Italy Road Trip

8 Days · May 2–9, 2026 · Northern Italy & Tuscany

Chyne, Czechia → Dolomites → Lake Garda → Tuscany → Home
8
Days
~2,730
km Total
4
Regions
25+
Must-See Spots
2
Countries

The Route

A loop from Chyne near Prague through the Austrian Alps into the Italian Dolomites, down to Lake Garda and Verona, deep into Tuscany for Florence and the rolling hills of Val d'Orcia, then back home through the Brenner Pass. Eight days of mountains, lakes, Renaissance art, medieval towers, and the best food in Europe — with three nights in Florence so you can actually slow down.

Chyne Innsbruck Bolzano Dolomites Lake Garda Verona Crema Bologna Florence Tuscany Chyne

The Route Map

All stops across the 8 days. Click a marker to see what awaits there. The dashed red line traces the rough driving route.

Start / End Day 1 Day 2 Day 3 Day 4 Day 5-6 (Florence) Day 7 Day 8
01 Day

Chyne → Innsbruck → Bolzano

Through Austria via Brenner Pass into South Tyrol
📅 Sat, May 2 ☉ ~620 km ⏱ ~6.5 hours driving ⛪ Overnight: Bolzano area

The big transit day. Head south from Chyne through Linz and Salzburg, cutting through the dramatic Brenner Pass (1,370m) into Italy. Break the drive with a stop in Innsbruck, then descend into the warm, wine-covered valleys of South Tyrol.

  1. 07:00 Depart Chyne

    Coffee, fuel up, D1 south toward Austria. Czech e-vignette must be active.

  2. 10:30 Linz — quick break

    Stretch legs, breakfast/Apfelstrudel at a rest stop. ~380 km down, ~240 to go.

  3. 12:30 Arrive Innsbruck

    Park at Congress Garage or Marktplatz. Walk into the Altstadt.

  4. 12:45 Innsbruck Old Town

    Maria-Theresien-Strasse, Golden Roof, Hofkirche. Nordkette peaks towering overhead.

  5. 14:00 Tyrolean lunch

    Schnitzel, Tiroler Gröstl, or Käsespätzle at a traditional Gasthaus.

  6. 15:15 Depart Innsbruck — A13 south

    Toll road climbs into the Alps. Keep camera ready.

  7. 15:45 Brenner Pass

    Cross into Italy at 1,370 m. Optional photo stop at Brenner village.

  8. 17:30 Check in, Bolzano

    Drop bags. South Tyrolean sunshine and palm trees alongside Alpine peaks.

  9. 18:30 Evening stroll

    Piazza Walther, Via dei Portici arcades, Duomo. Aperitivo at an enoteca.

  10. 20:30 Dinner at Wirtshaus Vögele

    Canederli, speck, Schlutzkrapfen, a glass of Lagrein. Historic spot since 1277.

Innsbruck Old Town Culture 📍

Compact Alpine capital surrounded by peaks. Walk Maria-Theresien-Strasse, see the famous Golden Roof (Goldenes Dachl) — a Gothic balcony covered with 2,657 fire-gilded copper tiles. The views of the Nordkette mountains from the old town are spectacular. Budget 1–1.5 hours.

Brenner Pass Scenic 📍

The historic gateway between Austria and Italy at 1,370m. Crossed by armies and traders for millennia. The motorway (A13/A22) tunnels through dramatic Alpine scenery. You’ll notice the landscape shift from Austrian green to Mediterranean warmth within minutes.

🍷 Bolzano / Bozen Must See 📍

The capital of South Tyrol — a unique fusion of Italian and Austrian culture. Stroll Via dei Portici, a covered arcade that has been a commercial hub for 1,000 years. Visit Piazza Walther with its stunning cathedral. Home to Otzi the Iceman, the world’s oldest intact human mummy (5,300 years old), at the South Tyrol Museum of Archaeology.

🍴 South Tyrolean Dinner Food 📍

End your first day with the region’s incredible cuisine: Canederli (bread dumplings), Speck (local cured ham), Kaiserschmarrn (shredded pancakes), paired with a glass of local Lagrein red wine. Try Wirtshaus Vogele — an institution since 1277.

Tip: Buy your Czech e-vignette at edalnice.cz and Austrian digital vignette at asfinag.at before you leave. A 10-day Austrian vignette is the best value for this trip. Italy uses distance-based tolls — pay at the toll booths (cards accepted).
02 Day

The Dolomites

Exploring South Tyrol’s jaw-dropping mountain scenery
📅 Sun, May 3 ☉ ~120 km loop ⏱ ~2.5 hours driving (scenic) ⛪ Overnight: Bolzano / Val Gardena area

A full day immersed in the UNESCO-listed Dolomites — jagged limestone peaks, emerald lakes, flower-filled meadows, and some of the most photographed landscapes on Earth. Start early to beat the crowds.

  1. 07:30 Early breakfast

    Grab coffee, pastries, and a picnic lunch (bread, speck, cheese) for the road.

  2. 08:30 Lago di Braies

    Arrive before the crowds. Parking reservation required in summer (braies.org).

  3. 09:00 Lakeside walk + rowboat

    Circular trail (1h) or rent a wooden rowboat (~€30/30min) on turquoise water.

