Ponte Vecchio bridge over the Arno River Medieval tower rising above the town of San Gimignano in Tuscany Cinque Terre colorful village houses on hillside Coastal hiking trail above Cinque Terre with the Ligurian Sea and coloured villages below

Best 28 Days in Italy — from Bolzano

Bolzano → Rome → Florence → Venice → Sorrento → Capri → Positano → Milan → Cinque Terre → Tuscany

28 days · 10 cities · 42 activities · route optimized by distance

A mix of art & culture, history, and walking tours. A moderate mix of walking and active experiences, mostly at your own pace. Includes 23 must-see landmarks.

Highlights: Colosseum, Roman Forum & Palatine Hill, Rome, Vatican Museums & Sistine Chapel, Rome, Uffizi Gallery, Florence, The Last Supper — Cenacolo Vinciano, Milan, Florence Cathedral & Brunelleschi's Dome Climb

Arriving Wed, Jul 1 Change

This variant starts in Bolzano instead of the default, with the route re-optimized from that entry point.

Your Route — ordered to minimize backtracking

42+ activities scored and ranked · route optimized across 10 cities

Where you'll stay
Hotel in Bolzano · From €100/night +4 more
See lodging →
Trip cost
~$3,767 total · $135/day
See budget →
Top picks
South Tyrol Museum of Archaeology — Ötzi the Iceman, Bolzano, Dolomites Hiking Day Trip — Alpe di Siusi (Seiser Alm) from Bolzano, Bolzano Old Town & Piazza Walther, South Tyrol
See itinerary →

Day-by-Day Schedule — heavy and light days alternate so you don’t burn out

Bolzano

Bolzano 8 stops · Open in Google Maps ↗
Day 1 Wed, Jul 1 Full Bolzano View on map
Morning Bolzano city street with mountains in the background in South Tyrol
South Tyrol Museum of Archaeology — Ötzi the Iceman, Bolzano$$~2 hrs

View Ötzi — a 5,300-year-old Copper Age mummy — through a refrigerated window and examine his intact copper axe and clothing

$14 Verified Mar 2026 Year-round indoor; excellent rainy-day option; closed Mondays 📍 Map
Afternoon Alpe di Siusi alpine meadow with Dolomite peaks and wildflowers in summer
Dolomites Hiking Day Trip — Alpe di Siusi (Seiser Alm) from Bolzano$$~7 hrs

Take the train to Castelrotto and gondola up to Europe's largest alpine meadow — loop trails from 2 to 6 hours with Dolomite peak panoramas

$38 Verified Mar 2026 Meadows accessible June–October; peak wildflowers July–August; gondola closed in winter 📍 Map
🏨 Hotel in Bolzano

Old Town / Gries

wifibreakfastair-conditioning
Travelers book: Hotel Greif €180-300/nightHotel Figl €110-180/nightHotel Laurin €100-170/night
Book Hotel in Bolzano from €100/night Affiliate link — we may earn a commission at no extra cost to you
Day 2 Thu, Jul 2 Moderate Bolzano View on map
Morning Buildings lining a street in Bolzano with mountain background, South Tyrol
Bolzano Old Town & Piazza Walther, South Tyrol$~2h 30m

Walk Bolzano's bilingual old town — Italian piazzas, Austrian konditorei, Gothic cathedral, and a morning produce market

Year-round; famous Christmas market in December; best weather April–June and Sept–Oct 📍 Map
Afternoon Person holding a wine glass with mountain panorama in South Tyrol
South Tyrolean Cuisine Experience$$~2 hrs

Dine on hearty South Tyrolean specialties — speck, Schlutzkrapfen, and Strudel — in a traditional Stube

$49 Verified Mar 2026 Year-round; summer best for outdoor activities; December for Christmas markets 📍 Map
🏨 Hotel in Bolzano

Old Town / Gries

wifibreakfastair-conditioning
Travelers book: Hotel Greif €180-300/nightHotel Figl €110-180/nightHotel Laurin €100-170/night
Book Hotel in Bolzano from €100/night Affiliate link — we may earn a commission at no extra cost to you
Day 3 Fri, Jul 3 Light Bolzano
Full Day Elegant building perched on a cliff in the Italian Alps
Merano Day Trip — Spa Town & Thermal Baths$$~6 hrs

