Title: Rocca of Montestaffoli in San Gimignano City Centre - Tours and Activities | Expedia.ca [Rocca of Montestaffoli Hotels](https://expedia.ca/Rocca-Of-Montestaffoli-Hotels.0-l632711416016093184-0.Travel-Guide-Filter-Hotels)[Rocca of Montestaffoli Car Rentals](https://expedia.ca/Car-Rentals-In-Rocca-Of-Montestaffoli.d632711416016093184.Car-Rental-Guide)[San Gimignano City Centre Vacations](https://expedia.ca/San-Gimignano-City-Centre.d553248635810302977.Destination-Travel-Guides) # Rocca of Montestaffoli Tours and Activities ![Photo "Rocca of Montestaffoli" by Robert Powell (CC BY-SA) / Cropped from original](https://mediaim.expedia.com/destination/3/228d09052bde0d65c3aab86fb1b243ef.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo](https://mediaim.expedia.com/destination/3/228d09052bde0d65c3aab86fb1b243ef.jpg) by [Robert Powell](https://www.panoramio.com/user/777952?with_photo_id=52766008) ([CC BY-SA](https://creativecommons.org/licenses/by-sa/3.0)) ## Visit Rocca of Montestaffoli Activities --- --- ## Plan a trip to see Rocca of Montestaffoli Price found within the past 48 hours. Click for updated prices. ![Residenza Florentia](https://images.trvl-media.com/lodging/2000000/1140000/1133600/1133528/4a95c46d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Residenza Florentia Historic Centre of Florence CA $1,483 per person Mar 10 - Mar 16 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Florence (FLR) 8.4/10 Very Good! (46 reviews) Location, accommodations, and communication. Simple but comfortable. A basic facilities, and nice AC, elevator, and luggage storage. Reviewed on Jun 12, 2025 ![Portrait Firenze - Lungarno Collection](https://images.trvl-media.com/lodging/1000000/810000/800600/800547/96b08b51_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portrait Firenze - Lungarno Collection Historic Centre of Florence CA $3,801 per person Mar 2 - Mar 7 found 3 hours ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 9.8/10 Exceptional! (299 reviews) Great location and got fantastic service from the hotel. Room was very clean and comfortable. Definitely my first choice for staying in Firenze! Reviewed on Nov 17, 2025 ![Villa Cora](https://images.trvl-media.com/lodging/1000000/30000/22600/22579/bc8037ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villa Cora Oltrarno CA $2,410 per person Feb 16 - Feb 21 found 15 hours ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 9.8/10 Exceptional! (467 reviews) Nice property and staff. Reviewed on Nov 13, 2025 ### Tours & day trips [See all 79 activities](https://expedia.ca/things-to-do/search?&rid=632711416016093184&location=Rocca+of+Montestaffoli&filter.categories=ToursDayTrips) ![Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch](https://mediaim.expedia.com/localexpert/236697/0f88e6e6-ef95-4a56-8618-2b7fc4f041a9.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch 12h 15m 7.8/10 152 reviews Free cancellation available CA $79 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/tuscany-in-1-day-pisa-san-gimignano-siena-with-lunch.a236697.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Chianti Wineries Tour with Tuscan Lunch and San Gimignano](https://mediaim.expedia.com/localexpert/3066812/0152b205-a96f-450d-b0ae-9ed1784446bc.jpg?impolicy=resizecrop&rw=500&rh=280) ### Chianti Wineries Tour with Tuscan Lunch and San Gimignano 8h 10/10 18 reviews Free cancellation available CA $307 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/chianti-wine-tour-with-lunch-visit-s-gimignano-organic-wineries-and-much-more.a3066812.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Tuscany Vespa Tour from Florence with Wine Tasting](https://mediaim.expedia.com/localexpert/3067216/186ed4da-a736-487d-9c27-f55c3c11482c.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscany Vespa Tour from Florence with Wine Tasting 8h 10/10 4 reviews Free cancellation available CA $324 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/tuscany-vespa-wine-tour.a3067216.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Truffle Hunting in Tuscany](https://mediaim.expedia.com/localexpert/3113978/a9f55ec7-b566-49c1-a7df-31ab6ac630ce.jpg?impolicy=resizecrop&rw=500&rh=280) ### Truffle Hunting in Tuscany 8h 10/10 1 review Free cancellation available CA $776 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/truffle-hunting-in-tuscany.a3113978.