Renaissance overload by day, bistecca alla fiorentina by night, and a countryside that sat behind 15th-century altarpieces. Two days in the city, the rest in Chianti and the Val d'Orcia.
Last reviewed July 2026
Euros, cash for the trattorias. Go April–May, or September–October; July and August the heat arrives and the city empties. Some English in the centre; a little Italian helps. Plan €150–400 a day before the splurges, round up, no more, and bring a two-pin adapter. Florence keeps Central Europe time.
Florence is heavily documented: every trattoria reviewed, every museum catalogued, every view photographed. The difficulty is not finding good things but sorting them. Below is the sorted version.
And then there's the rest of Tuscany: Chianti, Siena, the Val d'Orcia, Lucca, the Etruscan hills.
Two days in Florence, one in Chianti, the Val d'Orcia if you can spare it. You don't need to see Pisa unless you're dying for a touristy photo-op.
The city is best in April, May, and October. July and August in Florence run above 35°C with the museums at their busiest. The countryside handles the heat better. If your trip is mostly rural Tuscany, summer is fine.
Florence, plus five stretches of countryside around it. Pick one place to stay and drive out from it rather than changing hotels every night.
Oltrarno is the perfect neighborhood. The rest of the city center is beautiful, but full of tour groups by 10 a.m., which is not our vibe. Cross the Ponte Vecchio and go south to find the leather workshops and the trattorias. The city is better on the less-populated side of the river.
The stretch of land between Florence and Siena. Stone farmhouses, cypress alleys, Sangiovese in every direction. Greve, Radda and Panzano are the three towns worth stopping in. Visit a vineyard and get a little tipsy. Dario Cecchini's butcher shop is in Panzano, and that alone is a reason to visit.
The Piazza del Campo is the most beautiful piazza in Italy and we cannot recommend it enough. It is shell-shaped, paved in herringbone brick, and the Palio is run around its edge twice a summer. You don't need to stay overnight, but it is worth a day trip from Florence. Go without a plan and let yourself wander.
The rolling green hills of Pienza and Montalcino. A UNESCO-protected landscape that looks like a Sienese painting because it was one; these hills sat behind 15th-century altarpieces. Go in September, when the light is low and the harvest is on.
An intact Renaissance wall around a medieval city, flat, walkable, and inexplicably undervisited given what's here. Rent bikes and circuit the top of the wall. Eat at Buca di Sant'Antonio, open since 1782. We'd recommend a half-day if you're coming from Florence, but it is worth staying the night if you want the city quiet.
Eastern Tuscany. Cortona is the hilltop town with the Piero della Francesca frescoes in the Museo Diocesano and an antique market every month. Arezzo has the Basilica di San Francesco, with Piero's Legend of the True Cross fresco cycle, and a Saturday antiques market that Florentines drive out for.
Tuscan food is about unsalted bread, local olive oil, white beans, and a good steak. There are a lot of tourist traps here, and the list below is how we steer you clear of them.
Stand at the bar, and order an espresso rather than an Americano. Italian bars charge one price at the counter and a higher one for table service, which at the historic places is sometimes triple.
A Florence café founded in 1733 on the corner of Piazza della Repubblica, all Belle Époque chandeliers, mirrored walls, and lacquered panels. Stand at the bar and drink it fast; sit at a table and you're paying for the setting. At night it transforms into a full-on Negroni room, jacketed bartenders included.
Visit websitePrecise espresso, trained baristas, a real flat white, avocado toast that holds its own. The Oltrarno location on Via dello Sprone is the one to use.
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Courtesy of S.Forno
The Santo Bevitore team's Oltrarno bakery on Via Santa Monaca, run by Marco and Martina Baldesi with Stefano Sebastiani, the same trio behind Il Santo Bevitore. Long-ferment schiacciata, real croissants, sourdough with a morning queue. Sit at the communal table with an espresso and a slice of schiacciata with prosciutto, and get there before 10, because the almond croissants don't survive it.
Half flower shop, half café, a full restaurant after dark, inside an 1896 homewares store on Via de' Ginori with vaulted ceilings and plants on every surface. Brunch in the morning, live jazz and cocktails at night. Useful when you want something modern.
Visit websiteTuscan lunch is the longest meal of the day. Order the ribollita when it's cold. Eat late. Two hours at the table is normal.
A no-frills Florentine legend near Santa Maria Novella: white tiles, ten tables, handwritten menus, communal seating. Order the butter chicken (petti di pollo al burro, fried in an amount of butter nobody will defend) and the artichoke tart, with the tortellini en brodo as the third reason. Cash only, and reserve.
