Radda in Chianti Vacations from $966
Book a Hotel + Flight or Car together to unlock savings
Your Radda in Chianti Vacation
Lock in a Radda in Chianti vacation package and get set to experience the highlights of this city. Think about staying in the neighborhood of Badia Coltibuono, which is great for families, nature and walking. Meleto Castle, Castello di Albola and Il Molino di Grace Winery are just a few of the attractions worth checking out during your trip to Radda in Chianti. A few clicks is all it takes to craft a tailored Radda in Chianti vacation on Expedia.
The Latest Radda in Chianti Vacation Packages
- Aurum Firenze
Jan 19 - Jan 25Aurum Firenze + Flight
Historic Centre of Florence5 nights4.0 star property7.4/10 - Good (1,001 reviews)"My stay here was for the most part satisfactory. I would stay here again. The first few days the TVs in the entire hotel were not functioning. Then wifi had an issue but that only lasted a few hours. The included breakfast was basic with eggs and bread but good enough to energize you. I must admit the constant slamming of doors was an issue because it was loud"Reviewed November 4, 2026Roundtrip • New York (JFK) - Florence (FLR)JFK - FLR • 2 stops FLR - JFK • 1 stop$1,338$966found 3 hours agoper traveler - Aurum Uffizi
Jan 19 - Jan 25Aurum Uffizi + Flight
Historic Centre of Florence5 nights4.0 star property7.8/10 - Good (1,001 reviews)"Perfect location"Reviewed November 2, 2026Roundtrip • New York (JFK) - Florence (FLR)JFK - FLR • 2 stops FLR - JFK • 1 stop$1,471$1,012found 3 hours agoper traveler - Palazzo Monnalisa
Dec 26 - Jan 1Palazzo Monnalisa + Flight
Historic Centre of Florence5 nights5.0 star property9.0/10 - Wonderful (815 reviews)"Loved my stay! Beautiful room and property!"Reviewed November 1, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 2 stops$6,878$4,911found 1 day agoper traveler - Palazzo Lorenzo Hotel Boutique & Spa
Dec 26 - Jan 1Palazzo Lorenzo Hotel Boutique & Spa + Flight
San Lorenzo5 nights4.0 star property9.4/10 - Exceptional (627 reviews)Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 2 stops$6,339$4,550found 1 day agoper traveler - Villa Neroli - Place of Charme
Dec 26 - Jan 1Villa Neroli - Place of Charme + Flight
Coverciano5 nights4.0 star property9.6/10 - Exceptional (737 reviews)Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 2 stops$6,109$4,423found 1 day agoper traveler
Where to stay in and around Radda in Chianti
Villa
Villa is the ultimate destination for travelers seeking a romantic and cultural getaway in Tuscany. Nestled in Radda in Chianti, this charming village offers easy access to historic landmarks like the stunning Castello di Albola, the picturesque Piazza del Campo, and the breathtaking Siena Cathedral. With a peak in visitor arrivals from July to September, Villa provides an enchanting atmosphere for lovers and adventurers alike. Booking a stay here is a smart choice, ensuring you experience the best of Tuscany’s beauty and history.
Lucarelli
Experience the charm of Lucarelli, a delightful retreat for cultural enthusiasts and food lovers seeking a romantic getaway. Nestled in Radda in Chianti, this village invites you to explore the stunning Castello di Albola, unwind in the lively Piazza Matteotti, and admire the beautiful Church of Santa Maria Assunta. With a moderate flow of visitors throughout the year, Lucarelli is an ideal base for immersing yourself in Tuscany's rich history and vibrant culinary scene. Choosing Lucarelli as your stay guarantees a memorable experience in this picturesque region.
Volpaia
If you are a traveler seeking romance and cultural experiences, look no further than Volpaia, nestled in Radda in Chianti. This charming village offers easy access to stunning attractions like the historic Castello di Albola, the picturesque Piazza Matteotti, and the serene Church of Santa Maria Assunta. With a vibrant atmosphere that peaks from July to September, Volpaia is a perfect retreat for those wanting to indulge in outdoor adventures and local wines. Staying here ensures a delightful blend of history and leisure.