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Private Wine & Evo Oil Tasting with Tuscan Meal](https://mediaim.expedia.com/localexpert/1097610/05b7576c-1639-42cc-96ba-fce86bb904bd.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Wine & Evo Oil Tasting with Tuscan Meal 1h 30m Free cancellation available CA $89 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/wine-evo-oil-tasting-with-tuscan-meal.a1097610.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Cesani Wine Experience](https://mediaim.expedia.com/localexpert/3177828/1b2b9898-5d26-4def-a707-c7d7e4f007cf.jpg?impolicy=resizecrop&rw=500&rh=280) ### Cesani Wine Experience 1h 30m Free cancellation available CA $49 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/cesani-wine-experience.a3177828.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Private Tuscan meal with Wine and EVO oil tasting](https://mediaim.expedia.com/localexpert/1097603/e6a6f35d-6b38-4f32-9777-16145adb7681.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Tuscan meal with Wine and EVO oil tasting 1h 30m 10/10 1 review Free cancellation available CA $89 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/vineyard-tour-with-wine-olive-oil-tasting-and-tuscan-meal.a1097603.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Horseback Ride in S.Gimignano with Tuscan Lunch Chianti Tasting](https://mediaim.expedia.com/localexpert/3085681/15f4d4d1-7ea5-4d84-b9e5-7d365dca535e.jpg?impolicy=resizecrop&rw=500&rh=280) ### Horseback Ride in S.Gimignano with Tuscan Lunch Chianti Tasting 8h 10/10 6 reviews Free cancellation available CA $307 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/horseback-ride-lunch-winery-visit-wine-tasting-visit-s-gimignano-more.a3085681.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Agricola Poggio ai Laghi: Tasting of Wines, Oils and Vinegars](https://mediaim.expedia.com/localexpert/48760350/2219c541-6fde-41c5-ac71-ef4303238a1e.jpg?impolicy=resizecrop&rw=500&rh=280) ### Agricola Poggio ai Laghi: Tasting of Wines, Oils and Vinegars 1h 30m Free cancellation available CA $81 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/agricola-poggio-ai-laghi-tasting-of-wines-oils-and-vinegars.a48760350.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Private Wine & Oil Tasting with Lunch](https://mediaim.expedia.com/localexpert/1097624/5fcd50d5-cbb8-472f-85a1-f7132e12c883.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Wine & Oil Tasting with Lunch 1h 30m Free cancellation available CA $102 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/vineyard-tour-and-tasting-with-lunch-or-dinner.a1097624.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ### Classes & workshops [See all 22 activities](https://expedia.ca/things-to-do/search?&rid=632711416016093184&location=Rocca+of+Montestaffoli&filter.categories=ClassesWorkshops) ![Tuscan Cooking Class](https://mediaim.expedia.com/localexpert/3177810/362501bb-c03d-442f-bab5-f0d873263dc0.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscan Cooking Class 3h 10/10 2 reviews Free cancellation available CA $210 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/tuscan-cooking-class.a3177810.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Cooking Class: Italian Authentic Recipes with Lunch](https://mediaim.expedia.com/localexpert/48760354/15695096-597a-4270-9961-c13b9e1b4e89.jpg?impolicy=resizecrop&rw=500&rh=280) ### Cooking Class: Italian Authentic Recipes with Lunch 3h Free cancellation available CA $178 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/tuscan-and-italian-cooking-class-with-authentic-recipes.a48760354.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Barberino Tavarnelle: Truffle Hunt Tour with Lunch or Dinner](https://mediaim.expedia.com/localexpert/48107984/1488a9ec-3bef-4232-8441-34d80298e961.jpg?impolicy=resizecrop&rw=500&rh=280) ### Barberino Tavarnelle: Truffle Hunt Tour with Lunch or Dinner 3h Free cancellation available CA $380 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/barberino-tavarnelle-truffle-hunt-tour-with-lunch-or-dinner.a48107984.