The port city of Livorno serves as an ideal gateway to Tuscany’s finest wine regions. While most cruise visitors head straight to Florence or Pisa, savvy travelers use Livorno as a launching point for exceptional wine experiences. The standout tours head to Bolgheri, where prestigious Super Tuscans reign supreme, and the classic Chianti region, home to Italy’s famous red blend.
I’m especially fond of the family-run winery tours in Bolgheri, where you’ll often meet the winemakers themselves and taste wines that rarely make it to export. The half-day Chianti countryside tours offer great value, combining wine tastings with stunning views of cypress-lined hills and medieval villages.
For smart travel planning, check our carefully selected wine tours below, rated for quality and authenticity.
Key Points
- Terre del Marchesato Winery offers classic and premium wine tastings with guided tours, featuring acclaimed wines and excellent traveler recommendations.
- Agricola Tamburini Winery provides a private wine tasting experience with a family-owned winery, praised for exceptional wine quality and accessibility.
- Private tours from Livorno port offer flexible itineraries, including wine tastings in Chianti, Volterra, and San Gimignano, with high customer satisfaction.
- Specialized wine tours explore Tuscany’s top wine regions, such as Bolgheri, and include activities like pasta making and gelato sampling.
- Livorno offers various transportation options for wine tours, including private driver-led tours, providing flexibility, accessibility, and personalized experiences.
Bolgheri: Classic Wine Tasting With Winery Tour
Located in the picturesque Tuscan region, the Terre del Marchesato Winery offers visitors a delightful classic wine tasting experience with a guided tour of their historic grounds.
Founded in the 1950s, the winery has earned a reputation for excellence, boasting a Badge of Excellence and an impressive 93% traveler recommendation based on 282 reviews.
During the tour, guests can expect to explore the winery’s cellars and grounds while sampling a selection of their acclaimed wines, including the PAPEO DOC Bolgheri Bianco, the EMILIO PRIMO DOC Bolgheri Rosso, and the MARCHESALE DOC Bolgheri Superiore.
The tasting is accompanied by a light snack of bread and extra virgin olive oil, complementing the flavors of the wines. Knowledgeable, multilingual guides lead the experience, providing insightful information about the winemaking process and the region’s rich viticultural heritage.
With convenient daily tour times, wheelchair accessibility, and a flexible cancellation policy, the Terre del Marchesato Winery offers a true taste of Tuscan hospitality and a must-visit destination for any wine lover exploring the Livorno area.
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From Livorno: Siena, San Gimignano & Chianti Wine Excursions
This tour is priced at €760.00 per group (up to 4 participants) and offers free cancellation up to 24 hours in advance.
While not suitable for those with mobility impairments, the excursion promises a memorable exploration of Tuscany’s rich cultural and wine heritage.
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Bolgheri: Premium Wine Tasting With Winery Tour
Tucked within the prestigious Bolgheri wine country of Tuscany, the Terre del Marchesato winery offers a premium wine tasting and tour experience.
With a Badge of Excellence and 94% of travelers recommending the tour, this family-run winery is known for its monovarietal wines. The tour includes a guided exploration of the vineyards and cellars, providing insights into the winery’s history and production methods.
Guests can sample the estate’s premium wines, including Cabernet Sauvignon, Cabernet Franc, Merlot, and Petit Verdot, as well as taste the region’s renowned extra-virgin olive oil.
The experience is complemented by food pairings of bruschetta and EVO oil. The tour can be booked in advance for morning or afternoon options, with transportation provided to and from the meeting point.
The winery is wheelchair and stroller accessible, accommodating up to 16 travelers.
While the overall experience is highly rated, some reviews indicate a desire for more in-depth explanations during the tastings.
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Shore Excursion From Livorno: Tuscan Villages & Chianti Wine
Departing from the port of Livorno, this shore excursion takes visitors on a captivating journey through the picturesque Tuscan countryside and the renowned Chianti wine region.
Over the course of 8 hours, travelers will explore the historic villages of the Chianti area, soaking up the charming atmosphere and admiring the rolling hills dotted with vineyards.
The highlight of the tour is a visit to a traditional Chianti winery, where guests can learn about the winemaking process and indulge in a delightful wine tasting experience.