An Oltrarno classic on Borgo San Jacopo, open since 1945 and still in the same family, running Tuscan staples (bistecca, fried zucchini flowers, ribollita) beside the dishes regulars return for: celery, egg and bottarga salad, and parmesan-truffle fettuccine. Hard to book, and closed Tuesday and Wednesday, so plan around both.
An Oltrarno favorite on Via di Santo Spirito that stayed sharp without freezing in place. The seasonal menu leans contemporary: braised octopus, beef cheek with porcini, a vegetable-forward antipasti spread. Start at their wine bar Il Santino, three doors down, for the aperitivo.
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A fairy-lit dining room on Borgo Pinti, in the Santa Croce / Sant'Ambrogio quarter east of the Duomo (about a 10–15-min walk): vaulted brick ceiling, strings of lights, walls of family photographs, a welcome glass of prosecco. The ravioli stuffed with pecorino and pears is the signature; spaghetti Sorrentino is the second order. It is touristy. Book ahead and dress up.
Visit websiteFlorence does street food properly: a panino at the counter, a glass of red, twelve minutes total.
A counter inside the Mercato Centrale serving lampredotto, the fourth stomach of a cow braised in vegetable broth. Da Nerbone makes the classic version: a soft roll dipped bagnato in the broth, topped with salsa verde and a little peperoncino. About €6. Eat it standing, and don't overthink the anatomy.
The top floor of San Lorenzo's market: pasta made-to-order, Neapolitan pizza, panini, a fish counter; the ground floor is the traditional produce market for cheese, salumi, fruit. Busy, and good across most stands; open all day, no reservations.
Visit websiteFlorence's neighbourhood market near Piazza Ghiberti, mornings only. Go early, get a porchetta sandwich from one of the counters, eat it on a bench in the piazza; the trattoria stalls inside (Da Rocco, Trattoria Cibreo around the corner) are why you come.
Visit websiteDinner in Tuscany happens at 8 p.m. at the earliest. The dining rooms are small; book far ahead.
Dario Cecchini's sit-down restaurant in Panzano; he recites Dante while he cuts Chianina beef. Solociccia is the multi-course "butcher's cooking" set menu (no bistecca, all the other cuts) with Chianti flowing and lardo di Colonnata melting on warm bread. 40 minutes southwest of Siena.
Courtesy of Saporium FirenzeOne Michelin Star and a Green Star on Lungarno Benvenuto Cellini: executive chef Ariel Hagen cooks the produce grown at Borgo Santo Pietro, the Thottrup family's organic estate near Chiusdino. Florence sibling to Saporium at Borgo Santo Pietro. Tastings change with the seasons and the gardens. Book ahead in summer.
Visit websiteFlorence's three-Michelin-star institution: Italian-French technique on seasonal Tuscan ingredients, paired from the house cellar. Jackets recommended, service precise. Book a month ahead.
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Courtesy of Osteria di PassignanoSet beside the monumental medieval Abbey of Passignano, deep in Chianti Classico, Osteria di Passignano is a one-Michelin-star restaurant owned by the Antinori family, where Tuscan cuisine meets the history and the surrounding landscape. The experience moves from the vaulted dining rooms to the ancient cellars, where Badia a Passignano Chianti Classico Gran Selezione ages. Chef Matteo Lorenzini's cuisine brings together technique, seasonality and ingredients from the vegetable garden, making the dinner at Orto di Badia and cellar visit a natural way to discover the place in its fullest expression.
Visit websiteOne Michelin star inside the Ferragamo family's Lungarno Hotel: Tuscan cooking with seafood accents. Two tables on the balcony face the Ponte Vecchio directly; book one at sunset. In winter the dining room is candle-lit and stone-walled.
Visit websiteFlorence claims the Negroni as a hometown invention, and the city's bar program runs deep on it — Italian-spirits-only back bars, Tuscan wine lists, a proper aperitivo hour.
A tiny wine bar in a quiet square behind the Ponte Vecchio: forty wines by the glass, almost all from producers you can't get at home. Tell the bartender at the counter what you're in the mood for and let him take it from there.
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A narrow wood-paneled wine bar facing Palazzo Pitti with one of the deepest Tuscan wine lists in the city: deep into Sangiovese (Brunello, Vino Nobile, Chianti Classico Gran Selezione), with owners who'll talk through it properly. Order by the glass while you're learning, by the bottle when you're not.
Visit websiteInside a restored historic palazzo around a glass atrium: long-form drinks built on Italian botanicals, theatrical presentation, vaulted candlelit corners. Dress up; reserve.
Visit websiteA small dimly lit cocktail bar near Santa Maria Novella with a strict Italian-spirits-only back bar: Negronis, Americanos, less-famous local apéritifs done with reverence. About 20 seats inside, and a moody room.
