Exploring The Best of Tuscany – 7 Days Based In Florence

A week in Tuscany, based in Florence, blends art, history, and cuisine with idyllic countryside escapes. Explore Renaissance Florence, medieval towns, and vineyard landscapes, enjoying local flavours and unforgettable vistas.

Itinerary Overview

Destination: Tuscany, Italy

Duration: 7 Days / 7 Nights

Base Location: Florence

Airport: Florence Peretola (FLR)

When to Go

Late Spring (May–June) or early Autumn (September–October) for pleasant weather and fewer crowds than peak summer.

Transport

From the airport: take the ATAF bus (Line 1) or a 20-minute taxi ride to central Florence.

Around Florence: walking is easiest for the historic centre; occasional taxis or short tram rides for further spots.

Day trips: hire a car or join guided tours to reach Chianti, Siena, San Gimignano, and the Val d’Orcia region.

Budget Range

This 7-day Tuscany trip is moderately priced, with mid-range hotels, local meals, and wine tours; it suits travellers with a comfortable, mid-range budget.

Best For

Scenic countryside drives
Wine tasting & vineyard experiences
Iconic art and architecture
Medieval towns & villages
Food lovers & culinary tours
Photographers & Instagram-worthy spots
Relaxed walking and leisure days

Trip Highlights

Florence’s Duomo, Piazza della Signoria, and Ponte Vecchio
Chianti wine region vineyard tours and tastings
Siena’s Piazza del Campo and historic streets
San Gimignano’s medieval towers and Volterra’s artisan shops
Val d’Orcia’s rolling hills and hilltop towns of Pienza & Montepulciano
Panoramic sunset views from Piazzale Michelangelo
Authentic Tuscan cuisine experiences throughout

Local Cuisine to Try

Bistecca alla Fiorentina – Tuscan T-bone steak, grilled over wood or charcoal.
Ribollita – hearty vegetable and bread soup, a classic peasant dish.
Cantucci & Vin Santo – almond biscuits dipped in sweet dessert wine.
Chianti Classico or Brunello di Montalcino – local reds for wine lovers.
Gelato – Florence’s artisan gelaterias like Gelateria dei Neri or La Carraia

Best of Tuscany 7 Day Itinerary Summary

Over seven days, base yourself in Florence while venturing into the heart of Tuscany. Balance city exploration with countryside drives, wine tastings, and picturesque hilltop villages. This itinerary offers a mix of cultural landmarks, culinary delights, and Instagram-worthy landscapes.

Day 1: Arrival in Florence – Explore the Duomo, piazzas, and enjoy Tuscan dinner.
Day 2: Florence Art & Markets – Uffizi, Accademia, and local artisan shopping.
Day 3: Chianti Wine Tour – Vineyards, wine tastings, and rustic lunch.
Day 4: Day Trip to Siena – Piazza del Campo, Siena Cathedral, local gelato.
Day 5: San Gimignano & Volterra – Medieval towers, artisan shops, and scenic countryside.
Day 6: Val d’Orcia Countryside – Pienza, Montepulciano, and sunset over rolling hills.
Day 7: Florence Leisure Day – Brunch, last-minute shopping, and panoramic views from Piazzale Michelangelo.

Day By Day Itinerary

Day 1: Arrival in Florence – Iconic Duomo & Tuscan Flavours

Morning

Arrive at Florence Airport and take a 20-minute taxi or the ATAF Line 1 bus to your accommodation in the centre.
Start the day with an Italian breakfast at Caffè Gilli while people-watching in Piazza della Repubblica.
Walk to Florence Cathedral (Duomo di Santa Maria del Fiore) and marvel at Brunelleschi’s iconic dome.
Climb the Duomo Dome for panoramic views of Florence’s terracotta rooftops and the surrounding Tuscan hills.
Visit Giotto’s Campanile, the adjacent bell tower, for additional sweeping city vistas.
Stop at Battistero di San Giovanni to admire the famed bronze doors, known as the “Gates of Paradise.”

Afternoon

Enjoy lunch at Trattoria Mario, a local favourite serving traditional Tuscan fare like ribollita and pappa al pomodoro.
Stroll across Piazza della Signoria, the open-air museum of sculpture, spotting the replica of Michelangelo’s David.
Pop into Palazzo Vecchio, Florence’s historic town hall, for a quick glimpse of frescoed halls and medieval chambers.
Wander through the Mercato Centrale, browsing local cheeses, cured meats, and fresh pasta for snacks or souvenirs.
Sip an afternoon espresso at Ditta Artigianale, a specialty coffee shop loved by locals.
Walk along the Arno River to the Ponte Vecchio, exploring the jewellery shops lining the bridge.

