Chianti Region Romantic Vacations
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Top Romantic vacation packages in Chianti Region
Price found within the past 48 hours. Click for updated prices.
Villa Scacciapensieri Boutique Hotel
Scacciapensieri
Price was ￥336,164, price is now ￥238,784 per person
￥238,784
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.2/10 Wonderful! (440 reviews)
Delicious breakfast. Nice staff. Beautiful place to enjoy the gardens and the amenities.
Reviewed on Jun 7, 2026
Hotel Palazzo San Lorenzo & SPA
Price was ￥368,700, price is now ￥272,910 per person
￥272,910
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.4/10 Exceptional! (446 reviews)
Parking is tricky, but we found a free parking lot close by. Check-in was easy and Livia was a gem full of helpful tips and resources. Check out - the front desk guy wasn’t very helpful. We paid the city tax in cash and wanted our change in coins - just a few coins to use in town- very much needed in Italy and he wasn’t willing to provide coins or even break a ten. He offered no assistance. Overall the room, spa and property is nice. No restaurant during off season, but the breakfast provided was excellent.
Reviewed on Mar 20, 2026
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View all trips5* Romantic vacations in Chianti Region
Price found within the past 48 hours. Click for updated prices.
Hotel Le Fontanelle
Price was ￥1,039,225, price is now ￥976,985 per person
￥976,985
per person
Aug 26 - Sep 2
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.8/10 Exceptional! (99 reviews)
We stayed in Italy for 10 days and visited 5 different locations and this was clearly the best. We stayed here for 3 nights, and it did not disappoint. We wished we had stayed longer.
The facilities, grounds, and guest rooms are large and pristine. Everything is very clean. The food was exceptional including the breakfast and poolside bar which are easily forgotten with the amazing restaurants they have on site.
The overall service and hospitality are top tier, and it offers Tuscany views and grounds that are the best in the region.
Also, the location is close enough to visit several wineries, (We enjoyed the tour at Castello Di Ama), Siena and San Gimignano for great day trips if you want to venture out and see Tuscany.
Do not hesitate. Go ahead and book the Le Fontanelle. You may find some that are less expensive, but this resort offers a perfect combination of Chianti Living, value and A+ service. Worth every dollar/euro. You will create great memories.
Reviewed on Jun 9, 2026
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View all trips3 Night Romantic vacations in Chianti Region
Price found within the past 48 hours. Click for updated prices.
Villa Scacciapensieri Boutique Hotel
Scacciapensieri
Price was ￥336,164, price is now ￥238,784 per person
￥238,784
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.2/10 Wonderful! (440 reviews)
Delicious breakfast. Nice staff. Beautiful place to enjoy the gardens and the amenities.
Reviewed on Jun 7, 2026
Hotel Palazzo San Lorenzo & SPA
Price was ￥368,700, price is now ￥272,910 per person
￥272,910
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.4/10 Exceptional! (446 reviews)
Parking is tricky, but we found a free parking lot close by. Check-in was easy and Livia was a gem full of helpful tips and resources. Check out - the front desk guy wasn’t very helpful. We paid the city tax in cash and wanted our change in coins - just a few coins to use in town- very much needed in Italy and he wasn’t willing to provide coins or even break a ten. He offered no assistance. Overall the room, spa and property is nice. No restaurant during off season, but the breakfast provided was excellent.
Reviewed on Mar 20, 2026
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View all tripsTop Romantic Chianti Region Hotels
VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.
San Gimignano
Romance awaits at this villa, which features a garden and a hot tub. Couples will appreciate the in-room fireplaces and outdoor pool.
10/10 Exceptional! (120 reviews)
Couples like: hot tub, fireplace
Travelers say...
"Beautiful property. Spacious. Well equipped kitchen. Very accommodating host. Great location. Clean rooms. Cleaning service included. Only negative was the heat was turned off for the season but we had a few cold days. The stone house retains the cold."
Reviewed on Jun 3, 2026
Palazzo Leopoldo Dimora Storica & Spa
Via Roma 33 Radda in Chianti SI
Book a stay at this romantic hotel, featuring a spa and in-room massages. Couples will appreciate the hot tub, al fresco dining, and wine tasting rooms.
9.2/10 Wonderful! (289 reviews)
Couples like: full-service spa, couples spa treatments, al fresco dining, hot tub
Travelers say...
"The room was large and roomy and quiet. The breakfast was great! And the breakfast staff were very nice and helpful. The workout room was small but. Equipped for what we needed and there was never anyone else using it."
Reviewed on Jun 11, 2026
COMO Castello Del Nero
Strada Spicciano 7 Barberino Tavarnelle FI
For a romantic stay, consider this upscale hotel, featuring a spa, a Michelin star restaurant, and a garden. Couples will appreciate the hot tub and Egyptian ...
9.6/10 Exceptional! (137 reviews)
Couples like: full-service spa, couples spa treatments, Michelin star restaurant, hot tub
Travelers say...
"Everything was top notch and the food was amazing"
Reviewed on May 31, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
