Get a taste of Rome, Capri, and Positano with this 8 Day Italian Itinerary. Includes a day trip to Pompeii!
DAY 1 – ROME
When you arrive in Europe, flexibility is going to be your friend. Sometimes flights are delayed or your room at the hotel may not be ready. Or, it is ready and you need a quick nap before you can say Buongiorno to the Ancient City. This is why your first day on your Italian itinerary should include some buffer time as well as the opportunity to explore on your own time.
Call your hotel ahead of your arrival to make sure that (even if your room is not ready), they will hold your luggage for you. Flights from the US to Europe will often arrive in the early morning hours before hotel staff has had the chance to clean. In this case, you will want to grab a cab to your hotel, change out of your airplane clothes, and head to the nearest café for an espresso.
There is plenty to do in Rome without a tour guide. I recommend visiting the Trevi Fountain, Spanish Steps, Pantheon, and Piazza Navona during your first day wandering the city. If you’re looking for a place to stop for some shopping and for aperitivo, check out the Rinascente located close to the Spanish Steps.
DAY 2 – ROME
Now that you’ve had a day to rest and get your bearings, it’s time to see some of Rome’s most famous historical sights. I have always preferred booking tours through Viator, but make sure to always read reviews. We spent the morning on a small group tour of the Colosseum and Roman Forum before heading to the Vatican for our heading to the Vatican to tour the Museums and Sistine Chapel in the afternoon. Wear comfortable shoes and breathable clothing for this day in the summertime!
A friend recommended the restaurant Virginae near Piazza Navona for a traditional Roman dinner and it certainly did not disappoint. If you want an after-dinner drink in a cozy atmosphere, head to the Jerry Thomas Speakeasy. Call ahead to secure a table and when you arrive, look for a barred door with a little gold plaque and buzzer beside it.
DAY 3 – ROME to CAPRI
The next stop on our Italian Itinerary is the island of Capri. Capri can be tricky to get to, but by booking your transportation in advance you can save yourself some stress. We took the train to Naples (which you can book via ItaliaRail) and then hopped in a taxi to Molo Beverello, where the high-speed trains depart. You can book these ferries here.
Upon arrival in Capri, you’ll want to find transportation to your accommodation. We stayed at Hotel Weber Ambassador, which offered shuttles to and from the Marina (at 10 Euro per person) and free shuttles from the hotel to the city center. There are plenty of taxis around the island, but they can be on the pricier side.
There is endless fun to be had in Capri – from exploring cliffs and beaches to shopping along Via Camerelle. The views, food, and activities make Capri one of my Top 3 favorite places in the world. We explored the city until dinner time and headed to Ristorante Panorama for some of the best truffle pasta of my life. The views and food were so good that we came back the next night!
We opted for early reservations (because we didn’t book them far enough in advance to get a prime-time seating), but we ended up heading to another restaurant/bar each night after our early dinner for more drinks and some dessert. We checked out the Capri Rooftop Lounge Bar and the famous Taverna Anema e Core, both lively but very expensive (as everything in this city tends to be).
DAY 4 – CAPRI
The most important thing to do when visiting Capri? A boat tour and visit to the Blue Grotto. If there is one thing that you take from this Italian itinerary, let it me this! We booked a group tour through Laser Capri which took us around the entire island in about 2 hours for 18 euros each. Make sure to bring a tip for the Blue Grotto stop. Note: if it is a particularly windy day, the tour may not stop at the Blue Grotto. You will see all of the other major sites around the island, including the famous Faraglioni rock.
Grab a sandwich on your way back into the marina and take the Funicular or Bus (2 euros per person) back up to the city center. We opted to spend the afternoon at Marina Piccola, one of Capri’s beautiful public beaches. It was less than a five-minute walk from where we stayed! Grab a couple of Peronis and enjoy the crystal clear blue water.
After an afternoon of swimming we got ready for dinner, then window-shopped with gelato in hand to end the night.
