Chianti Region Honeymoon Vacations

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Flight and Honeymoon hotel deals in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel

CA $1,794
per person
Oct 12 - Oct 18
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.8/10 Excellent! (161 reviews)
Ac. Not working well Streets to get there not paved. Pitch black at night Staff at resto very rude!!

Reviewed on Aug 7, 2026

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

CA $4,163
per person
Oct 12 - Oct 18
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (218 reviews)
We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend.

Reviewed on Aug 5, 2026

Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World

CA $4,533
per person
Oct 12 - Oct 18
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.8/10 Excellent! (145 reviews)
The staff were excellent throughout — very friendly, attentive and always happy to help. Our room was lovely, comfortable and beautifully presented. Overall, we had a very enjoyable stay.

Reviewed on Aug 17, 2026

Hotel Le Fontanelle

Hotel Le Fontanelle

CA $4,758
per person
Oct 12 - Oct 18
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.8/10 Exceptional! (113 reviews)
Get away from it all at Hotel Le Fontanelle - Relax and Dine like the queen you are. Amazing staff, food, and unforgettable views - wish I was there right now.

Reviewed on Aug 22, 2026

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa

CA $1,805
per person
Oct 12 - Oct 18
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (296 reviews)
Very helpful and friendly staff, beautiful and spacious room, and wonderful location in the most lovely town in Tuscany. We loved our stay!

Reviewed on Aug 14, 2026

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5* Honeymoon holidays in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

CA $4,163
per person
Oct 12 - Oct 18
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (218 reviews)
We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while having breakfast - so it was easy to combine days by the pool with exploring one of Tuscany's most beautiful cities (and, inevitably, a bit of shopping to keep our teenage daughter happy). A fantastic place to stay, and one we'd happily recommend.

Reviewed on Aug 5, 2026

Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World

CA $4,533
per person
Oct 12 - Oct 18
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.8/10 Excellent! (145 reviews)
The staff were excellent throughout — very friendly, attentive and always happy to help. Our room was lovely, comfortable and beautifully presented. Overall, we had a very enjoyable stay.

Reviewed on Aug 17, 2026

Hotel Le Fontanelle

Hotel Le Fontanelle

CA $4,758
per person
Oct 12 - Oct 18
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.8/10 Exceptional! (113 reviews)
Get away from it all at Hotel Le Fontanelle - Relax and Dine like the queen you are. Amazing staff, food, and unforgettable views - wish I was there right now.

Reviewed on Aug 22, 2026

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4 Night Honeymoon holidays in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Belvedere di San Leonino

Belvedere di San Leonino

CA $1,079
per person
Nov 12 - Nov 15
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (194 reviews)
The most beautiful and breathtaking place to stay. The staff were lovely, the rooms were quiet, the views were exceptional. The breakfast was perfect. Idyllic!

Reviewed on Aug 11, 2026

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

CA $1,177
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (447 reviews)
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Honeymoon Hotels in Chianti Region

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI
  • 9 min drive from Antinori nel Chianti Classico
Book a stay at this luxury hotel in San Casciano in Val di Pesa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our ...
Villa I Barronci Resort & Spa
COMO Castello Del Nero

COMO Castello Del Nero

Strada Spicciano 7 Barberino Tavarnelle FI
  • 10 min drive from Antinori nel Chianti Classico
Book a stay at this luxury hotel in Barberino Tavarnelle. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Antinori nel Chianti Classico ...
9.6/10 Exceptional! (142 reviews)
"Great staff!"

Reviewed on Jun 27, 2026

COMO Castello Del Nero
Antico Borgo Poggiarello

Antico Borgo Poggiarello

Strada Di San Monti 12 Monteriggioni SI
  • 42 min drive from Antinori nel Chianti Classico
Book a stay at this golf residence in Monteriggioni. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Hedonistic Hiking and Alta Val ...
9/10 Wonderful! (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding."

Reviewed on Apr 27, 2025

Antico Borgo Poggiarello
See all 4,903 properties in Chianti Region
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.

Things to do

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

CA $40
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Uffizi & Accademia Timed Entry: Small Group Duomo Walking Tour

Uffizi & Accademia Timed Entry: Small Group Duomo Walking Tour

CA $79
per adult
96% of travellers recommend
Uffizi & Accademia Timed Entry: Small Group Duomo Walking Tour
Best of Florence Tour with Fast Track Accademia & Duomo

Best of Florence Tour with David at Accademia & Duomo (with VIP option)

CA $108
per adult
96% of travellers recommend
Best of Florence Tour with David at Accademia & Duomo (with VIP option)
See all activities in Chianti Region

More vacations you might like

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