15 Wine Tasting Shore Excursions in Livorno to Build a Port Day Around

1.Private Guided Tour to Pisa and local Wine Farm from Livorno port

★★★★★★★★★★5.0 · 19 reviews · 8 hours (approx.) Our pick

Leave Livorno with a private guide such as Valerio, Val, Dany, Miko, or Nicoletta for Pisa, medieval Lari, Castello dei Vicari, and a family-run wine farm dating to 1865. Expect flexible sightseeing, Tuscan views, a generous optional meal and wine tasting, and a return to port with your group only.

“We had the most amazing Tuscan experience with Nicoletta on this tour! It was exactly what we wanted after spending the previous day amongst the masses in Rome. Our first stop was in Pisa for an hour (more or less if you desire- it’s your tour) which was perfect to walk the grounds and get some great pictures. Afterwards, it was off to the countryside to visit a quaint village to include a castle and a family owned/run pasta making company! Last, it was off to a small winery where we experienced the most amazing lunch (bring a hearty appetite) with wine pairing! Everything was perfect and we are so…”

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2.Winery Tour & Wine Tasting with Food near Livorno & Pisa

★★★★★★★★★★4.9 · 15 reviews · 1.5 hours · from $58Best value

Visit the Etruscan Prince Warrior winery near Casale Marittimo with an English or Italian guide. Tour the vinification, barrel, and aging rooms, hear about the tomb in the vineyard, then taste four Costa Toscana and Montescudaio wines with cured meats, cheeses, and bread. Allow 1.5 hours, plus driving time.

“Opas oli erittäin osaava ja ystävällinen. Suosittelen lämpimästi. Hieno kokemus.”

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3.Florence and Wine Tasting Private Tour from Livorno

★★★★★★★★★★5.0 · 11 reviews · 9 hours (approx.)

You’ll ride from Livorno to Florence in a private air-conditioned vehicle, see the Duomo, Ponte Vecchio, and Piazza della Signoria, then head into Chianti for a winery visit, wine tasting, and light lunch. Drivers may include Alessio, Emanuele, Claudio, or Manuel. Florence time is about three hours.

“The tour organizer contacted me the night before and kindly let me know I had accidentally put Livorno Port as our pickup instead of La Spezia Port. We had originally planned to go to Florence from Livorno, but she assured me it was no problem and promised to make sure we had a fantastic day. She suggested changing the itinerary to avoid too much driving from La Spezia, and told us to leave it to her. Our driver, Emmanuel, picked us up promptly and took us to Portovenere for breakfast, followed by a leisurely stroll through the beautiful town and some shopping. Next, we visited Rio Maggiore, wandering the steep,…”

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4.PRIVATE EXCURSION: Volterra & San Gimignano + wine tastings (from Livorno Port)

★★★★★★★★★★5.0 · 7 reviews · 8 hours (approx.) · from $324

Meet an English-speaking driver at your cruise ship in Livorno at 8:00 am for a private day in Tuscany. Visit Volterra and San Gimignano, tour the Chianti hills, and enjoy a three-course farm lunch with five wine tastings, olive oils, and balsamic vinegar. Andrea and Laura are praised for friendly, well-informed guiding.

“This was an absolutely AMAZING tour! Laura was so great and very knowledgeable! We couldn’t have asked for a better tour guide! We ♥️ Italy!”

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5.Bella Toscana Private Tour: 2 Chianti Wineries and San Gimignano From Livorno

★★★★★★★★★★5.0 · 6 reviews · 7 hours (approx.) · from $445

From Livorno, Massimo drives you through Chianti to two historic wineries and medieval San Gimignano. Expect private transport, wine-making visits, tastings, and a generous Tuscan lunch at extra cost. The seven-hour outing suits cruise passengers who want personal guidance instead of a large group excursion.

