How to Solo Backpack Italy in 1 Month - The Ultimate Itinerary

Ciao, fellow travelers! If you're dreaming of espresso-fueled mornings, pasta by the seaside, and enough jaw-dropping architecture to make your camera storage cry, this one’s for you. In Fall 2021, I covered over 20 cities in just 26 days. If that sounds like your kind of adventure, read on. It’s absolutely worth it.

Hi, I’m Kevin. In Fall 2021, I embarked on the longest solo-backpacking trip of my life to explore everything that Italy has to offer. Along the way, I was adamant about seeing the common tourist attractions but also prioritizing my journey “off the beaten path.” Check it out!

What to Pack and What to Skip

Essentials:

• Comfortable walking shoes

• Quick-dry towel

• Power bank / portable charger

• Power adapter (Italy uses Type C, F, and L)

• Daypack or tote bag for short trips

Skip: Heavy books, too many clothes, or anything you won’t wear more than twice.

⚠️ Know Before You Go

Consider these tips before you arrive:

Scammers – In major tourist areas, especially in cities like Rome, Florence, and Venice, scammers offer "free" wristbands or friendship bracelets. They’ll try to tie one on you fast, then demand money. My advice, say “No, grazie”, avoid eye contact, and keep walking.

Bag Storage – Italy’s check-in times can be late (often after 2:00pm). Use “bag storage” or “luggage lockers” to stash your backpack for a few hours and explore hands-free.

Train Transport – Book high-speed trains in advance — they can and do sell out. For regional trains, you can usually wing it. If a train isn’t available, FlixBus is a solid long-distance alternative.

Dining Culture – Italians eat late. Like, 8:30 PM dinners are totally normal. Embrace the late lunch + espresso life.

My 4-Week Itinerary: Living Out of a Backpack in Italy

Venice → Milan → Lake Como

I kicked off my Italian adventure by landing in Treviso and catching a taxi to Venice. I had a great experience booking with the FREENOW app — easy to use and available in most major cities. Heads up, Venice is car-free. You’ll get dropped near Piazzale Roma and must take a vaporetto (water bus) or splurge on a gondola to reach the islands. I went for the gondola.

Venice Tips

• Stay 1–2 nights max — it’s stunning but small.

• Don’t miss St. Mark’s Basilica, Rialto Bridge, and the quiet canals of Cannaregio or Dorsoduro.

• Take a ferry to Burano (for colors) or Murano (for glassblowing).

• Skip dining in main piazzas — side street spots are tastier and cheaper.

Next Stop: Milan

Italy’s fashion capital. It's sleek, fast-paced, and worth a 24-hour stop, especially if you're not in shopping mode.

• Duomo di Milano: Climb 220+ steps for a golden hour rooftop view.

• Galleria Vittorio Emanuele II: For a glam walkthrough.

• Starbucks Reserve Roastery: A gorgeous coffee + tiramisu stop.

Then it was off to Lake Como — it’s out of the way, but you won’t want to skip this

From Milan, I hopped on a Frecciarossa high-speed train to Como San Giovanni (book in advance, especially in high season). The ride takes just over an hour and is stunning.

Where to Stay in Lake Como

• Como Town: Lakeside views conveniently located right off the Como San Giovanni train station on the southern end of the lake. This makes for an excellent base for exploring the surrounding areas and towns.

• Fjord-Like Landscapes: Romantic, scenic, and postcard-perfect

  • Bellagio: Situated at the junction of the lake’s two legs, this is an extremely attractive town yet less crowded and quieter than others in the vicinity.

  • Bellano: Located on the east side of the lake just to the north of Verbena, this lesser visited town features a pedestrian-only area in the center of town. This is a popular family-friendly option.

  • Menaggio: Located on the western shoreline, there is a youth hostel located here and is usually filled on the weekends. The pedestrian-only area in the heart of town is populated with coffee shops, gelaterias, a lakefront mini-golf course and snack bar, and several restaurants.

