Seven days across Tuscany — a Renaissance duomo and a private cooking class in Florence, medieval towers and a world-champion gelato in San Gimignano, a wine-country overnight at a working Chianti agriturismo, Siena’s shell-shaped piazza, the cypress-lined roads of the Val d’Orcia, and a leaning tower on the way home — with real hotels, real wineries, and 2026 prices for every stop.
Day 1Florence Arrival
A first afternoon in the Renaissance capital, arriving to a skyline still ruled by one red-tiled dome.
🚗 Rental Car Pickup — Florence Airport (FLR)
~20 minutes to the city center · from $55 USD / day
Florence’s small Peretola airport sits just north of the historic center — pick up the car now, but leave it parked for the next two days; the old town itself is walking-only, and the car only earns its keep once the trip heads into Chianti.
Europcar Florence Airport · europcar.com
🏛️ Piazza del Duomo & the Cathedral of Santa Maria del Fiore
~1.5 hours, self-guided · free to enter, ~$20 USD to climb the dome
Brunelleschi’s red-tiled dome, Giotto’s marble bell tower, and the Baptistery’s bronze doors, all facing one square in the heart of the old town — the obvious first stop, and worth returning to at dusk when the crowds thin out.
🍽️ Dinner — Trattoria near Santa Croce
~1.5 hours · $25–$35 USD / person
A first-night plate of bistecca alla fiorentina or pappa al pomodoro at one of the family-run trattorias tucked around Piazza Santa Croce, a few minutes’ walk from the Duomo.
🛎️ Overnight — Brunelleschi Hotel
From $220–$260 USD / night, for 2 people
A boutique hotel built around a 6th-century Byzantine tower and a medieval church, two blocks from the Duomo — one of the few hotels in Florence with its own private museum in the basement.
Brunelleschi Hotel · brunelleschihotelflorence.com
Day 2The Uffizi & a Florentine Cooking Class
A morning with the Medici’s art collection, an afternoon along the Arno, and an evening spent learning to cook the region’s food.
🖼️ Uffizi Gallery — Timed-Entry Tour
~2.5 hours, timed entry · ~$30 USD / person
Botticelli’s Birth of Venus, Michelangelo’s Doni Tondo, and room after room of Renaissance masterworks in the Medici family’s former administrative offices — book the timed slot in advance to skip the walk-up line, which can run over an hour in high season.
🌉 Ponte Vecchio & the Oltrarno
~1.5 hours, self-guided · free
Florence’s medieval bridge, lined with gold and jewelry shops that have traded there since the 16th century, then a wander into the quieter Oltrarno district on the far bank for leather workshops and artisan studios.
🍳 Market Tour & Cooking Class — Mama Florence
~4 hours · ~$110 USD / person
A morning-market walk through Mercato Centrale followed by a hands-on class making fresh pasta, a Tuscan main, and dessert in a home-style kitchen — a good introduction to the region’s food before a week of eating it.
Mama Florence · mamaflorence.com
🛎️ Overnight — Brunelleschi Hotel
From $220–$260 USD / night, for 2 people
A second night in the same tower-top rooms before the drive into the countryside tomorrow.
Day 3San Gimignano & the Chianti Hills
A medieval skyline of stone towers, the reigning gelato world champion, and a first night among the vineyards.
🚗 Drive — Florence to San Gimignano
~1 hour via the SR2 & SP1 · self-guided
A straightforward drive south through Chianti farmland, with the walled town’s 14 surviving medieval towers visible from the road long before the parking lots at its base.
🗼 San Gimignano Towers & Piazza della Cisterna
~2 hours, self-guided · free to walk, ~$5 USD to climb Torre Grossa
A hilltop town that once had 72 stone towers built by rival merchant families competing for status — 14 remain, and the climb up Torre Grossa gives the best rooftop view over the surrounding vineyards.
🍨 Gelato — Gelateria Dondoli
~30 minutes · ~$4–$6 USD / cone
The workshop of Sergio Dondoli, a multiple-time world gelato champion, on Piazza della Cisterna — the saffron and Vernaccia-wine flavors are the shop’s own inventions and worth the inevitable line.
Gelateria Dondoli · Piazza della Cisterna 4, San Gimignano
🍷 Chianti Wine Tasting — LivTours
~4 hours · ~$140 USD / person
A small-group afternoon at a family-run Chianti Classico vineyard, walking the cellar and tasting through several vintages paired with local cheese and cured meats.
LivTours · livtours.com
🛎️ Overnight — Agriturismo San Sano
From $160–$200 USD / night, for 2 people
A converted medieval hamlet in Gaiole in Chianti, with a pool overlooking the vineyards and its own small restaurant for a slower dinner than the day-trip crowds see.
