When planning to visit Italy, you will have to accept that it’s nearly impossible to see everything you want on one trip unless you plan to spend months exploring (one can only dream). Most of us have a limited amount of time to explore this wonderful country and its incredible sights. If you have just 5 days in Italy, what’s gonna be? You can choose a region and take in a perfect mix of historic sites, delicious cuisine, and beautiful landscapes.
It can be tempting to squeeze in as many places as possible into your trip, but this is a foolproof recipe for stress. You’ll be moving so often that you won’t have time to appreciate Italy’s beauty, plus you’ll be losing a lot of your time travelling from one place to the next.
Luckily, you can avoid this same amount of unnecessary stress by pinning down a focus and planning your trip with Designer Journeys. You can explore either your trip with a local guide or a 5-day Italy itinerary, which is the perfect mix of everything for you. We’ve gathered together 5 different ways to do a 5-day tour of Italy so that you can see which suits you best and start planning your perfect trip!
Post Contents
- Itinerary #1: The Classic Trio – Rome, Florence, Venice in 5 Days
- Itinerary #2: Island Escape – 5 Days in Capri, Italy
- Day 1: Arrival in Naples and Ferry to Capri
- Day 2: Exploring Capri’s Natural Beauty
- Day 3: Beaches and Gardens of Capri (Morning, Afternoon, Evening)
- Day 4: Day Trip to the Amalfi Coast
- Day 5: Relax and Departure
- Additional Tips
- Itinerary #3: The Eternal City – 5-Day Trip to Italy
- Day 1: Ancient Rome
- Day 2: More Ancient Rome and Iconic Sights
- Day 3: Vatican City and Beyond
- Day 4: Exploring Lesser-Known Neighborhoods
- Day 5: Day Trip to Tivoli
- Additional Tips
- Itinerary #4: The Mighty North – 5-Day Northern Italy Tour
- Day 1: Milan – The Fashion Capital
- Day 2: Lake Como – A Day of Elegance and Scenic Beauty
- Day 3: Lake Como – Exploring the Lakeside Villas
- Day 4: Verona – A Romantic Escape
- Day 5: Return to Milan and Departure
- Additional Tips
- Itinerary #5: Art, Fashion & Romance – Milan & Venice Itinerary of 5 Days
- Bonus Itinerary Inspiration: 5-Day Cinque Terre Tours!
- How to Design Your Own Trip to Italy
- More Information on Your 5-Day Italy Vacation
- Create Your Own Tour of Italy
Itinerary #1: The Classic Trio – Rome, Florence, Venice in 5 Days
Day 1: Rome – The Eternal City
Begin your Italian journey in Rome, often called the “Eternal City.” After arriving at Rome Fiumicino Airport, take a quick train or taxi to the city centre. Once settled, you can visit some of Rome’s most famous landmarks.
Morning: Ancient Rome
You can start your day early to avoid long lines at the Capitol. You can book advance tickets or a guided tour to fast-track your entry. After exploring the iconic Colosseum, continue to the Roman Forum and Palatine Hill, where you’ll walk through the heart of ancient Roman civilization.
At dusk, the Vatican dome is aglow, creating a stunning view of Rome’s architectural splendor.
Tip: Wear comfortable shoes as you’ll be walking over uneven terrain.
Afternoon: Capitoline Hill and Piazza Venezia
Head towards Capitoline Hill, where you’ll find spectacular views of Rome. Visit the Capitoline Museums if you have time. Afterwards, take a leisurely stroll to Piazza Venezia, stopping at Altare della Patria, an impressive monument dedicated to Victor Emmanuel II.
Piazza Venezia, Turismo Roma.
Lunch: Stop at a traditional Roman trattoria nearby for a classic pasta dish like cacio e pepe.
Evening: Piazza Navona and Pantheon
Wander through the charming streets of Rome, visiting the beautiful Piazza Navona and the magnificent Pantheon. The atmosphere here in the evening is vibrant, with street performers and quaint cafes around. End your day with dinner near the Trevi Fountain, where you can toss a coin in for good luck.
Trevi Fountain, Tridente, Trevi & the Quirinale, Rome.
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Day 2: Vatican City and Ancient Wonders
Dedicate half a day of your second full-day trip to the wonders of Vatican City, home to some of the world’s most famous religious and historical sites.
Morning: Vatican Museums and St. Peter’s Basilica
Start early at the Vatican Museums. Pre-book your tickets to avoid the long lines. Explore the incredible art collections and, of course, visit the Sistine Chapel. Afterwards, head into St. Peter’s Basilica—the sheer scale and architecture are awe-inspiring.
St. Peter’s Basilica, Rome, Italy.
Tip: Dress modestly when visiting religious sites, covering shoulders and knees.
Afternoon: Castel Sant’Angelo and River Walk
After lunch, walk along the Tiber River to Castel Sant’Angelo, a historical fortress with panoramic views of Rome. Enjoy a pleasant walk along the river, crossing picturesque bridges like Ponte Sant’Angelo.
The Tiber River: Central to Prosperity and Life in Ancient Rome.
