Ciao! Today on the blog, I’m sharing my complete Two Week Travel Itinerary to Italy. This was our first ever trip to Italy and we completely fell in love with the country. We traveled to Italy in late Spring/early Summer (May 24th – June 8th), and I think it was a really nice time to visit. It wasn’t too hot or too cold!
We started our adventure in Rome and made our way north, all the way up to Lake Como. The time we spent in each destination felt right and we weren’t rushed. From our travels, we have learned that we much prefer spending time in smaller cities versus big destinations like Rome or Barcelona. I think this itinerary is perfectly suited for someone who doesn’t mind going off the beaten path and wants to experience some “non-touristy” things.
At the end of the day, there will never be enough time to explore this amazing country, but we certainly tried to see as much as we could! I hope you find this travel guide helpful and informative if you are planning an upcoming trip to Italy. Saluti!
Table of Contents
Day 1 // Rome
Where We Stayed: St. Regis Rome
Transportation: We took a taxi from the airport to our hotel and then we walked around the city the rest of the day.
Itinerary:
- 8:00 AM – Landed in Rome
- 10:30 AM – Trevi Fountain
- 11:30 AM – Colosseum (We did not do a tour)
- 12:30 PM – Explored Trastevere
- 1:30 PM – Lunch in Trastevere at Il Comparone
- 3:00 PM – Pantheon and Piazza Navona
- 5:00 PM – Rooftop Bar at Eitch Borromini
- 7:30 PM – Dinner in Trastevere at Spirito DiVino
For more specifics on Rome, check out this blog post linked here.
Day 2 // Tuscany – Montepulciano
Where We Stayed: Locanda San Francesco
Transportation: We rented a car at the Rome Airport and drove up to Tuscany. We rented a car through National.
Itinerary:
- 8:30 AM – Pick Up Rental Car at Rome Airport
- 11:00 AM – Explore Monticchiello
- 12:30 PM – Lunch at Osteria La Porta
- 3:30 PM – Wine Tour at Tenuta Valdipiatta
- 5:00 PM – Check in to hotel in Montepulciano
- 6:00 PM – Explore/Walk Around Montepulciano
For more specifics and photos on Montepulciano, check out this blog post linked here.
Day 3 // Tuscany – Montepulciano
Where We Stayed: Locanda San Francesco
Transportation: We walked around the town of Montepulciano and used our rental car to get around to wineries outside of town.
Itinerary:
- 9:00 AM – Grab coffee in Montepulciano
- 9:30 AM – Explore/Take Photos around Montepulciano
- 12:00 PM – Wine Tour and Lunch at Avignonesi
- 4:00 PM – Cantina de’ Ricci in Montepulciano
- 5:30 PM – Wine at Enoteca La Dolce Vita
- 7:30 PM – Dinner at Ristorante Degli Archi
For more specifics and photos on Montepulciano, check out this blog post linked here.
Day 4 // Tuscany – Volterra
Where We Stayed: Borgo Pignano
Transportation: We continued to use our rental car throughout Tuscany.
Itinerary:
- 10:30 AM – Explore the town of San Gimignano
- 2:30 PM – Cooking Class at our hotel, Borgo Pignano
- 4:30 PM – Relax/Take photos at Borgo Pignano
- 6:00 PM – Sunset Cocktails at Borgo Pignano
- 8:00 PM – Dinner at Villa Pignano
For more specifics and photos on Borgo Pignano, check out this blog post linked here.
Day 5 // Tuscany – Volterra
Where We Stayed: Borgo Pignano
Transportation: We continued to use our rental car throughout Tuscany.
Itinerary:
- 12:00 PM – Guardastelle Wine Tour and Lunch
- 2:30 PM – Explore the town of Volterra
- 5:30 PM – Sunset Cocktails at Borgo Pignano
- 7:00 PM – Casual Dinner at Borgo Pignano
For more specifics and photos on Borgo Pignano, check out this blog post linked here.
Day 6 // Florence
Where We Stayed: The Westin Excelsior
Transportation: Florence is very walkable! We walked around the city and never needed a taxi.
Itinerary:
- 10:00 AM – Dropped off rental car at Florence Airport
- 10:45 AM – Check in to hotel
- 11:15 AM – Explore Florence
- 12:00 PM – Mercato Centrale for lunch
- 1:30 PM – Piazza della Repubblica
- 2:30 PM – Gelateria dei Neri
- 3:30 PM – Piazzale Michelangelo
- 5:00 PM – Cocktails at Enoteca Fuori Porta
- 6:30 PM – Rooftop drinks and dinner at Westin Rooftop Bar
- 8:30 PM – Live music and wine at Westin Lobby Bar
For more specifics and photos on Florence, check out this blog post linked here.
Day 7 // Florence
Where We Stayed: The Westin Excelsior
Transportation: Florence is very walkable! We walked around the city and never needed a taxi.
Itinerary:
- 7:00 AM – Pictures at Cathedral (Duomo)
- 8:30 AM – Cathedral Tour + Climbing the Dome and Bell Tower
- 10:00 AM – Walked around Florence
- 12:00 PM – Mercato Centrale for Lunch
- 2:00 PM – Boboli Gardens
- 3:30 PM – Drinks at Palazzo Vecchio
- 5:00 PM – Shopping in Florence
- 6:30 PM – Rooftop drinks at Westin Rooftop Bar
- 7:30 PM – Il Latini for Dinner
For more specifics and photos on Florence, check out this blog post linked here.