  4. 11:00 Drive to Val di Funes

    Scenic route via SS244 through Val Badia. ~1h 15min, spectacular throughout.

  5. 12:30 Santa Maddalena viewpoint

    The iconic Dolomites postcard: tiny church against the jagged Odle peaks.

  6. 13:30 Picnic lunch

    Meadow picnic or a stübele in Santa Maddalena with local cold cuts.

  7. 14:30 Adolf Munkel Trail

    Drive 15 min to Zanser Alm. Easy 1h 30min loop through meadows to the foot of the Geisler peaks — no lift needed, fully open in early May.

  8. 16:30 Drive to Alpe di Siusi area

    About 1h 15min via Bolzano. The high-altitude lifts (Seceda, Tre Cime road) only open from late May, so we stay lower today.

  9. 17:45 Alpe di Siusi cable car

    Funivia from Siusi/Seis runs year-round (weather permitting). Up to Compatsch for the meadow panorama.

  10. 19:30 Return to Bolzano

    Descend via Castelrotto. Shower, change.

  11. 21:00 Dinner in Bolzano

    Try a winery osteria — Gewürztraminer paired with pumpkin Schlutzkrapfen.

🏔 Lago di Braies Must See 📍

The crown jewel of the Dolomites. A pristine turquoise lake at the foot of Croda del Becco, surrounded by dense forest and sheer rock faces. Rent a wooden rowing boat or walk the easy lakeside trail (1 hour loop). Arrive before 9 AM — parking fills early. The water colour is surreal.

Val di Funes & St. Magdalena Photo Spot 📍

The most iconic postcard view in all of the Dolomites: the tiny church of St. Magdalena framed by the jagged Odle/Geisler peaks. The valley is serene, with traditional alpine farms and wildflower meadows. A spiritual experience even for non-hikers.

Alpe di Siusi (Seiser Alm) Scenic 📍

Europe’s largest high-altitude alpine meadow — a vast green plateau at 1,850m with the Sassolungo and Sciliar peaks as a backdrop. Take the cable car from Siusi and walk among wildflowers, wooden huts, and grazing cows. Feels like another planet.

🌲 Adolf Munkel Trail Scenic 📍

The signature Val di Funes walk — an easy ~6 km loop from Zanser Alm through alpine meadows to the foot of the Odle/Geisler peaks. No cable car required, accessible all season. The view of the jagged limestone wall rising directly out of green pasture is the “Dolomites moment” you came for. Allow 1h 30min – 2h.

Castel Roncolo Culture 📍

If you return to Bolzano with time to spare, visit this 12th-century castle perched on a cliff. Its walls are covered with remarkable medieval frescoes depicting courtly life, hunting scenes, and legends — the most complete secular medieval fresco cycle in Europe.

🎋 Renon Cable Car Scenic 📍

Right from Bolzano train station, glide above vineyards and forest to the Renon/Ritten plateau. Quiet villages, open meadows, and sweeping views back over the city. See the famous earth pyramids — natural clay pillars topped with boulders.

Tip: Early May is shoulder season — expect cool weather and snow patches above 2,000m. The high-altitude lifts (Seceda, Tre Cime road, most Dolomites pass roads) don’t open until late May/early June, so today sticks to lower-altitude walks and year-round lifts. Lago di Braies is still parking-friendly (the summer reservation system kicks in mid-May).
03 Day

Lake Garda & Verona

From the mountains to Italy’s largest lake and the city of Romeo & Juliet
📅 Mon, May 4 ☉ ~180 km ⏱ ~2.5 hours driving ⛪ Overnight: Verona / Lake Garda

Drive south through the wine-covered valleys of Trentino, watching the landscape transform from Alpine to Mediterranean. Lake Garda appears like a mirage — an enormous blue expanse backed by mountains. End the day in Verona, one of Italy’s most romantic cities.

  1. 09:30 Depart Bolzano

    A22 south along the Adige valley. Vineyards and castles on both sides.

  2. 11:30 Riva del Garda

    Coffee on the promenade, dramatic cliffs above. Short walk along the port.

  3. 12:30 Gardesana Orientale to Malcesine

    The lakeside road with tunnels, olive groves, and lake views at every bend.

  4. 13:00 Malcesine old town

    Castello Scaligero, cobbled lanes, harbour. Optional Monte Baldo cable car (~€25).

  5. 14:30 Lakeside lunch

    Lavarello (lake fish), risotto with Garda olive oil, chilled Lugana wine.

  6. 16:00 Drive to Sirmione

    ~1h 15min down the east shore. Stop at Lazise or Bardolino for a quick photo.

  7. 17:30 Sirmione peninsula

    Enter through the moated Rocca Scaligera. Walk to Grotte di Catullo Roman ruins.

  8. 19:00 Drive to Verona

    45 min on A4. Park at Parcheggio Arena near Piazza Brà, outside the ZTL.

  9. 20:00 Aperitivo at Piazza delle Erbe

    Spritz + cicchetti at a table on the square. Frescoed palaces all around.

  10. 21:00 Juliet’s Balcony + Ponte Pietra

    Evening walk through the old town. Views of the Roman theatre across the Adige.

  11. 22:00 Dinner

    Risotto all’Amarone or pastissada de caval at a Veronese osteria.