Accompanied by a knowledgeable guide, the tour offers an opportunity to discover the unique flavors and rich history of the Chianti wines.
With pickup and drop-off from the Livorno cruise port, this shore excursion provides a seamless way to take in the beauty and culinary delights of the Tuscan region.
Priced at $70.96 per person, it’s an ideal choice for those seeking an enriching and memorable day away from the port.
Read our full review: Shore Excursion From Livorno: Tuscan Villages & Chianti Wine Review
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Bolgheri: Sensorial Wine Tasting With Winery Tour
Nestled within the picturesque Bolgheri region, the Terre del Marchesato winery invites visitors to embark on a sensorial wine tasting journey. This highly-rated experience, boasting a 100% recommendation rate, offers a unique opportunity to explore the world of Italian viticulture.
The tour begins with a walking exploration of the winery’s historic vineyards, where guests learn about grape cultivation and the influential terroir.
Next, the guided sensorial tasting showcases three of the winery’s acclaimed wines: the Vermentino white, Cabernet Sauvignon red, and Merlot red. Accompanied by bruschetta drizzled with the estate’s own extra-virgin olive oil, the tasting is further enhanced by the use of printed cards and an aroma kit.
Accessible to all, this experience can accommodate up to 16 travelers and includes professional guidance, transportation, and all alcoholic beverages.
With a free cancellation policy and a reserve now, pay later option, the Bolgheri sensorial wine tasting is a must-try for oenophiles visiting the Livorno region.
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From Livorno: Siena and Chianti Day Trip With Wine Tasting
This day trip from Livorno offers travelers a chance to explore the UNESCO-listed town of Siena and the renowned Chianti wine region.
Priced from Kč 11,271 per person, the 8-hour small-group tour (limited to 8 participants) takes visitors through Tuscany’s scenic hills.
After visiting Siena’s Piazza del Campo and Gothic Cathedral, the tour continues to a local winery where guests can learn about winemaking and enjoy tastings.
The trip includes transportation, with pickup and drop-off at the port, as well as a knowledgeable guide who provides insights into Siena’s artistic and cultural heritage, including the annual Palio horse race.
Foldable wheelchairs can be accommodated with assistance.
The tour offers free cancellation up to 24 hours in advance for a full refund, and a reserve now & pay later option is available.
Read our full review: From Livorno: Siena and Chianti Day Trip With Wine Tasting Review
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Wine Tour Experience at Agricola Tamburini
Visitors looking to enjoy Tuscany’s renowned winemaking traditions can embark on a private wine tasting experience at Agricola Tamburini Emanuela, a family-owned winery located just a short drive from Livorno.
This intimate tour blends the family’s time-honored methods with modern techniques, allowing guests to sample prestigious Tuscan wines and extra virgin olive oil. During the experience, participants can discuss wine production with the winemakers and learn about the winery’s storied history.
With 100% of travelers recommending this activity, the wine tasting at Agricola Tamburini Emanuela promises an unforgettable glimpse into Italy’s renowned viticulture.
Booking is straightforward, with instant confirmation and flexible cancellation policies. Transportation to the winery is included, and the experience is accessible to most visitors, though strollers and service animals are allowed.
Reviews consistently praise the exceptional quality of the wines and the warmth of the family’s hospitality.
Read our full review: Wine Tour Experience at Agricola Tamburini Review
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Pisa and Florence Private Tour With Wine Tasting
Travelers seeking to explore the renowned landmarks of Pisa and Florence can embark on a private tour that also includes a picturesque wine tasting experience in the Chianti hills.
The tour provides round-trip private transportation, allowing visitors to relax and take in the scenic Tuscan countryside along the way. Highlights include the iconic Leaning Tower of Pisa and the architectural masterpieces of Florence, as well as a delectable lunch at a local restaurant.
The private wine tasting in the Chianti hills offers an opportunity to savor the region’s renowned vintages. The tour is equipped with luxury executive vehicles, air conditioning, and onboard WiFi, ensuring a comfortable and convenient experience.
Wheelchair-accessible transportation is available, and infants can participate by sitting on laps. With a 100% recommendation rate and an overall rating of 4.9/5 stars, this private tour is an excellent choice for those seeking to enjoy the rich cultural and culinary tapestry of Pisa, Florence, and the Chianti region.
