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.
Hotel Le Fontanelle
Price was $1,386, price is now $1,241 per person
$1,241
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
Hotel Palazzo San Lorenzo & SPA
Price was $1,472, price is now $1,355 per person
$1,355
per person
Aug 27 - Sep 2
found 11 hours ago
Roundtrip flight included
New York (NYC) 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
Palazzo Leopoldo Dimora Storica & Spa
Price was $1,892, price is now $1,653 per person
$1,653
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Florence (FLR)
9.2/10 Wonderful! (285 reviews)
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
Villa Scacciapensieri Boutique Hotel
Scacciapensieri
Price was $2,294, price is now $2,007 per person
$2,007
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) 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
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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 $1,386, price is now $1,241 per person
$1,241
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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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See all available trips from Columbus to Chianti Region
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 $1,119, price is now $1,054 per person
$1,054
per person
Aug 21 - Aug 23
found 24 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) 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
Relais Vignale & Spa
Price was $1,080, price is now $1,065 per person
$1,065
per person
Aug 21 - Aug 23
found 24 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Florence (FLR)
9.2/10 Wonderful! (293 reviews)
Beautiful views in the downtown area. The Pizza restaurant across stree is awesome and owner makes his own MELLONCello which is to die for. Get a Francis Espresson Martini at pool bar too.
Reviewed on Jun 1, 2026
Don't see what you're looking for?
See all available trips from Columbus to Chianti Region
View all trips4 Night Romantic vacations in Chianti Region
Price found within the past 48 hours. Click for updated prices.
Villa Scacciapensieri Boutique Hotel
Scacciapensieri
Price was $1,178, price is now $1,037 per person
$1,037
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Le Fontanelle
Price was $1,386, price is now $1,241 per person
$1,241
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
Don't see what you're looking for?
See all available trips from Columbus to Chianti Region
View all tripsHow to find a romantic Chianti Region vacation
How can I find the best Chianti Region vacation packages for couples?
To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.
How can I find cheap Chianti Region romantic packages for two?
For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.
How can I plan a great romantic trip to Chianti Region?
Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.
How much is a trip for two to Chianti Region?
Put a price on love with stunning deals for duos starting at just $1,037. Prices and availability are subject to change. Additional terms may apply.
Can I book Chianti Region spa packages for couples?
Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.
How can I book romantic weekend getaway packages in Chianti Region?
To book a loved-up break in Chianti Region, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).
Can I book a romantic trip to Chianti Region with free cancellation and/or flexible dates?
The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.
Why should I book my Chianti Region romantic holiday with Expedia?
If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?
Top 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
