The Ultimate 2-Week Italy Itinerary (Perfect for First-Time Visitors)

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I’ve lost count of how many times I’ve been to Italy, and I still never get tired of it! Italy is one of those destinations that never disappoints. No matter how high your expectations are, it somehow exceeds them. From ancient ruins and world-class art to simple pleasures like a perfectly made pizza or gelato, Italy is really equally about experiences as much as sights. This 14-day Italy itinerary is ideal if you want a clear plan but still crave freedom to wander, eat too much pasta, and discover hidden corners along the way. It’s realistic, flexible, and built around efficient train travel – perfect for seeing Italy without renting a car.

Route: Rome → Florence → Cinque Terre → Lake Como → Venice

Rome (Days 1–3)

Rome is the beating heart of Italy and the perfect place to start your journey. It’s easy to reach from everywhere and a place in Italy you really can't skip. While Rome can feel overwhelming at first, spending a few days here allows you to ease into Italy, adjust to the rhythm, and truly appreciate how layered and fascinating the city is.

Where to Stay in Rome

Best Budget Friendly Stays in Rome

Beehive Hostel ($100 per night)

Cozy, welcoming, and close to Termini; Its calm vibe and garden area make it feel more boutique than hostel.

New Generation Hostel ($180 per night)

A favorite for budget travelers who still want style; bright, modern rooms and a social lounge make it easy to meet other travelers.

Best Mid-Range Stays in Rome

Hotel Nazionale ($220 per night)

Stylish and centrally located with spacious rooms and historic interiors — perfect for history buffs who want comfort.

Hotel Artemide ($350 per night)

Elegant rooms on Via Nazionale with a rooftop restaurant and spa; great for relaxing after long days exploring Rome’s ancient sites.

Albergo del Senato ($420 per night)

Steps from the Pantheon with a stunning rooftop terrace; this feels like a classic Roman stay with modern service.

Best Luxury & Boutique Stays in Roma

Baglioni Hotel Regina ($700 per night)

Classic grand hotel on Via Veneto with opulent interiors and (for big splurges) incredible penthouse views of the city skyline.

Hassler Hotel ($1900 per night)

Celebrated for timeless elegance, Michelin-star dining, and panoramic views from its terrace over the Spanish Steps.

Rocco Forte Hotel De Russie ($2200 per night)

A leafy oasis near Piazza del Popolo with sumptuous service and a legendary wine bar — ideal for honeymooners or luxury lovers.

Daily Itinerary in Rome

Day 1: Wander the Historic Center

Arrive in Rome and keep things relaxed. After checking in, wander through the historic center, visiting the Pantheon and Trevi Fountain. End your first night with dinner and wine in Trastevere.

Guided Food Tour with Wine in Trastevere

This is for you, if you want to sample some amazing Italian food and wine with a local guide.

Day 2: Explore Colosseum and Ancient Rome

Spend the morning exploring ancient Rome with a guided Colosseum and Roman Forum tour. In the afternoon, climb Capitoline Hill and enjoy sunset views over the city.

Guided Tour of Colosseum private or with a small group

If you want to explore Colosseum with a guide, I highly recommend booking this tour.

Day 3: Visit The Vatican  

Start early at the Vatican Museums before the crowds arrive, then visit St. Peter’s Basilica. Spend the afternoon slowing down with gelato, shopping, and piazza hopping.

Book the best guided tour of the Vatican here

Traveling from Rome to Florence

Getting from Rome to Florence is fast and easy thanks to Italy’s high-speed trains. Trains run frequently and take about 1 hour and 30 minutes. Booking tickets in advance through Omio is essential during high season if you don’t have a lot of flexibility in your schedule and it often saves you money.

Florence (Days 4–6)

As the birthplace of the Renaissance, Florence is filled with masterpieces around every corner. It’s also a city best enjoyed slowly. Enjoy long lunches in the piazzas, stroll along the Arno in the evening, and watch the sunset views over terracotta rooftops.

Where to Stay in Florence

Best Budget Friendly Stays in Florence

B&B Hotel Firenze Novoli ($120 per night)

A favorite for budget-conscious travelers who still want comfort and clean, modern rooms.

Hotel Davanzati ($170 per night)

Classic Florentine charm with plenty of local character in every room.

PLUS Florence ($270 per night)

A hostel/hotel hybrid with lively social spaces and affordable private rooms.

Best Mid-Range Stays in Florence

Room Mate Luca ($200 per night)

Bright, modern design with friendly service and a location that’s hard to beat.