Visit websiteBorgo San Frediano's experimental cocktail bar: outlandish glassware, smoked drinks, fat-washed spirits, garnishes on their own plates. Younger and more design-school than the Locale crowd; no reservations, get there before 10 if you want a seat.
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Courtesy of Hotel Palazzo GuadagniA small rooftop bar above Palazzo Guadagni overlooking Piazza Santo Spirito: Bellosguardo Tower, the Boboli Gardens, the dome of Santo Spirito, the Florentine hills rolling out beyond. Order the Negroni and take a panoramic chair. Limited tables; book ahead in summer.
Visit websiteA rooftop terrace at the Lungarno Collection's Hotel Continentale, looking straight down at the Ponte Vecchio. The view is the reason to come; the price is high and the seating scarce. One drink, then dinner. Reserve before sunset in summer.
Visit websiteReal gelato is kept in covered steel containers rather than piled in mounds.
A neighborhood gelateria near Santa Croce: steel containers, lids on, honest prices, pistachio made from Sicilian pistachios rather than paste. The fig-and-ricotta in summer is the one to catch.
Visit websiteA Santa Croce institution: the Vivoli family started here in 1929 as a latteria and has been making gelato since 1930. The rice gelato is creamy and slightly grainy, and specific to this place. The line moves fast.
Visit websiteThe Buontalenti is the order: a mascarpone- and egg-rich vanilla named for the 16th-century Florentine architect, dense to the edge of too much. Go to the Campo di Marte original; the central location near the Duomo is fine if you're nearby.
Visit websiteA farm-to-table gelato shop in Santo Spirito: milk from a specific Mugello dairy, figs in summer from a farm an hour outside the city, nuts direct from Tuscan growers. Inventive seasonal flavors (ricotta and pear, fig and almond) beside the classics; real vegan options too.
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The wine is out here rather than in the city. Chianti first, then the Val d’Orcia if you have the third day, and you will want a car for both.
Order whatever is recommended. You'll learn the most over a long lunch in Chianti, if you start up a conversation with your waiter.
The four, briefly
The house wine. Black-rooster seal on the neck: that's real Chianti Classico.
€22–40 / bottleFive years in the cellar before release. The top one.
€60–250 / bottleSangiovese from Montepulciano, under a local name.
€30–90 / bottleFrench grapes, Tuscan soil, no DOC. Sassicaia and family.
€120–800+ / bottleThree of these four are Sangiovese; the differences come from soil, altitude and ageing rules.
Eleven hotels: four in Florence proper, one in Pienza, and six across the Tuscan countryside: Chianti, the Val d'Orcia, the Maremma. Click any card to expand the full picture.
A Renaissance palazzetto on Via dei Serragli, once a baker's home and shop, then a noble residence, then a philanthropic institution, now a seven-room boutique restored by an architect-owner who kept the bones intact: cotto floors, wooden ceilings, Renaissance pietra serena staircases, and an interior garden. Smart self-check-in, walkable to Pitti and Boboli, with the better Oltrarno restaurants within ten minutes.
A Renaissance palazzo in the centre, between the Duomo and Santa Croce, run as a hybrid artist residency and four-loft guesthouse. Tall ceilings, exposed fresco fragments, pared-back contemporary furnishings layered against the original Renaissance bones. Breakfast comes from S.Forno. A working creative space that you happen to also be sleeping in.
Thirteen individually-designed rooms inside a historic palazzo at Via Maggio 35: Oltrarno's main antique-dealer street. The work of architect Francesco Maestrelli with city natives Matteo Perduca and Betty Soldi (the calligrapher whose hand you'll see across the typography), every room has its own personality: antique Florentine furniture, hand-sourced fabrics, frescoed ceilings in select rooms, clawfoot tubs, hand-picked bookshelves. Breakfast included.
Courtesy of La Bandita TownhouseTownhouse Caffè · courtyard
Courtesy of La Bandita TownhouseLibrary lounge
Courtesy of La Bandita TownhouseTownhouse Caffè · interior
Courtesy of La Bandita TownhouseView toward Val d'OrciaPhotos courtesy of La Bandita Townhouse
John Voigtmann, the former New York record producer behind bands like the Strokes, Foo Fighters and Christina Aguilera, gave it all up for Pienza. He and his wife Ondine (a travel writer) converted a 15th-century former convent on Corso Il Rossellino 111 into this 12-room townhouse (four of them suites): pared-back rooms with exposed stone walls, beamed white-painted ceilings, a vinyl-record library lounge with an honesty bar. The Townhouse Caffè downstairs serves real Val d'Orcia food. Pienza itself is the bonus: cobblestoned, UNESCO-listed, and small enough to walk in twenty minutes.