  • Nesso: Located about halfway between Bellagio and Como, this is a very small town situated on Lake Como’s western leg.

  • Verbena: Along the eastern shoreline you’ll find this beautiful town with its charming villas and relaxing gardens.

Kev’s Tip: I took the 45-minute bus to Bellagio to explore the villages and towns nestled in the mountains. Bring cash for local transport and small shops.

Lake Como Highlights:

• Hike up to Punta Spartivento in Bellagio

• Visit Villa Melzi or Villa Serbelloni Gardens (seasonal)

• Grab lunch by the lake — grilled lake fish + a spritz is always a win

Genoa → Portofino → Cinque Terre

Genoa Highlights

Genoa makes a good pit stop if you want to avoid long travel days. It's not a must-see, but if you’ve got a few hours to kill:

• Palazzi dei Rolli: Stunning UNESCO-listed palaces

• Porto Antico & Aquarium: One of Europe’s biggest

• Spianata Castelletto: Hilltop views of the old city

Next: Portofino and Cinque Terre! If you’re not in a hurry, stop in Camogli — an underrated seaside village with charm and zero crowds.

Camogli Highlights

• Pastel-painted waterfront with trompe-l'œil facades

• Castello della Dragonara: Small but scenic

• Working fishing port and springtime Fish Festival (Sagra del Pesce)

Then on to Cinque Terre — five cliffside villages with hiking trails, pesto, and unreal views.

Getting to Cinque Terre:

• Train to La Spezia Centrale, then hop on the Cinque Terre Express

• Villages: Riomaggiore → Manarola → Corniglia → Vernazza → Monterosso

Get the Cinque Terre Train Card — unlimited train rides + hiking trail access

Places in Cinque Terre

1. Riomaggiore: Bold colors, sunset marina, local vibes

2. Manarola: Insta-famous view across the water, try Trattoria dal Billy

3. Corniglia: Quieter hilltop village — 380 stairs or shuttle up

4. Vernazza: Colorful harbor, perfect for lunch and lingering

5. Monterosso: Best beaches, flat terrain, and nightlife

Hiking Tips:

• The Sentiero Azzurro (Blue Trail) connects all five towns

• Check for trail closures due to landslides

• Wear real shoes — not flip-flops

Food Musts:

• Pesto with trofie pasta

• Monterosso anchovies

• Sciacchetrà sweet wine (hard to find outside the region)

Final Tips in Cinque Terre:

• Avoid mid-day crowds by staying overnight

• Download offline maps (spotty service)

• Sunsets = best in Manarola or Riomaggiore

• Carry cash — not all shops take cards

Florence → Pisa → Siena → San Gimignano

Florence is the Renaissance fantasy you picture in your head — all domes, sculptures, and centuries-old art. I stayed three nights to soak it all in, using it as a launchpad for day trips around Tuscany.

Top Things to do in Florence

1. Climb Brunelleschi’s Dome (Duomo di Firenze)
   463 steps to the top — your legs will hate you, but the views over the terracotta rooftops are unforgettable.

Book in advance. Early time slots = fewer crowds and dreamy lighting.

1. See Michelangelo’s David at the Galleria dell’Accademia
   Yes, it’s touristy. Yes, it’s worth it. The detail up close is mind-blowing.

2. Uffizi Gallery
   Botticelli’s Birth of Venus and dozens of other masterpieces.

Go in the afternoon — tour groups flood in early.

1. Watch Sunset from Piazzale Michelangelo
   Take a bottle of wine, climb the hill, and soak in the skyline. One of the best views in the city.

2. Eat at Mercato Centrale
   Grab a lampredotto sandwich if you're adventurous, or go with truffle pasta upstairs.

3. Chill at Biblioteca delle Oblate
   It’s a public library with a rooftop café and an unbeatable view of the Duomo.

4. Walk Across Ponte Vecchio
   Medieval bridge, gold shops, river views — classic Florence.

5. Explore Oltrarno
   Florence’s artsier side: less touristy, more local. Check out Piazza Santo Spirito and Bardini Gardens.