Lunch: Head to a small restaurant in Borgo Pio for delicious local fare.
Evening: Trastevere
Cross the river into Trastevere, one of Rome’s most charming neighbourhoods. Its narrow, cobbled streets are filled with character. Visit Santa Maria in Trastevere, a beautiful old church, before enjoying an evening of traditional Italian cuisine and local wines in one of the neighbourhood’s bustling trattorias.
The inside guide to Trastevere, Rome’s most emblematic neighbourhood.
Day 3: Florence – Art, Culture, and Culinary Delights
Catch a fast train to Florence, the cradle of the Renaissance and a city that boasts an array of art, architecture, and history.
Morning: Arrival and Piazza del Duomo
Take a fast train from Rome to Florence (approx. 1.5 hours). Once in Florence, head to the Piazza del Duomo. Climb to the top of the Cathedral of Santa Maria del Fiore (Duomo) for panoramic views of the city. Don’t miss the Baptistery of St. John and Giotto’s Bell Tower.
Milan Cathedral, Duomo and Vittorio Emanuele II Gallery at Piazza del Duomo.
Afternoon: Uffizi Gallery and Ponte Vecchio
After lunch, visit the Uffizi Gallery to see some of the world’s most famous Renaissance artworks, including pieces by Botticelli and Michelangelo. Afterwards, take a short walk to the Ponte Vecchio, Florence’s most iconic bridge, lined with jewellery shops.
Ponte Vecchio – The oldest and most famous bridge in Florence.
Lunch: Try a Florentine favourite like bistecca alla fiorentina (Florentine steak) at a nearby restaurant
Evening: Piazza della Signoria and Dinner
Piazza della Signoria.
Spend your evening around Piazza della Signoria, enjoying the vibrant atmosphere and historic statues. End your day with dinner at a traditional Florentine restaurant, tasting local dishes paired with Tuscan wine.
Day 4: Venice – Canals and Culture
For your quick trip and final days, take a fast train to Venice, one of the most iconic cities in the world, known for its canals, many bridges everywhere, and grand architecture.
Morning: Arrival and Piazza San Marco
Take a fast train from Florence to Venice (around 2 hours). Once in Venice, start your day in Piazza San Marco. Visit St. Mark’s Basilica, known for its opulent design and golden mosaics, and then head to the Campanile di San Marco (Bell Tower) for breathtaking views of the city.
St. Mark’s Basilica: a magnificent piece of history.
Tip: Pre-book skip-the-line tickets for St. Mark’s Basilica to save time.
Afternoon: Doge’s Palace and Grand Canal
After lunch, visit the Doge’s Palace, a masterpiece of Gothic architecture. Cross the Bridge of Sighs and learn about Venice’s fascinating history. Later, take a water taxi or vaporetto ride along the Grand Canal—a must for seeing Venice’s grand palazzos and vibrant city life from the water.
Doge’s Palace.
Lunch: Try cicchetti and Venetian tapas at a local bàcaro.
Evening: Explore the Rialto Area
In the evening, visit the Rialto Bridge and explore the surrounding area. It’s a great spot for shopping and dining. Enjoy dinner at a restaurant with a view of the canal, and perhaps try some Venetian seafood dishes, like squid ink pasta.
The Iconic Rialto Bridge: Venice’s Most Famous Landmark.
Day 5: Venice
Morning: Islands of Murano and Burano
Take a morning boat trip to the nearby islands of Murano and Burano. Murano is famous for its glass-making, and Burano for its colourful houses and lace-making traditions. These islands offer a tranquil escape from the bustling centre of Venice.
Murano in Venice.
Afternoon: Departure or Last-Minute Exploration
If you have time before your flight or onward journey, wander through Venice’s less touristy areas, such as Cannaregio or the Jewish Ghetto. If your departure is from Venice Marco Polo Airport, plan your transport in advance, as it can be tricky navigating Venice’s unique infrastructure.
Cannaregio, Venice’s Most Relaxing District.
Additional Tips
- Trains: Book fast train tickets in advance via Trenitalia or Italo for better prices and reserved seats. All main train stations in Rome, Florence, and Venice are well-connected by public transport.
- Queues: Purchase skip-the-line tickets where possible, especially for major attractions like the Colosseum, Vatican Museums, Uffizi Gallery, and Doge’s Palace.
- Travel Light: Venice, in particular, has many bridges and narrow streets, so it is advisable to travel with lighter luggage.
- Accommodation: Stay near major landmarks for convenience, especially in Venice, where getting around can take time.
Itinerary #2: Island Escape – 5 Days in Capri, Italy
Day 1: Arrival in Naples and Ferry to Capri
Morning: Arrival in Naples
Begin your trip by flying into Naples International Airport. Once you’ve collected your luggage, make your way to Molo Beverello or Calata di Massa port for your ferry to Capri. Ferries depart regularly, and the journey takes approximately 50 minutes.
The Architecture of Naples’ Historic Center.
Tip: Book your ferry tickets in advance to avoid queues and ensure a smooth transfer. If you have extra time, explore Naples briefly, grabbing a quick bite of Neapolitan pizza—the birthplace of the dish.
