Three Days in Florence & Tuscan Countryside: An Old-Money Inspired Journey Through Art, Heritage, and Rolling Hills
Florence is a city where the past never feels distant. You walk through narrow streets that once guided Michelangelo and da Vinci. You stand beneath cathedrals that took centuries to finish. You pass small workshops where the smell of leather still lingers in the air. Florence is refined without being loud – an old-money kind of elegance. Soft-spoken, confident, and rich in history.
Just beyond the city, lies the heart of Tuscany. One hour in any direction leads you to open hills, vineyards folded into the landscape, and roads lined with cypress trees. Tuscany is the quiet luxury of Italy – slow lunches, warm sunsets, and simple rustic charm.
This 3-day itinerary blends them together in a way that feels thoughtful, immersive, and deeply memorable.
A Little History
Florene was the beating heart of the Renaissance. The Medici family funded artists like Michelangelo , Botticelli, Brunelleschi, and da Vinci. They built banks, libraries, palaces, and galleries that shaped Europe for centuries.
Their influence gave Florence its character: understated beauty, and a refined sense of taste. Even today, the city moves at a soft, steady rhythm – cultured, elegant, and proud of its heritage.
WHEN TO VISIT?
Florence is best enjoyed from April to June and September to early October, when the weather is mild, the evenings linger with soft light, and the crowds are lighter. We personally recommend September – the city feels alive yet calm, perfect for leisurely strolls, open-air dining, and exploring Tuscany’s rolling vineyards in golden hues.
HOW TO GET THERE?
Florence is well connected by Italy’s high-speed trains.
- From Venice: Take a direct Frecciarossa or Italo train – the journey takes just over 2 hours, whisking you from the canals to the heart of Tuscany.
- From Rome: It’s even faster – about 1.5 hours by train, making Florence an effortless stop between the Eternal City and the northern lakes.
For arriving by air, Florence Airport (Amerigo Vespucci) is only 20 minutes from the city center, though most international travelers find Pisa Airport more convenient, with frequent train connections to Florence Santa Maria Novella station.
GETTING AROUND
Florence is best explored on foot. Most of its treasures – from the Duomo to Ponte Vecchio – are within walking distance, and getting lost in its winding alleys is half the charm. For longer routes, electric taxis and buses are convenient, but there’s nothing quite like wandering at your own pace with gelato in hand.
If you plan to explore beyond Florence – especially for a Tuscany day trip – renting a car offers flexibility and a touch of adventure. Driving through the rolling hills of Chianti or the winding roads to Siena feels cinematic, especially with the windows down and Italian jazz playing softly in the background
Just note that Florence’s historic center (ZTL zone) restricts private cars, so it’s best to collect your rental location just outside the zone or near the Santa Maria Novella train station.
WHERE TO STAY – REFINED AND ROMANTIC
Choosing the right base in Florence makes all the difference. Whether you prefer to wake up to cathedral bells or the Arno’s quiet shimmer, these stays capture the city’s absence – refined, historic, and effortlessly stylish.
- Portrait Firenze: Overlooking the Arno, this hotel is all about understated luxury. Its rooms feel like private residences, complete with plush fabrics and river views that glow at sunset. Perfect for couples seeking a private retreat in the City’s heart.
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- Hotel Calimala: A restored stone palace tucked behind the Duomo, where Renaissance grandeur meets contemporary flair. The rooftop terrace is a secret gem – ideal for aperitivo at dusk.
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- Antica Torre Tornabuoni: This 13th-century tower residence offers panoramic views of Florence, antique furnishings, and a sense of timelessness that captures the “old money” spirit beautifully.
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Day 1 - Florence: A Gentle Introduction
Morning: Duomo & Your First Steps in the City
Arrive at Piazza del Duomo early. The cathedral glows softly under the morning sun and feels almost private before crowds arrive.
Duomo Terraces (Old-Money Experience)
[Booking link: https://gyg.me/UNEQILee]
Choose the terrace climb, not the dome climb. The terraces let you walk along the marble exterior – intimate, cinematic, and far less crowded.
Pro Tip: Book 7:30 or 8:00 am slot for the quietest, dreamiest experience.
Afterward, enjoy your first cappuccino at Caffé Scudieri, with views overlooking the cathedral.
Outfit Inspiration for the Day
- A brown polo t-shirt (either tucked or untucked).
