Montegrossi

Travel Guide

Travel to Montegrossi for a blend of historical sites, local wineries, and the natural beauty of surrounding landscapes.

Montegrossi features a range of attractions that showcase its historical and cultural significance. You can visit notable sites like the Church of San Sigismondo and explore the Medieval Tower of Barbischio, both located nearby. For those interested in wine, several wineries such as Cantalici Winery and Volpaia are also in the vicinity, offering tastings and tours. Additionally, outdoor enthusiasts can enjoy the natural beauty of the Basso Merse Nature Reserve and Montagna Fiorentina, which provide opportunities for hiking and adventure tourism.

Spend some time exploring the nearby areas of Montegrossi, each with its unique charm. Radda in Chianti is known for its romantic ambiance and entertainment experiences, featuring the Castello di Radda Winery. Another nearby area, Gaiole in Chianti, offers a similar atmosphere and is home to Meleto Castle and Castello di Meleto Cantina. Additionally, Badia Coltibuono presents opportunities for both relaxation and enjoyment, rounding out the diverse experiences available in the surrounding neighborhoods.

The best time to visit Montegrossi is during the warm months of July to August, when you can expect mostly dry and sunny weather around 76°F. While this period tends to attract more visitors, the pleasant conditions make it ideal for outdoor activities and exploring nearby attractions. If you prefer a quieter experience, consider planning your visit outside the peak summer months, as the area can become busy during this popular time.

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is $103 total per night from Nov 30 to Dec 1
$103 total
per night
Nov 30 - Dec 1
Book a stay at this business-friendly hotel in Siena. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,012 reviews)
"Staff are very friendly and helpful. We appreciated the valet parking at no extra charge. Great location and stunning views from the terrace bar. The staff made it one of the best hotels we have stayed at in a very long time. Good value for the price."

Reviewed on Nov 9, 2026

Hotel Athena
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85 Siena SI
The price is $283 total per night from Dec 13 to Dec 14
$283 total
per night
Dec 13 - Dec 14
Book a stay at this luxury hotel in Siena. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Grand Hotel Continental Siena – Starhotels Collezione
Hotel Minerva

Hotel Minerva

3 out of 5
Via Garibaldi, 72 Siena SI
The price is $97 total per night from Nov 15 to Nov 16
$97 total
per night
Nov 15 - Nov 16
Book a stay at this family-friendly hotel in Siena. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. Popular ...
Hotel Minerva
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.
ApartHotel Anghel

ApartHotel Anghel

via Paolo Frajese 71 Siena SI
Book a stay at this business-friendly apartment in Siena. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Piazza del Campo and National ...
8.4/10 Very Good! (356 reviews)
"The staff were very friendly and helpful. I would recommend this hotel to any traveler"

Reviewed on Nov 1, 2026

ApartHotel Anghel
Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

4 out of 5
Via Norcenni 7 Figline e Incisa Valdarno FI
Book a stay at this family-friendly campground in Figline e Incisa Valdarno. Enjoy free parking, 7 outdoor pools, and 3 restaurants. Popular attractions Fashion ...
8.6/10 Excellent! (339 reviews)
"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family ..."

Reviewed on Sep 27, 2026

Hu Norcenni Girasole Village
Camping Village Il Poggetto.

Camping Village Il Poggetto.

3 out of 5
Via iI Poggetto 143 Rignano sull'Arno FI
Book a stay at this family-friendly campground in Rignano sull'Arno. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Fashion Groove and ...
8/10 Very Good! (86 reviews)
"This property was nice. We enjoyed our two nights in a home on property. The home was a little dated but overall nice. Getting to Florence was a bit challenging, due to the property being in an isolated area. On the weekends there are only two busses that so by the property... one in the morning ..."

Reviewed on Jun 3, 2026

Camping Village Il Poggetto.
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.

Things to do

Frequently asked questions

When is the best time to visit Montegrossi?
The best time to visit Montegrossi is from May through September, when travelers can enjoy warm, pleasant weather. For fewer crowds and better value, the quieter months of November through February are a good bet, offering cooler temperatures and a more relaxed atmosphere.
Can I book a refundable hotel in Montegrossi?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Montegrossi by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Montegrossi with Expedia?
Expedia makes it easier to plan your Montegrossi trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Montegrossi?
The best choice depends on your travel style. Hotels in Montegrossi can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Montegrossi trip on Expedia?
Once you've booked your Montegrossi trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Montegrossi trip?
Expedia offers customer support before, during, and after your Montegrossi trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Montegrossi?
If it's your first trip to Montegrossi, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Montegrossi hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Montegrossi hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Montegrossi

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