6. Shop the Leather Markets
   Florence is known for its leather — don’t forget to haggle (respectfully).

7. Start Your Day Like a Local
   Espresso at the bar. No takeaway. No milk after 11 a.m. Embrace it.

Best Florence Day Trips

Pisa

• Visit the Leaning Tower early to beat the crowds.

• Combine it with nearby Lucca for a chill afternoon bike ride around its Renaissance walls.

Chianti Wine Region

• Book a wine tour from Florence — many include tastings, lunch, and vineyard stops in Greve in Chianti.

• Try the Chianti Classico with the iconic black rooster seal.

San Gimignano & Siena

• San Gimignano is medieval tower heaven with world-famous gelato.

• Siena’s gothic vibes and historic city square make it worth at least a half-day.

Kev’s Pick | GetYourGuide

Pisa, Siena, San Gimignano & Chanti Tour

I took the Pisa, Siena, San Gimignano + Chianti tour via GetYourGuide — highly recommend. Early departures beat the crowds, and the wine tasting was top-tier.

Florence Travel Tips:

• Book major attractions a week ahead in peak season.

• Museums are usually closed Mondays.

• Some museums offer free admission on the first Sunday of each month.

• The city is super walkable — bring good shoes.

Rome

Rome is a chaotic, beautiful mix of ancient ruins and modern life. Every piazza, every alley, every ruin has a story to tell. Give yourself at least 3 days. This city’s layered and loaded with bucket-list moments.

Top Things to Do in Rome:

1. Colosseum + Roman Forum + Palatine Hill
   Book a guided or underground tour. Go early for the best light (and fewer crowds).

Kev’s Pick | GetYourGuide

Colosseum Underground, Arena & Forum Tour

Join a guided tour of Rome’s Colosseum, featuring exclusive access to the Underground chambers and arena floor. Discover the captivating history of Ancient Rome as your guide brings the past to life. Step into the Colosseum on a fun guided tour, with special access to the underground tunnels and arena floor. Your guide will share the amazing stories and secrets of Ancient Rome along the way! Dive into the wonders of Roman history with an immersive tour through the Ancient Rome archaeological park. You will spend 1 hour to see the Roman Forum and Palatine Hill. Allow your guide to point out the best places to capture the perfect picture as you tour the circumference of the Colosseum. Continue your tour through the Colosseum's different sections. Enter the underground chambers and learn about the Romans and the gladiators on a guided tour. Visit the underground chambers and hear stories of the gladiators and wild animals that were kept there. Walk onto the arena, the ground floor, and walk on the shoes of the gladiators.
See where the emperor would be perched, high above the arena floor, ready to decide the fate of another gladiator as he stood before a roaring Roman crowd. 

2. Vatican Museums + Sistine Chapel
It’s massive. It’s overwhelming. But it’s also a must.

Kev’s Pick | GetYourGuide

Museums & Sistine Chapel Skip-The-Line Entrance Ticket

Skip the long lines at the entrance to one of the world's busiest attractions with a skip-the-line ticket. See priceless works of art with skip-the-line entry to the Vatican Museums and Sistine Chapel. Admire the works of renowned artists such as Raphael, Michelangelo, and Leonardo da Vinci, admiring masterpieces from antiquity to Michelangelo's legendary frescoes.

3. St. Peter’s Basilica
Climb the dome (cupola) for epic views. The only way to see the dome is by booking a private tour or guide. The basilica itself is jaw-dropping.

Kev’s Pick | GetYourGuide

St. Peter’s Basilica, Papal Tombs and Dome Climb Tour

Enjoy an exclusive look at the Dome’s impressive mosaics then head further up to the top balcony. Gaze at the colourful marble, golden ceilings, and intricate mosaics that surround you. Learn about the renowned works of Renaissance and Neoclassic artists that are housed here. Next, head underground to the Basilica’s historic grottoes and visit St. Peter’s Tomb. Touch the ancient walls of the original 4th-century Basilica and admire its beautiful frescoes. Finish the tour in St. Peter’s Square and soak up its majestic architecture. 

