See Italy, One Train Ride at a Time

Thirty days, eight regions, countless memories — a step-by-step guide to seeing the best of Italy by train.

By: Rhonda Bannister

There is no better way to experience Italy than by train. From the grandeur of Rome to the quiet beauty of Umbria, the rolling hills of Tuscany, the culinary heart of Bologna, the canals of Venice, and the sparkling lakes of the north, travelling by rail allows you to see the country’s most beautiful landscapes effortlessly.

Your 30-day Itinerary

• Rome: The Eternal City (Days 1–4)
• Umbria: The Quiet Heart of Italy (Days 5–8)
• Florence and Tuscany: Art, Vineyards, and Hill Towns (Days 9–13)
• Bologna: Porticoes, Pasta, and Perfect Day Trips (Days 14–17)
• Venice: Wonders of the Floating City (Days 18–20)
• Verona: Romance and Hidden Corners (Days 21–23)
• Milan: Fashion, Art, and Modern Pulse (Days 24–26)
• Varenna and Lake Como: Northern Italy’s Serene Finale (Days 27–30)

Rome: The Eternal City (Days 1–4)

Rome, where ancient ruins and vibrant neighbourhoods await is the perfect beginning to your journey. Few cities balance grandeur and intimacy like Rome, a destination where history and romance intersect at every turn. For couples, the magic lies in exploring beyond the obvious. While the Colosseum and Vatican are essential, the quieter experiences create wonderful memories. Wandering through Trastevere’s cobbled alleys, lingering over a carafe of wine at a centuries-old Enoteca, or catching a sunset from the Pincio Terrace as the city glows gold. Plan to spend at least four days here to soak in the layers of history and daily life.

Must-sees include:

Colosseum and Roman Forum: Pre-book a guided tour to skip lines and fully grasp ancient Rome’s grandeur.

Vatican Museums and St. Peter’s Basilica: Early-access tours offer quieter moments with the Sistine Chapel’s awe-inspiring frescoes.

Pantheon and Piazza Navona: Perfect for evening strolls when crowds thin and fountains sparkle under lamplight.

Trevi Fountain: Toss a coin to guarantee your return.

Trastevere: Spend an evening wandering cobbled lanes, finishing with dinner at a classic trattoria like Da Enzo al 29.

The Jewish Ghetto: Europe’s oldest Jewish settlement, dating to the 2nd century B.C.

Where to stay: Choose a central hotel near Piazza Navona or the Spanish Steps for easy walking access to major sights. Boutique options like Hotel de’ Ricci combine luxury with Roman character.

For couples: Book a food tour for your first day as it’s the best way to discover the streets and neighbourhoods of Rome.

Travel Tip: Rome’s central station, Roma Termini, connects easily to the rest of Italy. High-speed trains (Frecciarossa or Italo) offer quick, comfortable service.

Read more: A three-day itinerary for Rome (especially for couples!)

Rail Logistics

1. Main hub: Roma Termini (also Tiburtina for some high-speed trains)
2. Next leg: Regional and InterCity trains to Umbria via Foligno or Terontola
3. Local transport: Metro for Vatican/San Giovanni; otherwise, walk or taxi

Umbria: Perugia and the Hill Towns (Days 5–8)

Take a regional train from Rome to Perugia, the capital of Umbria, for a four-day exploration of Italy’s “green heart.” Perugia is less traveled than neighbouring Tuscany yet every bit as captivating, offering a slower pace and a chance to immerse in Italy’s medieval heart. The city unfolds in layers,  cobblestone streets winding past frescoed churches, archways leading to hidden courtyards, and sweeping vistas of green valleys. Its university culture keeps the town lively, with cafés, wine bars, and jazz clubs tucked behind stone facades.

Outside the city, vineyards and hilltop towns like Assisi and Spello make for easy day trips, ideal if you want countryside charm without giving up city comforts.

