Title: Chianti Region Romantic Vacations 2026 | Expedia.com

![](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Chianti Region Romantic Vacations

## Book a Romantic Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to $1,045 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Top Romantic vacation packages in Chianti Region

Price found within the past 48 hours. Click for updated prices.

![Palazzo Leopoldo Dimora Storica & Spa](https://images.trvl-media.com/lodging/1000000/920000/911700/911656/95292913_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Palazzo Leopoldo Dimora Storica & Spa

$692

per person

Apr 12 - Apr 15

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

9.2/10 Wonderful! (272 reviews)

I booked a massage with my husband at the spa and was not very impressed by the whole process first of all the girl came in 10 minutes later and stopped at the 15 minute mark, even though she was late I felt like the massage did not massage us did not Put any effort into it. It was very lame as far as I’m concerned I’ve had many many massages in this was probably one of my worst and my husband, the same thing.

Reviewed on Sep 25, 2025

![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### COMO Castello Del Nero

Save 100% on your flight

$4,337

per person

May 17 - May 23

found 1 day ago

Roundtrip flight included

Washington (DCA) to Florence (FLR)

9.6/10 Exceptional! (131 reviews)

Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car).

Reviewed on Oct 25, 2025

![Hotel Le Fontanelle](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/4e848a61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Le Fontanelle

Save 100% on your flight

$2,912

per person

May 19 - May 25

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Florence (FLR)

9.8/10 Exceptional! (95 reviews)

Beautiful, serene location with wonderful hospitalty and service. Tons of options for activities that we unfortunately couldn't take advantage of due to limited time. Amazing staff! We will definitely be back!

Reviewed on Oct 20, 2025

![Villa Scacciapensieri Boutique Hotel](https://images.trvl-media.com/lodging/3000000/2700000/2693500/2693499/b46a6593_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Villa Scacciapensieri Boutique Hotel

Scacciapensieri

$1,725

per person

May 12 - May 18

found 21 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Florence (FLR)

9.2/10 Wonderful! (420 reviews)

The villa was wonderful and absolutely beautiful. My friends and I absolutely loved our stay here.

Reviewed on Nov 21, 2025

![Grand Hotel Continental Siena – Starhotels Collezione](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/8b42326b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre

$2,710

per person

Apr 3 - Apr 9

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

9.2/10 Wonderful! (571 reviews)

The best hotel in siena for sure, thank you!

Reviewed on Feb 23, 2026

Don't see what you're looking for?

See all available trips from Columbus to Chianti Region

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-03/2026-04-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 5\* Romantic vacations in Chianti Region

Price found within the past 48 hours. Click for updated prices.

![Grand Hotel Continental Siena – Starhotels Collezione](https://images.trvl-media.com/lodging/1000000/800000/796700/796662/8b42326b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre

$2,710

per person

Apr 3 - Apr 9

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

9.2/10 Wonderful! (571 reviews)

The best hotel in siena for sure, thank you!

Reviewed on Feb 23, 2026

![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### COMO Castello Del Nero

Save 100% on your flight

$4,337

per person

May 17 - May 23

found 1 day ago

Roundtrip flight included

Washington (DCA) to Florence (FLR)

9.6/10 Exceptional! (131 reviews)

Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car).

Reviewed on Oct 25, 2025

![Hotel Le Fontanelle](https://images.trvl-media.com/lodging/2000000/1620000/1614900/1614881/4e848a61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Le Fontanelle

Save 100% on your flight

$2,912

per person

May 19 - May 25

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Florence (FLR)

9.8/10 Exceptional! (95 reviews)

Beautiful, serene location with wonderful hospitalty and service. Tons of options for activities that we unfortunately couldn't take advantage of due to limited time. Amazing staff! We will definitely be back!

Reviewed on Oct 20, 2025

Don't see what you're looking for?

See all available trips from Columbus to Chianti Region

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-03/2026-04-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 3 Night Romantic vacations in Chianti Region

Price found within the past 48 hours. Click for updated prices.