Day 8 // Cinque Terre
Where We Stayed: Airbnb in Riomaggiore
Transportation: We took a train from Florence to La Spezia and then La Spezia to Riomaggiore. We booked the train tickets ahead of time. Once we were in Cinque Terre, we walked around the towns and used the train to get between towns. We bought a 2-day unlimited train pass to get between the towns of Cinque Terre. It was about $30 a person for a 2-day train pass.
Itinerary:
- 10:00 AM – Train to Cinque Terre
- 1:00 PM – Arrive in Riomaggiore
- 1:30 PM – Enoteca Dau Cila for Lunch
- 3:00 PM – Explore Riomaggiore
- 4:00 PM – Drinks @ A Pie de Ma
- 5:00 PM – Relaxing on our Airbnb balcony
- 7:30 PM – Trattoria La Grotta for Dinner
For more specifics and photos on Cinque Terre, check out this blog post linked here.
Day 9 // Cinque Terre
Where We Stayed: Airbnb in Riomaggiore
Transportation: We walked and used the trains to get between towns.
Itinerary:
- 8:30 AM – Explore Manrola
- 10:30 AM – Nessun Dorma for Pesto Cooking Class + Lunch
- 1:00 PM – Explore Vernazza
- 3:30 PM – Explore Monterosso + Cocktails on the Beach
- 7:00 PM – Dinner at Rio Bistrot in Riomaggiore
- 9:00 PM – Watch the sunset in Riomaggiore
For more specifics and photos on Cinque Terre, check out this blog post linked here.
Day 10 // Cinque Terre
Where We Stayed: Airbnb in Riomaggiore
Transportation: We walked and used the trains to get between towns.
Itinerary:
- 9:30 AM – Beach day in Monterosso
- 6:00 PM – Cocktails and Snacks at Bar O’Netto in Riomaggiore
- 8:00 PM – Take Away Dinner from Mamma Mia!
For more specifics and photos on Cinque Terre, check out this blog post linked here.
Day 11 // Bellagio, Lake Como
Where We Stayed: Hotel Du Lac
Transportation: We were coming from Cinque Terre, so we took 3 trains and a ferry to get to Lake Como. We took a train from Riomaggiore to Levanto, Levanto to Milan, and Milan to Varenna. Once we were in Varenna, we bought our ferry tickets to get over to Bellagio. It was about $10 for two ferry tickets to Bellagio.
Itinerary:
- 9:00 AM – Traveling to Lake Como
- 4:00 PM – Arrive in Bellagio + Check in to hotel
- 4:30 PM – Stroll around Bellagio
- 5:00 PM – Silk shopping at Azalea
- 5:30 PM – Cocktails at Hotel Metropole Bellagio
- 6:30 PM – Rooftop cocktails at Hotel Du Lac
- 8:00 PM – Dinner at Bellagio Restaurant & Bar (2nd floor of Hotel Du Lac)
For more specifics and photos on Lake Como, check out this blog post linked here.
Day 12 // Bellagio, Lake Como
Where We Stayed: Hotel Du Lac
Transportation: Bellagio is extremely walkable as there are only a few streets in town. If you want to visit other towns on the lake, a ferry is the best way to go. You can get day passes for the ferry or pay for each individual ride. There are also water taxis available that will take you to your destination more quickly. The water taxis are more expensive than the ferry, but it can be a good option if you are short on time.
Itinerary:
- 9:00 AM – Taking pictures + strolling around Bellagio
- 10:30 AM – Villa Melzi
- 12:30 PM – Lunch at Bstyle Bellagio
- 2:00 PM – Shopping at Rolando
- 2:30 PM – Cocktails on the water at Bar Sanremo
- 3:30 PM – Wine at Aperitivo et al
- 5:00 PM – Como Classic Boat Tour
- 7:30 PM – Dinner at Aperitivo et al
For more specifics and photos on Lake Como, check out this blog post linked here.
Day 13 // Bellagio, Lake Como
Where We Stayed: Hotel Bellagio
Transportation: See Day 12.
Itinerary:
- 10:00 AM – Cooking Class + Lunch at Salice Blu
- 3:00 PM – Truffle Hunting with Chef Luigi
- 6:00 PM – Cocktails at Princess Bar
- 7:30 PM – Dinner at Ristorante Terrazzo Barchetta
- 9:30 PM – Wine at Angolo DiVino
For more specifics and photos on Lake Como, check out this blog post linked here.
Day 14 // Bellagio, Lake Como
Where We Stayed: Hotel Bellagio
Transportation: See Day 12.
Itinerary:
- 11:00 AM – Ferry to Lenno
- 12:00 PM – Villa del Balbianello
- 1:30 PM – Lunch in Lenno at Bar Il Golfo
- 3:30 PM – Ferry to Bellagio
- 4:00 PM – Gelato at Gelateria del Borgo
- 6:00 PM – Rooftop cocktails at Hotel du Lac
- 7:00 PM – Dinner at Ristorante Bilacus
- 9:00 PM – Wine at Angolo DiVino
For more specifics and photos on Lake Como, check out this blog post linked here.
I hope this travel guide provided you with a nice layout of how to plan your trip to Italy. Again, the time in each designation felt right, and I don’t think I would change a thing in terms of how we split it up.
If you are wanting more Italy content, please reference the links below:
- Italy – What I Wore
- Rome In a Day
- Tuscany – Two Days in Montepulciano
- Tuscany – San Gimignano, Volterra, Borgo Pignano
- Two Days in Florence
- Cinque Terre Travel Guide
- Lake Como Travel Guide
As always, feel free to reach out with any questions or comments!
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