Highlights of Italy Itinerary

This itinerary is for those short on time who want to see many of the highlights of Italy. It has a little bit of everything, from the coast to the vineyards to the cities, which makes it perfect for a first trip to Italy. If you have more time, we’d highly recommend adding a day to your most desired locations or cutting out a stop entirely to slow the pace down.

High level plan: Fly into Naples, 3 days in Positano, 2 days in Rome, 2 days in Tuscany, 2 days in Florence, 2 days in Lake Como, fly out of Milan.

*If you can add a day, I would add another day to Tuscany. If you don’t have as much time, you may want to consider cutting Florence from your itinerary. Another popular stop would be to add Venice at the end.

Travel Day:

  • Fly into Naples. Most flights from the US arrive at night so plan to stay the night in Naples with an early departure the next day.
  • We stayed at an Airbnb walking distance to the central train station. It was nothing special, but close to some bars/night life.

Day 1:

  • Depart Naples early for Positano. We booked a shared shuttle service direct from Naples to Positano. It picked us up at 8am and we were in the heart of Positano by 10am. The van was very comfortable and the drivers were reliable so we recommend this as the easiest transport to Positano. Other options include taking a ferry or public bus service (from what we saw of the buses, I wouldn’t recommend).
  • Checked into our AirBnB. We stayed at a great spot walking distance to everything. It was steps from the beach and had the cutest little market right next door. They were also able to accommodate an early check-in. *Most airbnbs in Italy required us to meet the host in order to check-in so proper coordination and service to message via whatsapp was important.
  • Afternoon at Arienzo Beach Club. The perfect cure to jetlag was lounging at this picturesque Italian beach with drink service and lunch included. You will need to book in advance and can select from a few different inclusion packages. Your reservation also includes a roundtip boat ride to the beach. The seas were too rough the day we visited so we had a 20 min walk which is the other option for accessing this beach situated just south of Positano.
  • Dinner at Il Tridente. A beautiful patio dinner with a great ambiance. Reservations become available 14 days in advance so mark your calendar to book online as soon as they become available (at midnight Italy time). After dinner we stopped at a couple beach bars on our way home. The only late nightlife in Positano appeared to be the Music on the Rocks bar which is super touristy and charged a 50$ cover. A few friends recommended it for live music so could be worth it, but we passed.

Day 2:

  • Scooter tour along the coast. We rented Vespa scooters from Positano Scooters and drove the coast all the way to Salerno with stops along the way. It was a wild ride with traffic along the one lane road that follows the coast, but was a great way to see the many small towns with freedom to stop wherever we wanted.
  • We ate dinner in the courtyard at Al Palazzo . This Michelin guide restaurant was a short walk from our Airbnb and had a beautiful table setting under the lemon trees.

Day 3:

  • Private boat day to Capri. We booked this tour in advance through getyourguide, but unfortunately there were high seas the day we had originally planned and they had no availability the next day. We opted for a shorter tour (4 hours) that was available through BlueStar Positano – they have a shack right on the beach where we were able to find a last minute option. It was a private tour on a beautiful wooden boat with plenty of room to lounge up front and included drinks. It took us down the coast with stops at caves, swimming holes, cliffs to jump off and a brief docking in Amalfi. This was my favorite activity we did in Positano and a definite must-do. We would’ve loved to make it to Capri on the full day tour – guess we’ll have to go back.
  • Explore the town of Positano. Since our boat day got shortened we spent the morning wandering the charming steps of Positano filled with shops and gelaterias.
  • We had dinner overlooking the city at Adamo ed Eva. Getting to the restaurant was a hike up the many steps of Positano, but had beautiful views along the way.

Day 4:

  • Travel to Rome. From Positano we booked the same shuttle service back to Naples and took a train from there to Rome. Traffic delayed our shuttle which seemed pretty common and we missed our pre-booked train which was non-refundable. If you book train tickets in advance be sure to give yourself extra time or just wait to book train tickets until you arrive at the station.
  • Checked into our AirBnB in the Trastevere area which was an awesome place to stay. We definitely recommend Trastevere as the best neightborhood to stay in. If you need two bedrooms this AirBnB was perfect and had the sweetest host.
  • We had drinks at Piazza Navona, watched some street acts and then wandered to a few recommended bars (Il Goccetto, Salotto 42, and Ma Che Siete Venuti A Fa) on our way back to Trastevere for sunset at Belvedere del Gianicolo which is a park overlooking the city making for a great sunset spot.
  • We enjoyed a chef’s tasting dinner at the Michelin Star restaurant: Zia. It was an incredible culinary experience through 8+ courses.

Day 5:

  • We booked the Seven Hills APE tour through my vespa tours. This was a fun way to see the city with a private guide. You ride in an open air remake of the Ape Calessino vehicle which helps optimize the tour time. We parked at multiple stops where we got out and walked to additional sites. It was a great way to spend 3 hours learning about the history of the city from a local.
  • The afternoon was open to explore by foot. We downloaded the Rick Steve’s walking tour and visited the landmarks we didn’t hit on the Ape tour. This time could also be used to visit the Vatican. If that is your goal you should book entry tickets in advance before they sell out.
  • We had one of my favorite dinners of the trip at Taverna Trilussa where they make each pasta dish to order.