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Private Tour From Livorno Port to Chianti Wine Region
After disembarking at the Livorno port, travelers can embark on a captivating private tour that whisks them away to the renowned Chianti wine region.
This 5-star rated experience includes a scenic drive through the picturesque countryside, and free time to explore the charming town of San Gimignano at their own pace.
The tour offers the flexibility to include lunch or a wine tasting at a local winery, at an additional cost.
Travelers will enjoy the comfort of a Mercedes-Benz and the personalized attention of a dedicated driver/guide, who can tailor the itinerary to their preferences.
With a moderate fitness level required, the tour is also wheelchair accessible.
Positive reviews highlight the tour’s breathtaking views, exceptional wine and food, as well as the knowledgeable and accommodating guides.
This private excursion from the Livorno port provides a seamless and unforgettable way to take in the rich wine culture of the Chianti region.
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PRIVATE EXCURSION: Volterra & San Gimignano + Wine Tastings (From Livorno Port)
With a private excursion from the Livorno port, guests can embark on a captivating journey through the Tuscan countryside.
The tour offers visits to the historic centers of Volterra and San Gimignano, as well as an immersive experience at a traditional Tuscan farm, complete with a three-course lunch and five Chianti wine tastings.
Highlights include exploring the medieval charm of Volterra, savoring a Tuscan feast featuring homemade pasta, Pecorino cheese, and olive oils, and concluding the day with a stroll through the UNESCO-listed town of San Gimignano, where guests can indulge in a gelato tasting.
The tour includes private transportation with an English-speaking driver, bottled water, and ample time to return to the cruise ship.
Rated 5.0 out of 5 stars, this private excursion promises an authentic Tuscan experience, showcasing the region’s rich history, culinary delights, and world-renowned wines, all at a price of $282.60 per person, subject to group size.
Read our full review: PRIVATE EXCURSION: Volterra & San Gimignano + Wine Tastings (From Livorno Port) Review
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Bolgheri Wine Tour From Livorno
Embark on an extraordinary wine-centric adventure from the Livorno port with the Bolgheri Wine Tour. This private shore excursion takes you through Tuscany’s top villages and wine country, offering a chance to explore historic Volterra, stroll through the charming Bolgheri village, and savor the region’s renowned wines.
The tour includes a stop at a family-owned winery for a tasting, where you’ll sample Tuscan wines paired with local specialties. Along the way, you’ll enjoy scenic coastal drives and a brief stop in Castiglioncello for a refreshing gelato.
With private transportation and English commentary, the tour provides a seamless and personalized experience.
The Bolgheri Wine Tour is priced at $921.07 per group (up to 8 people) and features free cancellation up to 24 hours before the experience. Although not wheelchair accessible, the tour offers stroller and infant seat options, catering to the needs of all travelers.
With a 5.0 rating based on 2 reviews, this tour promises an unforgettable journey through Tuscany’s wine country.
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Exclusive Pisa and Wine Tour
This exclusive Pisa and Wine Tour offers a captivating blend of history, culture, and the renowned wines of the Tuscan region. Departing from Livorno, this private tour takes visitors on a journey to the iconic Leaning Tower of Pisa and a renowned local winery.
Guests will enjoy the comfort of a luxury executive Mercedes car or minivan, complete with air conditioning and bottled water. The knowledgeable driver-guide will provide live commentary throughout the tour, sharing insights into the history and architecture of Pisa.
After exploring the iconic landmark, the tour continues to a local winery for a guided wine tasting and a delicious lunch. This all-inclusive experience is perfect for those looking to enjoy the rich cultural and culinary traditions of the region.
With a maximum of 3 people, this private tour ensures a personalized and exclusive experience. However, it’s important to note that the tour isn’t wheelchair accessible and may not be suitable for certain medical conditions.
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Private San Gimignano Wine Tour From Livorno Port
Departing from the Livorno Port, this private wine tour takes visitors on an enchanting journey through the picturesque Tuscan countryside.
The tour includes multi-stop visits to the historic towns of San Gimignano and Volterra, where travelers can explore the architectural marvels and indulge in local delicacies.
