Florence & Tuscany Day Trip from Rome: High-Speed Train, Winery Lunch

Summary

Florence’s art-filled streets, Tuscan hills, family winery lunch and medieval towers in one day

You’ll step straight into Renaissance Florence before heading for a family-run Tuscan winery for lunch and wine tasting—all packed into one full day from Rome by high-speed train. Walk medieval San Gimignano’s lanes, taste fresh olive oil under open skies, and end your day tired in the best way possible.

What’s the experience like?

I’ll be honest—I almost skipped this Florence & Tuscany day trip from Rome because I thought it’d feel rushed. But there’s something about stepping off that high-speed train into Florence that wakes you up—like the city itself is stretching after a nap. Our guide, Chiara, was waiting right there at the station with this big grin, and somehow she made even the crowds around the Duomo feel like part of the show instead of an obstacle. The bells echoed off old stone and for a second I forgot about time tables or train tickets—just watched the light hit Brunelleschi's dome. I didn’t expect to laugh so much either; Chiara had stories about Michelangelo that made him sound more like someone’s stubborn uncle than a genius sculptor.

After wandering those tangled streets (and yes, Ponte Vecchio really does smell faintly of leather and river), we piled into a van and suddenly Florence was behind us. The drive out to the winery felt like flipping pages in a picture book—vineyards, olive groves, those cypress trees that look painted on. At the hilltop winery, the owners greeted us with handshakes and their dog immediately adopted me as her new best friend. We tasted five wines paired with salty prosciutto and bread still warm from the oven; I tried to take tiny sips but failed spectacularly. There was olive oil so green it looked fake, but tasted like sunlight and grass. Lunch was simple but somehow perfect—maybe it was just eating outside with strangers who suddenly felt like friends.

San Gimignano came next—a jumble of towers against blue sky. Our guide led us through narrow lanes where laundry flapped above our heads and locals argued (loudly) over espresso. Someone pointed out “the world’s best gelato” shop—I won’t argue, but my cone melted faster than I could eat it. By then my feet were tired but my head was buzzing in that good way you get after a long day outside your usual orbit. The ride back to Florence was quiet; most people dozed off or stared out at the fields rolling by. I kept thinking about that view from the winery terrace—the kind you try to memorize but never quite manage.

Step-by-step itinerary

Day 1 — Florence and Tuscany day tour

• Meet representative at Rome Termini
• Board high-speed train to Florence
• Arrive at Florence Train Station
• Guided walking tour of Florence landmarks
• Break in Florence
• Travel by van through Tuscan countryside
• Visit family-run hilltop winery
• Wine tasting and light lunch
• Drive to San Gimignano
• Guided walk and free time in San Gimignano
• Return to Florence Train Station by van
• Board train back to Rome

Top questions

How long is the Florence & Tuscany day trip from Rome?

The tour lasts a full day including travel by high-speed train between Rome and Florence.

Is lunch included on this tour?

Yes, a light lunch is included at a family-run winery in Tuscany along with wine tasting.

Do we have free time in San Gimignano?

Yes, after a short guided walk you’ll have free time to explore San Gimignano on your own.

How do we travel between Rome and Florence?

You’ll take a high-speed train both ways between Rome Termini Station and Florence.

Are entry fees or tastings included?

The winery tour includes tastings of five wines plus local meats, cheeses, breads, and olive oil—all included.

Is hotel pickup available?

No hotel pickup is included; you meet at Roma Termini Station in Rome for departure.

Is this tour suitable for travelers with limited mobility?

No, due to transportation logistics this tour isn’t accessible for wheelchairs or scooters.

Will there be a local guide throughout?

Yes, you’ll be accompanied by an expert local guide during your walking tour of Florence and visits in Tuscany.

What’s included

Your day includes round-trip high-speed rail tickets from Rome to Florence, guided walking tour of historic Florence with an expert local guide, private air-conditioned coach transport through Tuscany to San Gimignano and back, entry to a family-run hilltop winery for wine tasting paired with light lunch (local meats, cheeses, breads, olive oil), plus free time to wander San Gimignano before returning by train in the evening.