🏜 Riva del Garda Scenic 📍

The northern tip of Lake Garda, squeezed between towering cliffs. A charming waterfront town with a Venetian-era fortress, pebble beach, and views that stretch the length of the lake. Perfect for a morning coffee stop.

🏜 Malcesine Must See 📍

A gem on the eastern shore. Wander narrow cobblestone streets beneath the medieval Scaliger Castle. Take the Monte Baldo cable car (~€25 round trip) to 1,800m for some of the best panoramic views in all of Italy — the entire lake stretches below you.

🏜 Sirmione Must See 📍

A dramatic peninsula jutting into the southern lake, entered through the moated Scaliger Castle. Visit the Grotte di Catullo — ruins of a grand Roman villa (1st century BC) at the peninsula’s tip, one of the best-preserved Roman sites in northern Italy. Don’t miss the thermal springs.

🏛 Verona — Arena Must See 📍

The Arena di Verona — a Roman amphitheatre built in 30 AD, older than the Colosseum. Remarkably intact, it still hosts opera performances in summer for 15,000 spectators. Walk inside and feel the scale. Check if an evening opera is scheduled — a once-in-a-lifetime experience.

🏛 Verona — Old Town Culture 📍

Piazza delle Erbe — the vibrant main square with market stalls and frescoed palaces. Piazza dei Signori with Dante’s statue. Juliet’s House (Casa di Giulietta) with the famous balcony. Cross the ancient Ponte Pietra for evening views of the Adige river.

🍷 Bardolino Wine Wine 📍

The eastern shore of Lake Garda is Bardolino wine country. Stop at a lakeside enoteca for a glass of light, fruity Bardolino or Chiaretto rose with views over the water. The wine road between Lazise and Bardolino is beautiful.

Tip: If you can only pick two stops, choose Malcesine (with cable car) and Verona. Sirmione gets very crowded in summer — arrive before 10 AM or after 4 PM. Parking in Verona’s center is limited; use Parcheggio Arena near Piazza Bra.
04 Day

Verona → Crema → Bologna → Florence

Across the Lombardy plain, through Emilia-Romagna, into Tuscany
📅 Tue, May 5 ☉ ~380 km ⏱ ~4.5 hours driving ⛪ Overnight: Florence

A bigger driving day with two very different cultural stops. Head west through the Po Valley to the elegant Lombardy town of Crema, then south to Bologna for lunch, and finally through the Apennine hills into Tuscany. Arrive in Florence for a sunset that will leave you speechless.

  1. 08:30 Breakfast, depart Verona

    Quick espresso + brioche at a bar. Pick up the A4 westbound.

  2. 09:00 Arena di Verona — external photo

    Loop past the Roman amphitheatre on your way out. 10 min, no entry.

  3. 09:15 Drive to Crema

    ~1h 30min via A4, then A35 BreBeMi. Flat farmland of the Po plain.

  4. 10:45 Arrive Crema

    Park at Parcheggio Piazza Garibaldi, just outside the historic center.

  5. 11:00 Piazza del Duomo + CMBYN walk

    Pink-and-white cathedral, Palazzo Comunale, locations from the film.

  6. 13:00 Lunch: tortelli cremaschi

    The local sweet-savoury stuffed pasta at Trattoria Via Vai or Il Ridottino.

  7. 14:00 Depart for Bologna

    ~2h on A21 + A1 south. Refuel at an Autogrill if needed.

  8. 16:00 Bologna quick visit

    Park at Autosilo Staveco. Walk under porticoes to Piazza Maggiore + Due Torri.

  9. 17:00 Quadrilatero market

    Wander the medieval food quarter. Mortadella sandwich or gelato to go.

  10. 18:00 Depart for Florence

    A1 south through the Apennines (Variante di Valico). ~1h 15min.

  11. 19:45 Drop bags, park outside ZTL

    Garage Palazzo Vecchio or Parcheggio Beccaria. Never enter the ZTL by car.

  12. 20:30 Piazzale Michelangelo — sunset

    Taxi/bus 12 up the hill. The classic panorama of Florence glowing gold.

  13. 22:00 Dinner + Ponte Vecchio by night

    Santo Spirito or San Frediano trattoria, then cross the bridge lit up.

🏛 Crema Must See 📍

A hidden Lombardy gem and the setting of the film Call Me By Your Name. The elegant Piazza del Duomo is framed by the stunning 13th-century cathedral with its pink-and-white facade and the historic Palazzo Comunale. Wander Via XX Settembre and Via Mazzini for beautiful porticoes and boutiques. Don’t miss the tortelli cremaschi — a local sweet-savoury stuffed pasta that is utterly unique. The surrounding countryside (Moscazzano, Pandino) was used extensively in the film. Budget 1.5–2 hours.

🏛 Bologna — Quick Stop Food 📍

Italy’s food capital deserves at least a lunch stop. Walk under the famous porticoes (UNESCO-listed — 40 km of covered walkways!) to Piazza Maggiore. See the Two Towers (Asinelli & Garisenda). Eat authentic tortellini in brodo, tagliatelle al ragu, or mortadella on fresh bread. Budget 2 hours.

🏛 Piazzale Michelangelo Must See 📍

Your first stop in Florence. Drive or walk up to this hilltop terrace south of the Arno for the view of Florence — the Duomo, Palazzo Vecchio, Ponte Vecchio, and the Tuscan hills beyond. Come at sunset for golden light that makes the city glow. Free entry.

