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Escape to Chianti, Tuscany — where vineyard views, medieval charm, and Tuscan sunsets are part of everyday life! In this episode, we’re featuring 4 incredible homes for sale in Gaiole in Chianti.
From a historic apartment inside a castle to a renovated stone farmhouse with garden views, each property captures the rustic elegance and timeless charm of Tuscany. Whether you’re looking for a cozy hideaway, a rental investment, or a countryside retreat, these homes offer something unforgettable.
📍 Just minutes from wineries, olive groves, and historic Siena, Gaiole in Chianti is the heart of Tuscany’s wine country, and one of the most beautiful places in Italy to live or invest.
✨ Which home would you choose? You can find the property listing links below.
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🇮🇹 FEATURED PROPERTIES 🇮🇹
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🏡🔗 €250K – Elegant 1500s home with terracotta floors, fruit trees & WOW views https://rimmo.it/en/tuscany/buy/apartment/3-room-apartment/siena/gaioleinchianti/detail/5471/
🔗OMW 1 €185K – Sunny home in a borgo with pool, gym & rooftop terrace: https://www.idealista.it/en/immobile/27429202/
🔗OMW 2 €130K – Restored rustic home with private garden & beams from 1000 AD: https://www.idealista.it/en/immobile/32585903/
🔗OMW 3 €102K – Apartment inside a medieval castle with 3 bedrooms & charming finishes: https://www.idealista.it/en/immobile/32094538/
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📖 CHAPTERS 📖
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00:00 – Intro: 4 Homes for Sale in Chianti, Tuscany – Wine Country Dream Life
01:23 – Where is Gaiole in Chianti? Closest Airport & How to Get There ✈️
02:55 – Living in Chianti: Maps, Doctors, Hospitals & Daily Life Essentials 🏥
03:30 – Explore Gaiole in Chianti: Streets, Driving & Village Charm 🚗
05:43 – €250K Historic Stone Home with Sunset Terrace & Fruit Tree Garden 🌅
11:34 – Big Thanks to Our Wandering With Wine Family! 💛
11:50 – Where to Eat, Drink & Shop in Chianti: Local Tips & Hidden Gems 🥖🍷
13:47 – €185K Tuscan Rooftop Apartment with Pool, Gym & Panoramic Views 🏊♂️
17:28 – La Dolce Vita Wanderers Travel Tips!
19:34 – Learn Italian for Free for 7 Days with Lingopie
22:05 – Fun Stuff! Living Near Skiing, Hiking Trails & Nature in Chianti 🌿🏞️
25:42 – €130K Restored Rustic Apartment with Garden & Exposed Beams 🪵
28:03 – Wandering With Wine Family Shoutouts 🎉
29:10 – Everyday Life & Essentials in Chianti Tuscany: Schools, Hardware, Gas ⛽, Bakeries, Hair Salons & Local Shops ✂️🍞
30:28 –🌦️ Tuscany Weather Guide: What to Expect Year-Round
31:14 – Does Amazon Deliver to Gaiole in Chianti, Tuscany? 📦
31:34 – 📱 Mobile Service & Internet in Rural Italy: What You Need to Know
32:06 – €102K Castle Apartment with 3 Bedrooms & Stone Tavern in Chianti 🏰
33:51 – Recap: Which Chianti Home Would You Choose? 🏡
34:15 – Subscribe for More Stunning Homes in Italy! 🛎️
We included a paid promotion in this video to bring you even more value by partnering with brands that align with our content and can enhance your experience. This support helps us continue creating high-quality videos about affordable homes in Italy and beyond, while also sharing exclusive deals and opportunities with you. Thank you for your support and for helping us keep our channel thriving!
DISCLAIMER
Wandering with Wine is not a real estate agent or agency, we are not intermediaries, and we do not sell property. We search through hundreds of real estate listings to curate the best properties. Our content should not be considered advice, and you should consult a professional. We do not receive any sales commission from the properties we present. We do not assume responsibility for properties that may go under offer or have sold. Under no circumstance does the information provided represent a recommendation or advice and we strongly recommend that all buyers conduct thorough due diligence before completing a purchase. We are not responsible for the accuracy of the listings we present. All listing photo credits are given to the agent(s). This video is for entertainment purposes only.
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#ChiantiItaly #HomesForSaleInItaly #LivingInItaly #TuscanyRealEstate #ChiantiDreamHomes #ItalianCountryside #GaioleInChianti #ItalyHouseTour #BuyAHomeInItaly #WineCountryLiving #WanderingWithWine #ItalianProperty #ChiantiLifestyle
12 Comments
LEARN ITALIAN FOR 7 DAYS FREE AT LINGOPIE! https://learn.lingopie.com/wanderingwine.
Which Chianti home stole your heart? Let us know in the comments! 💬 Whether it’s the one with the Happy Hour Tower, the castle cottage, or that rooftop terrace with views for days, these homes are the definition of Italian charm.
We're here every Friday at 6p ET with new dream homes across Italy. Don’t forget to like, subscribe, and join the fam at Patreon or Buy Me a Coffee for sneak peeks, bonus properties & behind-the-scenes fun! ❤🇮🇹
Chianti!!!
This is for Laura…. the term for snack is lo spunito and "afternoon snack" is la meranda. I couldn't understand what the difference was until i lived mealtime in Italy. Your afternoon snack is slightly more abundant… thus tides this American over until italian dinnertime. I mean, lunch is over by one… dinner not until at least 8. You need a good afternoon snack!
biaggio….you kind of tickled my fancy….what kind of affordable properties can you find for us at la vagina….it would be funny if I like what I see and claim it my town….imagine telling people that I bought a property and live there…excuse the puns or innuendos….it's a strange world that we are living in, I wonder what is the history behind that town
This is a beautiful home you guys! Tell me you bought it! ….Jamie wife and Wonder Bread Biaggio! Yes I cought that comment !
NEW CHANNEL: "(just the) Tips from Uncle Biaggo".
Tip #1: do not pee in the pool.
Tip #2: Beware of eels in the lakes.
Tip #3: cafes are for meeting girls.
Tip #4: naked first, permission later.
YES! on the train ticket validation. The only "problem" I have ever had in Italy is when we didn't know to validate before we got on the train. 😢😢
Pouring the vino and grabbing some formaggio!! Ready set W3!!
Tuscan native here. Nice video guys. By the way, it's kilometers and not miles. Keep up the good work!
I liked all of them this time. I think it was the second omw that had a spiral stair, but I didn't see what was up there.
The last one was the best.
Ciao! Ciao!
Would they allow me to live in Italy if I don't like wine?😢
Oooooooh I love the main HHT. I mean property! It's fabulous! What a beautiful home that is. Just need that lotto win. I also love the 1st OMW – fantastic open-plan living for one – perfect. And the 2nd OMW is probably my favorite – it's beautiful! Thanks for finding these properties & sharing with us would-be Italians. It's so appreciated 🙏🙏 Have a great week you two – have fun exploring more properties for us. Salute! 🍷🍷🥂😘