Afternoon: Arrival in Capri and La Piazzetta
Upon arrival in Capri, you’ll dock at Marina Grande, the main port. Head to your hotel for check-in. Once settled, take the funicular from the port to La Piazzetta, the lively heart of Capri, often referred to by local guides as the “living room of the world.” Enjoy a coffee or aperitivo at one of the charming cafes, while people-watching in this glamorous square.
Capri: the beaches of the island of Campania.
Lunch: Try a Caprese salad at a local café—it’s a must in Capri, as it originates from the island.
Evening: Sunset at Anacapri
In the evening, take a short trip to Anacapri, Capri’s quieter and more relaxed town. Enjoy a sunset aperitivo with stunning views over the Bay of Naples. Anacapri is known for its more local atmosphere, offering a peaceful contrast to the bustling centre of Capri.
Day 2: Exploring Capri’s Natural Beauty
Morning: Blue Grotto and Boat Tour
Start your day with a visit to the Blue Grotto, Capri’s most famous natural wonder. Head down to Marina Grande and book a small boat tour that will take you inside the grotto. The sunlight reflects off the water, creating an ethereal blue glow inside the cave.
Grotta Azzurra – The Blue Grotto Capri.
Tip: Arrive early to avoid the busiest times, as there can be very long line up queues to enter the grotto, particularly in the summer.
Afternoon: Villa Jovis and Monte Solaro
After the boat tour, head to Villa Jovis, the ruins of Emperor Tiberius’s ancient palace. It’s a scenic hike up the hill, but the views are worth the effort, offering breathtaking vistas over the island and the sea. From there, make your way to Monte Solaro, the highest point on Capri. You can either hike or take the chairlift from Anacapri for panoramic views of the island.
Villa Jovis: the magnificent residence of Emperor Tiberius.
Lunch: Enjoy a leisurely meal at a traditional trattoria in Anacapri, where you can sample fresh seafood dishes such as spaghetti alle vongole (spaghetti with clams).
Evening: Dinner at Marina Piccola
Spend your evening at Marina Piccola, a serene bay with fantastic views of the Faraglioni Rocks. Choose a seaside restaurant for dinner, enjoying freshly caught seafood as the sun sets. The atmosphere is relaxed and romantic—ideal for unwinding after a day of exploring.
Day 3: Beaches and Gardens of Capri (Morning, Afternoon, Evening)
Morning: Beach Day at Marina di Mulo
Today is all about relaxation. Spend the morning soaking up the sun at one of Capri’s beautiful beaches, such as Marina di Mulo. This pebble beach is perfect for a laid-back day by the sea, offering crystal-clear waters and sunbeds for hire.
Marina Di Mulo Beach, Capri, Italy.
Tip: Capri’s beaches are often pebbled, so bring water shoes for comfort. Also, arrive early, as sunbeds can fill up quickly.
Afternoon: Giardini di Augusto and Via Krupp
After some time at the beach, make your way to the Giardini di Augusto. These terraced gardens offer stunning views of the Faraglioni Rocks and the sinuous Via Krupp, a serpentine pathway carved into the cliffs. Stroll through the lush gardens, admiring the vibrant Mediterranean flowers.
Augustus Gardens in Capri.
Lunch: Enjoy a relaxed lunch at a nearby café, where you can enjoy traditional Capri cuisine, such as ravioli capresi, stuffed with ricotta and marjoram.
Evening: La Piazzetta Nightlife
Return to La Piazzetta in the evening to experience Capri’s glamorous nightlife. The square comes alive with a chic crowd, and it’s the perfect spot to enjoy a cocktail while soaking in the island’s glamorous atmosphere. For dinner, consider a restaurant with a view offering refined cuisine that reflects Capri’s blend of luxury and simplicity.
Day 4: Day Trip to the Amalfi Coast
Morning: Ferry to the Amalfi Coast
Set out early for a five-day trip to the Amalfi Coast, one of Italy’s most iconic coastal destinations. Take a ferry from Capri to Positano or Amalfi, two of the most picturesque towns in the region. The journey itself is a delight, with stunning coastal views throughout.
The Towns of the Amalfi Coast.
Tip: Plan a great day trip out on this day carefully, as train station ferry schedules can vary, and it’s best to book tickets in advance during the high season.
Afternoon: Explore Positano or Amalfi
Spend the afternoon exploring either the beautiful villages of Positano or the Amalfi coast. In Positano, wander through narrow streets lined with pastel-coloured houses, luxury boutiques, multiple hotels, and cliffside restaurants. Visit the Amalfi Cathedral and enjoy coffee in the town’s charming piazza in Amalfi.
Positano, The Vertical City.
Lunch: Have lunch at a seaside restaurant and try a local delicacy like Scialatielli ai Frutti di Mare (homemade pasta with seafood).
Evening: Return to Capri and Sunset Views
After a day of exploration, return to Capri by ferry. For your evening, relax with a sunset aperitivo at a cliffside bar or restaurant, enjoying the island’s golden light as the day winds down.