Take a scenic 30-minute train to Merano, South Tyrol's elegant Belle Époque spa town

$27 Verified Mar 2026 Year-round; summer best for outdoor activities; December for Christmas markets 📍 Map
🏨 Hotel in Bolzano

Old Town / Gries

wifibreakfastair-conditioning
Travelers book: Hotel Greif €180-300/nightHotel Figl €110-180/nightHotel Laurin €100-170/night
Book Hotel in Bolzano from €100/night Affiliate link — we may earn a commission at no extra cost to you
Day 4 Sat, Jul 4 Moderate Bolzano View on map
Morning Medieval castle on a river surrounded by trees with mountain backdrop
Runkelstein Castle$~2 hrs

Visit the 'picture book of the Middle Ages' — a castle with Europe's largest secular medieval fresco cycle

$11 Verified Mar 2026 Year-round; closed Mondays; summer best for outdoor approach; December Christmas markets nearby 📍 Map
Afternoon Alpine houses below mountains on a sunny day in South Tyrol
Alto Adige Winery Visit & Tasting$$~2h 30m

Taste Italy's finest white wines at a South Tyrol winery with panoramic Dolomite views

$38 Verified Mar 2026 Year-round; summer best for outdoor activities; December for Christmas markets 📍 Map
🏨 Hotel in Bolzano

Old Town / Gries

wifibreakfastair-conditioning
Travelers book: Hotel Greif €180-300/nightHotel Figl €110-180/nightHotel Laurin €100-170/night
Book Hotel in Bolzano from €100/night Affiliate link — we may earn a commission at no extra cost to you
Day 5 Sun, Jul 5 Moderate Bolzano View on map
Morning
South Tyrol Wine Route (Alto Adige DOC)$$~3 hrs

Sample world-class Gewürztraminer and Pinot Noir along the vineyards encircling Bolzano

$33 Verified Mar 2026 Year-round; summer best for outdoor activities; December for Christmas markets 📍 Map
Afternoon
Free time in Bolzano$~4 hrs

Explore Bolzano at your own pace — cable cars, alpine villages, or cycling the valley floor

📍 Map
🏨 Hotel in Bolzano

Old Town / Gries

wifibreakfastair-conditioning
Travelers book: Hotel Greif €180-300/nightHotel Figl €110-180/nightHotel Laurin €100-170/night
Book Hotel in Bolzano from €100/night Affiliate link — we may earn a commission at no extra cost to you
Day 6 Mon, Jul 6 Light Bolzano
🏨 Hotel in Bolzano

Old Town / Gries

wifibreakfastair-conditioning
Travelers book: Hotel Greif €180-300/nightHotel Figl €110-180/nightHotel Laurin €100-170/night
Book Hotel in Bolzano from €100/night Affiliate link — we may earn a commission at no extra cost to you
Day 7 Tue, Jul 7 Light Bolzano
🏨 Hotel in Bolzano

Old Town / Gries

wifibreakfastair-conditioning
Travelers book: Hotel Greif €180-300/nightHotel Figl €110-180/nightHotel Laurin €100-170/night
Book Hotel in Bolzano from €100/night Affiliate link — we may earn a commission at no extra cost to you
Day 8 Wed, Jul 8 Light Bolzano
🏨 Hotel in Bolzano

Old Town / Gries

wifibreakfastair-conditioning
Travelers book: Hotel Greif €180-300/nightHotel Figl €110-180/nightHotel Laurin €100-170/night
Book Hotel in Bolzano from €100/night Affiliate link — we may earn a commission at no extra cost to you
Day 9 Thu, Jul 9 Light Bolzano
🏨 Hotel in Bolzano

Old Town / Gries

wifibreakfastair-conditioning
Travelers book: Hotel Greif €180-300/nightHotel Figl €110-180/nightHotel Laurin €100-170/night
Book Hotel in Bolzano from €100/night Affiliate link — we may earn a commission at no extra cost to you
Bolzano → Rome
4h ~€55 Train from Bolzano to Roma Termini via Verona (~4h)

Rome

Rome 7 stops · Open in Google Maps ↗
Day 10 Fri, Jul 10 Full Rome View on map
Morning
Colosseum, Roman Forum & Palatine Hill, Rome$$~4 hrs ★★★★★ 4.8 (192,047)