Hotel Calimala ($320 per night)

Stylish rooms tucked in medieval walls, a short stroll from Duomo and shopping streets.

Arte' Boutique Hotel ($430 per night)

This is a stylish and centrally located, just steps from the Duomo, with modern rooms and a cozy boutique feel.

Best Luxury & Boutique Stays in Florence

Duomo Luxury Florence ($500 per night)

This is a charming Hotel right by Florence’s iconic Duomo, offering stylish rooms with modern comforts and superb access to the city’s historic sites.

The St. Regis Florence ($1000 per night)

This is an elegant and historic hotel in the heart of Florence, offering classic luxury, a rooftop terrace with Duomo views, and an unbeatable central location.

Portrait Firenze ($1300 per night)

Ultra-chic suites by the Ferragamo family with river views and impeccable design.

Daily Itinerary in Florence

Day 4: Explore the Duomo and Ponte vecchio

Arrive by train from Rome and explore the Duomo area, Ponte Vecchio, and surrounding streets. Dinner in Santo Spirito is always a great choice.

Prebook your ticket to the top of the Duomo here

If you want to climb to the top of the Duomo to see the view over Florence, I recommend booking this one in advance as it often sells out during high season.

Day 5: Visit the Uffizi Gallery

Visit the Uffizi Gallery in the morning, followed by lunch nearby. Spend the afternoon wandering Oltrarno before heading up to Piazzale Michelangelo for sunset.

Guided tour of the Uffizi Gallery

If you are interested in art and history, I highly recommend doing a guided tour of the Uffizi Gallery.

Day 6: Wine tasting

Take a day trip into Tuscany, exploring Chianti vineyards or nearby hill towns, then return to Florence for a relaxed final evening.

Book a wine tasting tour to Chianti here

Explore multiple vineyards in Chianti. Taste and learn how the wine is made.

Explore the Val D'Orcia region on this tour

Explore the Val D'Orcia region, visiting Montalcino, Pienza og Montepulciano while tasting wine along the way.

Traveling from Florence to Cinque Terre

From Florence, take a regional train to La Spezia, then transfer to the local Cinque Terre train. The journey takes around 2.5–3 hours in total. Booking everything in advance through Omio is highly recommended. I advise you to catch an early train to get as much time as possible in Cinque Terre without stressing, especially if you want to see all five towns.

Cinque Terre (Days 7–8)

Cinque Terre is one of the most photographed regions in Italy – and it deserves the hype. You can easily explore the five different villages along the cliffside either by scenic walking trails or short train rides. Many come just for one day, but I highly recommend spending a couple of nights so you can enjoy the villages once the crowds leave.

Where to Stay in Cinque Terre

Accomodations in Cinque Terre is scarce and popular, which is reflected in the prices. I highly recommend booking something as soon as you know you are going there. My advice is to stay in one of the villages, but if your budget don't allow it, you can find more budget friendly accommodations in the closest city called La Spezia and take the train back and forth every day.

Best Places to Stay in Cinque Terre

Alla Marina Affitacamere ($170 per night)

This is a charming, family-run guesthouse set in a historic building right by Riomaggiore’s harbor, offering modern rooms with sea views just steps from the train station.

Affitacamere Rio Centrale ($200 per night)

Simple but beautifully situated right in town, perfect for beach days and sunset aperitivos.

La Vista Di Marina ($220 per night)

This is a stylish boutique hotel in Riomaggiore, offering elegant rooms with breathtaking sea views right above the marina.

La Malà ($250 per night)

Stylish mid-range with colorful interiors and a relaxed feel.

La Torretta Lodge ($900 per night)

Stylish boutique property with terraces, prosecco service, and one of the best views in town.

Hotel Porto Roca ($2100 per night)

This Hotel offers clifftop luxury with pool views over the Ligurian Sea. If you want to have the best of Cinque Terre, this is it.

Daily Itinerary in Cinque Terre

This time the itinerary will depend a bit based on the town you choose to base yourself in, so just mix and match accordingly.

Day 7: Explore Monterosso and Vernazza

Arrive from Florence, explore Monterosso and Vernazza, swim if the weather allows, and enjoy sunset by the harbor.

Day 8: Hike between villages

Hike between villages in the morning. Take pesto making class or just enjoy lunch at Nessun Dorma. End the day watching the sunset with a pizza or gelato in Riomaggiore. My two favourite towns are Manarola and Riomaggiore, so if you don't want to stress by visiting all towns in the days you have here, these are the two I would prioritize.