Evening

For dinner, head to La Giostra, a romantic trattoria in Oltrarno, serving bistecca alla Fiorentina and truffle pasta.
Finish the evening with a gelato from Gelateria dei Neri and a walk through the cobbled streets of the historic centre.
Optional: take in a nighttime view of the Duomo from Piazzale Michelangelo, accessible via taxi or a 20-minute walk

Transport Notes for the Day:

Walking is ideal in the historic centre; taxis or short tram rides recommended if carrying luggage.
All key sights—Duomo, Ponte Vecchio, Piazza della Signoria—are within 15–20 minutes’ walk from central hotels.

Highlights for Instagram/TikTok:

Panoramic view from the Duomo Dome
Sunset over the Arno from Ponte Vecchio
Close-ups of Tuscan dishes at Trattoria Mario
Street scenes in Piazza della Repubblica and Mercato Centrale

Day 2: Florence Art & Markets – Renaissance Masterpieces & Artisan Finds

Morning

Start with an Italian espresso and a pastry at Caffè Rivoire, right on Piazza della Signoria.
Head to the Uffizi Gallery early to avoid the crowds—home to Botticelli’s Birth of Venus and masterpieces by Leonardo da Vinci and Michelangelo.
Stroll through the Loggia dei Lanzi, an open-air sculpture gallery in Piazza della Signoria with works like Cellini’s Perseus.
Stop by Palazzo Vecchio if you missed it the previous day, to explore the Renaissance art and grand halls.
Walk across the Ponte Vecchio to the Oltrarno district, passing the goldsmiths’ shops and snapping photos

Afternoon

Enjoy lunch at Trattoria 4 Leoni, a classic Oltrarno spot known for pappardelle with wild boar and fresh bruschetta.
Explore Santo Spirito Square, a vibrant hub of artisan shops, leather ateliers, and local craft stores.
Visit Mercato di Sant’Ambrogio, a local food market away from tourist crowds
Take a short walk to Piazza Santa Croce to admire the church façade and surrounding leather workshops.
Stop for a gelato break at La Carraia Gelateria, widely regarded as one of Florence’s best.

Evening

Have dinner at Osteria Santo Spirito, a lively tavern serving traditional Tuscan dishes with a modern twist.
Enjoy cocktails with a view at Rooftop Bar La Terrazza del Principe, overlooking Florence’s rooftops and the Duomo.
End the evening with a stroll along the Arno River or stop for a photo at Piazzale Michelangelo for citywide views.
Optional: join an evening wine tasting in the Oltrarno district to sample Chianti and Brunello di Montalcino.

Transport Notes for the Day:

Walking is ideal—most art galleries and markets are in the historic centre.
A short taxi or tram ride may be needed to reach Oltrarno and Piazzale Michelangelo if you want to conserve energy.

Highlights for Instagram/TikTok:

Botticelli’s Birth of Venus at Uffizi
Artisan leather shops in Oltrarno
Street scenes at Santo Spirito and Mercato di Sant’Ambrogio
Sunset from Piazzale Michelangelo

Day 3: Chianti Wine Tour – Vineyards, Wine Tastings & Rustic Tuscan Lunch

Morning

Depart Florence after breakfast and pick up a rental car or join a guided wine tour from Piazza Santa Maria Novella—driving south into the rolling hills of Chianti.
Stop at Greve in Chianti, the main town, and wander through Piazza Matteotti, browsing local delis and artisan shops.
Visit the Chianti Classico Wine Museum, learning about the region’s winemaking history and tasting samples
Reach Castello di Verrazzano, a historic winery and castle offering guided tours of the cellars and vineyards.

Afternoon

Enjoy a rustic Tuscan lunch at Verrazzano’s estate, with pappardelle, ribollita soup, and Chianti Classico wines
Tour the vineyards with a wine expert, learning about Sangiovese grapes and the Chianti Classico production process.
Stop at a local olive oil farm nearby to taste freshly pressed Tuscan oils and learn about traditional production methods.
Drive to Panzano, a hilltop village famous for its butcher shops and scenic streets, ideal for post-lunch strolls.
Snap photos of the panoramic views of vineyards and olive groves from the village overlook.

Evening

Stop at Castellina in Chianti on your return route, wandering its medieval streets and artisan wine shops.
Enjoy an aperitivo at Enoteca Le Cantine, sampling local wines and small bites before heading back to Florence.
Return to Florence in time for a dinner at Trattoria da Ruggero, known for hearty Tuscan fare like bistecca alla fiorentina.

Transport Notes for the Day:

A rental car is ideal for flexibility, but guided wine tours offer stress-free transport and expert commentary.
Roads are narrow and winding; allow extra time for scenic stops and photo opportunities.