Book a timed entry to Rome's iconic Colosseum — free for EU youth under 18 — and walk the ancient Roman Forum

$20 Verified Mar 2026 Best March–May and Oct–Nov; summer very hot and crowded; open daily except 1 Jan and 25 Dec Book this experience → 📍 Map
Afternoon St. Peter's Basilica and Vatican Museums with Renaissance architecture
Vatican Museums & Sistine Chapel, Rome$$~4 hrs ★★★★★ 4.7 (143,802)

Pre-book Vatican Museums tickets to see the Sistine Chapel and Raphael Rooms without queuing for hours

$27 Verified Mar 2026 Fewer crowds Jan–Mar and Oct–Nov; closed Sundays except last Sunday of month (free entry); also closed major Italian public holidays Book this tour → 📍 Map
🏨 Hotel in Rome

Trastevere / Monti / Termini

wifibreakfastair-conditioning
Travelers book: Hotel Raphael €200-350/nightHotel Artemide €120-200/nightGenerator Rome €40-80/nightCapo Le Case Home 9 $100-200/nightMaddalena 6 - Pantheon $100-200/nightLa Porta Rossa di Borgo - Vatican Luxury Suite $100-200/nightVilla Spalletti Trivelli $100-200/nightArpinelli Relais $60-120/night
Book Hotel in Rome from €110/night Affiliate link — we may earn a commission at no extra cost to you
Day 11 Sat, Jul 11 Moderate Rome View on map
Morning Trevi Fountain at sunset with its baroque sculptural elegance
Pantheon, Trevi Fountain & Piazza Navona, Rome$~3 hrs

Visit the Pantheon, toss a coin in Trevi Fountain with the children, and stroll to Piazza Navona for gelato

$5 Verified Mar 2026 Best spring and autumn; Trevi Fountain extremely crowded in summer; Pantheon open daily, book online to avoid queues Book this experience → 📍 Map
Afternoon Renaissance art gallery with classical sculptures and paintings
Villa Borghese Gardens & Borghese Gallery, Rome$$~4 hrs

Reserve a mandatory 2-hour slot at the Borghese Gallery, then let the children ride bikes and row boats in Rome's loveliest park

$20 Verified Mar 2026 Gardens most beautiful April–May and September–October; gallery open Tue–Sun year-round; each 2-hour slot limited to 360 visitors — book at least 4 weeks ahead for April–September 📍 Map
🏨 Hotel in Rome

Trastevere / Monti / Termini

wifibreakfastair-conditioning
Travelers book: Hotel Raphael €200-350/nightHotel Artemide €120-200/nightGenerator Rome €40-80/nightCapo Le Case Home 9 $100-200/nightMaddalena 6 - Pantheon $100-200/nightLa Porta Rossa di Borgo - Vatican Luxury Suite $100-200/nightVilla Spalletti Trivelli $100-200/nightArpinelli Relais $60-120/night
Book Hotel in Rome from €110/night Affiliate link — we may earn a commission at no extra cost to you
Day 12 Sun, Jul 12 Light Rome
Full Day
Ostia Antica Archaeological Park Day Trip from Rome$$~8 hrs

Take a 30-minute train to Ostia Antica and walk Rome's ancient port city — better-preserved and far less crowded than Pompeii

$20 Verified Mar 2026 Best March–May and Sept–Nov; very exposed in summer heat 📍 Map
🏨 Hotel in Rome

Trastevere / Monti / Termini

wifibreakfastair-conditioning
Travelers book: Hotel Raphael €200-350/nightHotel Artemide €120-200/nightGenerator Rome €40-80/nightCapo Le Case Home 9 $100-200/nightMaddalena 6 - Pantheon $100-200/nightLa Porta Rossa di Borgo - Vatican Luxury Suite $100-200/nightVilla Spalletti Trivelli $100-200/nightArpinelli Relais $60-120/night
Book Hotel in Rome from €110/night Affiliate link — we may earn a commission at no extra cost to you
Day 13 Mon, Jul 13 Moderate Rome View on map
Morning Fresh homemade Italian pasta on a wooden table
Fresh Pasta Making Class in Rome$$~3 hrs

Make fresh ravioli, fettuccine, and pappardelle in a small-group Roman cooking class — great for children age 5+