DAY 5 – CAPRI TO POSITANO
On day five we checked out of Hotel Weber Ambassador after grabbing breakfast and headed to Marina Grande to catch a ferry to Positano. These ferries are about 20 euros per person and take about 30 minutes to an hour to complete the trip. Don’t forget your sunscreen if you plan to sit on the top level of the ferry!
I was naively unprepared for just how many stairs there are in Positano. We had to haul our luggage up about 3 flights of stairs and winding alleys to get to the main road where we were able to flag down a taxi. I recommend speaking with your hotel before you arrive in Positano to ensure you know the easiest (and least expensive) way to get to your accommodation.
We stayed at Hotel Punta Regina and I cannot recommend it enough. The staff was so helpful – our room was not ready when we arrived, however, they showed us where we could change into our bathing suits and took our luggage to the room while we headed upstairs to enjoy the pool. After a light lunch, long swim, and endless Aperol Spritzes, we made our way down to our room to get ready for dinner.
I made reservations at La Serra, a Michelin Starred restaurant located in Hotel Le Agavi. They arranged transportation to take us to the hotel. We enjoyed the most breathtaking views above Positano and 12 courses of luxuriously curated Mediterranean cuisine.
DAY 6 – DAY TRIP TO POMPEII
On our sixth day in Italy, we decided to take a tour of Pompeii. This tour picked us up at a designated spot in Positano and chauffeured us to Sorrento where we loaded onto a charter bus for the Lost City. If you are a history buff, you need to take a day trip to explore the archeological sites of this ancient city. Our tour included time to hike to the top of Mt. Vesuvius, so make sure to wear appropriate shoes and clothing! This was definitely something on my bucketlist, but if you are looking for a more relaxing vacay, I reccomend leaving this off of your Italian itinerary.
After our 8-hour excursion, we changed and had aperitivo on the rooftop of the Punta Regina before heading down to the beach to find some dinner. We walked through the alleys full of local shops along the way before ending up at Ristorante Buca di Bacco, a spot on the Spiaggia Grande. If you get a second wind after dinner, head to Music on the Rocks, a lively bar inside a cave on the coast.
DAY 7 – POSITANO
On our last day in Positano, we slept in and grabbed a late breakfast at our hotel. We wandered down to the Church of Santa Maria Assunta and soaked in some more of the sights before heading over to the main dock in Positano. There is a little bar on this dock called L’alternativa where you can get a spritz (or any drink you want!) at any time – no one will judge in Positano.
We decided to rent a half-day private boat excursion through our hotel on our last day on the Amalfi Coast. Hotel Punta Regina will set you up on a boat called the Alleria and the driver, Gianluigi, will take you to hidden beaches where you can cliff-jump and swim in the blue sapphire waters. We got a tour of the coast via boat and even stopped to pop prosecco in front of Amalfi.
By the end of the day we were exhausted from the sun and ready to relax. If you only have two people in your party, make a reservation at the Il Tridente Cocktail Club at Hotel Posiden. You can have drinks and a charcuterie that is more than enough food for dinner with one of the best views in Positano for much less than your typical dinner price.
DAY 8 – POSITANO TO ROME
There are plenty of ways to get back to Rome from Positano, but each of them will take you about half the day or more. We took a ferry to Salerno, then walked over to the train station from the marina. There we found our train and headed through Naples and back up to Rome. For our final night in Italy, we stayed at Le Meridien Visconti Rome.
Once we arrived in Rome we did some last-minute site seeing and shopping. We grabbed dinner and then wandered to find some gelato and sit in front of the Pantheon. We wandered the streets until the orange evening sky gave way to an inky twilight. Before retreating to the hotel and having to face our overflowing luggage that was begging to be repacked, we soaked in the last sounds of the city and wondered how soon we would be able to return.
I hope you found our Italian Itinerary helpful. Where should my next adventure be?
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