- Beige tailored trousers with a brown belt.
- Loafers in chestnut suede.
- Add a tortoiseshell sunglasses.
- And a slim watch for understated sophistication.
For Her:
Late Morning: Palazzo Vecchio, Piazza della Signoria & Window Wines
Walk to Piazza della Signoria – Florence’s historic political square. Statues line the piazza, and the Palazzo Vecchio stands tall.
Palazzo Vecchio Secret Passages
[Booking link: https://gyg.me/VLhaZk65]
A unique tour through hidden staircases and private Medici rooms.
Florence’s “Window Wines” (Vinaini)
One of the most charming old traditions in Florence is the wine windows – tiny openings in palace walls where noble families once sold wine directly to locals.
Visit 👇
Buchetta del Vino – Babae
A small window where wine is handed through the wall in a tiny glass. It feels like a secret Florentine ritual.
Sip your wine while standing along the narrow street, just as Florentines once did.
Lunch: La Giostra
Try the pear and pecorino pasta – a classic.
Afternoon: Uffizi Gallery
A slow, thoughtful museum experience.
Book your tickets: https://gyg.me/BdLh8sJ3
Highlights:
- Botticelli’s Birth of Venus
- Leonardo’s Annunciation
- Views over the Arno from the top-floor windows
Pro Tip: Don’t rush. One hour spent with a few masterpieces is worth more than scanning the entire gallery.
Evening: Golden View Firenze
The Arno becomes golden during sunset – a calm, elegant end to your first day.
Elevate Your Style for a Romantic Dinner Night
Day 2 - The Florence Locals Know & Love
Morning: Oltrarno, Artisans & Slow Coffee
Start your morning with a walk across Ponte Vecchio before the crowds arrive. The jewelry ships lining the bridge look like small treasure bixes with wooden shutters.
On the other side, Oltrarno welcomes you with quieter streets, local cafés, and artisans shaping leather, wood, and gold. These workshops are small family businesses, not tourist storefronts. You can watch someone hand-cut leather or shape a piece of jewelry the same way the ancestors did.
Have a breakfast at Ditta Artigianale. The coffee is strong, and the pastries come out warm. The streets outside feel relaxed, and it’s easy to fall into Florence’s slower rhythm here.
Pro Tip: Ask artisans about their work. Many families have practiced these crafts for generations.
Outfit Inspiration for Today
The look balances comfort for museums and class for cafés.
For Her:
- Long sleeve lightweight jumper with a soft, relaxed drape
- Tailored fabric skirt
- Chic ankle boots with a versatile design
- Compact leather crossbody
Mid-Morning: Boboli Gardens
Walk slowly toward the top for a panoramic city view. This is where Florence feels most peaceful.
Book your tickets: https://gyg.me/lwQjI0jm
Lunch: Mercato Centrale
Try:
- truffle pasta
- pizza al taglio
- crostine
- fresh mozzarella
- tiramisu upstairs
You get an honest taste of the city here.
Afternoon: Leather Shopping & Vivoli Affogato
After shopping, walk to Vivoli, one of Florence’s older gelaterias, famous for tradition, simplicity, and pure ingredients. Order an affogato – creamy gelato poured over hot espresso.
Evening: Santo Spirito
Choose a trattoria around the square and enjoy dinner in the warm evening air. Florence feels familiar at night, and Santo Spirito is the best place to feel that closeness.
Day 3 - Tuscany Day Trip: Vineyards, Hilltowns, and Golden Light
Morning: Driving into Tuscany
Start your morning by picking up a comfortable rental car for the day. This is the easiest, most relaxed way to explore Tuscany.
Driving out of Florence, the city fades into quieter neighborhoods, and then, without warning, Tuscany opens in front of you. Rolling hills stretch in long gentle waves. Rows of vineyards run across the slopes like straightened ribbons. Ancient stone farmhouses appear int he distance, surrounded by silvery olive trees.
With the windows down, you feel the breeze immediately – warm, earthy, carrying hints of grass and wildflowers. The roads through Chianti curve softly around hills, making the drive feel slow and graceful rather than rushed. Sunlight breaks through the trees and dances across the dashboard. It’s the kind of journey that makes you stop speaking for a moment just to breathe it in.
Even few kilometers, the landscape changes – sometimes narrow roads lined with tall cypress trees, sometimes wide valleys where the land opens all the way to the horizon. Tuscany was made for driving days like this.