$87 Verified Mar 2026 Year-round indoor activity; busiest classes in spring and autumn 📍 Map
Afternoon Authentic Italian pasta dish with traditional Roman cuisine
Trastevere Neighborhood Evening Walk, Rome$~3 hrs

Wander Trastevere's cobblestone lanes at sunset and eat supplì, cacio e pepe, and Roman pizza al taglio

Best April–June and Sept–Oct for outdoor dining; lively year-round; most restaurants close one day/week (varies by establishment) 📍 Map
🏨 Hotel in Rome

Trastevere / Monti / Termini

wifibreakfastair-conditioning
Travelers book: Hotel Raphael €200-350/nightHotel Artemide €120-200/nightGenerator Rome €40-80/nightCapo Le Case Home 9 $100-200/nightMaddalena 6 - Pantheon $100-200/nightLa Porta Rossa di Borgo - Vatican Luxury Suite $100-200/nightVilla Spalletti Trivelli $100-200/nightArpinelli Relais $60-120/night
Book Hotel in Rome from €110/night Affiliate link — we may earn a commission at no extra cost to you
Rome → Florence
2h ~€45 Frecciarossa from Roma Termini to Firenze SMN (1h30m)

Florence

Florence 7 stops · Open in Google Maps ↗
Day 14 Tue, Jul 14 Full Florence View on map
Morning Uffizi Gallery with Renaissance masterpieces and artworks
Uffizi Gallery, Florence$$~3 hrs

Book ahead for the Uffizi to see Botticelli's Birth of Venus, da Vinci's Annunciation, and the world's greatest Renaissance collection

$27 Verified Mar 2026 Fewer crowds Jan–Mar and Oct–Nov; closed Mondays; free entry first Sunday of each month; afternoon discount after 4pm from Jan 2026 📍 Map
Afternoon Florence Cathedral dome and rooftops viewed from Brunelleschi's lantern
Florence Cathedral & Brunelleschi's Dome Climb$$~3 hrs

Climb 463 steps to the top of Brunelleschi's revolutionary dome for 360° views over Florence's terracotta rooftops

$33 Verified Mar 2026 Book dome slots weeks ahead April–Oct; less crowded Nov–Mar; cathedral and monuments open daily (hours vary by component) 📍 Map
🏨 Hotel in Florence

Duomo / Santa Croce / Oltrarno

wifibreakfastair-conditioning
Travelers book: Hotel Davanzati €100-170/nightHotel Lungarno €180-300/nightPlus Florence Hostel €30-60/nightAppartamento Signoria $100-200/nightPenthouse Le Terrazze Duomo view $100-200/nightCritone Apartment in Palazzo Tempi $100-200/nightGarbo charm, Case Galante Apartments $100-200/nightB&B Emozioni Charme $60-120/night
Book Hotel in Florence from €95/night Affiliate link — we may earn a commission at no extra cost to you
Day 15 Wed, Jul 15 Moderate Florence View on map
Morning Michelangelo's David sculpture at the Accademia Gallery in Florence
Galleria dell'Accademia & Michelangelo's David, Florence$$~2 hrs

Book a timed slot to stand before Michelangelo's 5.17m marble David at the Galleria dell'Accademia

$22 Verified Mar 2026 Fewer queues Jan–Mar and Oct–Nov; closed Mondays; free admission on April 25, June 2, November 4, and first Sunday of each month in 2026 📍 Map
Afternoon Medieval tower rising above the town of San Gimignano in Tuscany
Tuscany Day Trip — San Gimignano, Siena & Chianti Vineyards$$~8 hrs

Join a small-group day tour through Chianti vineyards, medieval San Gimignano, and a Tuscan farmhouse lunch

$98 Verified Mar 2026 Harvest season Sept–Oct is most dramatic with wine-making; wildflowers May; avoid July–Aug heat; tours run year-round 📍 Map
🏨 Hotel in Florence

Duomo / Santa Croce / Oltrarno

wifibreakfastair-conditioning
Travelers book: Hotel Davanzati €100-170/nightHotel Lungarno €180-300/nightPlus Florence Hostel €30-60/nightAppartamento Signoria $100-200/nightPenthouse Le Terrazze Duomo view $100-200/nightCritone Apartment in Palazzo Tempi $100-200/nightGarbo charm, Case Galante Apartments $100-200/nightB&B Emozioni Charme $60-120/night
Book Hotel in Florence from €95/night Affiliate link — we may earn a commission at no extra cost to you
Day 16 Thu, Jul 16 Light Florence
Full Day
Chianti Classico Wine Tour from Florence$$~7 hrs