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Pici Class in a Tuscan Farm](https://mediaim.expedia.com/localexpert/50018697/ca16fa54-29ca-43f0-9d35-4d0c8b5fc76c.jpg?impolicy=resizecrop&rw=500&rh=280) ### Pici Class in a Tuscan Farm 3h Free cancellation available CA $202 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/pici-class-in-a-tuscan-farm.a50018697.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Home made Pasta Cooking Class in Tuscany](https://mediaim.expedia.com/localexpert/49469783/e893402c-50a5-41c4-aa23-e1c120e226f9.jpg?impolicy=resizecrop&rw=500&rh=280) ### Home made Pasta Cooking Class in Tuscany 3h Free cancellation available CA $243 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/san-gimignano-pasta-cooking-class-with-dinner-and-wine.a49469783.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Home Made Pizza Cooking Class in Tuscany with small group](https://mediaim.expedia.com/localexpert/49469755/c27f08db-6a0f-41bc-a526-be07f1ffb5a9.jpg?impolicy=resizecrop&rw=500&rh=280) ### Home Made Pizza Cooking Class in Tuscany with small group 3h Free cancellation available CA $243 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/san-gimignano-pizza-cooking-class-with-lunch-and-wine.a49469755.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Culinary School of Tuscany Private Tour from Florence](https://mediaim.expedia.com/localexpert/49895027/640690eb-7d13-44de-9f75-bdb83ec077b5.jpg?impolicy=resizecrop&rw=500&rh=280) ### Culinary School of Tuscany Private Tour from Florence 6h Free cancellation available CA $1,293 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/culinary-school-of-tuscany-private-tour-from-florence.a49895027.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Chianti - Vegetarian Gnocchi and Gelato with lunch or dinner](https://mediaim.expedia.com/localexpert/47231384/33b69af7-1555-41e9-8ab6-0b719c8dd532.jpg?impolicy=resizecrop&rw=500&rh=280) ### Chianti - Vegetarian Gnocchi and Gelato with lunch or dinner 3h Free cancellation available CA $251 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/vegetarian-gnocchi-and-ice-cream-cooking-class-with-lunch-or-dinner.a47231384.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Chianti - Tuscan Cooking Course with Vegetarian Lunch or Dinner](https://mediaim.expedia.com/localexpert/47147784/30879cf8-e698-4285-8b8c-72c0dbb49c94.jpg?impolicy=resizecrop&rw=500&rh=280) ### Chianti - Tuscan Cooking Course with Vegetarian Lunch or Dinner 3h Free cancellation available CA $243 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/cooking-class-tuscan-tradition-with-vegetarian-lunch-or-dinner.a47147784.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Chianti - Chef Secrets in Private Lessons with Michelin Starred Chef](https://mediaim.expedia.com/localexpert/47246127/f5b11568-fb79-499a-8e14-43ef496ee82a.jpg?impolicy=resizecrop&rw=500&rh=280) ### Chianti - Chef Secrets in Private Lessons with Michelin Starred Chef 3h CA $566 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/chef-secrets-in-private-cooking-lesson-with-starred-chef.a47246127.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ### History & culture [See all 18 activities](https://expedia.ca/things-to-do/search?&rid=632711416016093184&location=Rocca+of+Montestaffoli&filter.categories=HistoryCulture) ![Truffle Hunting in Tuscany](https://mediaim.expedia.com/localexpert/3113978/a9f55ec7-b566-49c1-a7df-31ab6ac630ce.jpg?impolicy=resizecrop&rw=500&rh=280) ### Truffle Hunting in Tuscany 8h 10/10 1 review Free cancellation available CA $776 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/truffle-hunting-in-tuscany.a3113978.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![CREMONA private tour: beautiful, historic close to Milan](https://mediaim.expedia.com/localexpert/47814951/87e0c85e-e011-45b1-8c5b-dce1420b9588.jpg?impolicy=resizecrop&rw=500&rh=280) ### CREMONA private tour: beautiful, historic close to Milan 2h Free cancellation available CA $558 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/cremona-private-tour-beautiful-historic-close-to-milan.a47814951.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Horseback Riding with Wine Tour from Florence](https://mediaim.expedia.com/localexpert/5027419/cc949c5b-e1f4-4dc8-93e2-112ab7aa3225.jpg?impolicy=resizecrop&rw=500&rh=280) ### Horseback Riding with Wine Tour from Florence 8h Free cancellation available CA $307 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/horseback-riding-wine-tour-from-florence.a5027419.