A 19th-century pink villa commissioned in the late 1860s by Baron Gustave Oppenheim, of the German banking dynasty, in honor of his young bride Eugenia Fenzi, designed by architects Pietro Comparini and Giuseppe Poggi. After the Baron left Florence, the villa passed to the former Empress Eugénie of France (widow of Napoleon III), who turned it into a salon for the Florentine nobility; it later took its current name from a subsequent owner, Egidio Cora. Today: frescoed ceilings and Salone degli Specchi, marble bathrooms, antique furniture, a heated outdoor pool, and a full spa with sauna, hammam, and ice fountain. South of the center on the edge of Boboli: quieter than the historic streets, with a free shuttle into the city every 30 minutes.
The Ferragamo family's Lungarno Collection includes four hotels in Florence, Portrait among them. Thirty-seven rooms and suites on the Lungarno Acciaiuoli: most river-facing, many with a balcony onto the Arno or the Ponte Vecchio itself. Interiors by Michele Bönan: tailored, residential, leather-trimmed, drawing on Florence's craftsmanship tradition and the birth of Italian haute couture in the 1950s. Caffè dell'Oro is on the ground floor; the same group's Borgo San Jacopo (one Michelin star) is across the bridge.
Photo: Matteo SerpiCastle suite with stone walls
Florentine Carlo and Milanese Aurora Baccheschi-Berti discovered the castle ruins in the 1980s and spent more than a decade restoring it; it opened as a boutique hotel in 2003. Their sons run it now: eldest son Brando oversees the wine, youngest son Corso (a Lausanne-trained hotelier) the front of house, with Neri also part of the family business. The kitchen pulls from the estate's organic gardens, and the whole property is still very much a working farm. Suites (each restored individually with antiques the family collected on travels) plus the separate private Villa La Vedetta. Two infinity pools facing the rolling Maremma hills. Remote: Siena's an hour, Pienza an hour and a half, and it is a long way from anything.
Villa Drones
Borgo
Villa Drones
Suites
Villa Interiors
Villa InteriorsCourtesy of Rosewood Castiglion del Bosco
A 5,000-acre Rosewood estate centred on a restored medieval hamlet in the Val d'Orcia. The estate is one of the historic producers of Brunello di Montalcino, with Castiglion del Bosco wines among the labels. Forty-two suites in restored farmhouses around the village; eleven private villas dotted across the hills. Ristorante Campo del Drago, two Michelin stars (first in the 2023 guide, second in the 2025) under Tuscan-born Executive Chef Matteo Temperini, is the estate's fine-dining room; Osteria La Canonica is the cooking school. The Club at Castiglion del Bosco is a private golf course that hotel guests can play.
Suite interior
Estate grounds
Suite bath
Heated infinity poolPhotos: Courtesy of Belmond
A medieval castle built in 998 on a wooded ridge between Florence and Siena, now a 39-room-and-suite Belmond property on an ancient Etruscan site. Terracotta floors, handwoven textiles, original stone walls; the spa lives in the former wine cellar. A heated infinity pool facing nothing but vineyard. Ristorante Tosca does an upscale version of Tuscan classics on a long stone terrace. The estate is the draw (roughly 4,200 acres of woodland, vineyards and walking trails); vintage Fiat tours, vespa rides, cooking classes and truffle hunts all run on the estate.
Frescoed, antique-furnished suite
Garden suite, doors to the pool
Trattoria sull'Albero, their tree-house dining room
La Casa dei Fiori Bianchi pool houseA boutique hotel built around a 12th-century villa on a 300-acre Tuscan estate, owned and developed by Jeanette and Claus Thottrup. Twenty-two individually designed rooms and suites, antique furniture in every one. The kitchen (Saporium, with executive chef Ariel Hagen) holds one Michelin Star and one Michelin Green Star, with the more casual Trattoria sull'Albero (a tree-house dining room around a spreading oak) on the estate. The on-site Seed to Skin laboratory (Jeanette Thottrup's botanical skincare line) grows ingredients for the spa and the product line. Three Michelin Keys 2025. About 40 minutes southwest of Siena, and you're there for the seclusion.
The estate now goes to sea. Satori is the group's hand-carved wooden schooner (teak and mahogany, built in the spirit of a 1920s sailing yacht), running private weekly charters off Italy and Greece. Five cabins, up to ten guests, Michelin-trained chefs from the Borgo kitchens cooking estate produce on board, plus an onboard spa. Booked whole, by enquiry only; itineraries are built with the captain and the Borgo concierge.
A restored medieval monastery and its hamlet in the Chianti countryside, near Siena: Castel Monastero runs as a wellness-led estate of about 68 rooms, suites and signature suites. The Contrada restaurant (the signature on the piazza, with Michelin Guide recognition) features the resort's seasonal program, with Gordon Ramsay involvement. Spa Monasterii does purifying spa treatments, yoga and meditation alongside the pools. Bigger and more conventional than Vicarello or Borgo Santo Pietro, but useful if you want full-resort amenities within easy reach of Siena and Chianti.