Visit two Chianti Classico estates for barrel tastings and a Tuscan lunch at an agriturismo in rolling vineyard country

$120 Verified Mar 2026 Harvest Sept–Oct brings vendemmia (grape picking); wildflowers May; avoid July–Aug summer heat; tours run year-round 📍 Map
🏨 Hotel in Florence

Duomo / Santa Croce / Oltrarno

wifibreakfastair-conditioning
Travelers book: Hotel Davanzati €100-170/nightHotel Lungarno €180-300/nightPlus Florence Hostel €30-60/nightAppartamento Signoria $100-200/nightPenthouse Le Terrazze Duomo view $100-200/nightCritone Apartment in Palazzo Tempi $100-200/nightGarbo charm, Case Galante Apartments $100-200/nightB&B Emozioni Charme $60-120/night
Book Hotel in Florence from €95/night Affiliate link — we may earn a commission at no extra cost to you
Day 17 Fri, Jul 17 Moderate Florence View on map
Morning Traditional Florentine leather crafting workshop and artisan goods
Florentine Leather Workshop — Make Your Own Piece, Oltrarno$$~3 hrs

Hand-stitch a leather wallet, card holder, or bracelet under the guidance of an Oltrarno master craftsman

$93 Verified Mar 2026 Year-round indoor activity; Florence leather workshops are a particularly rich experience in cooler months when the Oltrarno is less crowded 📍 Map
Afternoon Ponte Vecchio bridge over the Arno River with jewelry shops
Ponte Vecchio & Oltrarno Artisan Quarter, Florence$~2 hrs

Walk across the medieval Ponte Vecchio and browse Oltrarno's leatherworkers, bookbinders, and mosaic workshops

Year-round; most atmospheric April–June and September–October; artisan workshops and gold shops generally close Sundays 📍 Map
🏨 Hotel in Florence

Duomo / Santa Croce / Oltrarno

wifibreakfastair-conditioning
Travelers book: Hotel Davanzati €100-170/nightHotel Lungarno €180-300/nightPlus Florence Hostel €30-60/nightAppartamento Signoria $100-200/nightPenthouse Le Terrazze Duomo view $100-200/nightCritone Apartment in Palazzo Tempi $100-200/nightGarbo charm, Case Galante Apartments $100-200/nightB&B Emozioni Charme $60-120/night
Book Hotel in Florence from €95/night Affiliate link — we may earn a commission at no extra cost to you
Florence → Venice
2h ~€25 Frecciarossa or Italo from Firenze SMN to Venezia Santa Lucia (~2h)

Venice

Venice 4 stops · Open in Google Maps ↗
Day 18 Sat, Jul 18 Full Venice View on map
Morning St. Mark's Basilica golden facade and Piazza San Marco in Venice
St. Mark's Basilica & Doge's Palace, Venice$$~3 hrs

Enter St. Mark's golden Byzantine basilica and the Doge's Palace — book the Palace in advance to skip long queues

$46 Verified Mar 2026 Best March–May and Sept–Oct; avoid Nov–Jan acqua alta flooding season 📍 Map
Afternoon Scenic view of Venice's Grand Canal with historic palaces and gondolas
Grand Canal by Vaporetto & Gondola, Venice$$~2 hrs

Ride vaporetto Line 1 the full length of the Grand Canal past 200 Gothic and Renaissance palaces — then take a gondola through back canals

$98 Verified Mar 2026 Year-round; most pleasant April–May and September–October; vaporetto runs 24/7 📍 Map
🏨 Hotel in Venice

San Marco / Dorsoduro / Cannaregio

wifibreakfastair-conditioning
Travelers book: Hotel Danieli €350-600/nightHotel Al Ponte Antico €130-220/nightGenerator Venice €40-80/nightLa Corte Segreta $60-120/nightIn the heart of Venice $100-200/nightCasa ai Greci $100-200/nightThree Terraces $100-200/nightPalazzo San Severo Suite Apartments $60-120/night
Book Hotel in Venice from €120/night Affiliate link — we may earn a commission at no extra cost to you
Day 19 Sun, Jul 19 Light Venice
Full Day Colorful Burano island with vibrant houses reflected in canal waters
Murano Glass & Burano Lace Island Day Trip, Venice$~6 hrs

