First Italy Itinerary

Includes: Positano, Capri, Florence, Rome, Venice

Our 14-day Itinerary

4 nights in Positano

5 nights in Florence

3 Nights in Rome

1 night in Naples

Day 1 – Positano – Flew Boston to Naples

Pompeii and then on to Positano – arranged a car to pick us up at the airport to take us to Pompeii then to our hotel in Positano.

Hotel: La Rosa Dei Venti in Positano – small sort of like a bed and breakfast. The rooms were all different and each had a balcony overlooking Positano and the ocean (the Terryhenian Sea).

Lots of little restaurants up and down the street – some right on the street, some inside and some on terraces. Never had a bad meal. Can’t go wrong.

From here we had a driver take us to Ravello and Sorrento.

Day 2 – Ravello – spent a day up here. So pretty. Great shopping. Unbelievable views.

Day 3 – Capri and did the Blue Grotto (don’t forget to duck!).

Day 4 – Positano beach then later in the day we went to Sorrento – Cooking class at Villa Ida.

Day 5 – Train Florence (Firenze) from Naples (or Sorrento, I can’t remember).

Hotel: The De Rose Palace Hotel in Florence. This was close to the river and fairly easy walk to restaurants, Ponte Vecchio Bridge. The rooms were a bit dated, but I think it has been redone. Both of our rooms had Juliette balconies so you could open the windows and hear all that is going on along the street below.

Dining: Our favorite restaurant in Florence was La Martinicca. We went there at least twice, maybe 3 times. Great Tuscan cuisine in a basement space.

Days 6 & 7 – We wandered around Florence checking out Il Duomo, The Statue of David (we didn’t go to the original but there is a replica somewhere that we checked out), went across the river to a park on a big hill that we walked up and had such a gorgeous view of Florence and Il Duomo. Can’t remember the name of it. There were also people selling scarves, etc… up there.

Day 8 –Venice (Venezia) – day trip via train.

Day 9 –Tuscany bus tour. We did 3 walled cities – Sienna, San Gimignano and Montepulciano. Our last stop was a wine tasting at a mountain villa where they also do cooking classes, Tenuta Casanova.

Day 10 –Rome – train from Florence (3 nights in Rome)

Hotel: I don’t remember the name of the hotel, as it was not memorable. I barely fit into the shower (literally).

Dining: The dentist did make us a reservation for our last night at a restaurant near the Colosseum, Isodoro Restaurant, that brings various pasta dishes to the table for you to try – all for one price. In Rome, many restaurants do “apertivo” which is similar to tapas. Often they are complimentary small bites to have with a cocktail or just before dinner. We didn’t even ask at one sidewalk café and they kept bringing them.

Day 11 – Vatican City.

Day 12 – Site seeing day. Wandered around to find the typical tourist sites.

Day 13 – Rome to Naples (1 night)

Wandered around Rome to take in the beautiful gardens and statues, etc… in the morning and took the train to Naples to our hotel (wanted to be close to the airport for our flight home).

Day 14 – Flew home.

We had a wonderful vacation, but there are some things in hindsight that we would change.

• For one, we would end in Positano, rather than start. It would have been nice to have our busy vacation agenda behind us and just relax in Positano.
• We chose not to drive, but I think at least in Tuscany it would have been fun.
• We couldn’t wrap our heads around the train system before we went so, we chose not to drag our luggage to Venice and stay overnight. Next time I would and go to our next stop from Venice, or leave our big luggage with the concierge at the Florence hotel and only bring a carry on to Venice (however, you would have to go back to Florence).
• We would not recommend flying into and out of Naples. We could have done Rome for both or traveled North to South (or Vice Versa) and used two different airports for arrival and departure.
• We stayed pretty much in the middle section of Italy. We still want to see the North, Lake Como area and Cinque Terre, as well as the South in Sicily. So, when we plan our next trip we will incorporate some of these changes.