“Our guide, Massimo, warned us not to fall in love with Tuscany. We laughed—how could seven hours make us fall in love? Well, he was right. We stopped in Livorno on our cruise and wanted to go wine tasting in Tuscany. After lots of research, we booked this tour, and while it was expensive, it was worth every penny. It ended up being our favorite experience from our two-week trip. Massimo met us right at the cruise terminal (super easy!) and was incredibly knowledgeable and proud of his country. The drive itself was stunning—we stopped several times for photos—and our visit to San Gimignano was a highlight. The wineries were…”

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6.Pisa, Lucca, and Lunch at a Tuscan Winery from Livorno

★★★★★★★★★★5.0 · 5 reviews · 7 to 8 hours (approx.) · from $473

Travel from Livorno with an English-speaking driver such as Nikki, Sabrina, or Claudia. See Pisa’s Campo dei Miracoli, spend three hours in walled Lucca, then enjoy a homemade Tuscan lunch and 6 to 8 wine pairings at Fattoria Carmignani. The private tour lasts 7 to 8 hours, but lunch costs extra.

“We had a great tour with Nikki and Sabrina. We went to the leaning tower of Pisa, rode a bike on the city wall of Lucca and had lunch at a local winery. The overall experience is wonderful and it turned out to be the excursion that our family (7 adults and 5 kids) enjoyed the most among our four excursions in Italy.”

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7.Private Pisa, Pasta and Chianti Lovers Wine Experience Livorno Shore Excursion

★★★★★★★★★★5.0 · 5 reviews · 7 hours (approx.) · from $371

Leave Livorno with a private driver-guide and spend seven hours combining Pisa, the Leaning Tower, Pasta Martelli, and a winery near Terricciola. Emilia and Massimo are praised for personal service, flexible stops, and easy cruise timing. Pasta Martelli is closed Sundays and holidays, and lunch with wine tasting costs 40 euros extra.

“Great tour of Pisa, pasta making, and Winery. Massimo our guide was fantastic! Great food and wine at the winery”

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8.PRIVATE EXCURSION: Florence & Chianti with Wine Tasting Experience from Livorno

★★★★★★★★★★5.0 · 5 reviews · 8 hours (approx.) · from $248

Meet your English-speaking driver at the Livorno cruise port for an eight-hour private trip to Florence and the Chianti hills. Drivers including Andrew and Andreas tailor the city visit to your pace, then take you to a Tuscan farm for five wine tastings, including Chianti, Riserva, white wine, and Super Tuscan varieties.

“Our private tour began with easy pick up from our Livorno cruise ship terminal. Met by our guide/driver Andreas right on time, we headed to Florence via a very scenic route, passing fields of sunflowers and through the picturesque Tuscan hills. We arrived in Florence, stopping at a beautiful overlook of the city. We proceeded into the city center, parked the van, and headed out for our walking tour. We covered all the sights from the exterior as we did not have enough time to do the Uffizi Gallery, etc. we had read about the amazing sandwiches at Allantico… lived up to the hype!! After lunch we headed up to…”

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9.Private tour from Livorno port to Chianti Wine Region

★★★★★★★★★★5.0 · 5 reviews · 9 hours (approx.) · from $591

From Livorno port, your private English-speaking driver takes you through the Tuscan countryside to San Gimignano, then toward Chianti for views, photo stops, and an optional winery visit. Soni, Sonny, or Aldo may adapt the day to your ship schedule and interests. Lunch and wine tasting cost extra, and one winery accepts cash only.

“Soni was a phenomenal tour guide!! He has a clear sign for picking us up at port. The van was comfortable and air conditioned. He chatted with us and knew so much about the region. We loved getting to know him. He adjusted our tour path when we said other cities we were interested in so we could see them. He worked on our timeline. He gave us great recs on the best views and shops! Can’t say enough good things about the experience!”

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10.Private Chianti and SuperTuscan Tour 2 wineries with Light Lunch from Livorno

★★★★★★★★★★4.5 · 5 reviews · 7 hours (approx.) · from $490

Leave Livorno by private, air-conditioned minivan and spend about five hours among Chianti wineries and farms. You will visit two estates, taste wine at both, meet an owner, learn about cheese making, and enjoy a light lunch. Guides including Massimo, Matea, and Michel have led highly praised outings.