4. Trevi Fountain
Visit early or late to avoid crowds. Toss that coin right-hand-over-left-shoulder for good luck.

5. Pantheon
One of the best-preserved Roman buildings. Entry is low-cost or free depending on time/day. Don’t miss the open-air oculus.

6. Trastevere
Boho, artsy, and full of trattorias. Head here for dinner and live music.

7. Altar of the Fatherland (Piazza Venezia)
Massive monument. Climb (or elevator) for skyline views.

8. Spanish Steps
Great for photos — but note: no sitting or eating here (it's enforced).

9. Gianicolo Hill
Best local sunset view. Fewer crowds and daily noon cannon blast tradition.

10. Eat Everything
Try cacio e pepe, carbonara, or amatriciana. Grab pizza al taglio from Bonci, and don’t skip supplì (mozzarella-stuffed fried rice balls).

Kev’s Pick

Caupona Pompeii Restaurant

Caupona is a restaurant in Pompeii, Italy, that aims to recreate the experience of dining in ancient Rome. It offers a unique culinary and historical experience, with a focus on dishes inspired by Apicius' "De Re Coquinaria" and the Roman culture of the time. The restaurant is designed to resemble a Pompeian domus, with frescoes, wood tables, and terracotta dishes, and staff members often wear period costumes. 

Rome Travel Tips:

• Stay central, but not right next to Termini Station.

• Book all major attractions in advance.

• Rome is very walkable — bring a refillable bottle and use the public fountains (nasoni).

Getting Around Rome:

• Metro (A, B, C lines) is quick but limited.

• Buses/trams fill in the gaps — validate tickets onboard.

• Buy tickets at Tabacchi shops, stations, or newsstands.

• Skip taxis unless necessary — use apps like Free Now.

• Download Google Maps or Moovit for real-time routes.

Off-The-Beaten-Path:

Kev’s Pick

Civita di Bagnoregio

If you’re looking to go off the beaten track, Civita is the cliffside ghost town of your dreams and way off the beaten path. Civita di Bagnoregio is a hilltop village in central Italy. It’s accessed via a pedestrian bridge from the nearby ticket office in Bagnoregio village. The Porta Santa Maria gateway was built by the Etruscans. Founded in the 7th century, the Romanesque San Donato Church sits in the main square. Nearby is the Geological and Landslides Museum, whose exhibits document projects to shore up the village's eroding hillside.

Getting There (It’s a Trek, But Worth It)

Civita is remote — and that’s part of the charm. You can’t take a direct train, but here’s the best route from Rome:

Option 1: Train + Bus Combo

• Take a train from Rome Termini to Orvieto (about 1 hour 15 minutes)

• From Orvieto Scalo, catch a Cotral bus to Bagnoregio (roughly 45–60 minutes)

• From Bagnoregio, it’s a 15–20 minute walk or short local shuttle to Civita’s pedestrian bridge

Pro Tip: Cotral buses run only a few times a day. Check the bus schedule in advance and plan around it — or risk being stranded.

Naples → Pompeii → Sorrento → Amalfi Coast

After Rome, I headed south to Naples — raw, loud, chaotic, and full of flavor. Some people treat it as a layover, but trust me, Naples is a destination in its own right.

Things to Do in Naples:

1. Eat Your Way Through the City
   Start with a Pizza Margherita from L’Antica Pizzeria da Michele — yes, the one from Eat Pray Love. Try sfogliatella, sip an espresso standing at the bar, and don’t miss the street food (frittatina and cuoppo are musts).

Kev’s Pick | Viator

Naples Street Food Tour

Enjoy this pleasant walk through the history and the traditions of Naples while you taste the best this city has to offers about its culinary heritage!