Traveling from Cinque Terre to Lake Como

Travel from Cinque Terre to Lake Como via Milan. Take a train from La Spezia to Milan, then continue to Varenna. Total travel time is around 4–5 hours, making this a good day to start early.

Lake Como (Days 9–11)

After busy cities and sightseeing, Lake Como offers a completely different pace. Elegant villas, calm waters, and pastel-colored villages create a peaceful atmosphere that feels worlds away from Italy’s big cities.

This is also an area many choose to take a day trip to from Milan or other nearby cities, but I can tell you know that it will only feel stressed and be packed with people, so spend a couple of nights and enjoy this beautiful area a bit slower.

Where to Stay in Lake Como

There are multiple small towns to stay in around lake Como, and you'll probably have an amazing time no matter where you choose to base yourself, but my biggest tip is to not base yourself in the town called Como. Many people assume this is the best place to base yourself but in my opinion it's a huge mistake. The city in itself is nothing special compared to the smaller ones, and you'll end up traveling by boat quite far every day to visit places like Varenna or Bellagio. In my opinion it's much better to base yourself here. The train even goes all the way to Varenna. However, Como is bigger and more budget friendly so it all comes down to how you want to travel and what your budget looks like.

Budget friendly stays in Lake Como

Miralago B&B Apartments ($160 per night)

This is a charming, family-run B&B stay in the peaceful Pescallo bay of Bellagio, offering simple, comfortable rooms and some with lake views, just a 10-minute walk from the historic centre of town.

Locanda Della Maria ($170 per night)

This is a welcoming B&B in the quiet San Giovanni area of Bellagio, just steps from the ferry pier and Lake Como. they offer comfortable rooms and a hearty buffet breakfast, as well as easy access to the town center.

Hotel Don Ferrante ($180 per night)

This is a classic lakeside hotel in Bellagio’s Pescallo district, offering comfy rooms with lake views and an excellent on-site restaurant serving fresh regional cuisine just steps from the water.

Best Mid-Range Stays in Lake Como

Borgo Le Terrazze ($390 per night)

A stylish, elevated boutique property perched above Bellagio with refined design, beautiful views, and a peaceful atmosphere — perfect for a romantic or special-occasion stay with a splash of modern elegance.

Royal Victoria, by R Collections ($600 per night)

This is an elegant historic lakeside hotel right on Lake Como’s shore, offering panoramic water views, a swimming pool, lush gardens, a wellness centre, and two on-site restaurants — one overlooking Bellagio — all just steps from the ferry and village centre.

Hotel Belvedere ($850 per night)

A standout mid-range stay with spectacular panoramic lake views, terraced gardens, and a classic Italian lakeside vibe, plus an outdoor pool and spa facilities for extra relaxation.

Best Luxury Stays in Lake Como

Grand Hotel Villa Serbelloni ($1300 per night)

One of Lake Como’s most iconic and historic luxury hotels, set right on the water in Bellagio with opulent rooms, refined service, and timeless elegance that captures the Italian lakeside dream.

Mandarin Oriental ($1500 per night)

Although slightly outside the towns, this ultra-luxury lakeside resort offers world-class spa facilities, incredible dining, and serene lake views — ideal for a lavish Lake Como escape.

Daily Itinerary in Lake Como

Day 9: Explore Villas and Viewpoints

Arrive and settle in. Spend the evening strolling along the lake and visit one of the villas in the town you base yourself in or hike to the top of Varenna for some amazing views over the lake.

Day 10: Explore the villages

You can choose to either explore the different towns with the public ferry or book a private boat tour that takes you around the lake to see everything from the water. I do recommend a mix. Varenna and Bellagio needs to be explored on foot in my opinion, but you also need to take a boat ride at least once while here to admire the scenery from the water. Private boats will also take you past various villas and scenery you won't see from the public ferry.

My favourite boat tours around Lake Como

Private Boat Tour around the lake ( 2 Hours)

Private Tour on wooden boat with open bar (2 Hours & 4 Hours)

Private Boat Tour around Lake Como ( 6 Hours)

Day 11: Visit Villa del Balbianello

Villa del Balbianello is one of the most beautiful villas to explore, and also made famous from the Star Wars franchise. You can reach the nearest town with public ferry and walk for about 30 minutes to reach it, or catch a boat like the one below to also enjoy the scenery on the way there. Later on, enjoy a slow afternoon swimming or relaxing.

Guided boat tour with visit to Villa Balbianello

Arrive at Villa Balbianello in style with this guided boat tour. In addition you get to see more of Lake Como on the way.