What to Wear Today?
For Him:
- A deep olive linen shirt.
- Paired with slim-fit cream trousers for a refined yet relaxed aesthetic.
- The accessories can be repeated from previous days.
For Her:
Late Morning – San Gimignano Slow Wander
There is no need to rush here. The charm of San Gimignano comes from simple moments:
- Small shops displaying hand-painted ceramics
- Windows filled with local saffron jars.
- Panoramic terraces overlooking endless valleys
Stop for gelato at Gelateria Dondoli. Take it to one of the quieter side streets instead of the central square. The views are better, the breeze softer, and you can enjoy your cup without crowds around you.
If the sky is clear, climb to one of the town’s viewpoints. Tuscany stretches beneath you like an old tapestry – vineyards, cypress lines, and soft golden hills overlapping in the distance.
Lunch – A Vineyard Table in Chianti (The Real Old-Money Experience)
Arriving at a vineyard feels like stepping into a private property. Cypress trees line the driveway. Stone buildings sit quietly among vines. Olive trees shimmer silver-green in the breeze.
Choose a vineyard such as – Castello Vicchiomaggio and Castello La Leccia.
Lunch here isn’t simply “lunch”. It’s slow, generous, sun-splashed, and deeply Italian.
You sit a long wooden table overlooking fields of vines. The dishes arrive unhurried:
- Handmade pappardelle with local olive oil
- Tuscan bread still warm
- Sun-ripened tomatoes with basil
- Pecorino cheese and honey
- Chianti Classico poured gently into tall glasses
The atmosphere is peaceful. No loud music, no rush. Just conversation, softened by the countryside around you. This is the kind of experiences Italy does better than any country – elegant without excess, refined without effort.
Afternoon – Vineyard Walk & Golden Hour Through the Hills
Then return to car and continue driving through the countryside and pass along small stone villages, quiet roads lined with olive groves, lone cypress trees standing like century-old makers and sunlight flickering through the branches.
Optional on the drive back:
- Castellina in Chianti – medieval tunnels & romantic streets.
- Monteriggioni – tiny stone fortress village
Both are beautiful without crowds.
As you drive back toward Florence, the sky begins to change. the warm yellow becomes a deep golden orange and every turn in the road feels like a painting.
Evening – Florence at Sunset
This is where your journey settles. Tuscany behind you, Florence in front of you, and the feeling that these three days filled more than just your travel schedules – they filled your senses.
It’s a gentle, emotional end to a day that feels almost cinematic.
Insider Tips for Visiting Florence
- Visit the landmarks early or late in the day: Florence can get crowded, especially around the Duomo and Ponte Vecchio. Go early in the morning for soft golden light and quieter streets, or return after sunset when the city feels cinematic and calm.
- Reserve museum tickets in advance: Skip-the-line tickets for Uffizi Gallery and Accademia are worth every cent. Booking ahead saves you from long queues, giving you more time to wander through artisan streets and cozy wine bars.
- Walk instead of taking taxis: Florence is small enough to explore entirely on foot. The city’s cobblestone lanes, hidden courtyards, and terracotta rooftops are best appreciated when you’re not rushing from one spot to another.
- Dress the Part: Florence is a fashion-forward city – home to Ferragamo, Gucci, and Cavalli. You’ll feel at home in tailored neutrals, linen shirts or polo tshirts, and simple jewelry. Italians take pride in dressing well, even for coffee.
- Try the window wines: These historic “buchette del vino” – small wine windows from centuries past – are scattered around the city. Stop by Babae near Santo Spirito to enjoy a glass of local Chianti poured through one of them.
- Don’t skip the affogato at Vivoli: A Florence icon, Vivoli Gelateria – serves the city’s best affogato espresso poured over creamy vanilla gelato. It’s the perfect afternoon pick-me-up between museum visits.
- Sunset views are worth the climb: Head to Piazzale Michelangelo for panoramic views of Florence at dusk. Bring a small bottle of Chianti and watch as the city turns to gold – it’s one of those moments that stays with you.
- Consider a day trip to Tuscany countryside: If time allows, rent a car or book a tour to explore Chianti, Siena, or San Gimignano. Tuscany is just an hour away but feels like another world – all rolling vineyards, cypress trees, and soft countryside light.