The façade is the part you can stand and look at for nothing, and most people stop there. The list below sorts what needs booking ahead from what you can walk straight into.
What needs advance booking, what's free, and what's worth the drive.
Piazzale degli Uffizi 6 · Historic Center
Botticelli's Birth of Venus and Primavera are here, but so is everything else: Caravaggio, Titian, Raphael, Michelangelo drawings. Two hours minimum; four if you're thorough. Book the 8 a.m. slot and have the first rooms to yourself before the tour groups arrive at 9:30.
Via Ricasoli 58 · San Marco
The David is over five meters tall and carved from a single block of Carrara marble. The four unfinished Prisoners in the gallery leading up to it are almost as interesting: Michelangelo left them half-emerged from the stone, and no one has fully explained why. Forty-five minutes inside is enough; book ahead or queue an hour.
Piazza degli Strozzi · Historic Center
A 15th-century Renaissance palazzo that hosts contemporary art and historical exhibitions. Past shows: Marina Abramović, Olafur Eliasson, Donatello, Anselm Kiefer. The courtyard is open and free; the exhibitions are ticketed and worth checking before the trip. The stop for anything from the last 600 years that isn't strictly Renaissance.
Via delle Porte Sante · Oltrarno hills
A Romanesque basilica on the hill above Piazzale Michelangelo, free to enter. The Benedictine monks sing Gregorian vespers daily (currently around 5:30 p.m. in summer, earlier in winter; check the monastery's schedule the day you go). The marble facade catches the light in late afternoon.
Piazza dei Pitti 1 · Oltrarno
The Medici's private garden: formal Italian design with grottoes, fountains, a 17th-century horseshoe amphitheatre, and clear views across the city from the upper terraces. The Grotta di Buontalenti, near the entrance, has sculptures emerging from artificial stalactites.
Via della Scala 16 · Near Santa Maria Novella
On the site since 1221, when the Dominican friars began cultivating medicinal herbs here. The frescoed sales room is worth the visit on its own. Acqua di Santa Maria Novella, Pot Pourri and the Acqua di Rose are the ones to buy. Entry is free; you don't have to buy anything.
Piazza Santo Spirito to Ponte Vecchio
Cross the Ponte Vecchio first thing, before the jewelers open and the tour groups arrive, and walk south into the Oltrarno. The Piazza Santo Spirito has a market most mornings. Via Maggio is Florence's antique-dealer street. The leather workshops between Pitti and the Ponte Vecchio are open to visitors who ask.
Piazza del Duomo 9 · Historic Center
The museum that holds the original sculptures from the Duomo complex: Ghiberti's Gates of Paradise panels, Donatello's Mary Magdalene, the Pietà Bandini that Michelangelo began in his early 70s and couldn't finish. Gothic and early Renaissance sculpture, and rarely busy.
San Niccolò side · Walk up from Oltrarno
The view takes in Florence below, the Duomo, the Arno and the hills. Walk up from San Niccolò about 30 minutes before sunset; the kiosk sells a serviceable Aperol Spritz. Pair it with San Miniato vespers above.
Bargino · Via Cassia per Siena · 30 min from Florence
The Antinori Chianti Classico estate is built into the hillside, invisible from above and entirely underground. The tour covers the cellar, the architecture, and ends with a tasting of estate wines. Book the 10 a.m. slot.
Florence to Siena · 60 km · 1.5 hr
The wine road that runs south from Florence through the Chianti hills to Siena: the Tuscan wine drive. Stop in Panzano (Dario Cecchini's butcher), Greve (Tuesday market), and Radda (enoteca in the main piazza). Cypress alleys, stone farmhouses, harvest signs in September.
Siena · 1.5 hr from Florence by bus or car
The Piazza del Campo is shaped like a shell, paved in herringbone brick, and surrounded by Gothic palaces that haven't changed since the 13th century. Walk the medieval center, climb the Torre del Mangia for the full panorama, drink coffee at Il Magnifico on Via dei Pellegrini, and be done by early afternoon.
Pienza · 2 hr from Florence · Montalcino 30 min further
Pienza is a Renaissance town built to order by Pope Pius II in the 1460s: an urban-planning experiment in miniature, surrounded by a UNESCO-protected landscape. Drive the Strada della Bonifica for the cypress-lined hill views. Then go to Montalcino for Brunello di Montalcino from a producer you can't find elsewhere: Poggio di Sotto, Cerbaiona, Ciacci Piccolomini.