1. Wander Spaccanapoli
   This narrow slice through Naples' historic center is chaotic and full of life — scooters, locals yelling, laundry swaying overhead. Stop at Via dei Tribunali for more pizza and visit the Naples Cathedral.

2. Napoli Sotterranea or Catacombs of San Gennaro
   Explore the underground city or take a guided catacombs tour — eerie, fascinating, and less touristy than you’d expect.

Kev’s Pick | Viator

Pompeii & Vesuvius Trip With Italian Lunch

3. Pompeii + Mount Vesuvius Day Trip
Trains from Napoli Centrale to Pompeii Scavi run regularly (~35 min). Wear real shoes and bring sunscreen — this ancient city is massive and very exposed.

After morning pickup from locations in central Naples, relax during the scenic drive to Pompeii.  Begin with a walking tour of the ruins of the ancient Roman city of Pompeii, stopping to see the thermal baths, racy paintings in the Lupanare, the Basilica, Macellum (market square), and the formerly opulent residence known as the House of Faun. Your guide shares informative commentary about life in old Pompeii and the eruption of Mt. Vesuvius.  After your time at the ruins, enjoy a delicious pizza lunch or wine tasting (option selected at checkout). Next up, rejoin your driver and travel up Mt. Vesuvius to 3,280 feet (1,000 meters). Disembark there and follow your guide up a winding path that leads to the top of the volcano (this is a moderately challenging walk). Peer into the volcano crater and learn about the geology of the volcano from a volcanologist guide. Your tour ends with return to your starting point in Naples in the late afternoon.

4. Hike Vesuvius if you’re feeling adventurous — views into the crater and over the Bay of Naples are wild.

5. Castel dell’Ovo + Naples Waterfront
End the day strolling the Lungomare, grabbing gelato, and watching the sunset by the sea.

What to Avoid or Be Smart About:

• Naples is gritty. Stay alert, especially in crowded areas. Don’t flash valuables.

• Skip driving. Traffic is chaotic and rules are...suggestions.

• Avoid tourist trap restaurants in big piazzas, head a few streets away for better, cheaper food.

Sorrento → Amalfi Coast

From Naples, I hopped the Circumvesuviana train to Sorrento (cheap and ~1 hr 15 min). It’s packed and no-frills, but for a smoother ride, upgrade to the Campania Express.

Sorrento Highlights

• Marina Grande: Cozy fishing village with restaurants by the sea.

• Villa Comunale Park: Stunning views of the bay — especially at sunset.

• Limoncello tasting: It’s lemon central here. Sip it fresh.

• Day Trip to Capri: Ferries leave daily from the harbor. Go early for a full day.

Kev’s Pick | GetYourGuide

Sorrento Pizza Making Class

• Pizza or Cooking Making Class: Learn to prepare a real Neapolitan pizza and listen to the most well-kept secrets about its cooking process. Take part in an interactive pizza-making workshop in Sorrento and taste your creation.

Getting to the Amalfi Coast from Sorrento:

1. SITA Bus

   Cheapest (~€2–3), but crowded and slow.

   Sit on the right side leaving Sorrento for ocean views.

2. Ferry

   Fast, scenic, and less stressful. Worth the splurge for the views.

3. Private Transfer or Scooter

   Best for flexibility but $$$. Scooters are only for confident drivers — roads are tight and winding.

Where to Go Along the Amalfi Coast

• Positano: Bougie beach town, best for shopping and soaking it in.

• Amalfi Town: Historic with a famous cathedral and coastal charm.

• Ravello: High above it all, see epic views from Villa Rufolo and Villa Cimbrone.

Kev’s Pick | Viator

Amalfi Pasta Making Class

In Agerola: Enjoy practical lessons of fresh pasta various sauces for the condiments, after preparing the pasta and cooking it and then you get to taste everything. After eating, take a 10 minute excursion and visit the most beautiful place in the world. On the way back, say goodbye with an excellent homemade limoncello. Cooking lesson: tagliatelle, mozzarella and tiramisu

Time-Saving Tip: Don’t try to cram all 3 towns into 1 day. Pick 1–2 and slow down.

