Castel San Gimignano Vacations from $1,366
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Your Castel San Gimignano Vacation
With everything organized before you head off, our Castel San Gimignano vacation packages mean you can simply focus on enjoying your getaway. Whether you're staying in the neighborhood of Montegabbro, which is great for history, or someplace else, this lively city offers a wealth of discoveries. Make your trip to Castel San Gimignano even more fulfilling by including some sightseeing. Collegiate Church of Santa Maria Assunta, Piazza Duomo and Medieval Criminal and Torture Museum are some of the top attractions worth exploring. A few quick clicks is all it takes to put together your perfect Castel San Gimignano vacation on Expedia.
The Latest Castel San Gimignano vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
Price was $1,935, price is now $1,366 per person
$1,366
per person
Jul 16 - Jul 22
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (996 reviews)
Our experience was consistent with previous reviews. Location is ideal. Easy entrance into main attraction area and with rooms off an interior courtyard property is super quiet at night.
Rooftop terrace is ideal. Relaxing, great cocktails and a perfect way to end a day sightseeing in the crowds of Florence.
We didn't realize the restaurant is not open for dinner. Breakfast was crowded, food ok.
Overall a nice property.
Reviewed on May 17, 2026
Donati Luxury Tower Suites
Historic Centre of Florence
Save 100% on your flight
Price was $4,676, price is now $3,086 per person
$3,086
per person
Jul 18 - Jul 24
found 22 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (61 reviews)
Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable
Reviewed on May 23, 2026
Bernini Palace
Historic Centre of Florence
Save 100% on your flight
Price was $2,404, price is now $1,647 per person
$1,647
per person
Jul 16 - Jul 22
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (1,015 reviews)
Friendly staff and great location
Reviewed on May 19, 2026
The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World
Historic Centre of Florence
Save 100% on your flight
Price was $4,073, price is now $2,859 per person
$2,859
per person
Jul 6 - Jul 11
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
10/10 Exceptional! (18 reviews)
Outstanding hotel and a remarkable experience staying there. The room was large and beautifully decorated as the rest of the hotel. Service was impeccable and friendly. Food was great. Lovely and intimate atmosphere. Attention to details and distinctive effort to attend to our needs. The hotel manager and Lavinia at the front desk stood out, but everybody else was extremely helpful. I hope to return!
Reviewed on Nov 14, 2025
Il Rivalta - Place of Charme
Historic Centre of Florence
Price was $2,050, price is now $1,495 per person
$1,495
per person
Jul 16 - Jul 22
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (520 reviews)
Excellent property, beautiful spacious room. Great location and friendly staff. I loved it!!
Reviewed on May 21, 2026
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See all available trips from Columbus to Castel San Gimignano
View all tripsDiscover the most popular places to visit in Castel San Gimignano
Piazza della Cisterna
4.5/5(53 reviews)
Admire the palaces and towers that frame this beautiful square, which was once a medieval marketplace. Today, it’s a venue for cultural events.
Piazza Duomo
4.5/5(53 reviews)
Browse the collections of ancient art, which grace the walls of the medieval landmarks that surround this resplendent public square.
San Gimignano Communal Palace
3/5(1 review)
You can browse the exhibits at San Gimignano Communal Palace, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.
What to do in Castel San Gimignano
Chianti Half Day Wine Tour from Florence
$29
per adult
88% of travellers recommend
Tuscany Hiking Tour from Siena Including Wine Tasting
$71
per adult
100% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
$164
per adult
86% of travellers recommend
Castel San Gimignano Hotel Deals
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $241 total per night from Jun 3 to Jun 4
$241 total
Jun 3 - Jun 4
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"Good location. Bathroom was strange. Toilet behind door. Tricky at night. The shower leaks out of the shower wall, there was a weird smell in bathroom whole time. Room was clean and comfortable. Breakfast was good."
Reviewed on May 20, 2026
Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
$517 nightly
The price is $580 total per night from Jun 22 to Jun 23
$580 total
Jun 22 - Jun 23
Total with taxes and fees
9.2/10 Wonderful! (605 reviews)
"Loved the location Restaurant was outstanding!!"
Reviewed on May 14, 2026
Palazzo Ravizza
Pian dei Mantellini 34 Siena SI
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $166 total per night from Jun 15 to Jun 16
$166 total
Jun 15 - Jun 16
Total with taxes and fees
9.4/10 Exceptional! (801 reviews)
"View of this hotel is amazing! It has a beautiful yard to sit and have a drink and watch the Tuscany hills. Short walk to major attractions and good breakfast. I would highly recommend this hotel."
Reviewed on May 19, 2026
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.
Find the Best Castel San Gimignano Vacation Packages
Castel San Gimignano Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Closest Airport | Peretola Airport (FLR) |
Population | 150 |
Max Temp Winter | 50ºF |
Max Temp Summer | 85ºF |
Top Sights | Tenuta Torciano Winery, Sovestro in Poggio Winery and Museo Civico |
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- Visit Lucciana
- Visit Pignano
- Visit Val d'Elsa
- Borgatello Vacations
- Visit Borgatello
- Sovestro in Poggio Winery
- Ornithological Museum
- Piazza della Cisterna
- Museum of Sacred Art
- San Gimignano Vacations
- Rocca of Montestaffoli
- Fortress of Montestaffoli
- Piazza Luigi Pecori
- Archeological and Collegiate Church Museum
- Torre Grossa
- Medieval Criminal and Torture Museum
- San Gimignano Communal Palace
- Piazza Duomo
- Collegiate Church of Santa Maria Assunta
- Podesta's Palace
- Torre Rognosa
- Piazza delle Erbe
- Visit San Gimignano
- Visit Casole d'Elsa
- Fonti Medievali
- Sant'agostino Church
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.