Bagno a Ripoli · ~20 min south of Florence (pickup available)
Giulio and his dog Edda run small-group truffle hunts in the wooded hills outside Florence: white truffles in autumn and winter, black in summer. The hunt is about three hours through the forest; the morning ends with a multi-course truffle lunch at his family farmhouse, with estate wine and olive oil. Rain or shine.
Lucca · 1.5 hr from Florence by train
The Renaissance city walls are 4.2 kilometers of intact rampart with trees planted on top; you rent a bike at the gate and cycle the full circuit in forty minutes. Below: medieval towers, Roman amphitheatre outline, churches with Romanesque facades. Lunch at Buca di Sant'Antonio. Back by 5.
Castelnuovo dell'Abate · 10 km south of Montalcino
A Romanesque abbey in a field of cypresses south of Montalcino: pale travertine walls, three apses, an interior of austere columns and capitals. The hours are limited; arrive in the late afternoon. Free entry.
Chiusdino · 35 km southwest of Siena
Two sites, fifteen minutes apart. The Gothic abbey of San Galgano is roofless: its walls and arches stand open to the sky, with grass growing where the floor used to be. The Eremo di Montesiepi above it houses a sword embedded in stone, the actual Arthurian-legend version (sort of), placed there by the 12th-century knight-turned-hermit Galgano Guidotti. Detour territory between Florence and the coast.
Parco delle Cascine · Tuesday 8 a.m.–2 p.m.
Two kilometers of stalls in the riverside park, everything from Tuscan cheese and salumi to leather goods, clothes, and plants. Take the tram to Cascine (T1 line) and arrive by 9 before the produce runs low. The cheese counter at the far end is where you buy for the afternoon.
Via del Campuccio · Oltrarno
A purpose-built cooking school in the Oltrarno running small-group classes in fresh pasta, sauce, and tiramisu. Modern kitchen studio, professional Italian chefs, wine pairing throughout. Private classes available; book a couple of weeks ahead. The technique translates back to your own kitchen.
Inside Santa Croce · Via San Giuseppe 5R
A leather school housed inside the Basilica di Santa Croce, founded in 1950 by the Franciscan friars and the Gori and Casini families to teach the trade to WWII orphans. Today it functions as a workshop, retail space, and informal school: visitors walk through the working area, watch artisans tool leather by hand, and shop bags, belts, and stamped notebooks made on-site. Monogramming on the spot.
Via delle Belle Donne · Centro
Hand-embroidered linens, monogrammed tablecloths and nightwear, since 1967. The boutique on Via delle Belle Donne is small and quiet; the linens are monogrammed to order, and purchases are wrapped in tissue with wax-sealed ribbon. The tablecloths ship internationally.
Via dei Rondinelli 17 · Centro
A porcelain house founded outside Florence in 1735. The Rondinelli flagship is more cabinet of curiosities than store: the rooms are arranged like museum installations, plate patterns layered against painted ceilings. Even if you're not in the market for a €600 espresso set, walk in.
Piazza Lorenzo Ghiberti · Sant'Ambrogio · Mon–Sat mornings
A food market on the east side of the center, near Piazza Ghiberti. Inside: cheese, salumi, butchers, fresh pasta vendors, the trattoria stalls. Outside: produce stalls and a small clothes market. Get a porchetta panino and eat it on a bench in the piazza. Go before 10 a.m.
Piazza Santo Spirito · Oltrarno · Mon–Sat mornings
The Oltrarno's neighborhood square market: produce, local vendors, a few street food stalls, and the basilica facade as backdrop. Have a coffee at the bar on the corner and go before 10 a.m.
Saturnia · Southern Tuscany · 2.5 hr south of Florence
Steaming, aquamarine pools cascading over travertine terraces: the wild thermal springs of southern Tuscany. Free, open 24/7, naturally heated to about 37°C by sulphurous water from an extinct volcano. Go at dawn or after dark. Bring reef shoes; the rocks are slick. Skip the swimsuit jewelry; the sulphur tarnishes silver.
Launch sites near Siena · San Casciano · Chianti
A sunrise float across vineyards, olive groves, and the cypress-lined hills of the Val d'Orcia: about an hour airborne, depending on wind, and capped with a prosecco-and-pastry breakfast in a field on landing. Weather-dependent and not cheap. Book directly with a regional operator (Firenze Mongolfiere is the established name) rather than through a hotel concierge: same price, more flexibility on rescheduling.
Carrara · 1.5 hr northwest of Florence
A 4×4 drive into the active marble quarries where Michelangelo sourced the stone for the David: chalk-white cliffs cut into geometric terraces, still in extraction. The terrain is stark. Most tours include the quarry visit and a stop at the small mining museum. Closed-toe shoes required. Worth pairing with lunch in Carrara town or seafood at Marina di Carrara on the way back.