🌅 Ponte Vecchio at Night Scenic 📍

Cross Florence’s most famous bridge after dark. The medieval stone arches lit up, the Arno reflecting the lights, the jewellery shops shuttered with their wooden covers — pure magic. Walk to the middle for views both up and down the river.

🍴 Florentine Dinner Food 📍

Welcome to Tuscany with a proper dinner. Try Bistecca alla Fiorentina (the legendary T-bone, minimum 1.2 kg), ribollita (bread & vegetable soup), or pappardelle al cinghiale (wild boar pasta). Head to the San Frediano or Santo Spirito neighborhoods for authentic trattorias away from tourist traps.

Tip: Park outside Florence’s ZTL (restricted traffic zone) and use buses/trams or walk. Garage options: Parcheggio Beccaria or Garage Palazzo Vecchio. Driving into the ZTL without a permit means an automatic €80+ fine per camera that catches you.
05 Day

Florence — Renaissance Core

Accademia, Duomo, Uffizi — the Florence everyone comes for
📅 Wed, May 6 ☉ Walking day ⏱ ~12,000 steps ⛪ Overnight: Florence

Leave the car parked. Florence is best explored on foot. This city contains more Renaissance masterpieces per square meter than anywhere else on Earth. Pre-book timed tickets for the big museums — queues can exceed 3 hours without them.

  1. 08:30 Espresso + cornetto

    Breakfast standing at a local bar. Caffe Gilli or Ditta Artigianale.

  2. 09:15 Galleria dell’Accademia

    Pre-booked timed entry (accademia.org). Michelangelo’s David up close.

  3. 11:00 Walk to the Duomo

    Cattedrale di Santa Maria del Fiore. Enter the cathedral itself (free).

  4. 11:30 Climb Brunelleschi’s Dome

    463 steps, timed reservation required. Part of the combined Duomo pass (€30).

  5. 13:00 Baptistery + Campanile

    Gates of Paradise doors. Optional 414-step climb up Giotto’s bell tower.

  6. 14:00 Lunch at Mercato Centrale

    Upstairs food hall: fresh pasta, lampredotto sandwich, gelato, Chianti by the glass.

  7. 15:30 Uffizi Gallery

    Pre-booked timed entry (uffizi.it). Botticelli, Leonardo, Raphael, Caravaggio.

  8. 18:00 Piazza della Signoria

    Palazzo Vecchio courtyard, Loggia dei Lanzi open-air sculptures (free).

  9. 18:45 Aperitivo in the centre

    Negroni at Caffe Gilli or Procacci in Piazza della Repubblica. Watch Florence shift into evening.

  10. 20:00 Dinner: bistecca alla fiorentina

    Sostanza, Perseus, or any Santa Croce trattoria. Order it for two, rare, with a glass of Chianti.

The Duomo Complex Must See 📍

The Cattedrale di Santa Maria del Fiore — the largest church in Europe when it was built. Climb Brunelleschi’s Dome (463 steps) for vertigo-inducing views from inside and out. Also visit Giotto’s Campanile (414 steps, arguably better views because you see the dome) and the Baptistery with its gilded “Gates of Paradise” doors.

🎨 Uffizi Gallery Must See 📍

One of the world’s greatest art museums. See Botticelli’s Birth of Venus and Primavera, Leonardo da Vinci’s Annunciation, Caravaggio, Raphael, and Titian. Book timed entry at uffizi.it. Allow 2–3 hours minimum. Go early morning for smaller crowds.

🎨 Galleria dell’Accademia Must See 📍

Home of Michelangelo’s David — arguably the most famous sculpture in human history. The 5.17m marble giant is breathtaking in person. Also see Michelangelo’s unfinished “Prisoners” — figures seemingly struggling to free themselves from the stone. Book ahead.

Piazza della Signoria Culture 📍

Florence’s political heart since the Middle Ages. The imposing Palazzo Vecchio, a replica of David, the Loggia dei Lanzi with its open-air sculpture gallery (free!), and the Neptune Fountain. This is where Savonarola’s “Bonfire of the Vanities” took place.

Basilica di Santa Croce Culture 📍

The largest Franciscan church in the world and the final resting place of Galileo, Michelangelo, and Machiavelli. The frescoes by Giotto inside are among the most important in art history. The piazza outside is a lovely spot to rest.

👜 San Lorenzo Market Food 📍

The lively market around San Lorenzo church. Outdoor stalls sell leather goods (haggle!), while the indoor Mercato Centrale upstairs is a food hall paradise: fresh pasta, lampredotto (Florentine tripe sandwich — the street food of the city), gelato, and local wines. Lunch here.

Tip: Buy the combined Duomo pass (€30) for dome, campanile, baptistery, museum, and crypt. The dome requires a timed reservation. First Sunday of the month = free entry to state museums. Wear comfortable shoes — Florence is all cobblestones.
06 Day

Florence — Oltrarno & the slow side

Cross the river: Pitti, Boboli, artisan workshops, sunset at Piazzale Michelangelo
📅 Thu, May 7 ☉ Walking day ⏱ ~10,000 steps ⛪ Overnight: Florence (same hotel)

The other side of the Arno. Slower, quieter, full of artisan workshops and trattorias where Florentines actually eat. Pitti Palace and the Boboli Gardens give you Renaissance grandeur without Uffizi crowds, and a sunset climb to Piazzale Michelangelo and San Miniato is the postcard moment that makes the whole trip worth it.