Take the vaporetto to the Murano glass museum and glassblowing demos — kids love the fire — then ride to Burano's candy-colored houses

$27 Verified Mar 2026 Best April–June and September–October; avoid summer peak crowds on Burano 📍 Map
🏨 Hotel in Venice

San Marco / Dorsoduro / Cannaregio

wifibreakfastair-conditioning
Travelers book: Hotel Danieli €350-600/nightHotel Al Ponte Antico €130-220/nightGenerator Venice €40-80/nightLa Corte Segreta $60-120/nightIn the heart of Venice $100-200/nightCasa ai Greci $100-200/nightThree Terraces $100-200/nightPalazzo San Severo Suite Apartments $60-120/night
Book Hotel in Venice from €120/night Affiliate link — we may earn a commission at no extra cost to you
Day 20 Mon, Jul 20 Moderate Venice View on map
Morning
Venice Jewish Ghetto — the Original Ghetto$$~2h 30m

The world's first ghetto (1516) — where the word 'ghetto' was born, with five historic synagogues and a living community

$13 Open year-round; best spring and autumn 📍 Map
Afternoon St. Mark's Basilica and Campanile tower in Venice's Piazza San Marco
St. Mark's Square — Campanile, Basilica & Doge's Palace$~3 hrs

Stand in Venice's iconic Piazza San Marco and climb the Campanile bell tower for sweeping lagoon views

$11 Verified Mar 2026 Avoid November-January acqua alta flooding; summer extremely crowded
🏨 Hotel in Venice

San Marco / Dorsoduro / Cannaregio

wifibreakfastair-conditioning
Travelers book: Hotel Danieli €350-600/nightHotel Al Ponte Antico €130-220/nightGenerator Venice €40-80/nightLa Corte Segreta $60-120/nightIn the heart of Venice $100-200/nightCasa ai Greci $100-200/nightThree Terraces $100-200/nightPalazzo San Severo Suite Apartments $60-120/night
Book Hotel in Venice from €120/night Affiliate link — we may earn a commission at no extra cost to you
Venice → Sorrento
5h ~$65 Train Venice to Naples, then Circumvesuviana to Sorrento (~5h total, ~€55-70)

Sorrento

Sorrento Sorrento · Open in Google Maps ↗
Day 21 Tue, Jul 21 Full Sorrento
Morning Italian coastal town perched on clifftops above the Mediterranean
Sorrento Town Walk & Marina Grande$~3 hrs

Walk Sorrento's clifftop center, descend to the fishing harbor, and take in views of Vesuvius across the Bay of Naples

Year-round; summer very busy — mornings quieter
Afternoon
Capri Island Day Trip from Sorrento — Blue Grotto & Villa Jovis$$~8 hrs

Take the 30-minute hydrofoil to Capri and visit the Blue Grotto sea cave, Gardens of Augustus, and Villa Jovis

$22 Verified Mar 2026 Blue Grotto closed Nov-March; summer crowds; April-May ideal
Sorrento → Capri
30m ~$24 Ferry from Sorrento to Capri (~25min, ~€22)

Capri

Capri Capri · Open in Google Maps ↗
Day 22 Wed, Jul 22 Full Capri
Morning Blue glowing water inside the Blue Grotto sea cave on Capri island
Anacapri and the Blue Grotto, Capri$$~4 hrs

Take the bus to Anacapri and descend by rowboat into the Blue Grotto's eerily glowing sea cave

$33 Verified Mar 2026 Blue Grotto closes in rough seas; summer mornings offer best light and calmer water
Afternoon Capri island coastline with white limestone cliffs and turquoise water
Capri Town — Piazzetta, Gardens of Augustus, and Faraglioni Views$~3 hrs

Stroll to the clifftop park at the Gardens of Augustus — children love spotting the Faraglioni sea stacks from the viewpoint

$1 Verified Mar 2026 High season (July-August) is extremely crowded; May and September are ideal
Capri → Positano
51m ~$27 Seasonal hydrofoil Capri to Positano, ~50min, approx €22-28.