Departures from Pienza · Montalcino · San Quirico
Rolling hills, cypress alleys, ancient hill towns: the classic Tuscan landscape, on an e-bike, with the gradient handled for you. Multiple operators run half- and full-day routes that include wine tastings, picnic lunches, and stops at off-the-grid agriturismi. Beginner-friendly with the electric assist; routes mostly customizable. Late spring and September are the windows.
Greve · Radda · Castellina in Chianti
Small-group horseback rides through Chianti vineyards and wildflower meadows: most stables run 1- to 2-hour beginner-friendly trips, some longer with wine tastings or lunch included. The slower pace gives you the cypress alleys and stone farmhouses at a different scale than the SS222 drive. Spring and autumn are the seasons; summer afternoons get too hot.
Via dei Conti 22R · Centro
A good-looking yoga studio inside a historic Florentine building on Via dei Conti, with a glass-ceiling view of the San Lorenzo dome from inside the practice room. Vinyasa, kundalini, yin, and ashtanga, taught in both Italian and English. Drop-in friendly, with mat rental available. Useful when the museum days catch up with you.
Day one stays in Florence and the Oltrarno, which is mostly walking and looking up. Day two is the one that needs a car.
Day one in Florence and the Oltrarno, day two in Chianti and Panzano, day three in the Val d'Orcia. A car from day two.
Piazza San Marco · Central Florence
Schiacciata with prosciutto and stracchino, eaten standing, with espresso. Cash only, no queue before 8:30.
Piazzale degli Uffizi · Historic Center
The 8 a.m. ticket gets you ninety minutes before the tour groups arrive. Go straight to the Botticelli rooms on the second floor (Birth of Venus, Primavera), then work backwards through the early Renaissance galleries. Don't try to see everything; pick twelve rooms and take them slowly.
Via Rosina 2 · Mercato Centrale
Be at the door at noon. No reservations. Communal table, ribollita, half-portion of bistecca if you can justify it. They take cash only. Finish by 1:30 before the afternoon heat sets in.
Ponte Vecchio south · Piazza Pitti
Cross the Ponte Vecchio and go into the Oltrarno. Walk Via Maggio (antiques), drift toward Santo Spirito, then cut through to Palazzo Pitti. The Boboli Gardens are €10 and give you the city from above. The Grotta di Buontalenti is near the entrance.
Above Oltrarno · Walk from Piazzale
Vespers at 5:30 at San Miniato: fifteen minutes of Gregorian chant in an 11th-century basilica, free, no booking required. Then walk down to Piazzale Michelangelo for the sunset. Buy a drink from the kiosk and stand at the railing. One hour, total.
Via dei Palchetti 6 · Santa Maria Novella
No menu, shared tables, wine in carafes. Order the pappardelle with wild boar. They'll seat you when they're ready, the noise comes with the room, and it's over by 10. Book a week ahead, or stand in the walk-in queue at 8 on the dot.
Florence → Greve in Chianti · 45 min
Leave Florence before the traffic. Take the Strada Chiantigiana south, the SP222, not the autostrada. The first twenty minutes are the hills opening up around you. Stop in Greve for the Tuesday market if it's that day; otherwise, drive through and keep going south toward Panzano.
Via XX Luglio 11 · Panzano in Chianti
Cecchini's shop opens at 10. The shop itself (Chianina hanging, Dante on the walls, Chianti poured for visitors) is worth thirty minutes before the lunch reservation next door. Buy the lardo di Colonnata to eat in the car.
Via Chiantigiana 5 · Panzano in Chianti
The set-menu lunch at Cecchini's restaurant: lardo on warm bread, five courses of Chianina beef, Chianti flowing. It takes two hours.
Bargino · 30 min north of Panzano
The underground winery built into the hillside is architecturally significant in its own right. Stay for the afternoon tasting after lunch: wines you know in context you didn't have before. Book the 3:30 slot when you reserve lunch.
Piazza dei Pitti 16 · Oltrarno
Back in Florence by 7 p.m. Walk across the Ponte Vecchio to the Oltrarno and end the Chianti day with a glass of Brunello across from Palazzo Pitti. The owner knows the list. Ask what's open. Eat nothing heavy.
Florence → Pienza · 1.5 hr
Leave early. The Val d'Orcia in morning light: mist over the hills before 9, the cypress rows throwing long shadows. Take the Via Cassia (SR2) rather than the autostrada, and stop at the first hilltop that looks right.
Pienza · Val d'Orcia
The Renaissance town in miniature. Walk the main street, buy Pecorino di Pienza from one of the cheese shops (Marusco e Maria, or the shop inside the Palazzo Piccolomini courtyard), climb to the viewpoint behind the Duomo for the landscape photograph. An hour is enough; ninety minutes if you want it.
