Chianti Region Romantic Holidays

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

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    Save up to £750 when you book a flight and hotel together*
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    Packages with flights are ATOL protected

Top flight + Romantic hotel deals in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa

£343
per person
18 Oct - 21 Oct
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (297 reviews)
We had room 16 at the very top floor with beautiful views of the valley. The room has a separate sitting area with a pullout bed perfect for families. Also very conveniently located in the heart of Radda. Breakfast was lovely and the staff is so nice, even remembered our coffee preferences each morning. Only word of caution is there are no elevators to the rooms so if you have mobility concerns, this might not work. We did get our exercise to counteract all the lovely food!

Reviewed on 13 Sept 2026

Hotel Palazzo San Lorenzo & SPA

Hotel Palazzo San Lorenzo & SPA

Save 100% on your flight
£568
per person
25 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Florence (FLR)
9.4/10 Exceptional! (462 reviews)
Beautiful place, wonderful pool and great breakfast.

Reviewed on 1 Sept 2026

Villa La Borghetta Resort

Villa La Borghetta Resort

£437
per person
15 Oct - 18 Oct
found 1 day ago
Return direct flight included
London (LHR) to Florence (FLR)
7.8/10 Good! (91 reviews)
Beautiful experience!

Reviewed on 1 Jul 2025

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

Scacciapensieri
£551
per person
18 Oct - 25 Oct
found 12 hours ago
Return direct flight included
London (LHR) to Florence (FLR)
9.2/10 Wonderful! (457 reviews)
Just loved it!! This is a great place!!!

Reviewed on 14 Sept 2026

COMO Castello Del Nero

COMO Castello Del Nero

Tavarnelle Val di Pesa
Save 100% on your flight
£2,227
per person
25 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Florence (FLR)
9.6/10 Exceptional! (142 reviews)
The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back.

Reviewed on 11 Sept 2026

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5* Romantic holidays in Chianti Region

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

Hotel Le Fontanelle

Save 100% on your flight
£1,312
per person
25 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Florence (FLR)
9.8/10 Exceptional! (117 reviews)
Loved everything Overall Staff was amazing and very responsive Pool staff was great, lunches at pool was very good. Breakfast was excellent Room was amazing We did their wine making tour and tasting, worth the $32/pp Lots of great restaurant’s within reasonable driving range. Hotel dinner was very nice but expensive. I highly recommend this hotel, would definitely stay again

Reviewed on 11 Sept 2026

COMO Castello Del Nero

COMO Castello Del Nero

Tavarnelle Val di Pesa
Save 100% on your flight
£2,227
per person
25 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Florence (FLR)
9.6/10 Exceptional! (142 reviews)
The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back.

Reviewed on 11 Sept 2026

Borgo San Felice Resort

Borgo San Felice Resort

Save 100% on your flight
£1,853
per person
25 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Florence (FLR)
9.8/10 Exceptional! (89 reviews)
An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We especially loved the live piano music in the evenings; it added such a romantic and elegant touch to the entire experience. The service was one of the highlights of our stay. A special shout-out to **Herman at the pool**, who was always attentive and completely on point with everything we needed. We also had an amazing experience at **Poggio Rosso**, where **Matia provided top-notch service** and made our Michelin-starred dinner feel even more memorable. Every detail from the beautiful grounds and peaceful atmosphere to the food, wine, spa, and exceptional hospitality—made our time here unforgettable. Borgo San Felice gave us exactly the Tuscany experience we were hoping for and more. We absolutely loved our stay and would return in a heartbeat. Highly recommend! 🇮🇹🍷✨

Reviewed on 5 Sept 2026

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3 Night Romantic holidays in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa

£343
per person
18 Oct - 21 Oct
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (297 reviews)
We had room 16 at the very top floor with beautiful views of the valley. The room has a separate sitting area with a pullout bed perfect for families. Also very conveniently located in the heart of Radda. Breakfast was lovely and the staff is so nice, even remembered our coffee preferences each morning. Only word of caution is there are no elevators to the rooms so if you have mobility concerns, this might not work. We did get our exercise to counteract all the lovely food!

Reviewed on 13 Sept 2026

Villa La Borghetta Resort

Villa La Borghetta Resort

£437
per person
15 Oct - 18 Oct
found 1 day ago
Return direct flight included
London (LHR) to Florence (FLR)
7.8/10 Good! (91 reviews)
Beautiful experience!

Reviewed on 1 Jul 2025

Relais Vignale & Spa

Relais Vignale & Spa

£454
per person
18 Oct - 21 Oct
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (308 reviews)
Very nice property

Reviewed on 14 Sept 2026

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4 Night Romantic holidays in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa

£460
per person
18 Oct - 22 Oct
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (297 reviews)
We had room 16 at the very top floor with beautiful views of the valley. The room has a separate sitting area with a pullout bed perfect for families. Also very conveniently located in the heart of Radda. Breakfast was lovely and the staff is so nice, even remembered our coffee preferences each morning. Only word of caution is there are no elevators to the rooms so if you have mobility concerns, this might not work. We did get our exercise to counteract all the lovely food!

Reviewed on 13 Sept 2026

Relais Vignale & Spa

Relais Vignale & Spa

£597
per person
18 Oct - 22 Oct
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (308 reviews)
Very nice property

Reviewed on 14 Sept 2026

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How to find a romantic Chianti Region holiday

How can I find the best Chianti Region vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Chianti Region. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Chianti Region romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Chianti Region that start from £343. Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Chianti Region romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Chianti Region?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Chianti Region?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Chianti Region that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Chianti Region with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Chianti Region romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

Things to do

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

£21
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

£18
per adult
94% of travellers recommend
Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine
Michaelangelo's David

Accademia timed-entry Ticket with App Guide

£33
per adult
90% of travellers recommend
Accademia timed-entry Ticket with App Guide
See all activities in Chianti Region

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.