Florence is the cradle of the Renaissance—home to the Medici, Michelangelo’s David, and Brunelleschi’s audacious dome. Its compact historic center hums with art on every corner, from frescoed chapels to lively piazzas lined with centuries-old cafes. Yet the best of Tuscany lies just beyond: vine-striped hills, cypress-lined lanes, and stone villages frozen in time.

Across three days, you’ll savor Florence’s icons—the Duomo, Uffizi, and Ponte Vecchio—then roll into the countryside for Chianti wines and the medieval gems of Siena and San Gimignano, with Pisa’s Leaning Tower for good measure. Expect world-class museums by morning, leisurely lunches of ribollita and bistecca, and golden-hour views from Piazzale Michelangelo.

Practical notes: book major museums in advance; churches require shoulders/knees covered; Florence’s ZTL limits driving in the center (walk or taxi). The T2 tram connects Florence Airport (FLR) to the center in ~20 minutes, and high-speed trains bring you from Rome or Milan quickly and affordably. Pack comfy shoes—you’ll be on glorious stone streets much of the time.

Florence

Base yourself in Florence for all three nights—it’s the ideal launch pad for art, food, and Tuscan day trips. The city’s neighborhoods each have a mood: the Oltrarno for artisans and wine bars, Santa Maria Novella for transport convenience, and Santa Croce for buzzing nights near the Arno.

• Top sights: Duomo and Baptistery doors, Uffizi Gallery, Accademia (David), Ponte Vecchio, Basilica di Santa Croce, Pitti Palace & Boboli Gardens.
• Neighborhood flavors: Oltrarno’s botteghe (workshops), San Lorenzo’s Mercato Centrale food hall, Sant’Ambrogio market where locals shop.
• Signature tastes: bistecca alla fiorentina, pappa al pomodoro, wild boar ragù, schiacciata sandwiches, and gelato (always).
• Fun fact: Florence’s “wine windows” (buchette del vino) once dispensed vino straight from palazzi; some are serving again today.

Where to stay: Browse apartments with views or boutique hotels steps from the Duomo on VRBO Florence or compare central stays on Hotels.com Florence. Aim for the Duomo/Oltrarno for easy walks to everything.

How to get there: Fly into FLR (or nearby Pisa PSA/Rome FCO) and connect by train. Search flights and trains with Omio and European trains with Omio Trains. Examples: Rome–Florence high-speed train ~1h30 (~€25–60); Pisa–Florence regional ~1h (~€9).

Day 1: Arrival, First Sips, and a Sunset Stroll

Morning: Travel to Florence. If landing at FLR, hop on the T2 tram to Santa Maria Novella (~20 minutes) or a taxi (~15 minutes). If you’re coming by rail, Firenze S.M.N. station drops you right downtown. For booking, use Omio for flights and Omio Trains within Europe.

Afternoon: Check in and get your bearings with a gentle loop: Piazza del Duomo (admire the marble stripes and Ghiberti’s Baptistery doors), Via dei Calzaiuoli to Piazza della Signoria (open-air sculpture museum), then down to the Arno. Grab a quick, iconic sandwich at All’Antico Vinaio (schiacciata with porchetta and truffle cream) or a sit-down bowl of ribollita at Trattoria da Garibardi near San Lorenzo.

Evening: Toast your first night on a small-group tasting walk that threads hidden “wine windows,” neighborhood bars, and Florentine bites—ample enough to count as dinner.

Activity (Viator): Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe — a delicious primer on Tuscan flavors, history, and local wine culture. Book here.

After the tour, linger on the Ponte Vecchio as the goldsmiths’ shutters glow, then slip to Locale Firenze for a nightcap in a palazzo-turned-cocktail temple or up to SE·STO on Arno for skyline views of the Duomo.

Day 2: Siena, San Gimignano, Pisa — A Tuscan Classics Day

Let someone else drive while you chase the archetypal Tuscan scene: medieval Siena’s striped cathedral, turreted San Gimignano, vineyard lunch, and the Leaning Tower in Pisa. It’s a full, rewarding day with rolling panoramas between stops.

Activity (Viator): Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery — a well-paced, all-in-one countryside immersion (usually 11–12 hours; expect a morning departure near S.M.N.; typical range ~€80–120 depending on season and inclusions). Book here.

Typical flow: guided Siena walk (learn the Palio horse race lore in Piazza del Campo), rustic lunch with wine pairings at a Chianti estate (think pappa al pomodoro, pecorino, Sangiovese), free time in San Gimignano for gelato on the main square and stone-tower photos, then a golden-hour stop at the Piazza dei Miracoli in Pisa for that classic tower shot.

Back in Florence, keep dinner light: share bistecca alla fiorentina at Buca Lapi (historic cellar steakhouse) or go Oltrarno for wild boar pappardelle at Osteria del Cinghiale Bianco. For wine, the tiny Le Volpi e l’Uva pours stellar Tuscan labels by the glass.

Day 3: Masterpieces and Markets, then Departure

Morning: Fuel up with a cappuccino and flaky sfoglia at Caffè Gilli (1860s grande dame on Piazza della Repubblica) or a specialty pour-over at Ditta Artigianale (Via dei Neri). Then dive into the city’s crown-jewel museum with a guide who can thread the highlights and juicy backstories in two hours.

Activity (Viator): Uffizi Gallery Small Group Tour with Guide — priority entry and a focused route through Botticelli, Leonardo, and Caravaggio masterpieces. Book here.

Afternoon: Browse and lunch at Mercato Centrale: line up at Da Nerbone for the classic lampredotto panino (tripe, ask for salsa verde), snag truffle tagliolini from Il Tartufo, or fresh pasta at the upstairs counters. Wander San Lorenzo’s leather stalls, then cross to the Oltrarno for artisan studios along Via Maggio and Piazza Santo Spirito—ideal for last-minute gifts.

Evening (Departure): Pick up gelato at Gelateria dei Neri (pistachio or stracciatella) and stroll the Arno one last time. Grab your bags and head out: tram T2 to FLR (~20 minutes), or trains onward—Rome in ~1h30, Milan in ~1h55—bookable via Omio Trains. If flying beyond Europe, check connections on Omio.

More great eats and sips to slot in: Breakfast at Caffè Scudieri with a view of the Baptistery; lunch-only Trattoria Mario for hearty Tuscan plates (arrive early); truffle mini-panini at Procacci on Via Tornabuoni; aperitivo with a panoramic view at La Terrazza (Hotel Continentale); dessert at Gelateria Santa Trinita after crossing the bridge.

Booking tips: Reserve Uffizi/Accademia time slots several days ahead, and restaurants like Buca Lapi or Cinghiale Bianco a few days out. Bring a light scarf for church dress codes. Expect contactless payments widely accepted, but keep some euros for markets and small cafes.

In three days, you’ll trace Florence’s arc from gilded chapels to avant-garde cocktail bars, and from Botticelli’s Venus to cypress-swept horizons. The city’s magic lies in contrast—high art and humble trattorie, scholarly museums and sunlit piazzas—leaving you full of stories (and superb wine) to bring home.