Traveling from Lake Como to Venice

From Lake Como, travel back to Milan and catch a high-speed train to Venice. The journey takes around 3–3.5 hours in total and is easiest booked in advance through Omio.

Venice (Days 12–14)

Ending your Italy trip in Venice feels almost unreal. Once the day-trippers leave, the city becomes quiet, atmospheric, and incredibly romantic. It’s the perfect place to reflect on your journey and slow down one last time.

Yes, Venice can be pretty packed, but it’s for a good reason. It’s one of the most stunning places I’ve ever seen. However, you need to avoid doing a day trip and instead spend some time and venture a bit out of the main streets and wander freely.

Where to Stay in Venice

Best Budget Friendly Stays in Venice

Locanda Ca' Zose ($170 per night)

This is a charming and budget-friendly guesthouse in Venice’s Cannaregio district, offering simple, comfortable rooms in a peaceful canal-side location just a short walk from the train station and bustling city centre.

San Gregorio Apartments ($250 per night)

This is a bright, self-catering accommodations in a peaceful Venetian neighborhood, perfect for travelers who want space, flexibility, and a more local living experience just a short walk from public transport and key sights.

Maison Boutique Al Redentore ($300 per night)

This is a stylish boutique stay in Venice’s quieter Giudecca district, blending contemporary design with Venetian charm and offering easy water-bus access to St. Mark’s Square.

Best Mid-Range Stays in Venice

Monaco & Grand Canal ($500 per night)

This Hotel stands out for its front-row Grand Canal views, elegant Venetian character, and rare privilege of watching gondolas drift past from breakfast or your room—right in the heart of San Marco without feeling overly touristy.

Flora Hotel ($600 per night)

This is a romantic boutique hideaway near St. Mark’s Square, best known for its lush private courtyard garden that feels like a secret oasis in the heart of Venice.

Londra Palace Venezia ($800 per night)

This is a refined luxury hotel on Venice’s Grand Canal, known for its timeless elegance, spacious rooms with canal views, and a beautiful terrace where guests can enjoy breakfast or drinks overlooking the water.

Best Luxury Stays in Venice

Ca Maria Adele ($1000 per night)

This is a beautifully designed boutique hotel in Venice’s Dorsoduro district with uniquely decorated rooms overlooking the Santa Maria della Salute Basilica, a rooftop terrace for breakfast, and an intimate romantic atmosphere in a quiet yet central location.

The St. Regis ($1200 per night)

This is a luxurious waterfront palace hotel on the Grand Canal, offering elegant rooms, superb service, refined dining, and a lavish spa — all within walking distance of St. Mark’s Square.

The Gritti Palace ($1700 per night)

This is an iconic and opulent Grand Canal palace offering exquisitely furnished rooms, world-class service, refined dining, and a prime location just steps from St. Mark’s Square and Venetian landmarks.

Daily Itinerary in Venice

Day 12: Enjoy a stroll along the canal

Spend the day exploring Cannaregio, Venice’s most local-feeling district, with its canalside cafés and laid-back vibe. Enjoy the sunset, watch a concert or join a food tour.

Amazing activities for your first evening in Venice

Food and wine tour in the center of Venice with mini-cruise included

Vivaldi’s Four Seasons Live Classical Music Concert

Sunset Walking Tour with Food and Wine Tastings

Day 13: Visit the Highlights

Visit St. Mark’s Basilica, Doge’s Palace and the Rialto Bridge. Wander though the streets or take a gondola ride. End the day with dinner along a quiet canal in Dorsoduro.

Book Doge’s Palace & St. Mark’s Basilica Tickets here

Join a Rialto Market Food and Wine Lunchtime Tour

Day 14:  Visit the islands

Use your final day to visit the islands. Murano for glassmaking or Burano for colorful houses. If you’d rather stay in the city, wander Castello for a quieter side of Venice, pop into artisan workshops, and just enjoy the city.

Murano & Burano Guided Tour by Private Boat with Glassmaking

If you want to visit both islands, I recommend this private tour that takes you to all the highlights.

Final Thoughts: Ultimate 2 Weeks in Italy

This 2-week Italy itinerary gives you a perfect first taste of the country – history, art, coastline, lakes, and unforgettable cities – all connected by efficient train travel. It’s ideal if you want a clear plan without sacrificing spontaneity.

There are of course so many more places to visit, but if you want to see the highlights, this is the best route in my opinion.

I hope this helps you plan your upcoming adventure to Italy. If you have any questions about travel in Italy, or just want to follow along as I travel the world full time, don‘t hesitate to reach out to me on social media. I would love to connect and help out!

-Ingrid

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