trip to Castiglion Fiorentino.
    3. Decide your trip length: Think about how long you'd like to spend discovering Castiglion Fiorentino. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
    4. Combine your airfare and accommodations: Once you've settled on your dates and duration, lock in the perfect Castiglion Fiorentino vacation package for you.

    * Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.