Don’t Miss: An evening stroll along Corso Vannucci. At dusk, the city’s main boulevard becomes a stage where locals promenade, street musicians perform, and couples can slip into intimate wine bars overlooking the valley.

Perugia rewards couples who love food and authenticity. With its steep alleys and sweeping views, Perugia’s medieval old town makes an ideal base for day trips across the region.

Suggested day trips by train from Perugia:

Assisi: Visit the Basilica of St. Francis, a UNESCO World Heritage site adorned with Giotto’s masterful frescoes.

Spello: Wander flower-festooned lanes and admire Roman-era walls.

Gubbio: Ride the open-air cable car up Monte Ingino for panoramic vistas over rugged Umbrian countryside. (Note: Gubbio requires a bus connection from Perugia; no direct rail station.)

Orvieto: Discover its Gothic cathedral and intriguing underground tunnels carved by the Etruscans.

Where to stay: Historic hotels like Locanda della Posta in Perugia’s centre offer charm and walkability.

For couples: Share a wine tasting in Montefalco, or enjoy a quiet picnic overlooking the valley from Spello’s medieval walls.

Travel Tip: Trains in Umbria are slower; allow extra time for connections. A rental car isn’t necessary for this itinerary, though some couples prefer the flexibility.

Rail Logistics

1. Roma Termini → Perugia (Fontivegge): ~2–2.5 hours, often with one change at Foligno or Terontola
2. On arrival: Take the Minimetrò to Pincetto for Perugia’s old town

Florence and the Hill Towns of Tuscany (Days 9–13)

A two-hour train from Perugia will bring you to Florence, a Renaissance jewel and your base for the next five days.

Florence is the very definition of Renaissance romance, yet couples should look beyond the Uffizi queues to discover its quieter allure. Yes, Michelangelo’s David and Botticelli’s Venus deserve a viewing, but Florence reveals its most intimate side in its smaller details; the artisan workshops of Oltrarno, the hush of cloister gardens, or a glass of Chianti on a rooftop terrace as the Duomo dome glows at sunset.

For couples, Florence is best savoured slowly: early mornings crossing the Ponte Vecchio before crowds arrive, a gelato by the Arno in the afternoon, or an evening opera at Teatro della Pergola. The city also makes a perfect base for day trips  to Siena, San Gimignano, and the Tuscan hills. All are within easy reach, offering both wine-soaked adventures and landscapes that feel plucked from a painting.

Don’t Miss: Climbing to Piazzale Michelangelo just before sunset. It’s the most breathtaking view of Florence, where the dome of Brunelleschi, the Arno, and the Tuscan hills align in golden light. Bring a bottle of wine and join locals who gather to watch the city transform into night.

Suggested Day Trips:

Tuscany’s hill towns are within easy reach for day trips: Either book a private car/driver for the day or hire a car, scooter or bike and spend the day discovering the hill towns such as:

Montepulciano: Sample world-famous wines in atmospheric cellars while enjoying panoramic views from the medieval town centre.

San Gimignano: Stroll medieval lanes and admire the towers that earned it the nickname “Manhattan of the Middle Ages.”

Cortona: One of Tuscany’s most beautiful towns, perched high with stunning valley views.

Also consider:

Siena: Built around Piazza del Campo and dominated by a stunning Duomo, a masterpiece of Romanesque-Gothic architecture.

Pisa: Beyond the Leaning Tower, the town’s vibrant piazzas, rich cultural heritage, and riverside walks are a joy to discover.

Lucca: Well worth visitng, it’s one of the most fascinating and best-preserved medieval cities in Italy.

Where to stay: Boutique hotels like Hotel Lungarno, overlooking the Arno River, offer luxury and easy access to Florence’s treasures.

For couples: Book dinner at a Michelin-starred restaurant, or pack a picnic for a vineyard lunch with Chianti views.

Travel Tip: Regional trains connect Florence directly with Siena and Pisa. To reach San Gimignano, take the train to Poggibonsi, then a short bus ride.