Day 5: Relax and Departure
Morning: Visit Villa San Michele and Last-Minute Souvenirs
For your final morning, visit Villa San Michele in Anacapri, the former home of Swedish doctor and author Axel Munthe. The villa is surrounded by beautiful gardens with panoramic views over the island. Spending your last few hours on Capri is a peaceful and inspiring place.
Villa San Michele – Museums – Anacapri.
Tip: If you’re looking for souvenirs, this is a good time to browse Anacapri’s artisan shops, where you can find items such as hand-painted ceramics and locally made limoncello.
Afternoon: Departure from Capri
Have a light lunch at a seaside restaurant before heading back to Marina Grande for your ferry back to Naples. Ensure you leave plenty of time to catch your ferry, especially if you have a flight to catch.
Additional Tips
- Weather: Capri is best visited during the shoulder seasons (late spring and early autumn), when the weather is pleasant, but the crowds are fewer.
- Boat Tours: To avoid disappointment, book your Blue Grotto and island boat tours in advance, especially during peak season.
- Transport: Capri is car-free for tourists, so you’ll rely on taxis, buses, or walking. The island is small, but it’s quite hilly, so consider using the funicular from Marina Grande to the Piazzetta.
- Packing: Bring comfortable walking shoes, swimwear, sunscreen, and light clothing for exploring, as Capri’s streets are steep and cobbled.
- Dining: Capri’s food scene is renowned for its fresh seafood, citrus-infused dishes, and elegant dining options, so try to indulge in local specialities like ravioli capresi and torta caprese (a rich chocolate almond cake)
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Itinerary #3: The Eternal City – 5-Day Trip to Italy
Day 1: Ancient Rome
Morning: Colosseum and Roman Forum
Start your Roman adventure with a visit to the iconic Colosseum. Book a guided tour to skip the long queues and gain insights into the fascinating history of gladiatorial combat. After your tour, stroll through the Roman Forum, the heart of ancient Roman public life, where you can explore the ruins of temples, basilicas, and government buildings.
Colosseum morning in Rome, Italy.
Tip: Arrive early to enjoy a quieter experience before the crowds arrive.
Afternoon: Palatine Hill
After lunch at a nearby trattoria, head to Palatine Hill, the most famous of Rome’s seven hills. Here, you can explore the archaeological sites and enjoy spectacular views of the Forum and Circus Maximus. Take your time wandering through the lush gardens and ancient ruins.
Palatine Hill – Rome’s Mythic Past and Majestic Ruins.
Lunch: Try Pasta alla Gricia or Saltimbocca alla Romana at a local eatery in the vicinity.
Evening: Pantheon and Trevi Fountain
In the evening, visit the Pantheon, a marvel of ancient architecture. Afterwards, take a leisurely stroll to the Trevi Fountain. Toss a coin in to ensure your return for day trips to Rome! Finish your day with dinner in the Campo de’ Fiori area, where you can enjoy the lively atmosphere and sample Roman cuisine.
Trevi Fountain (Fontana di Trevi), Rome.
Dinner Tip: Look for restaurants offering outdoor seating for a lovely evening experience.
Day 2: More Ancient Rome and Iconic Sights
Morning: Vatican City – Vatican Museums
Dedicate the morning to the Vatican Museums. Pre-book a skip-the-line ticket or opt for a full guided tour or private tour to avoid the long queues. The museum houses an impressive collection of art, including the stunning Raphael Rooms and, of course, the world-famous Sistine Chapel, with Michelangelo’s iconic ceiling.
Vatican Museums, Rome, Italy.
Tip: Wear comfortable shoes, as you’ll be walking a lot.
Afternoon: St. Peter’s Basilica
After the museums, visit St. Peter’s Basilica. Climb to the top of the dome for breathtaking views of the Vatican and the whole city centre. Inside the basilica, take in the grandeur of Bernini’s Baldachin and Michelangelo’s Pietà.
St Peter’s Basilica | Vatican City, Borgo & Prati, Rome.
Lunch: Dine at Ristorante da Cesare al Casaletto, renowned for its Roman dishes.
Evening: Spanish Steps and Piazza di Spagna
In the evening, head to the Spanish Steps. Climb the steps for a beautiful view of the area, and then explore the chic shops in Via dei Condotti. Enjoy dinner at a restaurant overlooking Piazza di Spagna.
The Eternal Allure of the Spanish Steps.
Dinner Tip: Try Cacio e Pepe, a classic Roman pasta dish.
Day 3: Vatican City and Beyond
Morning: Vatican Gardens (Optional)
If you want a quieter experience, consider a morning visit to the Vatican Gardens (pre-booking required). These beautiful gardens offer a peaceful retreat with stunning views and interesting history.
Vatican Gardens: The Pope’s Personal Garden of Eden.
Afternoon: Explore Trastevere
After lunch, go to Trastevere, a charming neighbourhood with narrow cobbled streets. Visit Santa Maria in Trastevere, one of the oldest churches in Rome, known for its beautiful mosaics. Spend some time wandering through the vibrant streets, popping into local shops and cafes.