  1. 09:30 Slow breakfast at a bar

    Cappuccino + cornetto, watch the city wake up. No rush, no museum reservations to chase.

  2. 10:30 Cross Ponte Vecchio

    Walk over Florence’s medieval bridge. Browse the jewellery stalls, peek down the Arno from the centre.

  3. 11:00 Pitti Palace

    Medici residence turned museum complex. Palatine Gallery has Raphael, Titian, Caravaggio. Far less crowded than the Uffizi.

  4. 13:00 Boboli Gardens

    Renaissance terraced gardens behind Pitti. Cypress avenues, sculpture, the Kaffeehaus terrace with city views.

  5. 14:30 Lunch in Santo Spirito

    The most Florentine piazza. Try Trattoria Casalinga or Gusta Pizza on the corner.

  6. 16:00 Brancacci Chapel

    Masaccio’s frescoes (1424) — the moment Renaissance perspective was invented. Tiny chapel, profound impact. €10, ~30 min.

  7. 17:00 Artisan walk in San Frediano

    Leather workers, bookbinders, paper makers, frame restorers. The trades that built the Renaissance, still going.

  8. 18:00 Climb to Piazzale Michelangelo

    Either bus 12 or a scenic walk up Via di San Niccolò. ~25 min on foot, all uphill but worth every step.

  9. 18:30 San Miniato al Monte

    The most beautiful Romanesque church in Tuscany, just above Piazzale Michelangelo. If lucky, catch the monks’ Gregorian chant at evening vespers.

  10. 19:30 Sunset over Florence

    Back to Piazzale Michelangelo. Bottle of Chianti from the kiosk, dome and bell-tower glowing gold. The trip’s postcard.

  11. 21:00 Trattoria dinner in Oltrarno

    Trattoria Cammillo or 4 Leoni. Pappardelle al cinghiale, ribollita, a glass of Vernaccia.

🏛 Pitti Palace Must See 📍

Vast Renaissance palace bought by the Medici in 1549 as their main residence. Five separate museums under one roof — the Palatine Gallery is the highlight, with Raphael’s greatest portraits, Titian, Caravaggio, and Rubens hung salon-style across frescoed rooms. Far less crowded than the Uffizi.

🌳 Boboli Gardens Scenic 📍

16th-century terraced gardens behind Pitti Palace. Cypress avenues, an ancient Egyptian obelisk, the Grotta del Buontalenti, and views back toward the Duomo. The model for every formal European royal garden built afterwards. ~€10 combined with Pitti.

🎨 Brancacci Chapel Culture 📍

Tiny chapel inside Santa Maria del Carmine. Masaccio’s 1424 frescoes are the literal birth of Renaissance perspective — Michelangelo and Raphael came here to study. Reservation often required (~€10). Goes by quickly, but the impact on art history is incalculable.

San Miniato al Monte Must See 📍

Florence’s most beautiful church, hidden in plain sight on the hill above Piazzale Michelangelo. White and green marble facade from the 11th century. Free entry. If you can time it for evening vespers, the Benedictine monks sing Gregorian chant — one of the trip’s most quietly moving moments.

🌂 Piazzale Michelangelo Photo 📍

The terrace where every Florence postcard is shot. The Duomo, Palazzo Vecchio, Ponte Vecchio, and the Tuscan hills laid out in front of you. A bronze copy of the David in the centre. Bring a bottle for sunset — everyone does.

🍴 Oltrarno Trattoria Food 📍

Where Florentines actually eat. Trattoria Cammillo (since 1945) for traditional Tuscan classics — pappardelle al cinghiale (wild boar pasta), ribollita, bistecca. Or 4 Leoni in Piazza della Passera for a more modern bistro feel. Reserve ahead.

Tip: Pitti + Boboli combined ticket is the value play. If you’re tired of museums by now, just skip them and lean into the slow side — long lunch in Santo Spirito, walk the artisan streets, and head up early to claim a sunset spot at Piazzale Michelangelo. The chant at San Miniato is at 17:30 most days; check the board outside.
07 Day

Tuscan Countryside

Siena, San Gimignano & Val d’Orcia — the soul of Tuscany
📅 Fri, May 8 ☉ ~250 km loop ⏱ ~4 hours driving (scenic) ⛪ Overnight: Florence area / Val d’Orcia

The day many travellers say is the highlight of their entire Italy trip. Rolling hills, cypress-lined roads, medieval hilltop towns, world-class wine, and the golden light that inspired Renaissance painters. This is the Tuscany you see in films — and it’s even better in person.

  1. 09:00 Depart Florence

    Breakfast to go. SR2 Via Cassia south toward Poggibonsi.

  2. 10:30 Arrive San Gimignano

    Park at P2 (Giubileo) outside the walls. 5-min walk up to Porta San Giovanni.

  3. 10:45 Medieval towers + Torre Grossa climb

    Piazza della Cisterna, Piazza del Duomo, 54m tower climb for 360° Tuscany views.

  4. 12:30 Gelateria Dondoli

    World Gelato Champion — try Crema di Santa Fina or Vernaccia sorbetto.