Positano

Positano Positano · Open in Google Maps ↗
Day 23 Thu, Jul 23 Full Positano
Morning Positano's colourful cliffside houses cascading down to Spiaggia Grande on the Amalfi Coast
Positano Town Walk — Spiaggia Grande, Church of Santa Maria, and Boutiques$~3 hrs

Walk Positano's steep narrow lanes, photograph its pastel dome from the beach, and swim at Spiaggia Grande

July-August is packed; arrive at beach before 9am for a free spot
Afternoon Capri island coastline with turquoise water and dramatic limestone cliffs
Capri Day Trip from Positano by Ferry$$~9 hrs

Catch the morning hydrofoil to Capri, visit the Blue Grotto, and browse the glamorous Piazzetta before the return ferry

$22 Verified Mar 2026 Hydrofoil schedules run April-October; summer ferries fill up — book in advance
Positano → Milan
9h 30m ~$84 Bus + Circumvesuviana to Naples, Frecciarossa to Milan, ~9.5h, approx €70-85.

Milan

Milan 3 stops · Open in Google Maps ↗
Day 24 Fri, Jul 24 Full Milan View on map
Morning Leonardo da Vinci's Last Supper painting in the refectory of Santa Maria delle Grazie, Milan
The Last Supper — Cenacolo Vinciano, Milan$$~1 hr

Book months ahead to see Leonardo's Last Supper mural — only 40 visitors admitted every 15 minutes

$16 Verified Mar 2026 Year-round indoor; closed Mondays; tickets released quarterly — check cenacolovinciano.org for next release date 📍 Map
Afternoon Milan's Duomo cathedral with ornate Gothic spires and white marble facade
Milan Cathedral (Duomo di Milano) & Rooftop Terraces$$~3 hrs

Walk among 135 Gothic spires on the Duomo rooftop and admire 3,200 marble statues on Italy's largest cathedral

$24 Verified Mar 2026 Year-round; clear days in Nov–Mar offer the best Alps views from the rooftop 📍 Map
🏨 Hotel in Milan

Duomo / Brera / Navigli

wifibreakfastair-conditioning
Travelers book: Room Mate Giulia €130-220/nightHotel Berna €80-130/nightOstello Bello Grande €30-60/nightCozy Downtown Apartment $60-120/nightDesign apartment Porta Venezia $100-200/nightThe Art House $60-120/nightThe Street Milano Duomo | a Design Boutique Hotel $100-200/nightArtist Apartment $60-120/night
Book Hotel in Milan from €90/night Affiliate link — we may earn a commission at no extra cost to you
Day 25 Sat, Jul 25 Moderate Milan View on map
Morning Historic Galleria Vittorio Emanuele II with glass vault roof and luxury shops
Galleria Vittorio Emanuele II & Fashion Quadrilateral, Milan$~2 hrs

Walk through Milan's 1867 glass-vaulted arcade and stroll the Quadrilatero della Moda — Via Montenapoleone, Via della Spiga

Year-round; extra buzz during Fashion Weeks in February and September 📍 Map
Afternoon
Brera Design District and Bosco Verticale, Milan$~3 hrs

Walk through Milan's creative Brera quarter and photograph the iconic vertical forest skyscraper

Outdoor walking district — best in mild weather
🏨 Hotel in Milan

Duomo / Brera / Navigli

wifibreakfastair-conditioning
Travelers book: Room Mate Giulia €130-220/nightHotel Berna €80-130/nightOstello Bello Grande €30-60/nightCozy Downtown Apartment $60-120/nightDesign apartment Porta Venezia $100-200/nightThe Art House $60-120/nightThe Street Milano Duomo | a Design Boutique Hotel $100-200/nightArtist Apartment $60-120/night
Book Hotel in Milan from €90/night Affiliate link — we may earn a commission at no extra cost to you
Milan → Cinque Terre
3h ~$29 Intercity train from Milan Centrale to La Spezia Centrale (~3h, ~€20-35)

Cinque Terre

Cinque Terre Cinque Terre · Open in Google Maps ↗
Day 26 Sun, Jul 26 Full Cinque Terre
Morning Coastal hiking trail above Cinque Terre with the Ligurian Sea and coloured villages below
Cinque Terre Blue Trail Hike — Monterosso to Vernazza$~3 hrs

Hike the Sentiero Azzurro coastal trail from Monterosso to Vernazza along dramatic cliffside paths above the Ligurian Sea

$9 Verified Mar 2026 Trails close after heavy rain; July-August is very crowded — book early-morning starts
Afternoon Sandy beach of Monterosso al Mare with the old town and Ligurian cliffs behind
Beach Day at Monterosso al Mare, Cinque Terre$~4 hrs

Swim and sunbathe at Monterosso al Mare's sandy beach — the only proper beach in Cinque Terre — with views of medieval towers

Beach season June-September; Monterosso is quieter on weekdays
Cinque Terre → Tuscany
2h 30m ~$22 Train La Spezia to Pisa, drive or bus into Tuscany, ~2-3h total.

