This is our two week whirlwind trip around Italy. It is not for the slow paced traveler as there are early mornings, late nights, train travel, and a lot of moving hotels. However, if you want to see as much of the country as possibly in two short weeks and are up for a little bit of a crazy adventure, this is the trip for you! Check back soon for detailed posts on each location!
If you have any questions about this itinerary or want any tips about Italy travel please leave a comment below or send an email on the contact me page! I hope you enjoy your trip!
Day 0: Flight to Rome
Fly overnight to Rome. Be sure to try to get some sleep so you are ready to go first thing in the morning for a busy day!
Day 1: Rome
Most of the travel on this trip is via train, so start off your journey by taking the train Leonardo Express from the airport to Roma Termini station. Walk to your hotel and drop off your bags. Wander the streets and find a local restaurant for your first meal in Rome (I recommend pasta!). Now that you are successfully carb stuffed, trek over to the Colosseum and Roman Forum. We highly recommend downloading Rick Steve’s Audio Europe and listening to his tour of the Colosseum and Roman Forum while you walk around. After your tour, make your way to the Panthenon. Don’t be too scared of the line wrapped around the courtyard, it moves fast. For the last stop of the day walk up the Spanish Steps. If you have any interest in seeing the steps (or most other spots) without people covering them you will have to wake up and go at sunrise. For dinner, find another local spot and be sure to indulge in the liter of house wine! *As a note, water is usually not free and you will have to specifically purchase bottled water.
Where we stayed: AirBnB
Day 2: Naples
Take an early train from Rome to Naples. When you arrive in Naples check your bags at the station and go down to the Circumvesuviana train to Pompeii. This train will drop you off right in front of historic Pompeii. Spend your day exploring the amazing preserved history. Again, I highly recommend listening to the Rick Steve’s Audio Europe guide. It does a great job of telling you some of detailed information you would get on a guided tour, but it’s at your own pace. Once you get your fill of Pompeii hop back on the Circumvesuviana train to Naples. Grab your bags from the train station and check into your hotel. For dinner grab a slice of real Neapolitan pizza! After dinner wander down Via San Gregorio Armeno. The locals make and sell the most beautiful Nativity pieces.
Where we stayed: Hotel Piazza Bellini
Other activities: Naples Archeological Museum, Naples Underground Tour
Day 3: Capri
Hop on a morning ferry from Naples to Capri. When you arrive in Capri, if you are feeling brave, walk up the steep path of steps to your hotel to drop off your bags. Wander back down to the marina and have lunch at Salumeria Da Aldo. This is the best sandwich I have ever had in my entire life and I’m pretty sure my husband still dreams of this sandwich! (We got prosciutto, tomato, mozzarella, olive oil, and balsamic vinegar on ours.) After lunch take a boat tour around the island and stop at the blue grotto. Though it’s a little cheesy, inside the grotto was amazing and definitely worth a visit. After your boat tour, take a bus (pick up is right by the dock) to Anacapri. Take the chairlift up to the top of Monte Solaro for breath taking views! At the top there is a little snack shop, so you can actually sit and take in the views with a glass of wine or scoop of gelato. Back in Anacapri wander around the adorable town for all things lemon. For dinner venture back down to the marina and try Ristorante Lo Zodiaco for fresh seafood and some lemoncello!
Where we stayed: Capri Wine Hotel
Day 4: Sorrento/Positano
Today is one of the earliest days, but there is so much to see! Take the earliest ferry from Capri to Sorrento. Leave your bags at your hotel, grab a quick breakfast, and hop on the bus to Positano. If you are visiting during the high season and easily get carsick you may want to spend the extra money on taking the ferry. We visited in midseason and had no issues with the bus. Spend the morning exploring beautiful Positano. I highly recommend splurging on pair of custom made sandals. The experience of watching the cobbler make personalized shoes was so fun and they are some of the most comfortable shoes I own! For lunch visit the local grocery stop and grab a sandwich and a bottle of wine to take to go. Enjoy your lunch as a picnic on the beach and take in the beautiful views. If you are feeling extra adventurous you can go on to Amalfi from here, or you can return to Sorrento. We decided to head back to Sorrento and visit the lemon garden in the city. It was adorable! We then went for an early dinner and called it a night a little early.