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Private Day-Trip to Siena and San Gimignano](https://mediaim.expedia.com/localexpert/700800/06f9a81f-6b0a-489c-92a5-9cc8264ca226.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Day-Trip to Siena and San Gimignano 6h Free cancellation available CA $1,181 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/private-day-trip-to-siena-and-san-gimignano.a700800.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Siena Monteriggioni San Gimignano with Lunch&WineTasting Fullday from Flore...](https://mediaim.expedia.com/localexpert/1081372/170f659e-6389-483d-9369-030840699012.jpg?impolicy=resizecrop&rw=500&rh=280) ### Siena Monteriggioni San Gimignano with Lunch&WineTasting Fullday from Flore... 9h CA $1,941 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/siena-monteriggioni-san-gimignano-with-lunch-winetasting-fullday-from-florence.a1081372.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Chianti and San Gimignano - 2 Wineries with Pairing Lunch](https://mediaim.expedia.com/localexpert/1159906/08f3a397-1188-4800-bef8-fa725574f9b1.jpg?impolicy=resizecrop&rw=500&rh=280) ### Chianti and San Gimignano - 2 Wineries with Pairing Lunch 8h Free cancellation available CA $565 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/chianti-and-san-gimignano-3-wineries-and-lunch.a1159906.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![From San Gimignano: Chianti Wine tour with 2 wineries](https://mediaim.expedia.com/localexpert/44642727/7a35a83d-3a63-4209-bfbe-6166cbec6bdb.jpg?impolicy=resizecrop&rw=500&rh=280) ### From San Gimignano: Chianti Wine tour with 2 wineries 4h+ 10/10 1 review Free cancellation available CA $243 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/from-san-gimignano-chianti-wine-tour-with-2-wineries.a44642727.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Barberino Tavarnelle: Truffle Hunt Tour with Lunch or Dinner](https://mediaim.expedia.com/localexpert/48107984/1488a9ec-3bef-4232-8441-34d80298e961.jpg?impolicy=resizecrop&rw=500&rh=280) ### Barberino Tavarnelle: Truffle Hunt Tour with Lunch or Dinner 3h Free cancellation available CA $380 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/barberino-tavarnelle-truffle-hunt-tour-with-lunch-or-dinner.a48107984.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Private Guided Tour to three Supercar Museum](https://mediaim.expedia.com/localexpert/45668831/8e66fff8-763c-456a-9f34-b1e605c63e84.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Guided Tour to three Supercar Museum 8h Free cancellation available CA $1,124 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/private-guided-tour-in-supercar-museum.a45668831.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![San Gimignano private guide: Manhattan of the Middle Ages](https://mediaim.expedia.com/localexpert/47379923/64923ddf-4ee8-42a5-a952-d5360ec35350.jpg?impolicy=resizecrop&rw=500&rh=280) ### San Gimignano private guide: Manhattan of the Middle Ages 2h 8/10 1 review Free cancellation available CA $550 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/san-gimignano-private-and-guided-walking-tour.a47379923.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ### Adventure & outdoor [See all 6 activities](https://expedia.ca/things-to-do/search?&rid=632711416016093184&location=Rocca+of+Montestaffoli&filter.categories=AdventureOutdoor) ![Private Tuscan meal with Wine and EVO oil tasting](https://mediaim.expedia.com/localexpert/1097603/e6a6f35d-6b38-4f32-9777-16145adb7681.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Tuscan meal with Wine and EVO oil tasting 1h 30m 10/10 1 review Free cancellation available CA $89 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/vineyard-tour-with-wine-olive-oil-tasting-and-tuscan-meal.a1097603.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Tuscany Private Day Tour from Florence](https://mediaim.expedia.com/localexpert/50750395/52b7999a-b16f-4c52-aec1-efe98175473f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscany Private Day Tour from Florence 10h Free cancellation available CA $2,087 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/tuscany-private-day-tour-from-florence.a50750395.