Private Tuscany Shore Excursion: Vineyard Lunch, Wine & San Gimignano
Visit two family-run vineyards and enjoy free time in a medieval hilltop town, with port pick-up inc
If you'd rather spend your port day eating well and sipping wine than fighting crowds in Florence, this tour is for you. Your private guide and driver take you straight into wine country from Livorno, with no city traffic in sight. San Gimignano's medieval towers give you the culture fix, then a farmhouse lunch with olive oil and local wine slows everything down. A family-run vineyard rounds out the afternoon with one more tasting. This is Tuscany at its most relaxed, all from the port.
What You Get With This Tour
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Slow down in the Chianti hills
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Expert English-speaking guide
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Private vehicle and driver
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Port pickup and drop-off
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Free time in San Gimignano
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Farmhouse lunch and olive oil tasting
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Wine tasting at 2 estates
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Vineyard tour
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Private experience
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Guide tips
Tour Itinerary
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1
Your tour begins at the port of Livorno
Look for your guide and driver waiting dockside as you step off the ship. Settle into your private vehicle and watch the port give way to rolling Tuscan hills as you head inland. -
2
Wind through the heart of Chianti
The drive through the Chianti wine region is half the experience. Vineyards line the road in every direction, olive trees silver the hillsides, and your guide fills you in on why this stretch of Tuscany has been making poets and painters dizzy for centuries. -
3
Explore San Gimignano's medieval streets
Your guide walks you through the story of San Gimignano, a hilltop town where 14 medieval towers still pierce the sky, and the historic center has earned a spot on the UNESCO World Heritage list. After the intro, the town is all yours to explore. -
4
Taste olive oil and sit down to a farmhouse lunch
At a family-run organic farmhouse, you’re welcomed in for an olive oil tasting before a long, unhurried lunch. Antipasto, pasta, regional wine, and a sweet finish - this is the Italian slow food at its best. -
5
Tour an organic vineyard and taste more wine
Your second winery of the day takes a different approach, with biodynamic and organic methods that produce wines unlike anything in the average glass. Tour the estate, learn the process, and taste your way through the results. -
6
Your tour ends at the port of Livorno
Your driver gets you back to the cruise terminal with time to spare. It's been a full day of towers, tastings, and Tuscan wine, the kind that makes the ship feel very far from Chianti.
Additional Information
Discover what to expect, what's included, and everything you need to know before booking.
Good to know:
Accessibility: As this is a private tour, the itinerary can be accommodated to be wheelchair or mobility accessible. Please contact us in advance, after making the booking, to make the proper arrangements.
Please note: The itinerary of a private tour can be adjusted to your needs. Please reach out if you do not see a start time that fits for your party. We would be happy to check with our ticketing team to see if we can accommodate you.
Alcohol consumption: This tour includes wine tastings; participants should be of legal drinking age in Italy (18). Please bring a government-issued ID if you plan to partake.
Dietary restrictions: Please contact us in advance with any dietary restrictions so we can best accommodate your needs.
Your 9-hour tour includes:
Expert English-speaking guide
Private vehicle with a dedicated driver
Port pickup and drop-off at Livorno cruise terminal
Visit to San Gimignano with a guided introduction
Free time in San Gimignano
Organic farmhouse lunch with olive oil tasting
Wine tasting at a Chianti farmhouse
Guided tour and wine tasting at biodynamic vineyard
What to bring:
Comfortable walking shoes
Camera
Water bottle
Valid ID
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Customer Reviews
This was a top cruise day trip! Our private driver made it easy to get from cruise port to the Tuscan gems. The San Gimignano towers were stunning, the farm to table lunch was delicious, and the wines was poured freely. All the details were covered perfectly. We definitely felt pampered and full by the end when we were brought back to our ship. Thank you Flavia and The Tour Guy!
Walking through the streets of San Gimignano was lovely. We saw famous places and also quiet areas. It felt real and not rushed like some tours can be.
From ship to Chianti farms with San Gimignano the stop everything was great.! Wandered the towers and shopped a bit. Lunch and tastings were mouthwatering. Relaxed return to port. Ideal for couples or families, highly recommend.
Frequently Asked Questions
What to bring?
Since you will be walking around for much the day so wear comfortable shoes and bring sunscreen in the summer.
What if I don't see availability on the day I want to go?
Just reach out to us and we will try our best to accommodate your scheduling needs.
Is the cost of lunch and wine included in the price?
While a wine tasting and lunch is included in the tour price, we do not provide additional food and drink in San Gimignano.
What if my ship isn't docking in Livorno?
If you aren't docking in Livorno, just reach out to us via email or toll-free number. We'd still like to provide you with an unforgettable experience in Tuscany.
How many people can I bring?
If there are more than seven people in your group, please contact us prior to booking so we can sort out the details.
How do we arrange the timing of this shore excursion?
Please reach out to us upon booking to provide the exact time you'll disembark from your ship and we'll take care of the details.
What to bring?
Since you will be walking around for much the day so wear comfortable shoes and bring sunscreen in the summer.
Is this tour family-friendly?
Yes, this tour is a great fit for families. The pace is relaxed, with scenic drives, free time to explore San Gimignano, and a leisurely farmhouse lunch. Children are welcome, though please note the wine tastings are intended for guests aged 18 and over.
What if I have concerns about my mobility on this tour?
As this is a private tour, the itinerary can be adjusted to accommodate wheelchair or mobility needs. Please contact us after booking to make the proper arrangements.
Do you cater to dietary restrictions?
Please contact us in advance with any dietary restrictions or allergies, and we'll do our best to accommodate.