Day 5: Tuscany
Take another early train from Sorrento back to Rome. Pick up a rental car and start your drive through the stunning Tuscan countryside. Stop in Assisi and visit the Basilica di San Francesco d’Assisi. The views from the top of the city are some of the best we saw during our trip. Continue on from Assisi to your agriturismo. We stayed in the old villa at Vignamaggio Winery. Waking up to the sprawling views of Tuscan hills covered in wine vines and olive groves was unbelievable. If you want a nice place to relax and escape, this is your spot!
Where we stayed: Vignamaggio
Other activities: San Galgano Abbey
Day 6: Tuscany
Spend a lazy morning at your agriturismo and take in the Tuscan morning views. Start your day with a tour of a winery in the morning. We opted for a small family run winery, but there are also world famous and much larger wineries in the area. For lunch be sure to check out Dario Cecchini Antica Macelleria Cecchini Oficina. We did the family style lunch and had a blast getting to meet others from around the world! Out of all of the activities we did on the entire trip, this was our favorite. Be warned, it is a ton of meat and you will leave stuffed to the max. Finish your day with another winery tour or a dinner and wine pairing. Our agriturismo offered a sunset tour of the winery with a dinner and wine pairing. It was such an amazing dinner, but we wish we had planned it for a different day so we didn’t have such a huge lunch and dinner planned on the same day.
Wineries we visted: Montefioralle, Vignamaggio
Day 7: Tuscany
After another lazy morning, take your car to Pisa. We opted to just see the leaning tower and not actually take a tour of the area. After lunch, drive on to Lucca and drop off your car. We highly recommend staying inside the ancient city walls to get a true feeling of the city. We spent the afternoon exploring the streets. We stumbled upon a fashion market in the city park, which goes to show that you never know what kind of cool things you can find when you wander a bit. We ended the night having dinner at La Bottega Dell’Oste Lucca. I had a delicious plate of pasta and John got a meat and cheese tray (which we came to find out was meant to be an appetizer for four; the waiter thought he was crazy when he ordered it!)
Where we stayed: Lucca Hotel Guest Apartment Margherita
Other activities: Siena
Day 8: Lucca
Lucca was my favorite city in Italy and though it is small, it should not be overlooked. Start your morning off by renting bikes and biking the city walls. Spend the rest of the day exploring the city. Lucca is called the city of 100 churches so be sure to stop by a couple. (*Lucca also has some nice leather shops which may be worthwhile visiting if you’re not stopping in Florence.) Walk up all the steps in Torre Guinigi for beautiful views of the city. Late in the day take a train up to Riomaggiore and check into your hotel. Be sure to get a good night’s sleep for tomorrow!
Where we stayed: AirBnb
Other activities: Torre Guingi
Day 9: Cinque Terre
Get started early today, in fact, the earlier the better. I recommend taking the train up from Riomaggiore to Monterosso and starting your hike there, but you can also start at Riomaggiore and hike up. Be sure to check out the link below to check the status of the trails before you go. The direction we went ended up leaving the harder hikes for later in the day. The trail from Monterosso to Vernazza was the easiest and from Corniglia to Manarola was the hardest. Unfortunately when we were there the main trail from Manarola to Riomaggiore was closed, so we took a train the last little bit back. We thought hiking this direction was a good choice because we weren’t exhausted halfway through and didn’t make up some excuse to stop halfway. After such a long day we opted for a seafood cone and a bottle of wine for dinner before passing out in bed super early.