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Private E-bike Tour in Chianti from San Gimignano](https://mediaim.expedia.com/localexpert/3084432/06d5ddb5-46ac-4e92-8585-9817311729c6.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private E-bike Tour in Chianti from San Gimignano 6h Free cancellation available CA $616 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/e-bike-tour-and-wine-tasting-from-san-gimignano.a3084432.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![San Gimignano: Bike tour in the Tuscan Hills](https://mediaim.expedia.com/localexpert/48233488/bce0be68-ea33-4b02-85bb-4c4a7591b940.jpg?impolicy=resizecrop&rw=500&rh=280) ### San Gimignano: Bike tour in the Tuscan Hills 4h Free cancellation available CA $874 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/from-certaldo-bike-tour-in-the-tuscan-hills.a48233488.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Explore Chianti's Beauty: E-Bike Tour & Wine Tasting](https://mediaim.expedia.com/localexpert/45716506/d10ae431-1dc0-45af-a410-dd709d50ff7f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Explore Chianti's Beauty: E-Bike Tour & Wine Tasting 4h CA $210 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/guided-chianti-e-bike-tour-with-wine-tasting.a45716506.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ![Mensanello Valley Wine and Olive Tasting Hike](https://mediaim.expedia.com/localexpert/50000479/6c1559bd-8d4a-492b-90cf-83f4873edd79.jpg?impolicy=resizecrop&rw=500&rh=280) ### Mensanello Valley Wine and Olive Tasting Hike 3h Free cancellation available CA $178 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/mensanello-valley-wine-and-olive-tasting-hike.a50000479.activity-details?&rid=632711416016093184&location=Rocca+of+Montestaffoli&swp=off) ### Popular places to visit ![Piazza delle Erbe which includes heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/158000/158235-Piazza-Delle-Erbe-San-Gimignano.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Piazza delle Erbe Watch the world go by and admire San Gimignano’s medieval architecture from the comfort of a café terrace at this central square. [](https://expedia.ca/Piazza-Delle-Erbe-San-Gimignano-City-Centre.d6105350.Vacation-Attraction) ![San Gimignano Communal Palace](https://mediaim.expedia.com/destination/1/4141def83d312f3c3eca793393c14faa.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### San Gimignano Communal Palace 4.5/5(2 reviews) You can browse the exhibits at San Gimignano Communal Palace, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours. [](https://expedia.ca/San-Gimignano-Communal-Palace-San-Gimignano-City-Centre.d6105356.Vacation-Attraction) ![Piazza Duomo showing heritage architecture and a church or cathedral](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/158000/158214-Piazza-Duomo-San-Gimignano.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Piazza Duomo 4.5/5(20 reviews) Browse the collections of ancient art, which grace the walls of the medieval landmarks that surround this resplendent public square. [](https://expedia.ca/Piazza-Duomo-San-Gimignano-City-Centre.d6105352.Vacation-Attraction) ![Collegiate Church of Santa Maria Assunta](https://mediaim.expedia.com/destination/2/cab42bcac22cfa9a6c61d9efc4ffdf16.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Collegiate Church of Santa Maria Assunta 4.5/5(7 reviews) You can browse the exhibits at Collegiate Church of Santa Maria Assunta, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours. [](https://expedia.ca/Collegiate-Church-Of-Santa-Maria-Assunta-San-Gimignano-City-Centre.d6105346.Vacation-Attraction) ![Piazza della Cisterna which includes street scenes, a city and a square or plaza](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157885-San-Gimignano.