  5. 13:00 Drive to Siena

    ~50 min south on SR2. Park at Parcheggio Il Campo or Fontebranda.

  6. 14:00 Lunch near Piazza del Campo

    Pici all’aglione or pappa al pomodoro. Osteria le Logge if you can book.

  7. 15:30 Siena Duomo

    Striped marble façade, Pisano pulpit, Piccolomini Library frescoes.

  8. 16:30 Piazza del Campo

    Sit on the sloping bricks. Optional 400-step climb up Torre del Mangia.

  9. 17:30 Drive to Pienza

    ~1h south via SR2 + SP146 through Val d’Orcia. The iconic cypress road.

  10. 18:30 Pienza — pecorino + panorama

    Tasting at a formaggeria, walk the town wall for sweeping Val d’Orcia views.

  11. 19:30 Chapel of Vitaleta

    Short pullover on SP146. Tiny chapel in a cypress-lined field at golden hour.

  12. 20:15 Montepulciano wine tasting

    Descend into a tufa-rock cantina (De’ Ricci or Contucci). Vino Nobile straight from barrel.

  13. 21:30 Dinner on Piazza Grande

    Pici al ragù di cinghiale with another glass of Nobile. Stars over Tuscany.

  14. 23:30 Return to Florence (or stay over)

    ~1h 45min via A1. Better option: overnight at a Val d’Orcia agriturismo.

🏛 Siena Must See 📍

One of Italy’s most beautiful cities. The shell-shaped Piazza del Campo is unlike any other square in the world — a sloping brick amphitheatre where the famous Palio horse race happens twice a year. The Cathedral is a masterpiece of Gothic architecture with its striking striped marble facade. Budget 2–3 hours.

🏛 San Gimignano Must See 📍

The “Medieval Manhattan” — a UNESCO World Heritage town famous for its 14 surviving medieval towers (originally 72!). Wander cobblestone streets, climb the Torre Grossa for panoramic views, and try the award-winning gelato at Gelateria Dondoli on Piazza della Cisterna. Magical at any time of day.

🌿 Val d’Orcia Photo Spot 📍

A UNESCO-listed landscape of gentle clay hills, lone cypress trees, golden wheat fields, and winding white roads. The drive along SP146 between Pienza and San Quirico d’Orcia is the most iconic — you’ll recognize it from every Tuscany postcard. Stop at the Chapel of Vitaleta — a tiny chapel in a cypress-lined field.

🍷 Montepulciano Wine 📍

A majestic hilltop town with sweeping views of Val d’Orcia and Val di Chiana. Home to Vino Nobile di Montepulciano, one of Italy’s oldest and most prestigious wines. Visit underground wine cellars carved into the tufa rock beneath the town. Piazza Grande at the top is stunning.

🏛 Pienza Must See 📍

The “Ideal City of the Renaissance” — redesigned by Pope Pius II in the 15th century. A tiny jewel of a town with a perfect piazza, a cathedral with a stunning view from behind the altar, and the best Pecorino cheese in Italy. Walk to the town wall for an unforgettable Val d’Orcia panorama.

🏛 Monticchiello Scenic 📍

A hidden gem — a tiny medieval village reached via a winding white road (strada bianca). The approach road, flanked by cypress trees with rolling hills behind, is one of the most photographed scenes in Tuscany. The village itself has a terrace overlooking Pienza. Few tourists make it here.

Tip: This is a long day. Start with San Gimignano (morning, fewer crowds), then Siena for lunch, then drive the Val d’Orcia loop through Pienza and Montepulciano. Alternatively, split into two days if you can afford the extra night. Roads are winding but well-paved.
08 Day

Return to Chyne

North through the Brenner Pass back to Czechia
📅 Sat, May 9 ☉ ~850 km ⏱ ~8.5 hours driving ⛪ Home sweet home

The long drive home. Start early, take it easy, and make a couple of stops to break up the journey. The route north through the Adige valley is beautiful in itself — vineyards, castles, and the Alps growing larger ahead of you. You’ll be home by evening with a head full of memories.

  1. 07:30 Early checkout

    Last Italian espresso + cornetto standing at the bar. Load the car.

  2. 08:00 Depart Florence

    A1 north through the Apennines. Aim to clear Bologna before rush hour.

  3. 10:00 Coffee stop near Modena

    Quick Autogrill break. Stretch, fuel up, grab a panino for later.

  4. 12:00 Trento

    Park near Piazza Dante. 45-min walk: Piazza Duomo frescoes, Castello del Buonconsiglio from outside.

  5. 13:30 Lunch in Trento

    Pizzeria or polenta & luganega sausage at a traditional osteria.

  6. 14:45 Depart Trento — A22 north

    Back up the Adige valley. Castles on the cliffs: Castel Beseno, Castel Firmiano.

  7. 16:00 Last South Tyrolean espresso

    Quick stop at Brenner services. Buy speck, cheese, and a bottle of Lagrein as souvenirs.

  8. 16:30 Cross into Austria

    A13 north down to Innsbruck. Fill up in Austria — fuel is cheaper than Italy.

  9. 18:30 Salzburg (optional)

    If energy allows: 45-min Altstadt stroll, Mozart’s birthplace, Mozartkugel to go.

  10. 20:00 Dinner stop near Linz

    Proper sit-down meal. Schnitzel and a cold Stiegl before the last stretch.