Trattoria da Enzo al 29, authentic Trastevere restaurant.
Lunch: Enjoy a traditional Roman meal at Trattoria Da Enzo in Trastevere.
Evening: Roman Jewish Ghetto
In the evening, visit the Jewish Ghetto, known for its rich history and delicious food. Stop by Portico d’Ottavia, where you can explore the ruins and enjoy a meal at a local restaurant. Be sure to try Carciofi alla Giudia (Jewish-style artichokes).
The Portico d’Ottavia.
Dinner Tip: Look for a restaurant with outdoor seating to soak in the atmosphere.
Day 4: Exploring Lesser-Known Neighborhoods
Morning: Testaccio and Local Markets
Start your day in Testaccio, a neighbourhood known for its authentic Roman food scene. Visit the Testaccio Market to sample local delicacies and fresh produce. Take a guided food tour to get the most out of your culinary experience.
Testaccio a district not yet discovered by tourists.
Tip: Bring an appetite for tasting various local specialities.
Afternoon: Explore the Aventine Hill
After lunch, head to Aventine Hill. Visit the Basilica of Santa Sabina, and don’t miss the famous keyhole at the Priory of the Knights of Malta, which offers a unique view of St. Peter’s Basilica framed by lush greenery.
Aventine Hill In Rome Is A Beautiful Escape From The Chaos.
Lunch: Try Supplì, rice balls filled with mozzarella, at a nearby trattoria.
Evening: Dinner in Monti
Spend your evening in the Monti district, known for its trendy vibe and artisan shops. Explore the area before enjoying dinner at a local restaurant. Monti has a vibrant bar scene, perfect for a nightcap after dinner.
Monti: Rome’s historical and hippest neighborhood.
Dinner Tip: Opt for a restaurant that offers homemade pasta for an authentic experience.
Day 5: Day Trip to Tivoli
Morning: Journey to Tivoli
Take a morning train or bus to Tivoli (about 30 km from Rome). Start your day at Villa d’Este, renowned for its beautiful gardens and impressive fountains. Stroll through the lush grounds and admire the stunning Renaissance architecture.
Villa d’Este: the Tivoli villa of the baroque.
Tip: Arrive early to beat the crowds and enjoy the tranquillity of the gardens.
Afternoon: Hadrian’s Villa
After lunch, head to Hadrian’s Villa (Villa Adriana), a UNESCO World Heritage site. Explore the extensive ruins of the ancient Roman villa and marvel at the grandeur of the complex, including pools, gardens, and temples.
Hadrian’s Villa | Roman architecture, UNESCO, ruins.
Lunch: Enjoy a meal at a local tavern in Tivoli, trying dishes like Saltimbocca or Porchetta.
Evening: Return to Rome
After a day of exploration, return to the city centre of Rome in the late afternoon. Spend your fourth day’s final evening enjoying a leisurely dinner, perhaps revisiting your favourite spot or trying a new restaurant.
Dinner Tip: Celebrate your first trip here with a meal at a rooftop restaurant for stunning views of the city at night.
Additional Tips
- Rome Transport: Use the Metro, buses, or trams for easy access around the city. Consider purchasing a Roma Pass for unlimited public transport and discounted entry to attractions.
- Ticket Reservations: Pre-book tickets for major attractions like the Colosseum, Vatican Museums, and Villa d’Este to save time and avoid long lines.
- Cultural Etiquette: Respect local customs, especially when visiting religious sites. Dress modestly, covering shoulders and knees.
- Dining Reservations: Popular restaurants can fill up quickly, so it’s advisable to make reservations, especially for dinner.
Itinerary #4: The Mighty North – 5-Day Northern Italy Tour
Day 1: Milan – The Fashion Capital
Morning: Duomo di Milano
Start your adventure in Milan with a visit to the magnificent Duomo di Milano, the city’s iconic cathedral. Climb to the rooftop for breathtaking views of the city centre and to admire the intricate Gothic architecture up close.
Duomo di Milano : Myths and legends.
Tip: Pre-book your tickets online to skip the long queues.
Afternoon: Galleria Vittorio Emanuele II
After exploring the Duomo, head to the Galleria Vittorio Emanuele II, Italy’s oldest shopping mall. Enjoy a leisurely lunch at one of the cafes inside while soaking in the elegant atmosphere. Don’t forget to take a few photos of the stunning mosaics and glass dome.
Galleria Vittorio Emanuele II – Shopping arcade in Milan.
Lunch: Try a classic Milanese dish like Risotto alla Milanese at Ristorante Savini.
Evening: The Last Supper
In the evening, visit Santa Maria delle Grazie to see Leonardo da Vinci’s famous mural, The Last Supper. Ensure you book your tickets well in advance, as they sell out quickly. After your visit, enjoy dinner at a nearby restaurant.
Santa Maria delle Grazie – Museo.
Dinner Tip: Ristorante da Vinci is a great choice, offering traditional Italian cuisine in a lovely setting.