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Piazza della Cisterna 4.5/5(17 reviews) Admire the palaces and towers that frame this beautiful square, which was once a medieval marketplace. Today, it’s a venue for cultural events. [](https://expedia.ca/Piazza-Della-Cisterna-San-Gimignano-City-Centre.d6105348.Vacation-Attraction) #### Fortress of Montestaffoli You can learn about the history of San Gimignano with a trip to Fortress of Montestaffoli. Discover the area's beautiful countryside and wineries. [](https://expedia.ca/Fortress-Of-Montestaffoli-San-Gimignano-City-Centre.d553248621532497703.Vacation-Attraction) --- ## Best Lodging Options Near Rocca of Montestaffoli ## Check availability on hotels close to Rocca of Montestaffoli [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=632711416016093184&startDate=2025-12-23&endDate=2025-12-24)[Dec 23 - Dec 24](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=632711416016093184&startDate=2025-12-23&endDate=2025-12-24) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=632711416016093184&startDate=2025-12-24&endDate=2025-12-25)[Dec 24 - Dec 25](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=632711416016093184&startDate=2025-12-24&endDate=2025-12-25) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=632711416016093184&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025)[Dec 26 - Dec 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=632711416016093184&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=632711416016093184&startDate=02%2F01%2F2026&endDate=04%2F01%2F2026)[Jan 2 - Jan 4](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=632711416016093184&startDate=02%2F01%2F2026&endDate=04%2F01%2F2026) ![Hotel Leon Bianco](https://images.trvl-media.com/lodging/2000000/1320000/1315000/1314959/f531fd35_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Leon Bianco Piazza Della Cisterna 13 San Gimignano SI [](https://expedia.ca/San-Gimignano-Hotels-Hotel-Leon-Bianco.h1314959.Hotel-Information) ![L'Antico Pozzo](https://images.trvl-media.com/lodging/1000000/920000/915500/915432/dc667d35_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### L'Antico Pozzo Via San Matteo 87 San Gimignano SI [](https://expedia.ca/San-Gimignano-Hotels-LAntico-Pozzo.h915432.Hotel-Information) ![Residenza d'Epoca Palazzo Buonaccorsi](https://images.trvl-media.com/lodging/6000000/5940000/5933000/5932999/71d708e5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Residenza d'Epoca Palazzo Buonaccorsi Via San Matteo, 95 San Gimignano SI [](https://expedia.ca/San-Gimignano-Hotels-Residenza-DEpoca-Palazzo-Buonaccorsi.h5932999.Hotel-Information) ![san gimignano apartment in historical center, courtyard and fast free wifi](https://images.trvl-media.com/lodging/34000000/33590000/33582100/33582090/f9c68b50_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### san gimignano apartment in historical center, courtyard and fast free wifi San Gimignano Siena [](https://expedia.ca/San-Gimignano-Hotels-San-Gimignano-Apartment-In-Historical-Center.h33582090.Hotel-Information) ![La Casa di Ines](https://images.trvl-media.com/lodging/118000000/117150000/117149900/117149866/12ea27d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Casa di Ines Via delle Romite 2 San Gimignano SI [](https://expedia.ca/San-Gimignano-Hotels-La-Casa-Di-Ines.h117149866.Hotel-Information) ![Hotel Bel Soggiorno](https://images.trvl-media.com/lodging/3000000/2550000/2541800/2541764/caa423d4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Bel Soggiorno Via San Giovanni 91 San Gimignano SI [](https://expedia.ca/San-Gimignano-Hotels-Hotel-Bel-Soggiorno.h2541764.Hotel-Information) ![La Cisterna](https://images.trvl-media.com/lodging/3000000/2530000/2520300/2520221/0063883f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Cisterna Piazza Della Cisterna 23 San Gimignano SI [](https://expedia.ca/San-Gimignano-Hotels-La-Cisterna.h2520221.Hotel-Information) ![RELAIS SANTA CHIARA - TUSCANY CHARME](https://images.trvl-media.com/lodging/1000000/900000/897600/897561/98a56ee9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### RELAIS SANTA CHIARA - TUSCANY CHARME Via Giacomo Matteotti, 15 San Gimignano SI [](https://expedia.ca/San-Gimignano-Hotels-Relais-Santa-Chiara-Hotel.h897561.Hotel-Information) ![B&B Palazzo Tortoli](https://images.trvl-media.com/lodging/25000000/24130000/24124100/24124035/b9eedc7c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### B&B Palazzo Tortoli Piazza Della Cisterna 22 San Gimignano SI [](https://expedia.ca/San-Gimignano-Hotels-BB-Palazzo-Tortoli.h24124035.Hotel-Information) [See all 3,371 properties in Rocca of Montestaffoli](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=632711416016093184) 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.