Guests will travel in a luxury executive Mercedes car or minivan, equipped with air conditioning and onboard WiFi for easy photo uploads.
The tour’s highlights include a walking tour of San Gimignano’s iconic towers, and tastings of Volterra’s renowned ice cream, cheese, or wine.
Conveniently, the tour includes hotel or port pickup and drop-off, as well as bottled water, lunch, and optional wine, cheese, or truffle tastings.
The tour is wheelchair accessible and suitable for most travelers, with confirmation received within 48 hours of booking.
Priced at $900.13 per group (up to 7 people), this private wine tour has received a perfect 5.0-star rating from previous guests.
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Tuscany Countryside From Livorno: Private Volterra, San Gimignano & Wine Tasting
Explore the picturesque Tuscan countryside on this private tour from Livorno. Your journey will take you to the charming medieval towns of Volterra and San Gimignano, with a stop for wine tasting along the way.
Travel by air-conditioned minivan with an English-speaking driver, who’ll provide flexibility and personalized attention throughout the day.
In Volterra, you’ll discover the town’s impressive Etruscan heritage and Roman ruins. Then, venture to the hilltop town of San Gimignano, known for its striking skyline of medieval towers.
Enjoy a Tuscan-style lunch, and for an additional €30, partake in a wine tasting at a local vineyard.
This tour isn’t wheelchair accessible but can accommodate strollers and infants. With a starting price of $350.63 per person and free cancellation up to 24 hours in advance, it’s a flexible and hassle-free way to explore the Tuscan countryside from Livorno.
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Livorno Shore Excursion: Pisa, Lucca and Wine Experience Private Day Trip
For cruise passengers seeking to experience the highlights of Pisa, Lucca, and Tuscan wine, this private day trip from Livorno offers a tailored and hassle-free excursion.
Designed around cruise schedules, the tour includes pickup and drop-off at the port, as well as visits to the iconic Leaning Tower of Pisa, Pisa Cathedral, Lucca Cathedral, Amphitheatre Square, and a local winery.
Travelers will be transported by air-conditioned minivan and accompanied by a knowledgeable driver/tour leader. While wine tasting at the winery is an optional extra cost, the tour includes a lunch stop, ensuring a well-rounded experience.
With a maximum of just your group, the private format provides a more personalized adventure compared to large bus tours.
Recent reviews praise the tour’s blend of top sights and Tuscan wine, as well as the guide’s expertise and engaging personality.
For those seeking an efficient yet immersive shore excursion from Livorno, this private day trip promises an enjoyable and memorable experience.
Read our full review: Livorno Shore Excursion: Pisa, Lucca and Wine Experience Private Day Trip Review
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Wine Tour Bolgheri Half Day Shore Excursion From Piombino Port
Whisked away from the Piombino Port, travelers embark on a captivating half-day shore excursion to the charming villages of Bolgheri and Castagneto Carducci.
The private driver-led tour offers convenience, allowing guests to explore at their own pace while taking in scenic views of the famous Cypress Avenue and medieval Bolgheri.
In Bolgheri, visitors enjoy free time for sightseeing and lunch, with opportunities for shopping and local dining.
The tour then continues to Castagneto Carducci, where guests can visit the home of renowned poet Giosuè Carducci.
While the driver provides commentary, they aren’t licensed guides, so museum and monument entry is self-guided.
The tour includes air-conditioned minivan transport, port pickup and drop-off, and free Wi-Fi.
Wine tastings are available for an additional €35 per person.
With a 5.0 rating from previous travelers, this excursion is priced at $788.59 per group, allowing up to 8 participants.
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Private Pisa, Pasta and Chianti Lovers Wine Experience Livorno Shore Excursion
As travelers disembark at the Port of Livorno, they embark on a private guided shore excursion that immerses them in the quintessential Tuscan experiences of Pisa, pasta, and Chianti wine.
The tour begins with a visit to the iconic Leaning Tower of Pisa, a UNESCO World Heritage Site. Next, participants explore a pasta factory, learning the art of traditional Italian pasta making.
The experience culminates with a tasting lunch at a local winery, where they can savor the flavors of Chianti. The excursion is tailored to the cruise schedule, with guaranteed refunds for delays and free transport to the next port if the departure is missed.
