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.
Slow down in the Chianti hills
Expert English-speaking guide
Private vehicle and driver
Port pickup and drop-off
Free time in San Gimignano
Farmhouse lunch and olive oil tasting
Wine tasting at 2 estates
Vineyard tour
Private experience
Guide tips
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.
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.
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.
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.
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.
For Reference Only. Itineraries are subject to change
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Start times are in the product’s local time
Free cancellation up to 7 days in advance!
Mon, 30 Mar 2026
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4.88
151 Ratings
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Eloise F.
Verified Review
January 22, 2026
Amazing Full Day Trip During Our Cruise
Tanish B.
Verified Review
January 22, 2026
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!
Lovely Streets
Zachary P.
Verified Review
January 10, 2026
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.
Matheo D.
Verified Review
January 09, 2026
Farm Wine Fiesta
Luisa B.
Verified Review
December 29, 2025
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.
Archer K.
Verified Review
December 28, 2025
Family Friendly
Aurora A.
Verified Review
December 17, 2025
We did this with our family and everyone enjoyed it. The kids stayed interested and the adults felt relaxed. It was a nice mix of learning and just enjoying the countryside of Chianti.
Ridhi E.
Verified Review
December 16, 2025
Chianti Charm Burst
Dev B.
Verified Review
December 06, 2025
Fantastic private shore day. Seamless from Livorno port through hills to San Gimignano. Towers and streets perfect for exploring. Farmhouse wines olive oil and lunch hit all right notes.
Imogen K.
Verified Review
November 25, 2025
Gimi Towers Glory
Arthur K.
Verified Review
November 24, 2025
Loved the whole flow of this excursion. Port to Tuscany in luxury ride. San Gimignano charmed with its history. Wine tour lunch combo at the farm was delicious beyond words.
Sweet Memory
Sara M.
Verified Review
November 12, 2025
This experience gave us sweet memories of Tuscan. We talked about it even after getting back to the ship. It was a lovely part of our trip.
Nice Balance
Stella B.
Verified Review
November 01, 2025
There was a nice balance between walking listening and free time. We never felt bored or overwhelmed.
Comfort All Day
Aliyah S.
Verified Review
November 01, 2025
Luxury transport made the tour super comfortable. Our driver took care of every detail. We just enjoyed the ride and the beautiful scenery.
Aliyah J.
Verified Review
November 01, 2025
Wine Country Wow
Philipp A.
Verified Review
October 20, 2025
This tour exceeded hopes. Driver got us from the ship quick then headed to San Gimignano's towers. Free time there was great for pics. Chianti farm offered tasty lunch and plenty of wine sips. Private and wheelchair friendly too. What a gem.
Christian W.
Verified Review
October 18, 2025
Tasty Olive Oil
Aarav W.
Verified Review
October 17, 2025
Tried the best olive oil I’ve ever had in my life! Learned how it’s made and enjoyed dipping fresh bread. A tasty and fun moment.
Aarav H.
Verified Review
October 16, 2025
Wonderful Lunch
Avani S.
Verified Review
October 13, 2025
Lunch under the trees felt dreamy. Everything on the table was made with love.
Avani Z.
Verified Review
October 10, 2025
True Tuscan Adventure
Felix L.
Verified Review
October 09, 2025
Every stop was fascinating. The medieval towers, stunning countryside, and delicious wines made it a real adventure. So glad we joined this group!
Gentle Day
Fletcher S.
Verified Review
October 08, 2025
This felt like a gentle day out instead of a busy tour. Perfect for older travelers and families who want to enjoy without rushing.
Excellent Plan
James M.
Verified Review
October 05, 2025
The tour had the right balance of rest and exploration. Never felt rushed.