Agriturismo San Sano · agriturismosansano.it
Day 4Siena’s Piazza del Campo
A shell-shaped medieval square, a striped marble cathedral, and a slow dinner before heading back to the vineyards.
🚗 Drive — Gaiole in Chianti to Siena
~45 minutes via the SR408 · self-guided
A scenic backroad south out of the Chianti hills into Siena, Florence’s historic rival city.
🏛️ Piazza del Campo & Siena Cathedral
~3 hours, self-guided · free for the piazza, ~$18 USD for the Duomo complex
A fan-shaped brick square that hosts the twice-yearly Palio horse race, ringed by cafes, and a striped black-and-white marble cathedral a few blocks up the hill with an inlaid marble floor rarely fully uncovered outside of a few weeks each year.
🍽️ Dinner — Il Campo
~1.5 hours · $30–$40 USD / person
A restaurant with outdoor tables directly on the Piazza del Campo itself — the view of the square at dusk is the draw as much as the Tuscan menu of pici pasta and grilled meats.
Il Campo · Piazza del Campo 50, Siena
🛎️ Overnight — Agriturismo San Sano
From $160–$200 USD / night, for 2 people
A second night back at the vineyard hamlet in Gaiole in Chianti, a short drive north of Siena.
Day 5Into the Val d’Orcia
A drive through the postcard hills south of Siena, and a hill-town evening built around a single ingredient: pecorino cheese.
🚗 Scenic Drive — Chianti to Pienza via the Val d’Orcia
~1.5 hours via the SR2 & SP146 · self-guided
The single most photographed stretch of road in Tuscany — golden wheat fields (or plowed brown earth, depending on season), lone farmhouses, and the winding cypress-lined driveways that appear on a thousand postcards, with pullouts near San Quirico d’Orcia for the classic shots.
🧀 Pienza Old Town & Pecorino Tasting
~2 hours, self-guided · ~$10–$15 USD for a tasting flight
A Renaissance “ideal city” commissioned by Pope Pius II, its main street lined with shops selling the region’s pecorino di Pienza sheep’s-milk cheese in every stage of aging, several offering tastings paired with local honey and jam.
🛎️ Overnight — Relais Val d’Orcia
From $170–$210 USD / night, for 2 people
A countryside hotel just outside Pienza with rooms looking straight out over the Val d’Orcia’s rolling wheat fields — the terrace at sunset is the reason to book a room with a view here rather than sleeping in town.
Relais Val d’Orcia · Pienza, Val d’Orcia
Day 6Montepulciano & the Hot Springs of Bagno Vignoni
A historic wine cellar built into a Renaissance palazzo, and an afternoon soak in water that’s been running hot since Roman times.
🍷 Wine Tasting — Cantina Contucci, Montepulciano
~1.5 hours · ~$20–$30 USD / person
A 13th-century palazzo cellar in the center of Montepulciano, still family-run, where Vino Nobile di Montepulciano ages in enormous oak barrels beneath frescoed ceilings — one of the oldest continuously operating wineries in the region.
Cantina Contucci · contucci.it
♨️ Bagno Vignoni & La Posta Hotel Day Spa
~2.5 hours · ~$45–$60 USD / person for spa access
A tiny village built around a steaming rectangular pool in its main square — fed by the same volcanic springs the Romans and Medici bathed in — where the historic pool itself is now look-but-don’t-touch, but the adjoining hotel’s thermal pools are open to day visitors for a soak with the same mineral-rich water.
La Posta Hotel Day Spa · lapostahotel.it
🍽️ Dinner in Pienza
~1.5 hours · $25–$35 USD / person
A last relaxed evening back in Pienza’s old town, with a table looking out over the same valley crossed by car two days earlier.
🛎️ Overnight — Relais Val d’Orcia
From $170–$210 USD / night, for 2 people
A second night on the terrace above the wheat fields.
Day 7Pisa & Departure
One last stop at Italy’s most famous architectural mistake, then the drive back to Florence to close out the week.
🚗 Drive — Val d’Orcia to Pisa
~2 hours via the SI-PG-FI & FI-PI-LI · self-guided
A longer final drive west across Tuscany, timed to reach Pisa by mid-morning before the Piazza dei Miracoli fills with day-trip buses.
🗼 Leaning Tower of Pisa
~1.5 hours · ~$27 USD / person to climb
The 12th-century bell tower that’s been tilting since before it was finished, still open to climb its 251 spiral steps for a view over the Piazza dei Miracoli’s cathedral and baptistery — timed-entry tickets for the climb are worth booking a day or two ahead in high season.
🚗 Departure — Rental Car Return, Florence Airport
~1 hour from Pisa · self-guided
A short final drive back to Florence to return the car, closing the loop on a week that ran from a Renaissance dome to a wine cellar to a tower that never quite falls over.
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