Tuscany

Tuscany Tuscany · Open in Google Maps ↗
Day 27 Mon, Jul 27 Full Tuscany
Morning Iconic cypress tree-lined road winding through Val d'Orcia hills in Tuscany
Val d'Orcia Scenic Drive — Brunello Vineyards and Medieval Villages$$~7 hrs

Drive through UNESCO-listed Val d'Orcia, stopping at cypress-lined roads, Pienza village, and a Brunello di Montalcino tasting

$27 Verified Mar 2026 Cypress trees and rolling hills most photogenic in spring wildflowers or autumn gold
Afternoon
Tuscany's Medieval Hill Towns — Montepulciano and San Gimignano$~7 hrs

Drive between hilltop Montepulciano and tower-studded San Gimignano for wine tastings and medieval streetscapes

Summer is busy but evenings are magical; autumn harvest season adds colour and activity
Day 28 Tue, Jul 28 Tuscany
Checkout & Depart

Check out of your hotel, grab a final breakfast, and head to the airport. Safe travels from Tuscany!

Where You’ll Stay

Estimated total: €1,808–€2,712

Trip Budget Estimate

$3,767 estimated total per person
$135 per day
Lodging $2,260
Activities $1,131
Transport $376

Estimates based on listed activity prices and hotel rates. Actual costs vary by season, availability, and personal spending.

Typical range for Italy

$2,800 – $14,000 per person for 28 days

Budget: $100/day — Hostels, pizza al taglio, regional trains Mid-range: $250/day — Boutique hotels, trattorias, high-speed rail Luxury: $500/day — 5-star hotels, fine dining, private tours

Similar Destinations

Similar vibes, fewer crowds — destinations our algorithm rates as close matches to Italy.

Plan Your Trip

Practical guides to help you prepare for Italy.

🧳 Practical Info for Italy

📄 Visa
Schengen Area — visa-free for up to 90 days for US, UK, CA, AU citizens. EU/EEA nationals have freedom of movement.
💵 Tipping
Coperto (cover charge) is common at restaurants. An additional 10% tip is appreciated for good service but not required.
💱 Currency
Euro (€ EUR). Cards widely accepted in cities; carry cash for small shops and rural areas.
🔌 Power
230V, Type C/F/L plugs. US/CA travelers need a plug adapter and possibly a voltage converter for older devices.
📶 Connectivity
SIM cards available at airport shops (TIM, Vodafone, WindTre). Free WiFi common in hotels and cafés.
🚨 Emergency
112 (general emergency), 118 (ambulance)

🚄 Getting Around Italy

🚄 Rail

Trenitalia and Italo run high-speed trains between Rome, Florence, Milan, and Naples. Book 2-4 weeks ahead for 30-50% savings.

🚄 Rail

Regional trains connect smaller towns without advance booking. Validate tickets before boarding.

🚌 Bus

FlixBus covers routes between smaller cities at budget prices.

Frequently Asked Questions

Is 10 days enough for Italy?

10 days lets you cover Rome, Florence, Venice, and one coastal area (Amalfi or Cinque Terre) comfortably without rushing.

Should I book Italian trains in advance?

Yes — Trenitalia and Italo high-speed trains are 30-50% cheaper when booked 2-4 weeks ahead. Regional trains don't require booking.

What is the best time to visit Italy?

April-June and September-October offer warm weather without peak summer crowds. August is when many Italians vacation and some local shops close.

How much does 10 days in Italy cost?

Budget: $100-130/day. Mid-range: $200-300/day. Luxury: $500+/day. A coperto (cover charge) of €2-3 is standard at restaurants.

Do I need a visa for Italy?

Italy is in the Schengen Area. US, UK, Canadian, and Australian citizens can visit visa-free for up to 90 days within any 180-day period.

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