Day 2: Lake Como – A Day of Elegance and Scenic Beauty
Morning: Travel to Lake Como
Take an early morning train from Milan to Como (about 1 hour). Upon your train station arrival, explore the charming town of Como. Visit the Como Cathedral and take a stroll along the lakefront promenade to soak in the stunning and beautiful scenery below.
The Timeless Allure of Lake Como’s Beaches.
Tip: Purchase your train tickets in advance for the best prices.
Afternoon: Bellagio Boat Tour
After lunch in Como, hop on a ferry to Bellagio, often referred to as the “Pearl of the Lake.” Enjoy the picturesque views of the surrounding hills and elegant villas. Spend the afternoon exploring Bellagio’s cobbled streets, beautiful gardens, and quaint shops.
Bellagio: Lake Como Shared Boat Tour.
Lunch: Try the local specialities at Ristorante La Punta, which has a stunning view of the lake.
Evening: Dinner in Bellagio
Spend your evening dining in Bellagio, perhaps at Ristorante Salice Blu, which offers delicious regional dishes and an extensive wine list. After dinner, enjoy a leisurely walk along the lakeshore, taking in the peaceful ambience as the sun sets over Lake Como.
Day 3: Lake Como – Exploring the Lakeside Villas
Morning: Visit Villa Carlotta
After breakfast, take a ferry to Tremezzo to visit Villa Carlotta, which is famous for its beautiful gardens and art collection. Spend your morning wandering through the lush gardens, enjoying the stunning views of the lake and surrounding mountains.
The Italian gardens of lake Como – Villa Carlotta in Tremezzo.
Tip: Check the local guide on the villa’s website for any events or guided tours available during your visit.
Afternoon: Varenna and Villa Monastero
In the afternoon, take a short ferry ride to Varenna, a charming small town known for its colourful houses and romantic lakeside atmosphere. Visit Villa Monastero, a historic villa with beautiful gardens. Enjoy lunch at a lakeside café in Varenna.
Varenna – The Enchanting Gem of Lake Como.
Lunch: Consider Ristorante La Vista, which offers wonderful views and delicious Italian dishes.
Evening: Return to Como
Return to Como in the evening. For dinner, choose a local restaurant such as Il Ristorante di Paolo or Ristorante Caffe’ D’Artisti for some authentic Italian cuisine. After dinner, enjoy a stroll around the illuminated lakefront, reflecting on the beauty of the day.
Day 4: Verona – A Romantic Escape
Morning: Travel to Verona
Depart from Como early in the morning and take a train to Verona (approximately 2–2.5 hours). Upon your next train arrival, start your exploration at the Arena di Verona, an ancient Roman amphitheatre still used for concerts and operas.
The Verona Arena: theatre in Verona, Italy.
Tip: Pre-book your tickets for the Arena if you wish to catch a show during your stay.
Afternoon: Juliet’s House and Piazza delle Erbe
After visiting the main church and the Arena, stroll over to Casa di Giulietta (Juliet’s House), where you can see the famous balcony. Then, head to Piazza delle Erbe, the vibrant market square surrounded by historical buildings and cafes. Enjoy lunch at one of the restaurants in the square, sampling local dishes.
Juliet’s House in Verona City Centre.
Lunch: Try Tortellini di Valeggio, a traditional pasta dish, at Ristorante Maffei.
Evening: Explore Verona’s Streets
Spend the same day of your evening wandering the charming streets and beautiful villages of Verona, discovering hidden gems and enjoying the local atmosphere. Consider having dinner at Osteria le Vecete, known for its delicious pasta and intimate setting.
Tip: Try a glass of local Valpolicella wine to complement your meal.
Day 5: Return to Milan and Departure
Morning: Visit Sforza Castle
Before heading back to Milan, take some time to visit Sforza Castle in Verona, a magnificent fortress with museums and beautiful grounds. After a day exploring the castle, enjoy a leisurely breakfast at a local café.
Castello Sforzesco in Milan, ancient fortress now museum.
Afternoon: Return to Milan
Travel back to Milan by train (about 1.5 hours). Upon arrival, spend your two-day trip, the first night and the last day, shopping in the fashion capital. Head to the Quadrilatero della Moda (Fashion District) for high-end boutiques, or explore the Corso Buenos Aires for a more affordable shopping experience.
Quadrilatero della Moda – Milano.
Tip: If you have time, visit Castello Sforzesco and the surrounding Sempione Park for a leisurely walk.
Evening: Farewell Dinner
Enjoy a farewell dinner at a restaurant like Trattoria Milanese or Ristorante Cracco for a memorable final meal in Italy.
Dinner Tip: Sample Milanese risotto or Ossobuco to get an authentic taste of the region.
Additional Tips
- Travel by Train: Northern Italy has an excellent train network, making travel between cities quick and convenient. Consider purchasing Eurail Pass or Trenitalia tickets in advance for the best deals.
- Timing: Try to start your days early to avoid crowds at major attractions and maximise your time in each city.
- Dining Reservations: Popular restaurants may fill up quickly, especially during peak tourist seasons, so it’s advisable to make reservations ahead of time.