Montalcino · 30 min from Pienza
Drive to Montalcino, the hill town of Brunello. Lunch at Osteria Porta al Cassero: pici al cinghiale, ribollita, a glass of Brunello di Montalcino Rosso. Walk up to the medieval fortress after for the view.
Bagno Vignoni · 15 min from Montalcino
A medieval village whose central piazza is a Renaissance thermal pool, not swimmable (the swimmable version is nearby at Posta Marcucci) and an unusual piece of architecture. The walk around the old thermal mills takes twenty minutes. Go before the light shifts at 4 p.m.
Bagno Vignoni → Siena → Florence
Take the road through Siena. Enter the city, park outside the walls, walk into the Piazza del Campo one time with no agenda. Have one more coffee, then drive north to Florence.
Need this built around your actual trip? That's what Upon Request is for.
Build My ItineraryThe dishes that define Tuscany, and when to order them.
Tuscany has both, and they are not interchangeable: white is the rare, expensive one, black the year-rounder. Check which is in season the week you're going, then find where to eat it.
Shaved over pasta, never cooked.
When it's in season
The hills around San Miniato (an hour west of Florence) are a white-truffle zone, alongside Alba in Piedmont and Acqualagna in the Marche.
Tagliolini al tartufo bianco: egg pasta, butter, parmigiano, freshly shaved truffle at the table. The truffle should be the size of a small egg and the waiter should weigh it in front of you. It should be shaved at the table, not pre-sliced.
A plate at a top restaurant runs €80–160 in season. Yes, that's the truffle, not the pasta. The white truffle festival in San Miniato runs the last three weekends of November. Go for the producer stalls.
In Florence: Trattoria Cammillo, Il Santo Bevitore, Borgo San Jacopo. Out of town: lunch at Pepenero in San Miniato itself, at the source. Or book a hunt with Giulio + his dog Edda (Bagno a Ripoli, just south of Florence) and eat what you find.
Sliced, sauced, sometimes warmed. Available all year, peaks in summer. Order without guilt.
When it's in season
Mostly Crete Senesi (south of Siena) and the hills around San Miniato. The summer black (scorzone) peaks May through August; the prized winter black (uncinato) overlaps the white truffle window in late autumn.
Crostini neri (the Tuscan black-truffle crostino of chicken liver, capers, anchovy and truffle), pici al tartufo nero, scrambled eggs with shaved black truffle. It holds up to heat unlike the white, so it goes into sauces.
A plate runs €18–35 at a trattoria, about a quarter of the white price. You can order it casually. You can order it at lunch. You can have it on a sandwich.
Almost any good trattoria in Florence will have it on the menu. The countryside agriturismi around Siena and San Miniato tend to shave it more generously than city restaurants.
Practical things: bread, museums, heat, cars, coffee, tipping, churches.
Tuscan bread is unsalted: sciocco, literally "insipid." It is designed to carry the flavor of prosciutto, olive oil, and ribollita rather than compete with them. You will stop noticing within a day.
Book the Uffizi and Accademia in advance, at least ten days ahead in high season, two weeks to be safe. Walk-up queues at both can run two to three hours. The booking fee is €4. Everything else in Florence can be walked into.
July and August in Florence are hot: 35°C+, crowds, heat radiating off stone. The Uffizi is air-conditioned; the city is not. Schedule museum mornings, long lunches in the shade, and nothing outdoors between 1 and 4 p.m. The countryside is more manageable.
You need a car for Chianti, Val d'Orcia, Cortona, and almost everything in the countryside. You do not need one in Florence, because the ZTL (limited traffic zone) covers the entire historic center and tourists driving in get fined automatically by camera. Rent the car on day two, leave it at the hotel for day one.
Espresso at the bar is €1.20–1.50. The same espresso at a table costs €3–4. That is a service charge for table seating, not a scam. Take it at the bar and move on. The exception is when you genuinely want to sit; then pay the difference without resentment.
The Oltrarno, south of the Arno, is where we'd base a stay: the streets are quieter, the leather workshops are walkable, and the Ponte Vecchio is close enough to use rather than photograph.
Tipping is not culturally expected in Italy. The coperto (cover charge) that appears on restaurant bills (€2–4 per person) is the conventional add. Leave coins on the bar for espresso, round up at lunch, and tip €5–10 at a dinner you genuinely loved. More than that is not expected.
Shoulders and knees covered: this applies to every church in Tuscany, including the Duomo and Santa Croce. The dress code is actively enforced at major sites; you will be turned away without warning. Carry a scarf or light layer in your bag from April through October. It takes thirty seconds to put on.
$85, one time.
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