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Open Photo by Earl Baron
Sassicaia Wine Area Vacations from $1,155
Book a Hotel + Flight or Car together to unlock savings
Top destinations in Sassicaia Wine Area
Marina di Bibbona
Marina di Castagneto Carducci
Bolgheri
Donoratico
La California
San Giusto
Bolgheri I
Val Canina
Fornaci
The Latest Sassicaia Wine Area Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Il Pelagone Hotel & Golf Resort Toscana
Aug 25 - Aug 31Il Pelagone Hotel & Golf Resort Toscana + Flight
Gavorrano6 nights4.0 star property8.2/10 - Very Good (15 reviews)"The staff was very friendly and accommodating but the first room I got smelled like mildew. Asked for a new room and got upgraded at no charge to one of the newer buildings. Beautiful location but even the new room was uncomfortable, minus the smell, all the furniture was dated and the room was dark. I don't think I would return but really appreciated the staff for doing their best."Reviewed October 17, 2024Roundtrip • New York (NYC) - Pisa (PSA)JFK - FLR • 1 stop FLR - JFK • 1 stop$1,512$1,155found 1 day agoper traveler - Il Leccio Luxury Resort
Sep 4 - Sep 9Il Leccio Luxury Resort + Flight
Santa Margherita Ligure4 nights5.0 star property8.8/10 - Excellent (12 reviews)"Great location, rooms, pool and food"Reviewed August 31, 2025Roundtrip • New York (JFK) - Pisa (PSA)JFK - GOA • 1 stop GOA - JFK • 1 stop$3,192$2,533found 1 day agoper traveler - The Poet Hotel
Sep 4 - Sep 9The Poet Hotel + Flight
La Spezia Historic Centre4 nights4.0 star property9.2/10 - Wonderful (1,001 reviews)"Overall, an enjoyable experience"Reviewed July 20, 2026Roundtrip • New York (JFK) - Pisa (PSA)JFK - GOA • 1 stop GOA - JFK • 1 stop$1,571$1,265found 1 day agoper traveler - SPLENDIDE RIVIERA
Aug 26 - Aug 31SPLENDIDE RIVIERA + Flight
Rapallo4 nights4.0 star property10/10 - Exceptional (27 reviews)"It was wonderful overall."Reviewed July 21, 2026Roundtrip • Boston (BOS) - Pisa (PSA)BOS - PSA • 1 stop PSA - BOS • 1 stop$2,017$1,650found 1 day agoper traveler - Rosabianca Boutique Hotel
Aug 26 - Aug 31Rosabianca Boutique Hotel + Flight
Rapallo4 nights4.0 star property9.2/10 - Wonderful (99 reviews)"Rosabianca is truly an amazing place. The staff is outstanding, and the way they treated us was incredible, paying attention to every detail during both check-in and check-out. The team is professional, well-educated, and genuinely kind. The views are beautiful, and the food is excellent. I will definitely visit Rosabianca many more times. "Reviewed January 12, 2026Roundtrip • Boston (BOS) - Pisa (PSA)BOS - PSA • 1 stop PSA - BOS • 1 stop$1,840$1,529found 1 day agoper traveler
Discover the most popular places to visit in Sassicaia Wine Area
Sassicaia Wine Area Hotel Deals
Tombolo Talasso & Beach Resort
Tombolo Talasso & Beach Resort5.0 star property
2.7 mi from Sassicaia Wine Area
8.8 out of 10, Excellent, (146 reviews)
8.8/10
Excellent
(146 reviews)
"Where as we enjoyed our time here we did have a bit of an issue with our room temperature. We asked for it to be lowered as it was 81 degrees.
We found out, after a very uncomfortable night and requesting 2 more times, that the AC was not working. As an aside: we could not open a window as our room was on the 1st floor and only had doors to a common area. We were moved to a new room.
Other than that- the staff was lovely the pools and Spa are great. Location is wonderful with close...
$358 nightly
The price is $401
$401 total
Jul 29 - Jul 30
Total with taxes and fees
8.8 out of 10, Excellent, (227 reviews)
8.8/10
Excellent
(227 reviews)
$324 nightly
The price is $362
$362 total
Aug 3 - Aug 4
Total with taxes and fees
Relais Sant'Elena
Relais Sant'Elena5.1 mi from Sassicaia Wine Area
10.0 out of 10, Exceptional, (77 reviews)
10/10
Exceptional
(77 reviews)
"This place is truly heaven on earth. The property is a spectacular private farmhouse nestled in the heart of the Tuscan countryside, offering complete tranquility and breathtaking beauty in every direction. Set in a peaceful valley, it is surrounded by stunning 360-degree views of rolling hills, forests, open fields, and the picturesque town of Bibbona in the distance. It’s a great place to host a wedding or offsite or simply just relax
The setting feels timeless; an authentic Tuscan landscape...
$489 nightly
The price is $540
$540 total
Jul 26 - Jul 27
Total with taxes and fees
Punti Di Vista B&B Food&Wine Experience
Punti Di Vista B&B Food&Wine Experience5.2 mi from Sassicaia Wine Area
9.4 out of 10, Exceptional, (3 reviews)
9.4/10
Exceptional
(3 reviews)
$159 nightly
The price is $178
$178 total
Jul 26 - Jul 27
Total with taxes and fees
8.8 out of 10, Excellent, (46 reviews)
8.8/10
Excellent
(46 reviews)
"Great hotel staff, charming people and charming place. The only downside was the A/c that wasn’t cool enough but I would definitely come back. "
$121 nightly
The price is $137
$137 total
Jul 26 - Jul 27
Total with taxes and fees
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
"Tutto perfetto, struttura molto accogliente e personale professionale e gentile."
$319 nightly
The price is $351
$351 total
Jul 31 - Aug 1
Total with taxes and fees
Csa Hotel Beach & Park
Csa Hotel Beach & Park4.2 mi from Sassicaia Wine Area
9.0 out of 10, Wonderful, (4 reviews)
9.0/10
Wonderful
(4 reviews)
"Everything was great !"
$182 nightly
The price is $204
$204 total
Jul 31 - Aug 1
Total with taxes and fees
Relais dei Molini
Relais dei Molini2.7 mi from Sassicaia Wine Area
10.0 out of 10, Exceptional, (8 reviews)
10/10
Exceptional
(8 reviews)
"We were so happy we found this gem of a resort. Small, intimate yet luxurious. The breakfast breads and cakes are incredible. And the view is like from a movie. We hope to be back. Thank you for your hospitality."
$236 nightly
The price is $264
$264 total
Jul 27 - Jul 28
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.