- Cultural Etiquette: When dining in Italy, it’s customary to wait for the host to invite you to sit down. Also, remember that service charges are often included in the bill.
Itinerary #5: Art, Fashion & Romance – Milan & Venice Itinerary of 5 Days
Day 1: Milan – The Fashion Capital
Morning: Quadrilatero d’Oro
Begin your Milan adventure in the famous Quadrilatero d’Oro, the luxury shopping district. Here, you’ll find iconic fashion houses such as Gucci, Prada, and Versace. Spend the morning exploring the high-end boutiques and enjoying the glamorous atmosphere.
Quadrilatero d’Oro, Milan.
Tip: If you’re interested in fashion, consider booking a personal shopping experience for insider knowledge on Italian designers.
Afternoon: Pinacoteca di Brera
After a morning of shopping, make your way to the Pinacoteca di Brera, one of Italy’s most important art galleries. Marvel at masterpieces by Italian masters, including Caravaggio and Raphael. Don’t forget to visit the Orto Botanico di Brera, the beautiful botanical garden adjacent to the gallery.
Pinacoteca di Brera – Museum & Art Gallery in Milan.
Lunch: Enjoy lunch at Ristorante Nabucco in the Brera district, which is known for its delicious pasta dishes.
Evening: Duomo di Milano
In the evening, visit the Duomo di Milano. Climb to the rooftop for spectacular views of the city at sunset. Once back on the ground, explore the surrounding Piazza del Duomo.
Cathedral of Light Duomo di Milano’s New Lighting.
Dinner: Dine at Ristorante Cracco, a Michelin-starred restaurant offering modern Italian cuisine in an elegant setting.
Day 2: Milan – More Cultural Delights
Morning: Castello Sforzesco
Start your day with a visit to Castello Sforzesco, a historic castle surrounded by beautiful gardens. Explore the museums within the castle that showcase art, archaeology, and ancient history.
The Castello Sforzesco, a landmark of Milan.
Tip: Stroll through Sempione Park behind the castle for a relaxing morning.
Afternoon: Santa Maria delle Grazie
After lunch, head to Santa Maria delle Grazie to see Leonardo da Vinci’s The Last Supper. Be sure to book your tickets in advance, as they often sell out quickly.
Santa Maria delle Grazie and Da Vinci last supper.
Lunch: Try Trattoria Milanese for traditional Italian dishes.
Evening: Navigli District
In the evening, explore the Navigli District, famous for its picturesque canals and vibrant nightlife. Enjoy an aperitivo by the water, a pre-dinner drink accompanied by snacks.
Navigli, Milan: the Coolest District in the City.
Dinner: Dine at Ristorante Al Porto, known for its seafood and lovely canal views.
Day 3: Venice – The City of Canals
Morning: Travel to Venice
Take a direct train from Milan to Venice (about 2.5 hours). Upon arrival, head to Piazza San Marco, the main square of Venice. Marvel at the stunning St. Mark’s Basilica and its intricate mosaics.
Venice, Italy.
Tip: Arrive early to avoid crowds and enjoy the square’s beauty.
Afternoon: Doge’s Palace
Visit the Doge’s Palace, the former residence of the Doge of Venice. Explore the opulent rooms, the Bridge of Sighs, and the fascinating history of the Venetian Republic. After your guided tour, take a leisurely stroll through the charming streets of Venice.
Exploring the Doge’s Palace in Venice.
Lunch: Enjoy lunch at Ristorante Antico Pizzico, known for its authentic Venetian cuisine.
Evening: Gondola Ride
In the evening, experience a romantic gondola ride through the canals of Venice. This is a must-do for couples and offers a unique perspective of the city’s beauty.
Gondolas: Venice canal ride is all romance and no schlock.
Dinner: Dine at Osteria alle Testiere, a small and intimate restaurant famous for its seafood dishes.
Day 4: Venice – Art and Architecture (Morning, Afternoon, Evening)
Morning: Rialto Market
Start your day at the Rialto Market, where you can sample local produce and enjoy the lively atmosphere. After a few hours exploring the market, cross the Rialto Bridge, one of Venice’s most famous landmarks.
The Rialto fish market in Venice.
Tip: Arrive early to see the market in full swing and try some fresh cicchetti (Venetian tapas).
Afternoon: Peggy Guggenheim Collection
In the afternoon, visit the Peggy Guggenheim Collection, an impressive modern art museum housed in her former home. The museum features works by artists such as Picasso, Kandinsky, and Pollock.
Venice Museum: Peggy Guggenheim house museum.
Lunch: Enjoy lunch at Caffè Guggenheim on the museum grounds.
Evening: Stroll and Dinner
Spend the evening strolling through the picturesque streets of Venice. As night falls, the city takes on a magical quality.
Dinner: Experience a delightful meal at Corte Sconta, a hidden gem known for its seafood and warm ambience.
Day 5: Final Day in Venice
Morning: Basilica di San Marco
On your last morning in Venice, visit St. Mark’s Basilica to admire its stunning architecture and breathtaking mosaics. Take your time to explore the interior and climb the bell tower for panoramic views of the city.