Highlights for Instagram/TikTok:

- Vineyards rolling over Chianti hills
- Wine tasting at Castello di Verrazzano
- Panoramic village views from Panzano or Castellina
- Rustic Tuscan lunch with local wine pairing

Day 4: Day Trip to Siena – Medieval Streets, Piazza del Campo & Gelato Treats

Morning

Depart Florence early, either by rental car (about 1.5 hours) or bus/train to Siena for a scenic ride through Tuscany.
Arrive in Siena and start at Piazza del Campo, the iconic shell-shaped square famous for the Palio horse race. Take your time to admire the Palazzo Pubblico and its Torre del Mangia.
Grab a quick morning espresso and cantucci biscuit at Nannini Café, a historic spot just off the square.
Climb the Torre del Mangia for panoramic views of Siena’s red-tiled rooftops and surrounding Tuscan hills
Wander through the narrow cobbled streets, spotting artisan workshops and boutique shops

Afternoon

Visit Siena Cathedral (Duomo di Siena), marveling at the intricate black-and-white striped marble exterior
Stop at Santa Maria della Scala, a former hospital turned museum, to explore medieval frescoes and historic halls.
Enjoy a leisurely lunch at Osteria Le Logge, serving traditional Tuscan dishes such as pici pasta with wild boar ragù.
Indulge in gelato from La Vecchia Latteria, renowned for creamy, authentic flavours like ricotta-honey and dark chocolate.
Walk up to Basilica of San Domenico for a quiet moment and beautiful views of the city from the hilltop.
Browse local stores for Siena specialties, including panforte, a spiced fruit and nut cake, and hand-painted ceramics.

Evening

Enjoy an aperitivo at Enoteca Italiana, sampling Chianti wines and local snacks before departing.
Stroll along the Piazza Salimbeni and admire the historic palaces lit up as evening descends.
Head back to Florence by car or bus, timing your return to catch a sunset over the Tuscan countryside if possible.

Transport Notes for the Day:

Driving gives flexibility to explore nearby scenic villages around Siena.
Public transport (bus or train) is reliable and stress-free, but walking in Siena is easiest on foot due to its medieval streets.

Highlights for Instagram/TikTok:

Panoramic views from Torre del Mangia
Piazza del Campo’s medieval charm
Siena Cathedral’s stunning interior
Artisan streets and Tuscan gelato

Day 5: San Gimignano & Volterra – Medieval Towers, Artisan Shops & Scenic Countryside

Morning

Depart Florence early by rental car or join a guided day tour, heading towards San Gimignano (approx. 1.5 hours).
Arrive in San Gimignano and wander into the Piazza della Cisterna, the heart of the town surrounded by medieval towers.
Climb the Torre Grossa, the tallest tower in town, for panoramic views of the town’s rooftops and the surrounding vineyards.
Stop at Gelateria Dondoli, famous worldwide, and try flavours like saffron & pine nut or Vernaccia sorbet.
Browse Via San Giovanni and nearby streets for artisan shops selling local ceramics, leather goods, and handmade jewelry.

Afternoon

Enjoy a Tuscan lunch at Trattoria Chiribiri, known for fresh pappardelle and local cured meats.
Drive or take a short trip (approx. 40 minutes) to Volterra, a quieter medieval town with Etruscan roots.
Visit Piazza dei Priori, one of Italy’s oldest town squares, and admire its historic palaces.
Stop at Volterra Cathedral (Duomo di Volterra) to see its Romanesque architecture and 12th-century frescoes.
Explore artisan alabaster workshops, unique to Volterra, and pick up a small souvenir.
Walk along the medieval city walls for sweeping views of the Tuscan countryside and vineyards beyond.

Evening

Return to San Gimignano for an early dinner at Ristorante La Mandragola, serving classic Tuscan cuisine.
Enjoy a sunset stroll along the town’s cobbled streets, capturing golden light between the medieval towers.
Head back to Florence in the evening (approx. 1.5-hour drive), listening to the soundtrack of the Tuscan countryside.

Transport Notes for the Day:

Driving is highly recommended to maximise time and flexibility between San Gimignano and Volterra.
The towns themselves are best explored on foot; parking is usually on the outskirts with short walks into centres.

Highlights for Instagram/TikTok:

Iconic medieval towers of San Gimignano
Gelato at Gelateria Dondoli
Alabaster workshops and artisan crafts in Volterra
Panoramic Tuscan countryside views

Day 6: Val d’Orcia Countryside – Pienza, Montepulciano & Sunset Over Rolling Hills

Morning

Depart Florence early by rental car for a full-day excursion to the Val d’Orcia, about 2–2.5 hours south of Florence.
Arrive in Pienza and stroll through Piazza Pio II, surrounded by historic palaces and the Pienza Cathedral.
Sample local pecorino cheese at a traditional shop like La Buca delle Fate, perfect for a morning snack.
Wander through Via del Casello and browse small artisan shops offering handmade crafts, olive oils, and ceramics.
Take a short drive to Sant’Anna in Camprena, a picturesque spot for classic Tuscan landscape photography.

