Chianti Region Romantic Vacations 2026

Top Romantic vacation packages in Chianti Region

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

Villa San Lucchese

$1,105

per person

Nov 17 - Nov 21

found 22 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Florence (FLR)

9.4/10 Exceptional! (354 reviews)

The place itself is beautiful!!

Reviewed on Oct 13, 2026

COMO Castello Del Nero

Tavarnelle Val di Pesa

$3,616

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip flight included

New York (JFK) to Florence (FLR)

9.6/10 Exceptional! (145 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 Sep 11, 2026

Hotel Palazzo San Lorenzo & SPA

$2,412

per person

Dec 26 - Jan 2

found 9 hours ago

Roundtrip non-stop flight included

Seattle (SEA) to Florence (FLR)

9.4/10 Exceptional! (470 reviews)

Palazzo Leopoldo Dimora Storica & Spa

$2,147

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip flight included

New York (JFK) to Florence (FLR)

9.2/10 Wonderful! (302 reviews)

Amazing historical hotel in a beautiful town, 10 out of 10.

Reviewed on Sep 28, 2026

Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre

$1,607

per person

Nov 17 - Nov 21

found 22 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Florence (FLR)

9.2/10 Wonderful! (633 reviews)

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5* Romantic vacations in Chianti Region

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

Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre

$1,607

per person

Nov 17 - Nov 21

found 22 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Florence (FLR)

9.2/10 Wonderful! (633 reviews)

COMO Castello Del Nero

Tavarnelle Val di Pesa

$3,616

per person

Dec 27 - Jan 2

found 1 day ago

Roundtrip flight included

New York (JFK) to Florence (FLR)

9.6/10 Exceptional! (145 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 Sep 11, 2026

Don't see what you're looking for?

See all available trips from Columbus to Chianti Region

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3 Night Romantic vacations in Chianti Region

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

COMO Castello Del Nero

Tavarnelle Val di Pesa

$5,020

per person

Dec 10 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Florence (FLR)

9.6/10 Exceptional! (145 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 Sep 11, 2026

Don't see what you're looking for?

See all available trips from Columbus to Chianti Region

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4 Night Romantic vacations in Chianti Region

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

Hotel Palazzo San Lorenzo & SPA

$1,207

per person

Nov 20 - Nov 24

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Florence (FLR)

9.4/10 Exceptional! (470 reviews)

Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre

$1,607

per person

Nov 17 - Nov 21

found 22 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Florence (FLR)

9.2/10 Wonderful! (633 reviews)

COMO Castello Del Nero

Tavarnelle Val di Pesa

$5,539

per person

Dec 10 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Florence (FLR)

9.6/10 Exceptional! (145 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 Sep 11, 2026

Don't see what you're looking for?

See all available trips from Columbus to Chianti Region

View all trips

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 $1,105. 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.

San Gimignano

5 min drive from Tenuta Torciano Winery

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

Palazzo Leopoldo Dimora Storica & Spa

Via Roma 33 Radda in Chianti SI

44 min drive from Tenuta Torciano Winery

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! (304 reviews)

Couples like: full-service spa, couples spa treatments, al fresco dining, hot tub

Travelers say...

"Amazing historical hotel in a beautiful town, 10 out of 10."

Reviewed on Sep 28, 2026

COMO Castello Del Nero

Strada Spicciano 7 Barberino Tavarnelle FI

18 min drive from Tenuta Torciano Winery

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! (145 reviews)

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

Travelers say...

"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 Sep 11, 2026

See all 4,862 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.