Chianti Region Romantic Vacations 2026

Top Romantic vacation packages in Chianti Region

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

Palazzo Leopoldo Dimora Storica & Spa

$1,293

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip flight included

Washington (WAS) 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

COMO Castello Del Nero

Save 100% on your flight

$2,295

per person

Oct 27 - Nov 1

found 24 hours ago

Roundtrip non-stop flight included

Tel Aviv (TLV) to Florence (FLR)

9.6/10 Exceptional! (142 reviews)

Great staff!

Reviewed on Jun 27, 2026

Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre

$1,787

per person

Oct 2 - Oct 4

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (624 reviews)

Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back

Reviewed on Aug 18, 2026

Villa Scacciapensieri Boutique Hotel

Scacciapensieri

$1,369

per person

Oct 2 - Oct 4

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (454 reviews)

Hotel Le Fontanelle

$1,472

per person

Oct 20 - Oct 22

found 4 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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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5* Romantic vacations in Chianti Region

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

Hotel Le Fontanelle

$1,472

per person

Oct 20 - Oct 22

found 4 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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

COMO Castello Del Nero

Save 100% on your flight

$2,295

per person

Oct 27 - Nov 1

found 24 hours ago

Roundtrip non-stop flight included

Tel Aviv (TLV) to Florence (FLR)

9.6/10 Exceptional! (142 reviews)

Great staff!

Reviewed on Jun 27, 2026

Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre

$1,787

per person

Oct 2 - Oct 4

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (624 reviews)

Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back

Reviewed on Aug 18, 2026

Don't see what you're looking for?

See all available trips from Columbus to Chianti Region

View all trips

3 Night Romantic vacations in Chianti Region

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

Villa Scacciapensieri Boutique Hotel

Scacciapensieri

$1,369

per person

Oct 2 - Oct 4

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (454 reviews)

Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre

$1,787

per person

Oct 2 - Oct 4

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (624 reviews)

Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back

Reviewed on Aug 18, 2026

COMO Castello Del Nero

$13,619

per person

Oct 2 - Oct 4

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.6/10 Exceptional! (142 reviews)

Great staff!

Reviewed on Jun 27, 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.

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 $1,293. 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

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.

10/10 Exceptional! (122 reviews)

Couples like: hot tub, fireplace

Travelers say...

"My family of 10, 2 grandparents, two adult children and their spouses plus 4 teenagers spent a wonderful week at that the Villa Iris. The house is lovely and has air conditioning. The 6 bedrooms with 6 bathrooms were great to have. Every day we went went to a different hill town, explored them and ..."

Reviewed on Jul 25, 2026

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.

9.2/10 Wonderful! (297 reviews)

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

Travelers say...

"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

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! (142 reviews)

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

Travelers say...

"Great staff!"

Reviewed on Jun 27, 2026

See all 4,902 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.