Day 6:

  • We rented a car in Rome and drove north to the Tuscany. This is the one leg of the trip it helps to have a vehicle so we booked a one-way rental with pickup in Rome and drop off in Florence.
  • We visited Avignonesi Vinyard where we had booked a tasting tour with lunch included. It was amazing to walk through the whole wine making process. This organic vineyard was so detailed in their approach which was fascinating to learn about. The lunch was also incredible. Each course was paired with tastings that we all shared and enjoyed.
  • We purchased a few bottles of our favorite wines from Avignonesi and enjoyed them at the pool of our Airbnb which was conveniently located just steps away. We played bocce ball on the grounds and enjoyed a more laid back afternoon. For dinner we went to La Dogana Enoteca which overlooked the rolling hills of Tuscany.

Day 7:

  • We planned a picnic overlooking a picturesque view of a curved road lined with cypress trees. This spot was away from crowds and a nice little place to live in the moment. There is another famous view of a curved driveway lined with Cyprus trees that was a bit farther out of the way from us, but is even more picturesque if you have time for a longer road trip.
  • We drove to Montepulciano and explored the charming town for the rest of the day.

Day 8:

  • Drive to Florence and return rental car.
  • Checked into our AirBnB that was very close to the famous Ponte Vecchio Bridge and walking distance to everywhere we explored. I have also stayed at Hotel Botticelli which was also a great location and wonderful stay.
  • We visited the Accademia Gallery to see the famous statue of David and learn about the amazing sculptures by Michelangelo. It is a small museum which makes for a quick, but fascinating stop. Leading up to the David statue you get to see Michelangelo’s process of carving into marble through multiple of his intentionally unfinished works. We had booked a ticket with a scheduled time in advance which is highly recommended to avoid a long wait.
  • After visiting the museum we used the Rick Steve’s walking tour to explore more of the landmarks in Florence, stopped in a few bars to get out of the rain, did some leather shopping and had gelato along the way. Sean played tour guide for our group – reading all the fun Rick Steve’s facts, but it is also available as an audio guide that can be downloaded.
  • For dinner we enjoyed steak Fiorentina at Dall’Oste Chianineria – which is the 27th ranked steakhouse in the world by world steaks 101. The steak was fantastic, but the wait staff does rush you through the meal which was very different then most Italian restaurants.

Day 9:

  • We booked a cooking class through Airbnb called the Art of Pasta. It was informative, hands-on, and delicious. You can book it through Airbnb or through their website here. We learned how to make various types of pasta from scratch then enjoyed them as a group with 4 different sauces. The chef was a joy to talk to and very experienced with time spent working in Michelin star restaurants. We left the experience delighted and extremely full after 4 plates of tasty pasta.
  • To work off the pasta we did the climb up the dome of Cathedral of Santa Maria del Fiore. After the 463 steps you are rewarded with expansive views of Florence. It is one of the best ways to see the city and definitely worth the steps. It is not recommended for people who suffer from claustrophobia as it is a tight spiral staircase to the top. You can buy tickets for a scheduled entry time in advance here.
  • We had drinks at View on Art Rooftop which had an incredible elevated view of the cathedral. Another great rooftop with views of the cathedral is at the Grand Hotel Cavour.

Day 10:

  • From Florence we hopped on the train to Varenna, Lake Como. It was a 3.5 hour train ride with one transfer in Milan. We booked our tickets in advance through ItailiaRail.com to ensure we had seats on the early morning departure.
  • Once in Varenna everything was walking distance from the train station which is one of the main reasons we chose Varenna as our home base in Lake Como. It was very accessible and a picturesque little town. We checked into our accommodations at Alberga Milano – a boutique hotel overlooking the lake with stunning balcony views.
  • We visited Villa Monstera which was also walking distance from Varenna. There was a small café and nice outdoor seating area along the water so we enjoyed a bottle of wine with lunch in the gardens.
  • After lunch we hiked up to Castello di Viezio. This short 30 min hike has two possible routes – one starting just past Villa Monstera: we followed these directions. Entry to the Castle grounds cost $4/person. The castle affords visitors panoramic views of Lake Como and opportunities to see falconry.
  • In the evening we had booked a private boat tour with a drop off in Bellagio through Taxi Boat Varenna. The 1 hour tour was a great way to see a few landmarks on the lake and hear from a local while also providing our transport to Bellagio. There we explored the town, had drinks in the square, and had dinner at Silvio. To get back to Varenna we caught the ferry which runs about every two hours. The head chef/owner/fisherman and staff at Silvio were incredible and even drove us in their personal vehicle to ensure we made it to the ferry in time.

Day 11:

  • We rented a small boat to explore the entirety of the lake on our own. I rented the boat in advance through https://www.lakecomoboat.eu/ . They text me the day before to confirm our pickup time and location, but prior to that they were unreachable and had me nervous we weren’t confirmed – perhaps why they were so affordable. Good to know they are legit and the boat was great. No special licenses were required to rent the boat. We enjoyed cruising the lake, taking a dip in the water, and attempting to explore a few of the other towns. We would’ve made more stops, but found it challenging to find public docking at most towns along the water. Docking was easiest near Hotel Grand Tremezzo and in Menaggio. We were able to see almost every town from off the shores and had a great time relaxing in the beautiful surroundings.
  • We spent our last night exploring Varenna. It is a very small town, but has a nice walk along the lake and a few places to grab a drink. Bar II Molo is the most popular.

Travel day – We flew out of Milan Airport. It was an earlier flight so instead of taking the train we booked a private shuttle through https://city-airport-taxis.com/ . Just like our shuttle to Positano they were reliable and the shuttle was very comfortable.

I hope you enjoyed this post and it helps you plan your own trip to Italy one day! We will definitely be back for more! If you have any questions feel free to leave a comment.

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