  11. 23:30 Arrive Chyne

    Home sweet home. Unpack tomorrow.

🏛 Trento Culture 📍

A perfect halfway stop in the Adige valley. Elegant Piazza Duomo with its painted frescoes, the imposing Castello del Buonconsiglio, and excellent cafes. The city hosted the famous Council of Trent (1545–1563) that shaped European history. Budget 1–1.5 hours for a walk and coffee.

Rovereto Culture 📍

Just north of Trento, this small city punches above its weight. Home to MART (Museum of Modern and Contemporary Art of Trento and Rovereto) — one of Italy’s most important modern art museums. Also features a Venetian-era castle and the Peace Bell, the largest ringing bell in the world.

🏔 Salzburg (Quick Stop) Scenic 📍

If you have energy for one more stop, Mozart’s birthplace is right on the route. The Altstadt (old town) is compact and UNESCO-listed. Walk along the Salzach river, see the Hohensalzburg fortress from below, grab a Mozartkugel (chocolate). A 45-minute stroll is enough for a taste.

🍴 Last Italian Coffee Food 📍

Before you cross the Brenner back into Austria, stop at an Autogrill or a local bar in South Tyrol for one last proper Italian espresso. Savour it — you’ll miss the coffee quality the moment you leave Italy. Grab some Speck, cheese, and wine as souvenirs.

Tip: Depart by 7–8 AM to arrive home comfortably by evening. The A22 through the Brenner gets congested on weekends (especially Sundays). Consider driving back on a weekday if possible. Fill up on fuel in Austria — it’s cheaper than Italy. Stop every 2 hours to stay fresh.

What to Eat & Drink

Each region has its own culinary identity. Here’s what not to miss.

Canederli (Knodel)

South Tyrol

Bread dumplings with speck, cheese, or spinach. A hearty mountain dish that is pure comfort. Served in broth or with butter.

Speck Alto Adige

South Tyrol

Dry-cured, lightly smoked ham aged for 22+ weeks. Cut paper-thin, it’s a world apart from generic prosciutto. Buy some to take home.

Kaiserschmarrn

South Tyrol / Austria

Shredded fluffy pancakes with raisins, dusted with powdered sugar, served with plum compote. The emperor’s dessert.

Tortellini in Brodo

Bologna

Tiny hand-folded pasta parcels in a clear, rich broth. Bologna’s signature dish. Accept no substitutes — the real thing is transcendent.

Bistecca alla Fiorentina

Florence / Tuscany

A massive T-bone from Chianina cattle, grilled rare over oak. Minimum 1.2 kg, served for sharing. Drizzled with olive oil. Life-changing.

Ribollita

Tuscany

Hearty Tuscan bread soup with cannellini beans, cavolo nero, and vegetables. Twice-cooked (“reboiled”) — humble peasant food elevated to art.

Pecorino di Pienza

Val d’Orcia

World-famous sheep’s milk cheese aged in walnut leaves, ash, or hay. Buy it fresh in Pienza’s shops and pair with honey and walnuts.

Pici all’Aglione

Southern Tuscany

Hand-rolled thick spaghetti with a robust garlic and tomato sauce. A Sienese specialty — simple, rustic, and incredibly satisfying.

Gelato

Everywhere

Italy’s gift to the world. Look for “artigianale” (handmade) and natural colours. Try pistachio, stracciatella, or nocciola. Multiple times daily is acceptable.

Lagrein & Gewurztraminer

South Tyrol

The region’s signature wines. Lagrein is a dark, velvety red; Gewurztraminer a floral, aromatic white. Both unique to this alpine terroir.

Vino Nobile di Montepulciano

Montepulciano

One of Italy’s oldest designated wines (since 1685). A prestigious Sangiovese-based red. Visit underground cellars carved into volcanic rock.

Brunello di Montalcino

Montalcino

Tuscany’s most celebrated wine — powerful, complex, and age-worthy. Even a glass at a local enoteca is worth it. Budget for a bottle to bring home.

Practical Tips

🚗 Driving & Tolls

  • Czech e-vignette required for motorways — buy at edalnice.cz
  • Austrian digital vignette required — 10-day option is best value (~€11.50)
  • Italy uses distance-based tolls at booths — credit cards accepted
  • Brenner Pass toll is separate from the Austrian vignette (~€11)
  • Speed limits: Austria 130 km/h, Italy 130 km/h (110 in rain)
  • Austrian winter tire requirement: Nov 1 – Apr 15

⚠ ZTL Zones

  • Italian cities have ZTL (Zona Traffico Limitato) — restricted areas
  • Cameras photograph your plate; fines arrive months later (~€80+)
  • Florence, Siena, Bologna, Verona all have ZTL zones
  • Park outside ZTL and walk/bus in
  • Your hotel may be able to register your plate for ZTL access
  • GPS often routes through ZTL — watch for signs with red circles

💰 Money & Costs

  • Italy, Austria, and Czech Republic all use different pricing
  • Czech Republic uses CZK (Czech koruna), Austria and Italy use EUR
  • Cards accepted almost everywhere in Italy and Austria
  • Fuel is most expensive in Italy, cheapest in Czech Republic
  • Tip in Italy: not expected but rounding up is appreciated
  • Museum tickets: book online to save time and sometimes money