Colle Petroso
Immerse yourself in Colle Petroso, where cultural enthusiasts and food and wine lovers can easily access the stunning Castello di Albola, the charming Piazza del Campo, and the modern City Hall in Castellina in Chianti. This picturesque village, nestled in Radda in Chianti, offers a romantic backdrop and a vibrant atmosphere, particularly thriving from July to September. Choosing Colle Petroso for your stay ensures a memorable Tuscan experience filled with history and charm.
Cignano
Travelers seeking a blend of culture, luxury, and nature will find Cignano to be the ideal base for their vacation in Radda in Chianti. Nestled in this picturesque region, visitors can explore nearby attractions like the stunning Piazza del Campo, the majestic Siena Cathedral, and the historic Monteriggioni Castle. Cignano offers easy access to beautiful outdoor scenery and activities such as karting. Choosing Cignano for your stay ensures a memorable experience in the heart of Tuscany.
Discover the most popular places to visit in Radda in Chianti
What to do in Radda in Chianti
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Chianti Half Day Wine Tour from Florence
SMALL-GROUP Wine Safari: Tuscany Wine Tasting Tour from Florence
Radda in Chianti Hotel Deals
Hotel Palazzo San niccolò & Spa
Hotel Palazzo San niccolò & Spa"Great stay!"
Palazzo Leopoldo Dimora Storica & Spa
Palazzo Leopoldo Dimora Storica & Spa"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!"
"One of the best hotels I have ever stayed at. We loved every minute. The hotel and buildings are stunning, the landscaping and surrounding area is so picturesque, and the facilities, especially the spa, are top quality. The food was incredible. A little bit on the pricey side for dinner, but certainly fine dining. Breakfast was great - the pastries are all made fresh. Every single staff member was super friendly and accommodating. Special mention to Jessica, who gave me one of the best...
"We arrived by bike and there was not means of other transportation to the town."
Tenuta CorteDomina
Tenuta CorteDomina
La Locanda Volpaia
La Locanda Volpaia
"What a wonderful stay! The location, food and wine were amazing. But the best part was the staff!!! Everyone was so welcoming and accommodating. Do not miss the wine tour!!!"
Frequently Asked Questions
How much does a Radda in Chianti vacation package cost?
You'll find cheap prices from $966 on Expedia for your Radda in Chianti escape. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Radda in Chianti costs.
What are the cheapest months to go to Radda in Chianti?
If you're hoping to book a cheap Radda in Chianti vacation package, consider planning a trip in October, November and December. You'll generally find better prices on accommodations and flights during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Radda in Chianti?
Typically, a few days is great for a Radda in Chianti vacation. With a well-planned itinerary, you can see all the leading attractions such as Borgo di Vescine - Tenute di Castelvecchi, as well as explore some hidden treasures along the way.
Is it worth booking a vacation package to Radda in Chianti?
Radda in Chianti has all the ingredients you need for a fantastic trip — views, walking trails and dining are just the start. Whether you'd like to visit attractions such as Castello di Albola and Castello di Radda Winery, or take the path less traveled, you'll find plenty to see and do on your Radda in Chianti vacation.
How to find the best Radda in Chianti package deals?
Start your search for a Radda in Chianti package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Radda in Chianti package deal right away, simply play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Radda in Chianti escape off to a flying start.
Is it cheaper to book a Radda in Chianti vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Radda in Chianti vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Radda in Chianti?
If you've got your Radda in Chianti travel dates locked in, book early to snap up some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Radda in Chianti?
- Choose when to go: Check your calendar and pack your bags. Your favorite season and the type of activities available will also help you decide when to escape to Radda in Chianti.
- Set a budget: Factor in costs such as flights, food and transportation when working out how much to put aside for your trip to Radda in Chianti. Then, select a property that works with your budget, whether that's a low-cost option or a lavish getaway.
- Use Expedia's trip planning tool to discover Radda in Chianti: Research every part of your trip to Radda in Chianti with this handy planner. Invite friends or family to collaborate on a group trip, search for hotels or things to do and make bookings.
- Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to get to in Radda in Chianti. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your accommodations and airfare: After you've nailed down your travel dates and duration, book the ideal Radda in Chianti vacation package for you.
- Book any day trips or activities: Now to the fun part — organizing everything you want to do and see. Explore some of the best things to do in Radda in Chianti and book your tickets early to save time (and maybe some dollars too!).
Does Expedia offer Book Now, Pay Later Radda in Chianti vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Radda in Chianti break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.