Tuscany Itinerary: How to Plan the Perfect 4 or 7 Day Trip

Cobblestone alleys that echo with history. Golden hills dotted with cypress trees. Long lunches that stretch into lazy afternoons. Tuscany is one of those places that gets under your skin in the best way.

Whether you’ve only got a few days or you’re dreaming of a week or longer, we’ve laid out two flexible itinerary options to help you make the most of your time—plus the kind of local tips we’d text a friend before their trip. With Florence, Siena, and the Tuscan countryside all within reach, your adventure can be as quick or as leisurely as you like.

Want even more detail? Our Florence & Tuscany Guide has everything from restaurant picks to Google Maps pins and winery links. It’s built to help you travel smarter, whether you’re visiting for two days or ten.

🧳 Before You Go: Tips for Planning Your Time in Tuscany

• Home Base Strategy: With 4 days, choose either Florence or Siena as your base—both give you access to regional highlights. With 7 or more days, we recommend starting in Florence and then heading to the countryside for a few nights.
• Getting Around: You won’t need a car in Florence or Siena, but it’s worth renting one for exploring the countryside. Just be mindful of ZTL (restricted traffic) zones in historic centers.
• When to Go: Spring and fall are ideal, with mild weather and fewer crowds. In summer, plan for early starts and take refuge in shady piazzas or wine cellars during the heat.
• Book Ahead: Must-sees like the Uffizi, winery visits, and popular agriturismos book up fast. Reserve Uffizi tickets directly via uffizi.it—timed entry is essential.

🚗 4-Day Tuscany Itinerary

Short on time? You can still experience the essence of Tuscany—art, food, wine, and those dreamy hill town views—in just four days.

Day 1: Florence’s Icons

Start with the big hitters. Climb to the top of Brunelleschi’s dome for sweeping city views, then admire Ghiberti’s bronze Baptistery doors. Visit the Uffizi (book in advance!) for Botticelli’s Birth of Venus and Caravaggio’s drama, or the Accademia to see David up close. Cap it off with a sunset aperitivo overlooking the Arno and a bistecca alla fiorentina at a classic trattoria.

JAM Tip: Head to Piazzale Michelangelo or the steps of San Miniato al Monte for panoramic views without the rooftop prices.

Day 2: Artisan Florence or Siena Strolls

Still in Florence? Spend your day across the Arno in the Oltrarno. Watch leatherworkers in action, browse marbled paper shops, and wander through Boboli Gardens. Reward yourself with gelato made from seasonal fruit.

If you’ve based yourself in Siena, spend the day exploring the city’s medieval center. Visit the striped Duomo, peek into the Piccolomini Library, and soak in the rhythm of life in Piazza del Campo.

Day 3: Day Trip to San Gimignano or Chianti

Rent a car and head out to San Gimignano for its towering skyline and crisp Vernaccia wine. Prefer reds? Tour a few Chianti vineyards with a Viator wine experience so you can enjoy every sip without worrying about the drive.

Day 4: Market Browsing and One Last View

Spend your final morning shopping for souvenirs—cantucci cookies, olive oil (look for the DOP label), or hand-stitched leather goods. Grab a last espresso and pastry at the bar before heading out.

🍷 7-Day Tuscany Itinerary

With a full week, you can slow down—adding vineyard visits, cheese tastings, and those quiet countryside mornings that make Tuscany unforgettable.

Day 1: Arrive in Florence

Check in and stretch your legs with a golden-hour stroll along the Arno. End your travel day with a negroni and a bowl of tagliatelle with wild boar ragu.

Day 2: Renaissance Treasures and Rooftop Views

Hit the essentials: climb the Duomo, visit the Uffizi or Accademia, and wander the Piazza della Signoria. Pause for a long lunch near the Arno, and book a rooftop table for a sunset drink.

Day 3: Florence’s Slower Side

Explore the Oltrarno. Start with espresso at a neighborhood bar, peek into artisan studios, and climb up to San Miniato for panoramic views. In the afternoon, unwind in the gardens or visit Palazzo Pitti. Cap it off with dinner on a quiet side street—somewhere the menu is still handwritten.

JAM Tip: Book a Florence cooking class or food tour to get insider food tips while tasting your way through the city.

Day 4: San Gimignano + Drive to Siena

Pick up a rental car and head to San Gimignano. Climb a tower, try local saffron dishes, or browse for ceramics. Then continue to Siena for check-in and a quiet dinner in the medieval center.

Day 5: Siena, In Depth

Spend the day exploring Siena. Visit Saint Catherine’s birthplace, the striking striped cathedral, and learn about the Contrade districts and their fierce pride in the Palio horse race. Sip a cappuccino under the shell-shaped curve of Piazza del Campo.

Day 6: Val d’Orcia Wine Country

Set out early for a scenic drive through the Val d’Orcia. Stop in Pienza for pecorino and picture-perfect views, then visit Montepulciano or Montalcino for Vino Nobile or Brunello tastings.

JAM Tip: It’s hard to beat a guided winery tour with transport—especially in a region where the wine is this good.

Day 7: Slow Start, Scenic Return

Spend your final morning sipping espresso on a terrace or walking through olive groves. If time allows, stop in Volterra or Colle di Val d’Elsa on your way back to Florence or Rome.

✨ Final Thoughts: Planning for 7 Days or Longer

The beauty of Tuscany is that it doesn’t ask you to rush. Whether you’re here for four days or stretching it to a week or more, you’ll leave with sun-warmed memories—and a longing to return.

Ready to plan your own trip? Our Florence & Tuscany digital guide makes it easy:

• 75 handpicked recommendations from hill towns to hidden cafés
• Easy-to-follow daily recs (not rigid itineraries—just what’s worth your time)
• Restaurant, wine, and gelato picks we’d fly back for
• Downloadable Google Maps pins
• Trusted Viator experiences to book before your trip

If you’re also visiting Rome, Milan, or the Amalfi Coast, check out our full Italy Guide Collection. Each one is written from experience—with the kind of detail and honesty you won’t find in free blogs.