📷 Booking Ahead

  • Uffizi Gallery — timed entry essential (uffizi.it)
  • Accademia Gallery — timed entry essential
  • Duomo dome climb — timed reservation required
  • Most high-altitude Dolomites lifts open from late May (Seceda from 22 May 2026)
  • Lago di Braies — parking reservation may be required in peak season
  • Verona Arena opera — summer performances sell out fast

🌞 Best Time to Visit

  • May–June: ideal — warm, green, fewer crowds than July/August
  • September–October: harvest season, golden light, wine festivals
  • July–August: hot (35°C+), very crowded, expensive
  • Dolomites passes open late May – late October
  • Val d’Orcia is golden in June and again in late October

📱 Useful Apps

  • Google Maps / Waze — navigation with traffic
  • Tollguru — estimate toll costs for your route
  • Park4Night — find parking spots across Europe
  • TheFork — restaurant reservations in Italy
  • Tiqets / GetYourGuide — skip-the-line museum tickets

Book Before You Go

What needs to be locked in ahead of time, in rough order of urgency. Florence museums and the right hotels go first — the rest can wait but shouldn’t be left to the last week.

🏠 Accommodation — book first

  • Bolzano — 2 nights (May 2 & 3). Same hotel both nights ideally.
  • Verona / Lake Garda — 1 night (May 4). Verona inside or just outside the ZTL.
  • Florence — 3 nights (May 5, 6, 7). Same hotel for all three.
  • Florence or Val d’Orcia — 1 night (May 8). Optional agriturismo if you want to stay south.
  • Look for hotels that can register your plate for ZTL access (Florence, Verona).

🎨 Florence museums — timed tickets

  • Galleria dell’Accademia (David) — accademia.org. Book 2–4 weeks ahead.
  • Uffizi Galleryuffizi.it. Book 2–4 weeks ahead, even more for weekends.
  • Brunelleschi’s Dome — combined Duomo pass (€30) at duomo.firenze.it. Timed climb, books up.
  • Pitti Palace + Boboli — combined ticket, less urgent but still book ahead.
  • Brancacci Chapel — reservation often required, small capacity. Book direct via museicivicifiorentini.comune.fi.it.

🚗 Vignettes & tolls

  • Czech e-vignetteedalnice.cz. Buy before leaving.
  • Austrian digital vignetteasfinag.at. 10-day option (~€11.50) is best for this trip.
  • Brenner Pass — pay at the toll booth in cash or card; not covered by the Austrian vignette.
  • Italian motorway tolls — pay at booths as you go (cards accepted).

🍴 Restaurants — reserve ahead

  • Florence: Sostanza, Trattoria Cammillo, 4 Leoni — reserve 1–2 weeks ahead.
  • Bolzano: Wirtshaus Vögele — popular, book a few days ahead.
  • Verona: Antica Bottega del Vino — reserve, especially weekends.
  • Tuscan agriturismo dinners — if you stay over, book your table when you book the room.
  • Use TheFork app for easy Italian restaurant bookings.

🏔 Outdoors & transport

  • Lago di Braies parking — check braies.org; the summer reservation system kicks in around mid-May.
  • Funivia Alpe di Siusi — verify operating dates (early May is shoulder season).
  • Most high-altitude Dolomites lifts (Seceda, Lagazuoi) and pass roads only open from late May — not relevant for May 2–9.
  • Lucca bike rental — walk-up only, no booking needed.

💼 Documents & insurance

  • Passports — check expiry; for Czech citizens, ID card is sufficient inside Schengen.
  • EHIC / European Health Insurance Card — free, get it from your insurer before leaving.
  • Travel insurance — recommended for cancellation cover and non-EHIC costs.
  • Car insurance Green Card — check yours covers Italy and Austria.
  • Driver’s licence — EU licence accepted; carry it on you, not in the boot.

Estimated Budget (2 people)

Category Details Estimate
Fuel ~2,600 km, avg. 7L/100km, ~€1.75/L €320
Tolls & Vignettes CZ vignette + AT vignette + Brenner + IT tolls (x2 ways) €120
Accommodation 6 nights, mid-range hotels/B&Bs (€80–140/night) €600–850
Food & Drink Restaurants, cafes, gelato, wine (€60–100/day for 2) €420–700
Museums & Attractions Uffizi, Accademia, Duomo, cable cars, castles €150–200
Parking City garages and lots (~€15–30/day in Florence) €80–120
Total Estimate €1,700–2,300

Packing Checklist

Documents

  • ID / Passport
  • Driver’s license
  • Car registration & insurance
  • European breakdown cover
  • E-vignettes (CZ + AT)
  • Hotel confirmations
  • Museum reservations

Clothing

  • Comfortable walking shoes
  • Light layers (alpine mornings are cool)
  • Sunhat & sunglasses
  • Light rain jacket
  • Something nice for dinner out
  • Warm fleece for Dolomites

Gear

  • Phone car mount & charger
  • Offline maps downloaded
  • Power bank
  • Camera / good phone camera
  • Reusable water bottle
  • Sunscreen SPF 50

Car Kit

  • Warning triangle (required by law)
  • Reflective vest (required)
  • First aid kit
  • Spare bulb kit (required in some countries)
  • Headlight beam deflectors
  • CZ/AT country sticker if not on plates