Winter Note: I visited in December, chilly but crowd-free. The hikes, the peaceful cliff walks, the festive lights? Worth it.

Potenza → Ostuni → Bari → Alberobello

Once I wrapped up the Amalfi Coast, I headed inland — a route most travelers skip, but one I highly recommend. If you want to see the quieter, more authentic side of Italy, this stretch delivers.

How to Get from Amalfi to Potenza to Ostuni

Step 1: Amalfi → Salerno

• Take a SITA bus (~1 hr 15 min) or a ferry (seasonal, more scenic) to Salerno.

Step 2: Salerno → Potenza

• From Salerno Centrale, catch a regional train to Potenza Centrale (~1 hr 45 min).

• Trains run every few hours — check ahead on Trenitalia.

Kev’s Tip: Spend a night in Potenza. It’s quiet, festive in winter, and gives you a breather from the usual tourist circuit.

Step 3: Potenza → Metaponto → Ostuni

• Take a regional train from Potenza to Metaponto (~1.5 hrs).

• From Metaponto, transfer to a bus or train to Ostuni (~1 hr). You may need to pass through Taranto or Brindisi, so check local timetables.

It’s a full day of transit — download offline maps, bring snacks, and enjoy the scenery.

What to Do in Ostuni (The White City)

This hilltop stunner is called La Città Bianca for a reason. Its whitewashed buildings seem to glow in the sun — especially at golden hour.

Top Things to Do in Ostuni

• Centro Storico: Wander narrow alleys and white-stone arches. Every corner is camera-worthy.

• Ostuni Cathedral: A 15th-century Gothic-Romanesque mix with a unique rose window.

• Artisan Markets: Shop for ceramics, linen, olive oil, and local food.

• Sunset at the City Walls: Grab a bottle of wine and take in sweeping views of olive groves and the Adriatic.

Bonus: Take a quick ride to Marina di Ostuni for beaches and chill beach clubs.

Ostuni → Bari → Alberobello

After soaking up Ostuni, I made my way to the final stop: Alberobello — the land of trulli.

Step 1: Ostuni → Bari

• Take a Trenitalia regional train from Ostuni to Bari Centrale (~45–50 min).

• Ostuni station is about 3 km from the city center — take a short taxi or local bus to avoid walking.

Step 2: Bari → Alberobello

• Walk to Bari Largo Sorrentino Bus Terminal (near Bari Centrale).

• Catch FSE Bus 100 or 145B to Alberobello (~1.5 hrs).

Kev’s Tip: Use Rome2Rio or the FSE site to check schedules — they aren’t always listed on Google Maps.

Alternative: You can also take the FSE regional train via Putignano, but it’s slower and requires a transfer.

What to Do in Bari & Alberobello

If you have time between transfers, visit the capital of Italy’s Puglia region: Bari

• Bari Vecchia: Get lost in the Old Town’s maze of alleys, orecchiette pasta makers, and hidden churches.

• Basilica di San Nicola: Pilgrimage site with Santa Claus’ remains (seriously).

• Castello Svevo: A 12th-century fortress near the water.

Stop-in to experience the world-famous trulli — whitewashed, cone-roofed stone houses that look like something out of a fairytale. Alberobello’s trulli is recognized as a UNESCO World Heritage Site.

• Trulli Districts: Explore both Rione Monti (more touristy) and Aia Piccola (more local).

• Trullo Sovrano: A two-story trullo turned museum. Worth the €2–3 entry.

• Eat local: Burrata, capocollo, olive oil, and wine — all fresh and regional.

Alberobello is walkable and perfect for a short, slow-paced final stop.

Final Verdict

Italy in one month? It’s totally doable. My biggest piece of advice: be flexible, stay organized, and embrace the chaos. From gondolas to ruins, cliffside hikes to underground tombs, this trip taught me to go slow when I could, say yes to the detours, and never turn down house wine.

-Kevin