Priced from $328.65 per person, the tour offers exceptional value, as evidenced by the 5.0 rating from previous travelers who praised the personal service, unique experiences, and exceptional food and wine.
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Florence and Wine Tasting Private Tour From Livorno
Travelers seeking to explore the charms of Florence and indulge in the rich winemaking traditions of Tuscany can embark on a private day trip from the port of Livorno.
This 5-star tour offers round-trip transport and a winery stop in the Tuscan hills, providing a seamless and flexible experience. The tour includes time-saving transport from the cruise ship, a back-to-port guarantee, and an English-speaking driver offering commentary throughout the journey.
The highlight of the tour is the opportunity to enjoy a Tuscan wine tasting and light lunch at a local winery, which can be added for an additional 60 Euros per person.
This break in the return drive allows travelers to savor the flavors of the region. The tour features a private air-conditioned vehicle, accessibility for infant seats, wheelchairs, and strollers, as well as the convenience of free cancellation up to 24 hours before the experience.
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Full-Day Pisa Private Guided Tour With Visit to Local Wine Farm
Though the charm of Florence may beckon, this full-day private tour from Livorno offers a captivating opportunity to explore the historic city of Pisa and indulge in the rich winemaking traditions of the Tuscan countryside.
Guests are picked up from the Livorno Port Center at 9:00 AM and whisked away to witness the iconic Leaning Tower of Pisa, with the option to climb to the top for stunning views. After an hour in Pisa, the tour ventures into a quaint village, where travelers can discover a local castle and a family-run pasta-making company.
The highlight of the day, however, is the wine experience at a nearby winery. Guests are treated to a light lunch and a chance to savor the region’s finest vintages.
With private transportation and personalized attention from knowledgeable guides, this tour promises an intimate and unforgettable journey through Pisa and the Tuscan wine country.
Travelers are advised to secure pricing for the wine tasting and meals in advance to avoid any surprises.
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Wine Tour Bolgheri Half Day Shore Excursion From Livorno Port
This half-day shore excursion from Livorno Port offers wine enthusiasts an immersive exploration of the renowned Bolgheri wine region.
Guests can expect to visit the picturesque town of Bolgheri, known for its scenic Tuscan countryside. The tour includes a drive along the iconic Cypress Avenue, leading to the medieval center of the town, where participants can freely explore, shop, and dine.
The itinerary also features a visit to Castagneto Carducci, the home of celebrated Italian author Giosuè Carducci. For those interested, wine tastings are available for an additional €35, payable on-site.
The tour is conducted in a private, air-conditioned vehicle with complimentary Wi-Fi, and pickup and drop-off at the Livorno port are included. While the drivers provide commentary, they aren’t licensed guides and can’t enter museums or churches.
This half-day excursion is priced at $788.59 per group of up to 8 participants and can be booked with a free cancellation up to 24 hours prior to the start.
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Bolgheri Wine Tour & Extra Virgin Olive Oil Tasting Experience From Livorno
If you’re seeking an immersive experience in Bolgheri’s renowned wine and olive oil region, this private tour from Livorno is an excellent choice.
The tour includes visits to a winery and an olive grove, where you’ll have the opportunity to taste local wines and extra virgin olive oils. You’ll also explore the historic streets of Bolgheri and enjoy a refreshing gelato.
During the tour, you’ll travel from Livorno to Bolgheri, where you’ll visit the iconic Viale dei Cipressi for picturesque photographs.
The guided tour provides an in-depth look at the winemaking and olive oil production processes, allowing you to learn about the selection and appreciation of these local specialties.
With private transportation and the choice of two meeting times, this tour offers a convenient and personalized experience.
The tour has received exceptional reviews, with a perfect overall rating of 5.0 stars, indicating a high level of satisfaction among previous participants.
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The Sum Up
Livorno offers a variety of wine tours that cater to different preferences. Visitors can enjoy classic wine tastings, premium experiences, and sensorial explorations in the renowned Bolgheri region. Plus, they can combine wine tasting with visits to historic Tuscan villages, Pisa, and Florence. These tours provide a well-rounded experience, allowing travelers to enjoy the rich wine culture and scenic landscapes of the area.