Basilica di San Marco in Venice.
Tip: Book a guided tour to learn about the basilica’s fascinating history.
Afternoon: Last-minute Exploration and Departure
Spend your last afternoon exploring any sights you may have missed, such as the Church of Santa Maria della Salute or the Gallerie dell’Accademia. Enjoy a final stroll along the canals, soaking in the romance of Venice.
Gallerie dell’Accademia.
Lunch: Grab a quick bite at Trattoria da Fiore before heading to the main train station again.
Evening: Departure from Venice
Depart from Venice, either returning to Milan or heading to your next destination. If time permits, enjoy a farewell aperitivo at a canal-side bar before you leave.
Additional Tips
- Transportation: Use Italy’s efficient train system for travel between Milan and Venice. Book tickets in advance for the best prices.
- Cultural Etiquette: When visiting churches, dress modestly. Cover your shoulders and knees as a sign of respect.
- Dining Reservations: Popular restaurants can fill up quickly, so consider making reservations ahead of time, especially for dinner.
- Weather Preparedness: Venice can be quite humid, especially in summer, so dress comfortably and stay hydrated.
Bonus Itinerary Inspiration: 5-Day Cinque Terre Tours!
If you’d like to mix up your itinerary or create your own Italy itinerary, then this is your chance to indulge in one of the most divine spots in the country by travelling to the Cinque Terre from Florence.
Travelling from many different cities in Italy’s northern and central regions—Florence or Pisa is one of the most popular ways to add this destination to your itinerary—allows you to easily capture the best of Cinque Terre in one day.
These itineraries can be customized by our Local Designers in Italy to deliver the perfect experience, whether you’re looking to conquer Cinque Terre in a day or over 5 days!
How to Design Your Own Trip to Italy
Designing your own Italy trip allows you to focus on what excites you the most, whether it’s art, history, food, or nature. Consider mixing bustling cities like Rome and Florence with quieter destinations like the Amalfi Coast or Tuscany’s rolling hills. Fast trains make it easy to travel between cities, so plan your itinerary around the places that inspire you the most. Here’s how to design a memorable experience tailored to your interests:
Select Your Destinations:
- Consider mixing bustling cities like Rome and Florence with quieter destinations such as the Amalfi Coast or the rolling hills of Tuscany.
- Each location offers unique attractions: explore the Eternal City for its ancient landmarks, savour the delicious food of Tuscany, and relax amidst the beautiful landscapes of the Amalfi Coast.
Plan your itinerary:
- Fast Trains: Italy boasts an efficient fast train network, making it easy to travel between cities. For instance, you can take a direct train from Rome to Florence in under two hours.
- Create a day-by-day itinerary focusing on the attractions that inspire you most, such as the Sistine Chapel, St. Peter’s Basilica, the Doge’s Palace, or the Leaning Tower of Pisa.
Consider Day Trips:
- Plan day trips from your base cities. For example, from Rome, you can easily visit Pompeii or take a scenic journey to the Amalfi Coast.
- While in Florence, consider a half-day trip to Siena or San Gimignano to experience charming small towns and beautiful scenery.
More Information on Your 5-Day Italy Vacation
When to Go to Italy:
The best times to visit are during the shoulder seasons of spring (April to June) and autumn (September to October). During these months, the weather is generally mild, and the crowds are smaller, allowing for a more enjoyable experience at famous landmarks without the long lines.
What to Pack for 5 Days:
- Comfortable Shoes: You’ll be doing a lot of walking, so invest in good footwear. Many attractions are within walking distance, and cobblestone streets can be challenging.
- Layers: The weather can be unpredictable, so packing layers will help you adjust to changing conditions throughout the day.
- Camera: Don’t forget your camera or smartphone to capture the amazing views and beautiful villages you’ll encounter.
Trip to Italy Cost:
Expect to budget around £100 to £150 per day. This includes accommodation, meals, transportation, and entrance fees to attractions. The cost can vary based on your choices; a private tour might increase your budget but offers a more tailored experience.
Create Your Own Tour of Italy
Whether you follow one of these suggested itineraries or craft your unique adventure, a five-day trip to Italy presents a wonderful opportunity to delve into the country’s rich cultural tapestry.
- World-Famous Landmarks: Visit iconic sites like the Colosseum, Roman Forum, Piazza San Marco, and Vatican Museums.
- Hidden Gems: Seek out lesser-known spots, such as the Jewish Ghetto in Rome, or local markets in Florence, like the San Lorenzo Market.
- Food Scene: Enjoy Italy’s renowned food scene, from fine dining to casual eateries. Be sure to try local specialities wherever you go.
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Italy is a place where each day holds the promise of new discoveries. By crafting your own journey, you can completely immerse yourself in its enchanting charm and rich history. Our Local Designers in Italy possess extensive knowledge of the country and excel at tailoring trips to suit your budget, travel preferences, and interests. By entrusting our Local Designers with your vision, you can transform your dream Italy trip into a reality. Pack your bag and get ready for the unforgettable in Italy. Bon voyage!!!