Read more: Here’s how to spend 48 Hours in Florence!

Rail Logistics

1. Perugia → Firenze SMN: ~1.5–2.5 hours; sometimes change at Terontola
2. Florence ↔ Siena: ~1.5 hours by Regionale
3. Florence ↔ Pisa: ~50 minutes by Regionale
4. Florence ↔ Lucca: ~1h20–1h40

Bologna: Culinary and Cultural Capital (Days 14–17)

Travel by high-speed train (about 40 minutes) to Bologna, the vibrant capital of Emilia-Romagna and Italy’s undisputed food capital.

Often bypassed for Florence or Venice, Bologna is Italy’s under-the-radar gem; a city couples will fall for precisely because it feels so lived-in. Its medieval towers, arcaded porticoes, and terracotta rooftops form a rich backdrop for one of Italy’s most rewarding culinary scenes. If food is your shared passion, Bologna is unmissable: tagliatelle al ragù, tortellini in brodo, and mortadella sliced paper-thin are staples best enjoyed in trattorias where recipes haven’t changed in generations.

The city’s university – Europe’s oldest – infuses Bologna with youthful energy, giving nights in the Piazza Maggiore a lively, convivial feel. By day, couples can climb the Asinelli Tower for a panorama of red-tiled rooftops, or wander portico-covered streets to hidden courtyards and elegant cafés.

Bologna also serves as a hub for easy train trips; Modena for balsamic vinegar, Parma for prosciutto, and Ravenna for mosaics, making it a practical base for exploration.

Don’t Miss: Aperitivo under the porticoes of Via Zamboni, followed by a late-night gelato at Cremeria Cavour. 

Suggested day trips by train:

Modena: Explore traditional balsamic vinegar houses and visit the Ferrari Museum.

Parma: Taste prosciutto and Parmigiano-Reggiano at their source.

Ravenna: Admire glittering Byzantine mosaics in UNESCO-listed basilicas.

Where to stay: Central hotels like Hotel Corona d’Oro place you steps from Piazza Maggiore and Bologna’s vibrant markets.

For couples: Take a cooking class together, or enjoy an aperitivo in a hidden courtyard restaurant discovered beneath the porticoes.

Travel Tip: Day trips from Bologna are easy and frequent; trains run hourly to Modena, Parma, and Ravenna.

Rail Logistics

1. Florence → Bologna: High-speed ~35–45 minutes
2. Bologna ↔ Modena: ~20–30 minutes
3. Bologna ↔ Parma: ~1 hour
4. Bologna ↔ Ravenna: ~1h15–1h30

Venice: The Floating City (Days 18–20)

From Bologna, board a high-speed train to Venice Santa Lucia station—the only station where you step directly onto the Grand Canal.

Few cities spark debate like Venice: is it overcrowded or the most romantic place on earth? For couples, the answer lies in how you experience it. Skip the midday tourist crush around St. Mark’s and instead embrace Venice’s quieter rhythms; morning walks along misty canals, evenings when the lanterns glow, or detours into quiet sestiere  (neighbourhoods) where laundry hangs over silent alleys.

Yes, gondola rides are cliché, but drifting beneath bridges at sunset remains one of travel’s enduringly intimate moments. For those seeking depth, explore the islands: Murano for glass, Burano for its riot of colors, or Torcello for peaceful ruins and countryside charm. Art lovers can linger in the Peggy Guggenheim Collection, while food-focused couples should try cicchetti, Venetian tapas,  paired with wine in a tiny Bacari.

Don’t Miss: A late-night wander through Piazza San Marco after the crowds have vanished. The square feels like your private ballroom, with only the sound of footsteps echoing under the arcades.

Related: Three dreamy days in Venice: what to do and see, and where to sleep and eat

Highlights:

Piazza San Marco: Visit early morning or late evening when crowds thin and the square shimmers with mystery.