![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### COMO Castello Del Nero

Save 100% on your flight

$2,246

per person

May 26 - May 29

found 5 hours ago

Roundtrip non-stop flight included

Prague (PRG) to Florence (FLR)

9.6/10 Exceptional! (131 reviews)

Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car).

Reviewed on Oct 25, 2025

Don't see what you're looking for?

See all available trips from Columbus to Chianti Region

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-03/2026-04-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## 4 Night Romantic vacations in Chianti Region

Price found within the past 48 hours. Click for updated prices.

![Palazzo Leopoldo Dimora Storica & Spa](https://images.trvl-media.com/lodging/1000000/920000/911700/911656/95292913_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Palazzo Leopoldo Dimora Storica & Spa

$692

per person

Apr 12 - Apr 15

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

9.2/10 Wonderful! (272 reviews)

I booked a massage with my husband at the spa and was not very impressed by the whole process first of all the girl came in 10 minutes later and stopped at the 15 minute mark, even though she was late I felt like the massage did not massage us did not Put any effort into it. It was very lame as far as I’m concerned I’ve had many many massages in this was probably one of my worst and my husband, the same thing.

Reviewed on Sep 25, 2025

Don't see what you're looking for?

See all available trips from Columbus to Chianti Region

[View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-03/2026-04-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=FLR&NumRoom=1&NumAdult=2&NumChild=0&paandie=true)

## How 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 and visiting outside busy months of . 

####  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 $692\. Stay during the quiet season, in , for breaks to make your bank balance smile. 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. 

####  What’s the best time of year for a romantic vacation in Chianti Region? 

 Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience. 

####  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.](https://images.trvl-media.com/lodging/20000000/19400000/19394100/19394094/eadad249_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.

 San Gimignano 

- 29 min drive from Antinori nel Chianti Classico

Romance awaits at this villa, which features a garden and a hot tub. Couples will appreciate the in-room fireplaces and outdoor pool.

[](https://expedia.com/San-Gimignano-Hotels-Villa-Iris-SAN-Gimignano-Luxury-6-Rooms-EN-Suite.h19394094.Hotel-Information)

![Palazzo Leopoldo Dimora Storica & Spa](https://images.trvl-media.com/lodging/1000000/920000/911700/911656/95292913_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Palazzo Leopoldo Dimora Storica & Spa

Via Roma 33 Radda in Chianti SI

- 35 min drive from Antinori nel Chianti Classico

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.

[](https://expedia.com/Radda-In-Chianti-Hotels-Palazzo-Leopoldo-Dimora-Storica-Spa.h911656.Hotel-Information)

![COMO Castello Del Nero](https://images.trvl-media.com/lodging/2000000/1280000/1279800/1279768/5908bcb2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

COMO Castello Del Nero

Strada Spicciano 7 Barberino Tavarnelle FI

- 10 min drive from Antinori nel Chianti Classico

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! (133 reviews)

Couples like: full-service spa, couples spa treatments, Michelin star restaurant, hot tub

Travelers say...

Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car).

Reviewed on Oct 25, 2025

[](https://expedia.com/Barberino-Tavarnelle-Hotels-COMO-Castello-Del-Nero.h1279768.Hotel-Information)

[See all 4,820 properties in Chianti Region](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=603148)

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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## More Vacation Ideas

[Flights to Chianti Region

](https://expedia.com/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[

Chianti Region Hotels

](https://expedia.com/Chianti-Region-Hotels.d603148.Travel-Guide-Hotels)[

Vacation Rentals in Chianti Region

](https://expedia.com/Chianti-Region-Vacation-Rentals.d603148.Travel-Guide-VacationRentals)[

Car Rentals in Chianti Region

](https://expedia.com/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide)[

Chianti Region Vacations

](https://expedia.com/Chianti-Region.d603148.Destination-Travel-Guides)[

Things to do in Chianti Region

](https://expedia.com/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)

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

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