“They stopped at the Capponi winery was fabulous. The host was gracious gave us a great tour of the facility and a wonderful understanding of their wines. She then had us taste six different wines and provided some like snacks to go along. A fabulous opening act. I wish I could say the same about the second. Prior to going I asked if the experience was suitable for my wife who uses a walker. I was assured it was. Upon getting there the hostesses who were quite gracious asked if we wanted to skip the tour because of her disability and go directly to eating lunch. We indicated you know…”

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11.Florence & Pisa Shore Excursion with Chianti Wine Tasting

★★★★★★★★★★5.0 · 4 reviews · 9 hours (approx.) · from $440

You’ll travel privately from Livorno to Pisa, Florence, and San Michele a Torri with an English-speaking driver. See the Field of Miracles, Florence’s main squares, and Piazzale Michelangelo, then taste Chianti wines, local meats, and olive oils at a family winery. Guide Sarah can also help shape your limited time in Florence.

“Sarah our guide was wonderful, she knew without limited time in Florence and Pisa all of the highlights and took us to the most picture worthy spots. She made reservations for lunch at a delightful little off the beaten path restaurant that was delicious and very old-world which was perfect. All in all she helped solidify our love of Italy and would request her again she was that good. It was like touring the city with a friend that new were all the best places were hidden. I hope to see her again she was a treasure. The family winery was a must see as well the wine, meats and…”

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12.Siena, San Gimignano & Chianti Wine Excursions

★★★★★★★★★★5.0 · 3 reviews

Travel from Livorno by air-conditioned minivan to San Gimignano and Siena, then stop at a Tuscan farm for two wine tastings. Guide Massimo is praised for his humor, local advice, photo stops, and well-paced touring. Lunch is not included, and the wine tasting costs €30 per person.

“This tour was the absolute best we did & the highlight of our trip! Both villages are incredibly pretty & unique. Great shopping too. We shopped in San Gimignano, had an amazing lunch at a family owned & operated restaurant in Siena. Then the winery tasting ith Antipasto was divine. Our driver Massimo was so funny, knowledgeable and had all the best advice to make it a sensational day for us. He gave us plenty of time at each place to explore & stopped along the way for photos etc. Nothing was too much trouble and he entertained us tge whole way. Do yourself a favour and do this tour…”

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13.Pisa, Lucca and wine experience Private Day Trip

★★★★★★★★★★5.0 · 3 reviews · from $416

Spend about eight hours with a private driver and tour leader visiting Pisa and Lucca from Livorno. See the Leaning Tower, cathedral sights, Lucca’s San Martino and San Michele churches, Via Fillungo, and Amphitheatre Square, then stop at a winery. Massimo is named as one guide associated with the experience. Wine tasting costs extra.

“Massimo was a wonderful guide for our day in Pisa and Lucca. We also had a stop at a winery that we found so very enjoyable.”

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14.San Gimignano and Winery Experience with Lunch from Livorno

★★★★★★★★★★5.0 · 3 reviews · 7 to 8 hours (approx.) · from $204

Travel from Livorno to San Gimignano and two Tuscan wineries in a small group with an English-speaking driver. You will have time for town views, shops, gelato, Chianti and Super Tuscan wines, extra-virgin olive oil, and a local lunch of cheese, ham, salami, and other fresh products. Cruise-port pickup and return are included.

“I have used a lot of drivers in Tuscany but hands down Maximo was the best. Everything was perfect. I was concerned about lunch and left it to them. They told me it would be a light lunch it was a five course meal with pairings. Wineries were all different but all deserve 5 stars. Never rushed beautiful day and lots of fun with Maximo.”

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15.Private San Gimignano Wine Tour from Livorno Port

★★★★★★★★★★5.0 · 3 reviews

Leave Livorno Port with Enzo Dellaria in a private Mercedes car or minivan for a nine-hour day in San Gimignano and Volterra. Expect guided walks, medieval towers, alabaster buildings, cathedral art, Tuscan countryside views, and the option to add wine or cheese tasting. Lunch and tasting fees cost extra.

“Wonderfull tour of san gimignano and volterra. Enzo was punctual and very knowledgeable during the tour. the wine tasting was great and the views of san gimignano during it were breathtaking. san gimignano and volterra towns are also breathtaking and well worth visiting. overall we had a fantastic day enjoying the tuscan countryside and towns. thanks again Enzo!”

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