Basilica di San Marco: Golden mosaics beneath a Byzantine dome; terrace and those iconic views of the city.

The Doge’s Palace: Cross the Bridge of Sighs and imagine prisoners’ final glimpses of freedom.

Secret Venice: Wander beyond San Marco to the Dorsoduro and Cannaregio districts, where locals sip spritzes and laundry flutters between windows. A Spritz at sunset in Venice is not a cliché – it’s a rite of passage!

Where to stay: Boutique hotels like Ca’ Maria Adele in Dorsoduro offer intimate luxury away from the crowds.

For couples: Share a gondola ride at sunset, or discover a hidden canal-side restaurant where you’re the only tourists.

Travel Tip: Take a Vaporetto (water bus) across the lagoon to the islands of Murano and Burano: the first famous for glass-blowing, the second for its candy-coloured fishermen’s houses.

Rail Logistics

1. Bologna → Venezia S. Lucia: ~1h30
2. Venice transport: ACTV waterbus passes for 48/72 hours

Verona: Romance, History and Hidden Corners (Days 21–23)

After Venice’s intensity, a comfortable one-hour train ride brings you to Verona; the city of Romeo and Juliet, but so much more – its charm goes far beyond Juliet’s balcony. Couples will find a city where Roman ruins, medieval palaces, and lively piazzas blend seamlessly into an atmosphere both romantic and authentic. The Arena di Verona, still hosting operas under the stars, is one of Italy’s most dramatic settings for a shared cultural experience.

The city lends itself to leisurely exploration: climbing Torre dei Lamberti for panoramic views, wandering across the Ponte Pietra at sunset, or sipping Amarone in cozy wine bars. Verona is also compact enough for unhurried strolling, ideal for couples who want a balance of history, dining, and downtime.

Its location in Veneto makes it easy to extend your journey to nearby Lake Garda or Valpolicella’s vineyards, but Verona itself deserves at least a few nights to sink into its rhythms.

Don’t Miss: An evening performance at the Arena. Whether opera or concert, the experience of sitting in a 2,000-year-old amphitheater as music fills the night is unforgettable.

Highlights:

Piazza delle Erbe: Once a Roman forum, now a lively market square.

Juliet’s House: Worth a quick visit for the famous balcony and bronze statue.

Arena di Verona: Summer opera performances in a spectacular Roman amphitheatre.

Giardino Giusti: Peaceful Renaissance gardens perfect for afternoon strolls.

Where to stay: Due Torri Hotel, a historic property near the old city centre.

For couples: If visiting in summer, book opera tickets well in advance for an unforgettable evening under the stars.

Travel Tip: Verona’s compact size makes it entirely walkable; taxis are rarely needed.

Rail Logistics

1. Venezia S. Lucia → Verona Porta Nuova: ~1 hour

Milan: Fashion, Art and Modern Pulse (Days 24–26)

Milan is Italy’s modern face,  sleek, stylish, and buzzing with energy. At first glance, it may feel more business than romance, but couples who lean into its rhythm will discover a city that seduces through fashion, design, and culture. Begin with the icons: da Vinci’s Last Supper, the Duomo’s spires, and the grand Galleria Vittorio Emanuele II. 

For couples, Milan’s appeal lies in its contrasts: contemporary art museums beside centuries-old churches, Michelin-starred dining alongside humble trattorias, cutting-edge boutiques near family-run bakeries.

Don’t Miss: Aperitivo in the Navigli district. As the sun sets, couples can share cocktails and cicchetti along the canals, watching Milanese life unfold in style.

Highlights:

The Duomo: Take the rooftop walk among Gothic spires and gargoyles.

The Last Supper: Book months in advance for Leonardo’s masterpiece.

Brera District: Art galleries, designer boutiques, and intimate trattorias.

Quadrilatero d’Oro: Fashion houses and luxury shopping.