Afternoon

Continue to Montepulciano, perched on a hilltop and renowned for its Vino Nobile wine.
Stop for a wine tasting at Cantina Contucci or Cantina Nardi, exploring historic wine cellars and sampling regional wines.
Enjoy a rustic Tuscan lunch at Osteria Acquacheta, famous for its bistecca alla fiorentina and hand-rolled pici pasta.
Stroll through Piazza Grande, Montepulciano’s central square, taking in Renaissance architecture and local artisan shops.
Visit Palazzo Comunale and, if you’re up for it, climb the tower for sweeping views of Val d’Orcia’s rolling landscapes.

Evening

Head towards Bagno Vignoni, a tiny village with a thermal water square, ideal for a golden-hour stroll.
Find a scenic viewpoint along the countryside roads to watch the sunset over the rolling Val d’Orcia hills.
Return to Florence in the evening (approx. 2.5-hour drive), stopping for gelato or a quick espresso along the way.
Enjoy dinner at La Giostra, a charming trattoria famous for its Tuscan specialties like pear and pecorino ravioli.

Transport Notes for the Day:

Driving is essential to explore multiple towns in Val d’Orcia efficiently.
Narrow streets and hilltop towns are best explored on foot once parked; allow extra time for parking near historic centres.

Highlights for Instagram/TikTok:

Pienza’s Renaissance streets and piazza views
Scenic rolling hills with cypress trees
Montepulciano wine cellars and tasting experiences
Golden-hour sunset over Val d’Orcia

Day 7: Florence Leisure Day – Brunch, Last-Minute Shopping & Panoramic Views

Morning

Start your day with brunch at Ditta Artigianale, one of Florence’s top cafés serving coffee, avocado toast, and pastries.
Take a slow walk through Oltrarno, Florence’s artisan quarter, browsing leather goods, jewellery, and ceramics.
Stop for a gelato at Gelateria La Carraia, a local favourite known for creamy flavours and Instagram-worthy presentation.

Afternoon

Head to Via de’ Tornabuoni, Florence’s luxury shopping street, for last-minute souvenirs or designer pieces.
Explore Mercato di Sant’Ambrogio for local food treats like truffle products, olive oil, and fresh focaccia to take home.
Relax at Caffè degli Artigiani, a hidden café tucked along a quiet side street, perfect for a mid-afternoon espresso.
If desired, visit the Boboli Gardens for a peaceful walk among sculptures, fountains, and manicured greenery.
Grab a light lunch at Trattoria La Casalinga, serving authentic Tuscan fare in a cozy, traditional setting.

Evening

Make your way to Piazzale Michelangelo in time for golden-hour views—walk up or take a short taxi ride.
Enjoy an aperitivo at La Loggia Café on the piazza terrace, sipping a spritz while soaking in the cityscape.
End your Florence adventure with a relaxed dinner at Buca Lapi, one of the city’s oldest trattorias.
Take a slow stroll back through the city centre, passing illuminated landmarks like the Duomo and Piazza della Signoria.

Transport Notes for the Day:

Central Florence is easily walkable; taxis are optional for Piazzale Michelangelo or if carrying shopping bags.
Leave extra time to navigate narrow streets and stop at hidden artisan shops or viewpoints along the way.

Highlights for Instagram/TikTok:

Brunch at trendy cafés with photogenic interiors
Artisan shopping in Oltrarno and Via de’ Tornabuoni
Gelato selfies on Ponte Vecchio
Sunset panoramas from Piazzale Michelangelo

Photo Inspiration

Itinerary Map

Make It Happen

Find Flights

Recommended Hotels

Hotel Delle Camelie

Budget

A cosy, well-reviewed hotel offering clean, comfortable rooms with traditional decor, located within easy walking distance of Santa Maria Novella train station and central Florence.

Via Montebello 7,

50123 Florence

Hotel L’Orologio

Mid Range

Stylish, boutique hotel with elegant rooms featuring a rooftop terrace, breakfast service, and walking distance to Ponte Vecchio and Piazza della Signoria.

Piazza Santa Maria Novella 24,

50123 Florence

Tivolo Palazzo Gaddi

Luxury

Elegant, boutique hotel offering spacious, classic-style rooms, a refined breakfast service, and a central location just a short stroll from Florence’s main sights and Santa Maria Novella station.

Via del Giglio 9

50123 Florence