Information for Hiking Trails: https://cinqueterreinsider.com/2014/09/26/current-status-of-the-cinque-terre-sentiero-azzuro-coastal-trail-september-2014/
Day 10: Florence
Another bright and early train ride will get you into Florence with a whole day ahead of you. Take a morning tour of the Brunelleschi Duomo and the cathedral. For lunch, stop by the Market of San Lorenzo. Be sure to get there before they close up the downstairs market for the day to see the wonderful variety of fresh food they offer. The shops have everything from seafood to spices to fresh bread. Upstairs you will find actual restaurant options. Here we ventured out from the standard pizza or pasta and tried dumplings just to mix it up a little. After lunch keep exploring. There are so many different historic sites in this city that there is definitely a spot for everyone. We wandered through the Medici palace and churches because I just finished a Netflix show about the Medici before our trip and I was a little obsessed. As you wander around the city be sure to keep your eye out for a quality leather shop. I think we brought home something leather for just about everyone in our family. Spend the rest of the day exploring, there’s so much to see!
Where we stayed: AirBnb
Day 11: Florence
Start your morning off with a visit to Accademia to see Michelangelo’s David. After visiting the museum wander over to Piazza della Signoria to see a replica of the statue, as well as many other works of art. If interested, this would be a great time to visit the Uffizi Gallery (we opted to skip it this trip). From there you can walk past the statues lining the Piazzale degli Uffizi and then onto the Ponte Vecchio bridge. Grab a pizza from Gusta Pizza (if you are lucky they will make yours in the shape of a heart). Spend the afternoon exploring the Bobli Gardens. There was so much to see here that we could have wandered the gardens for hours. I’m still not sure that we actually made it around the whole thing. To return to the city, walk across the Ponte Santa Trinita to get a great view of the Ponte Vecchio bridge from afar. At night walk over to the Piazza della Repubblica to watch the street entertainment.
Day 12: Venice
Arrive in Venice on an early train and drop your bags off at your hotel. Take a ferry over to the island of Burano. Explore the colorful little town and pick up something lace as a souvenir. There isn’t a ton to do on the little island, but it was a beautiful spot for lunch. From Burano take the ferry back to Venice, or stop at Murano to see the local glass blowing. Once back in Venice, take a 6PM gondola ride through the Grand Canal. Pro tip: if you go before 7pm it is cheaper and you still get a sunset tour. It’s also a good idea to try to split a ride with more people as one gondola is the same price no matter how many people ride.
Where we stayed: Ca’ Bonvicini
Day 13: Venice
Spend sunrise in St. Mark’s square to see it before it is packed with people. After breakfast take the Hidden Passages tour of Doge’s Palace and then spend a few hours exploring the palace after the tour. Spend your afternoon wandering the streets of Venice. Stop for an aperitivo and aperol spritz with the locals before a late dinner.
Other activities: Verona
Day 14: Venice / Rome
Spend a lazy morning seeing anything else you missed in Venice. Hop on a train from Venice to Rome. We decided to stop halfway in Bologna for lunch and tracked down some real spaghetti bolognese! This time in Rome we stayed in the Trastevere neighborhood. Spend the evening exploring the area.
Where we stayed: AirBnB
Other activities: Jewish Ghetto, Campo Fiore
Day 15: Rome
On your last day in Rome, wake up early to fit in all the remaining activities. Start with a tour of the Vatican Museum and Sistine Chapel. Rick Steve’s Audio Europe has a great audio guide to listen along to! After your tour wander St. Peter’s square. If you are lucky and able to get tickets in advance, take a tour of the Vatican Scavi and see the bones of St. Peter. The tour ends in St. Peter’s Basillica. You can listen to the Rick Steve’s Audio Europe guide here too. Spend the evening visiting any other sites on your list like the Trevi Fountain.
Day 16: Fly Home
Check out and fly home.
Notes:
Reservations:
* We used the location sites to book all of our tickets. I highly recommend this over using any third party sites.
*Book your train tickets ahead of time if you are confident you can make the trains on time.