Navigli Canals: Evenings come alive with aperitivo culture and canal-side dining.

Where to stay: Room Mate Giulia offers sleek, central accommodation.

For couples: Book a fashion district shopping tour, or enjoy Milan’s legendary nightlife in the Navigli district.

Travel Tip: Trains from Milano Centrale reach Lake Como in under an hour.

Rail Logistics

1. Verona Porta Nuova → Milano Centrale: ~1h10–1h20
2. Milano Centrale → Varenna-Esino: ~1h05–1h20 by Trenord

Varenna and Lake Como: Serenity and Splendour (Days 27–30)

End your month-long journey in the serene beauty of Lake Como. Take a direct regional train from Milan to Varenna, one of the lake’s most enchanting villages. Lake Como is where Italy slows down, inviting couples to linger among water, mountains, and villa gardens. Its villages, Bellagio, Varenna, Menaggio, sit like jewels along the lake, each offering cobbled lanes, waterfront promenades, and trattorias with tables just steps from the water. For couples, the charm lies in the simplicity of days spent ferry-hopping between towns, strolling through manicured gardens like Villa Carlotta, or sipping Prosecco as boats drift by. The lake also offers opportunities for adventure: hiking trails above Varenna, boat rentals for private cruising, or funicular rides up to Brunate for sweeping views.

Don’t Miss: A sunset ferry ride between Varenna and Bellagio. The shifting light on the water, with villas and cypress trees silhouetted against the mountains, is as romantic as Italy gets.

Highlights:

Villa Monastero: Lakeside botanical gardens with dramatic mountain backdrops.

Castello di Vezio: Hike up for panoramic lake and Alpine views.

Ferry excursions: Explore Bellagio, Menaggio, and Tremezzo by boat. Buy a multi-ride ferry ticket for flexibility.

Bernina Express: Take a spectacular day trip to St. Moritz from nearby Tirano, climbing through the Swiss Alps.

Where to stay: Hotel du Lac or Albergo Milano, both featuring lake-view terraces perfect for morning coffee or evening wine.

For couples: Book a lakefront dinner table at sunset, or take the scenic Bernina Express together for breathtaking Alpine views.

Travel Tip: Direct trains run from Varenna → Tirano (~1h48). From there, connect to the Bernina Express for one of the world’s most scenic train rides (reservations required).

Rail Logistics

1. Milano Centrale → Varenna-Esino: ~1h05–1h20
2. Ferries: Frequent triangle service between Varenna, Bellagio, and Menaggio
3. Bernina Express: Varenna → Tirano (~1h45), then panoramic train to Switzerland

If You Go

Rail Tickets:

1. Book high-speed Frecciarossa and Italo tickets in advance for the best prices
2. Use regional trains for shorter journeys (Florence–Siena, Milan–Varenna)
3. Rail passes (like the Eurail Italy Pass) rarely offer savings for this specific itinerary

Best Time to Travel:

1. Ideal: Late April–June or September–October
2. Avoid: July–August can be uncomfortably hot and crowded

Budget Considerations:

1. Expect €150-300 per night for recommended hotels (couples)
2. Train tickets: €50-150 for high-speed routes, €15-30 for regional services
3. Meals: €80-120 per couple for dinner at quality restaurants

Packing Tips:

1. Comfortable walking shoes are essential for cobblestones
2. Layer clothing for variable weather
3. Pack light; you’ll carry bags on and off trains frequently

Dining:

1. Reserve popular restaurants in Florence, Bologna, and Milan well ahead of time
2. Try regional specialties: truffle pasta in Umbria, bistecca alla Fiorentina in Florence, ragù in Bologna, carbonara in Rome

Over 30 days, this journey takes you through Italy’s most iconic cities and landscapes, from Roman ruins to Renaissance splendour and lakeside serenity. You’ll ride sleek high-speed trains and leisurely regional lines, creating memories to last a lifetime – one train ride at a time.